MONOSACCHARIDE PARTICLES MODIFIED BY A HYDROPHOBIC CHAIN ​​AND CYCLODEXTRIN.

Abstract

The present invention relates to particles comprising at least one monosaccharide modified with a hydrophobic chain, at least one cyclodextrin, and optionally a molecule of therapeutic or cosmetic interest; their preparation process; a pharmaceutical or cosmetic composition comprising them; and their use for the prolonged release of molecules of cosmetic or therapeutic interest. It also relates to said modified monosaccharide.

Description

Title of the invention: PARTICLES OF MONOSACCHARIDES MODIFIED BY A HYDROPHOBIC CHAIN ​​AND CYCLODEXTRIN. TECHNICAL FIELD OF THE INVENTION

[0001] The present invention relates to particles comprising at least one monosaccharide modified with a hydrophobic chain, at least one cyclodextrin, and optionally a molecule of therapeutic or cosmetic interest, their preparation process, a pharmaceutical or cosmetic composition comprising them, and their use for the prolonged release of molecules of cosmetic or therapeutic interest. It also relates to said modified monosaccharide. STATE OF THE ART

[0002] The encapsulation of active ingredients in particles has been developed with a view to allowing better control of the release of the active ingredients and / or to isolate them from the environment in which they are found in order to avoid any degradation or any unwanted interaction.

[0003] Microparticles (whose size is between 1 and 1000 pm) and nanoparticles (whose size is less than 1 pm) can be obtained by three main classes of processes: (1) physicochemical processes based on variations in solubility of the materials used for encapsulation under the effect of variations in temperature or pH, (2) mechanical processes such as extrusion for example and (3) chemical processes during which the synthesis of the membrane which makes up the particle, generally based on polymer, and the encapsulation of the active substances take place simultaneously.

[0004] Microencapsulation and nanoencapsulation techniques such as nanoprecipitation, solvent emulsion-evaporation, salting-out or solvent emulsion-diffusion generally use surfactants and organic solvents (Salatin et al. 2018).

[0005] Concerning mechanical processes, they often use complex equipment. In addition, the increase in temperature constitutes a significant loss of energy and can lead to partial or total denaturation of heat-sensitive active ingredients.

[0006] Finally, among category (3) of processes, the methods by polymerization or polycondensation, if they have the advantage of not using solvents, have the disadvantage of using extremely reactive products capable of reacting with the substances to be encapsulated. For example, in the case of the emulsion polymerization of alkylcyanoa- acrylates, polymerization reagents can chemically react with the active ingredient to be encapsulated. This causes a partial or total loss of the effectiveness of the formulations. This method also involves extreme variations in pH, which also causes the degradation of some or all of the active ingredient (Mirchandani et al. 2021).

[0007] Thus, the methods of encapsulating molecules of interest pose several problems.

[0008] The main problem remains the toxicity due to the solvents, surfactants, or reagents used during encapsulation, as well as the extreme variation in pH during the preparation process. In some cases, heating or strong agitation is also necessary, which is the cause of a loss of energy and time. In addition, the molecules to be encapsulated may undergo degradation due to the solvents, surfactants, and reagents used, variations in pH, or even the strong agitation or heating necessary for the manufacture of the particles, leading to therapeutic ineffectiveness of the particles obtained.

[0009] Encapsulation processes, in particular by interfacial polycondensation or by solvent emulsion-diffusion, are long because they generally involve several steps, with additional purification steps to remove excess reagents, solvents or surfactants often being necessary.

[0010] Finally, when encapsulation is possible, the encapsulation yield is generally low and the release of the encapsulated active substance is most often uncontrolled, a “burst release” effect being classically observed.

[0011] There therefore remains a need for a method of encapsulating molecules of therapeutic or cosmetic interest which is simple, does not involve the use of toxic ingredients, while limiting the degradation of the encapsulated active substances.

[0012] Cyclodextrins (CDs) are cyclic oligosaccharides composed of α-(1,4)-linked glucopyranose chains. For example, alpha-cyclodextrin (α-CD) is composed of six glucose units in chair conformation linked by α-1,4 glycosidic bonds ([Fig.l]). CDs appear as a conical frustum. The apolar cavity of CDs is lined by hydrogen atoms linked to the C3 and C5 carbon atoms and by oxygen atoms forming ether bonds, while on the outside, we find hydroxyl groups (Del Valle 2004). The amphiphilic nature of CDs, both hydrophilic on the outside and hydrophobic on the inside, allows them to include hydrophobic molecules in their cavity to form inclusion complexes (Diaz-Salmeron et al. 2018).In addition, the cavity contains water molecules whose presence is energetically unfavorable (polar-apolar interaction), which allows substitution by guest molecules of less polarity than water (Rekharsky et al. 1998).

[0013] Studies have highlighted the possibility of forming self-assembled systems such as micelles, nanoparticles or vesicles by non-covalent interactions between a-CD and a hydrophobic guest molecule. Such systems are similar to colloids intended to vectorize active substances in the pharmaceutical field, to protect vitamins in the food industry or to stabilize / protect active substances against heat or light or to control the release of active substances in the cosmetic field (Crini et al. 2021).

[0014] Similarly, several a-CD molecules can thread along another linear molecule "axis" by forming inclusion complexes, the resulting assemblies being called polyrotaxanes. Spherical nanoparticles of polyrotaxanes were thus obtained after mixing a-CD and PEG modified with cinnamic acid at each end of the PEG (Zhang et al. 2014). Nanorods and microrods were also obtained by mixing tetradecane with a-CD solution (Mathapa et al. 2013).

[0015] Finally, nano- and micro-platelets could be obtained by the hierarchical assembly in water of a-CD and polysaccharides hydrophobically modified by C16-C18 alkyl chains. The formation of structured and cohesive platelets is induced by the interaction of the alkyl chains grafted onto the polysaccharides with the a-CD molecules and the self-organization of the inclusion complexes with each other makes it possible to form a multilayer structure (Ahmed et al. 2018). International application WO 2013 / 150193 describes in particular the formation of nanoplatelets resulting from the interaction between a chitosan modified with an alkyl chain and a-CD. However, the nanoplatelet shape makes it difficult to encapsulate an active ingredient as well as its controlled release. Furthermore, the compositions obtained do not have a rheofluidifying character which is of interest in particular for topical application. Summary of the invention

[0016] Surprisingly, the Applicant has discovered that particles comprising at least one monosaccharide modified by a hydrophobic chain and a cyclodextrin make it possible to effectively encapsulate hydrophilic molecules of interest while having a simple and versatile preparation process. In addition, the compositions obtained have good shear-thinning properties which are interesting for topical application.

[0017] A first subject of the invention therefore relates to particles comprising: - at least one compound of the following formula: [Chem. (I)] in which - n represents 0 or 1; - M represents a residue of a monosaccharide, preferably of an al-dohexose, of which an OH group, preferably the OH group in the anomeric position, is replaced by the group -X-(AY)nZ and of which one or more -OH groups are optionally replaced by an -OSO3H group and / or of which a -CH2-OH group is optionally replaced by a -COOH group; X represents -O-, -S-, -NRr, -OC(O)-, -SC(O)-, -bKRJQO)-, -OC(S)-, -SC(S)-, or -N(Ri)C(S)-, the first atom of the groups being linked to M; - A represents a spacer, the spacer being a (Ci-C2o)alkyl chain, in particular (Ci-Ci5)alkyl, in particular (Ci-Cio)alkyl, and preferably (Ci-C8)alkyl, optionally interrupted one or more times by one or more units chosen from the group consisting of -O-, -S-, -NR2-, -C(O)-, and -C(S)-, and / or optionally substituted with one or more groups chosen from the group consisting of a halogen atom, -NO2, -CN, -OR3, -SR4, and -NR5R6; Y represents -O-, -S-, -NR7-, -C(O)-, -C(S)-, -OC(O)-, -C(O)O-, -SC(O)-, -C(O)S-, -N(R7)C(O)-, -C(O)N(R7)-, -OC(S)-, -C(S)O-, -SC(S)-, -C(S)S-, -N(R7)C(S)-, or -C(S)N(R7)-; - R1 to R7 represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group (eg (C1-C4)alkyl); and - Z represents a saturated or unsaturated hydrocarbon chain, in particular saturated, linear or branched, preferably linear, comprising from 4 to 40 carbon atoms, in particular 6 to 28 carbon atoms, preferably 12 to 24 carbon atoms; and - at least one cyclodextrin, preferably α-cyclodextrin.

[0018] According to a particular embodiment of the invention, the particles further comprise at least one molecule of therapeutic or cosmetic interest.

[0019] A second subject of the invention relates to a process for preparing the particles according to the invention comprising the mixture: - at least one compound of formula Chem. (I) as defined above; - at least one cyclodextrin, preferably α-cyclodextrin; and - optionally a molecule of therapeutic or cosmetic interest.

[0020] A third subject of the invention relates to a compound of the following formula: [Chem. (I)] in which - n represents 0 or 1; - M represents a residue of a monosaccharide, preferably of an aldohexose, of which an OH group, preferably the OH group in the anomeric position, is replaced by the group -X-(AY)nZ and of which one or more -OH groups are optionally replaced by a group -OSO3H and / or of which a group -CH2 -OH is optionally replaced by a group -COOH; X represents -O-, -S-, -NRr, -OC(O)-, -SC(O)-, -N(Rj)C(O)-, -OC(S)-, -SC(S)-, or -N(Ri)C(S)-, the first atom of the groups being linked to M; - A represents a spacer, the spacer being a (Ci-C2o)alkyl chain, in particular (Ci-Ci5)alkyl, in particular (Ci-Cio)alkyl, and preferably (Ci-C8)alkyl, optionally interrupted one or more times by one or more units chosen from the group consisting of -O-, -S-, -NR2-, -C(O)-, and -C(S)-, and / or optionally substituted with one or more groups chosen from the group consisting of a halogen atom, -NO2, -CN, -OR3, -SR4, and -NR5R6; Y represents -O-, -S-, -NR7-, -C(O)-, -C(S)-, -OC(O)-, -C(O)O-, -SC(O)-, -C(O)S-, -N(R7)C(O)-, -C(O)N(R7)-, -OC(S)-, -C(S)O-, -SC(S)-, -C(S)S-, -N(R 7)C(S)-, or -C(S)N(R7)-; - R1 to R7 represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group; and - Z represents a saturated or unsaturated hydrocarbon chain, in particular saturated, linear or branched, preferably linear, comprising from 4 to 40 carbon atoms, preferably 6 to 24 carbon atoms.

[0021] A fourth subject of the invention relates to a cosmetic or pharmaceutical composition comprising particles according to the invention and at least one cosmetically or pharmaceutically acceptable excipient.

[0022] A fifth subject of the invention relates to the use of particles according to the invention comprising at least one molecule of cosmetic interest for the prolonged release of the molecule of cosmetic interest.

[0023] The invention also relates to a method for the prolonged release of a molecule of cosmetic interest comprising the administration, for example by route topically, to a person in need of an effective quantity of particles according to the invention comprising the molecule of cosmetic interest.

[0024] A sixth subject of the invention relates to particles according to the invention comprising at least one molecule of therapeutic interest, for their use as a medicament, preferably as a prolonged-release medicament.

[0025] The invention also relates to the use of particles according to the invention comprising at least one molecule of therapeutic interest, for the preparation of a prolonged-release medicament.

[0026] The invention also relates to a method for the prolonged release of a molecule of therapeutic interest comprising the administration, for example topically, to a person in need thereof of an effective quantity of particles according to the invention comprising the molecule of therapeutic interest. DETAILED DESCRIPTION OF THE INVENTION Definitions

[0027] For the purposes of the present invention, the term "monosaccharide" means a compound of formula H-(CHOH)x-CO-(CHOH)yH with x and y representing, independently of one another, an integer ranging from 0 to 5 provided that 2 < x+y, and in particular x+y = 2, 3, 4, 5, 6, 7, 8 or 9, and preferably x+y = 4 or 5, the monosaccharide possibly being in a linear form represented by the abovementioned formula or possibly being in a cyclized form by reaction of the CO function (aldehyde or ketone) with one of the OH groups to form a hemiacetal or hemiketal group. Preferably, the monosaccharide is in cyclized form. The monosaccharide may be an aldose which carries an aldehyde function (when x or y is 0) or a ketose which carries a ketone function (when neither x nor y is 0). It will preferably be an aldose. Preferably, the monosaccharide is a hexose (comprising 6 carbon atoms), i.e. x+y = 5, and in particular an aldohexose.The monosaccharide may be of the dextrorotatory (D) or levorotatory (L) type, preferably of the dextrorotatory (D) type. The monosaccharide may be in particular allose, altrose, glucose, mannose, gulose, idose, galactose, talose, ribose, arabinose, xylose, or lyxose. Preferably, it will be mannose, galactose or glucose, and in particular D-mannose, D-galactose or D-glucose.

[0028] In the context of the present invention, one or more -OH groups of the monosaccharide are optionally replaced by an -OSO3H group and / or a -CH2 -OH group of the monosaccharide is optionally replaced by a -COOH group.

[0029] For the purposes of the present invention, the term "monosaccharide residue" means a monosaccharide as defined above from which an OH group has been removed and which is linked to the rest of the molecule by the carbon atom originally bearing the OH group removed.

[0030] For the purposes of the present invention, the term “alkyl” group means a saturated, linear or branched hydrocarbon chain.

[0031] For the purposes of the present invention, the term “(CrCx)alkyl” group means an alkyl group as defined above, comprising from 1 to x carbon atoms. Thus, a (Ci-C6)alkyl group comprises 1 to 6 carbon atoms and may be, for example, a methyl, ethyl, isopropyl, tert-butyl, pentyl, or hexyl group. Similarly, a (Ci-C2o)alkyl group comprises 1 to 20 carbon atoms and may be, for example, a methyl, ethyl, isopropyl, tert-butyl, pentyl, hexyl, or decyl group.

[0032] For the purposes of the present invention, the term “(C2-C6)alkenyl” group means a linear or branched hydrocarbon chain comprising at least one double bond and comprising 2 to 6 carbon atoms. For example, ethenyl or allyl groups may be mentioned.

[0033] For the purposes of the present invention, the term "aryl" means an aromatic hydrocarbon group, preferably comprising from 6 to 10 carbon atoms, and comprising one or more fused rings, such as, for example, a phenyl or naphthyl group. Advantageously, this is phenyl.

[0034] For the purposes of the present invention, the term "aryl-(Ci-C6)alkyl" means an aryl group as defined above, linked to the rest of the molecule via a (Ci-C6)alkyl chain as defined above. By way of example, the benzyl group may be mentioned.

[0035] For the purposes of the present invention, the term "(Ci-C6)alkyl-aryl" means a (Ci-C6)alkyl group as defined above, linked to the rest of the molecule via an aryl group as defined above. By way of example, the tolyl group (CH3Ph) may be mentioned.

[0036] For the purposes of the present invention, the term “halogen atom” means fluorine, chlorine, bromine and iodine atoms.

[0037] For the purposes of the present invention, the term "cyclodextrin" means a cyclic oligosaccharide composed of glucopyranose links linked in α-(1,4). Preferably, the cyclodextrin comprises 6, 7 or 8, in particular 6, glucopyranose links.

[0038] In the present invention, by "cosmetically or pharmaceutically acceptable" is meant that which is useful in the preparation of a cosmetic or pharmaceutical composition which is generally safe, non-toxic and neither biologically nor otherwise undesirable and which is acceptable for cosmetic or pharmaceutical use, in particular human pharmaceutical use.

[0039] For the purposes of the present invention, the term “ambient temperature” means a temperature of between 8 and 40°C, preferably between 15 and 30°C, in particular from 20 to 25°C.

[0040] For the purposes of the present invention, the term "protecting group" means a group which selectively blocks a reactive site in a multifunctional compound such that a chemical reaction can be carried out selectively at another unprotected reactive site in the meaning conventionally associated with it in synthetic chemistry.

[0041] For the purposes of the present invention, the term "O-protecting group" means any substituent that protects the hydroxyl group, i.e., a reactive oxygen atom, against undesirable reactions, such as the O-protecting groups described in "Greene's Protective Groups In Organic Synthesis," 4th edition, 2007, John Wiley & Sons, Hoboken, New Jersey. A hydroxyl group protected by an O-protecting group may be, for example, an ether, an ester, a carbonate, an acetal, and the like. In particular, the O-protecting groups include a (Ci-C6)alkyl group optionally substituted by one or more (especially 1 to 3) halogen atoms (such as chlorine atoms), such as methyl, ethyl, tert-butyl, and 2,2,2-trichloroethyl groups; an aryl-(Ci-C6)alkyl group, such as benzyl, the aryl ring being optionally substituted by one or more methoxy groups, such as benzyl (Bn) and p-methoxybenzyl (PMB) groups;a trityl group of formula -CAr iAr2Ar3, such as triphenylmethyl (also called trityl - Tr), (4-methoxyphenyl)diphenylmethyl (also called methoxytrityl - NMT) and bis-(4-methoxyphenyl)phenylmethyl (also called dimethoxytrityl - DMT); a substituted methyl group of formula -CH2ORGp2 or -CH2SRGp2 (in particular -CH2ORGP2), such as methoxymethyl (MOM), benzyloxymethyl, 2-methoxyethoxymethyl (MEM), 2-(trimethylsilyl)ethoxymethyl and methylthiomethyl; a substituted ethyl group of formula -CH2CH2ORGP2 or -CH2CH2SRGP2 (in particular -CH2CH2ORGP2), such as ethoxyethyl (EE); a silyl group of formula -SiRGp3RGp4RGp5, such as trimethylsilyl (TMS), triethylsilyl (TES), t-butyldimethylsilyl (TBS or TBDMS) and t-butyldiphenylsilyl (TBDPS) groups;a carbonyl group of formula -CO-RGP6, such as acetyl (Ac), pivaloyl (Piv or Pv) and benzoyl (Bz) groups, or of formula -CO2-RGP7, such as allyloxycarbonyl (Alloc) and 9-fluorenylmethyloxycarbonyl (Fmoc) groups; or a tetrahydropyranyl (V) (THP) or tetrahydrofuranyl (V) group; ;

[0042] with Arb Ar2 and Ar3 representing, independently of each other, an aryl, such as phenyl, optionally substituted by one or more methoxy groups; RGP2 representing a (Ci-C6)alkyl group (such as methyl or ethyl) optionally substituted by an aryl group (such as phenyl), (Ci-C6)alkoxy (such as methoxy) or trialkylsilyl (such as SiMe3); RGP3, Rgp4 and RGP5 representing, independently of each other, a (Ci-C6)alkyl or aryl (such as phenyl) group; and RGP6 and RGP7 representing, independently of each other, a (Ci-C6)alkyl, (C2-C6)alkenyl, aryl, aryl-(Ci-C6)alkyl or 9-fluorenylmethyl group.

[0043] In particular, it is an acetyl group.

[0044] For the purposes of the present invention, the term "leaving group" means a chemical group which can be easily displaced by a nucleophile during a nucleophilic substitution reaction, the nucleophile being, for example, an alcohol, thiol or amine function. Such a leaving group may more particularly be a halogen atom such as a chlorine or bromine atom, a sulfonate, an N-succinimidyloxy group, a 4-nitro-phenyloxy group, a pentafluorophenoxy group or an N-benzotriazoloxy group. The sulfonate may in particular be a -OSO2-RLG group with RLG representing a (Ci-C6)alkyl, aryl, aryl-(Ci-C6)alkyl or (Ci-C6)alkyl-aryl group, said group being optionally substituted by one or more halogen atoms such as fluorine atoms. The sulfonate can be in particular a mesylate (-OS(O2 )-CH3), a triflate (-OS(O)2-CF3) or even a tosylate (-OS(O)2-(p-Me-C6H4)).

[0045] By "activated form" of the COOH or CSOH group is meant, for the purposes of the present invention, a COOH or CSOH group in which the OH unit of the COOH or CSOH function has been replaced by an activated leaving group (LG) allowing the coupling of the COOH or CSOH group in an activated form with a hydroxyl (OH), thiol (SH) or amino (NH) function by formation of a (thio)ester (C(OO, C(O)-S, C(S)-O, C(S)-S) or (thio)amide (C(O)-N, C(S)-N) bond and release of the LG-H compound. The activated forms may be activated (thio)esters, activated (thio)amides, anhydrides or (thio)acyl halides such as (thio)acyl chlorides. The activated (thio)esters include derivatives formed by the reaction of the COOH or CSOH group with N-hydroxybenzotriazole or N-hydroxysuccinimide. Compound of formula Chem. (I)

[0046] The present invention relates to a compound of the following formula: [Chem. (I)] (^1F>X4A-YV M, X, A, Y, n and Z being as defined above, and at least one cyclodextrin, preferably α-cyclodextrin.

[0047] Preferably, M represents an aldohexose residue, in particular mannose, galactose or glucose, and more particularly D-mannose, D-galactose or D-glucose, one or more -OH groups of which are optionally replaced by an -OSO3H group and / or one -CH2-OH group of which is optionally replaced by an -COOH group. Preferably M represents a mannose residue, more particularly D-mannose, one or more -OH groups of which are optionally replaced by an -OSO3H group and / or one -CH2-OH group of which is optionally replaced by a -COOH group. Preferably, M represents a mannose residue, in particular D-mannose.

[0048] Advantageously, X represents -O-, -NRr, -OC(O)-, or -N(Ri)C(O)-; in particular -O- or -N(Ri)C(O)-; in particular -O- or -NHCO-, the first atom of the groups being linked to M. Preferably, X represents -O-.

[0049] According to a first embodiment of the invention, n = 0 and the AY motif is absent.

[0050] According to a second preferred embodiment of the invention, n is equal to 1 and the AY pattern is present.

[0051] In this embodiment, A advantageously represents a (Ci-C20)alkyl chain, in particular (Ci-Ci5)alkyl, in particular (Ci-Cio)alkyl, and preferably (CrC 8)alkyl, optionally interrupted one or more times by one or more units chosen from the group consisting of -O-, -NR2-, and -C(O)-, and / or optionally substituted with one or more groups chosen from the group consisting of a halogen atom, -OR3, and -NR5R6. In particular, A advantageously represents a (Ci-C20)alkyl chain, in particular (Ci-Ci5)alkyl, in particular (Ci-Cio)alkyl, and preferably (Ci-C8)alkyl, optionally interrupted one or more times by one or more -O- units and / or optionally substituted with one or more -OR3 groups, such as OH.Preferably, A represents a (Ci-C20)alkyl chain, in particular (Ci-Ci5)alkyl, in particular (Ci-Cio)alkyl, and preferably (CrC8)alkyl, such as a -(CH2)m- chain with m representing 1, 2, 3, 4, 5, 6, 7 or 8, in particular 2 or 3, in particular 3. A may also represent a -CH2CH2-(O-CH2CH2)P- chain with p = 1, 2, 3, 4 or 5, in particular 1.

[0052] Similarly, in this embodiment, Y advantageously represents -O-, -NR7-, -C(O)-, -OC(O)-, -C(O)O-, -N(R7)C(O)-, or -C(O)N(R7)-; in particular -OC(O)-, -C(O)O-, -N(R7)C(O)- or -C(O)N(R7)-; more particularly -N(R7)C(O)- or -C(O)N(R7)- (eg -NHC(O) or -C(O)NH-); preferably -N(R7)C(O)- such as -NHC(O)-, the first atom of the groups being linked to A.

[0053] According to a preferred embodiment, n is equal to 1, A represents a chain -(CH2)m- with m representing 1, 2, 3, 4, 5, 6, 7 or 8, in particular 2 or 3, in particular 3, and Y represents -OC(O)-, -C(O)O-, -N(R7)C(O)- or -C(O)N(R7)-, in particular -N(R7)C(O)- or -C(O)N(R7)- (eg -NHC(O) or -C(O)NH-), preferably -N(R7)C(O)- such as -NHC(O)-, the first atom of the groups being linked to A.

[0054] Preferably, Z represents a saturated or unsaturated, linear hydrocarbon chain of 4 to 40, in particular 6 to 28, preferably 12 to 24 carbon atoms.

[0055] According to a preferred embodiment, n is equal to 1, X represents -O- or -N(Ri)C(O)- such as -NHCO- preferably -O-, A represents a chain -(CH2)m- with m representing 1, 2, 3, 4, 5, 6, 7 or 8, in particular 2 or 3, in particular 3, and Y represents -N(R7)C(O)- or -C(O)N(R7)- (eg -NHC(O) or -C(O)NH-), preferably -N(R7)C(O)- such as -NHC(O)-, the first atom of the groups being linked to A.

[0056] According to one embodiment, n is equal to 1, X represents -O- or -N(Ri)C(O)- such as -NHCO- preferably -O-, A represents a chain -(CH2)m- substituted by an OH group with m representing 1, 2, 3, 4, 5, 6, 7 or 8, in particular 2 or 3, in particular 3, and Y represents -N(R7)C(O)- or -C(O)N(R7)- (eg _NHC(O) or -C(O)NH-), preferably -N(R7)C(O)- such as -NHC(O)-, the first atom of the groups being linked to A.

[0057] According to another embodiment, n is equal to 1, X represents -O- or -N(Ri)C(O)-such as -NHCO- preferably -O-, A represents -CH2CH2-(O-CH2CH2)P- with p = 1, 2, 3, 4 or 5, in particular 1 and Y represents -N(R7)C(O)-, N(R7) being linked to A.

[0058] According to another embodiment, n is equal to 0, X represents -O- or -N(Ri)C(O)-, preferably -N(Ri)C(O)- such as -NHCO-, the first atom of the groups being linked to M.

[0059] Preferably, the molecule of formula Chem. (I) corresponds to the following formula Chem. (II) (this compound is called ML in the experimental part, including the figures):

[0060] [Chem. (II)]

[0061] Process for the preparation of the compound of formula Chem. (I)

[0062] The compound of formula Chem. (I) may be prepared by a preparation process comprising a coupling reaction at X and a coupling reaction at Y, when Y is present, the coupling reaction depending on the nature of X and Y.

[0063] When n= 0, the preparation process advantageously comprises a step of coupling MrXi with X2-Z, for which: - Mi representing a group M as defined above optionally in a protected form, and preferably in which the -OH groups are in a protected form and therefore substituted by an O-protecting group such as an acetyl; - Z is as defined above; - Xi and X2 each represent a reactive chemical group capable of reacting together to form a group X as defined above.

[0064] According to a first embodiment, the group Xi is a group -OH, -SH or -NRi H and the group X2 is a leaving group, in particular as defined above, or a group -COOH or -CSOH optionally in an activated form.

[0065] According to a second embodiment, the group Xi is a leaving group, in particular as defined above and the group X2 is a group -OH, -SH or -NRiH.

[0066] In this embodiment, when the group Xi is located in the anomeric position of the monosaccharide M, Xi may in particular be a group -OCO-R8 with R8 representing a (Ci-C6)alkyl group such as methyl. Preferably, the other OH groups of the monosaccharide M will be in a protected form. The coupling reaction of this group Xi with X2 representing a group -OH, -SH or -NRiH may then be carried out in the presence of a Lewis acid.

[0067] Lewis acids are well known to those skilled in the art. They can be chosen from boron trihalides such as boron trifluoride (eg BF3.OEt2), phosphorus pentahalides, arsenic pentahalides and antimony pentahalides.

[0068] The coupling step between Xi and X2 making it possible to form the pattern X is well known to those skilled in the art.

[0069] When Mi represents a group M in a protected form, an additional deprotection step will be necessary to obtain the desired Chem. I compound.

[0070] When n = 1, according to a first alternative, the preparation method may comprise the coupling of MrXi with X2-AYZ, for which Mb Xb X2, A, Y and Z are as defined above.

[0071] The molecule X2-AYZ can be prepared by coupling between X2'-A-Yi and Y2-Z, for which A and Z are as defined above and X2' represents a group X2 as defined above, optionally in a protected or inactivated form. Yi and Y2 each represent a reactive chemical group capable of reacting together to form a group Y as defined above. The chemical groups Yi and Y2 can be chosen according to Table 1 below. The coupling step between Yi and Y2 making it possible to form the unit Y is well known to those skilled in the art.

[0072] [Tables 1] 1st reactive group (Yi or Y2) 2nd reactive group (Yi or Y2) capable of reacting with the 1st reactive group OH, SH or NHR7 COOH or CSOH or an activated form such as C(O)C1 OH, SH or NHR7 Leaving group such as a halogen atom or a sulfonate C(O)Hal or C(S)Hal MgHal

[0073] Hal represents a halogen atom such as Br or Cl, R7 is as defined above.

[0074] When n = 1, according to a second alternative, the preparation process can understand the coupling of MrX-A-Yi with Y2-Z, for which Mb X, A, Yb Y2 and Z are as defined above.

[0075] The molecule MrX-A-Yi can be prepared by coupling between MrXi and X2-A-Yi', for which Mb Xb X2, A and Z are as defined above, and Yf ​​represents a group Yi as defined above optionally in a protected or inactive form.

[0076] In the context of the present invention, "inactive form" means that the group Y / is not capable of coupling with Y2 to form a Y unit. When Yf represents a group Yi in a protected or inactive form, it will be deprotected or activated so as to obtain the group Yi before carrying out the coupling reaction. The deprotection or activation reaction can be carried out in situ, that is to say that the deprotection or activation reaction can be carried out during the same reaction step as the coupling. The deprotection or activation reaction can also be carried out in one or two reaction steps.

[0077] For example, when Yi represents -NH2j, then Yf can be a halogen atom or an N3 group. Halogen atoms (eg Br or Cl) can be easily substituted by an azide, this azide can then be reduced to an amine group in the presence of a phosphorus(III) derivative such as triphenylphosphine (Staudinger reduction). Thus, for example, Yf can represent a bromine or chlorine atom or an N3 group when Yi represents an NH2 group.

[0078] The compound Chem. (I) thus obtained can be separated from the reaction medium by methods well known to those skilled in the art, such as for example by extraction, evaporation of the solvent or by precipitation and filtration.

[0079] The compound may further be purified if necessary by techniques well known to those skilled in the art, such as by recrystallization if the compound is crystalline, by distillation, by column chromatography on silica gel or by high performance liquid chromatography (HPLC). Particles

[0080] The present invention also relates to particles comprising: - at least one compound of formula Chem. (I), and - at least one cyclodextrin, preferably α-cyclodextrin.

[0081] The compound of formula Chem. (I) is as defined above.

[0082] In a particularly preferred embodiment, the particles according to the invention comprise: - at least one compound of the following formula: [Chem. (II)] - at least one α-cyclodextrin.

[0083] The molar ratio between the compound Chem. (I) and the cyclodextrin is advantageously from 1 to 20, preferably from 5 to 10.

[0084] Advantageously, the particles according to the invention may have a hydrodynamic diameter ranging from 10 nm to 10 pm, preferably from 40 nm to 4 pm, more preferably from 200 nm to 2 pm and / or a number average diameter DMET ranging from 10 nm to 10 pm, in particular from 20 nm to 1 pm, in particular from 50 nm to 300 nm.

[0085] The hydrodynamic diameter can be determined by dynamic light scattering (DLS), in particular from a suspension of the particles in water, more particularly according to the method described in the experimental part. The particles according to the invention suspended in a solvent such as water can form aggregates and be in the form of a nanogel. The hydrodynamic diameter makes it possible to measure the size of these aggregates.

[0086] The number average diameter DMET can be determined by transmission electron microscopy (TEM) which makes it possible to obtain a distribution of the number diameters of the particles, the average of which is called DMET. This diameter can be measured more particularly according to the method described in the experimental part. In this case, the diameter measured is that of the particles taken individually, and not of the aggregates.

[0087] The particles according to the invention may further comprise at least one molecule of therapeutic or cosmetic interest, whether hydrophilic or lipophilic.

[0088] The molecule of therapeutic interest may be a substance, hydrophilic or lipophilic, belonging to classes I and III of the Biopharmaceutical Classification System, namely: antibiotics, peptides such as antimicrobial peptides (for example e.g., temporins), antiviral agents, antiparasitic agents (e.g., metronidazole or fluconazole), antihistamines (e.g., cimetidine), analgesics (e.g., paracetamol), vitamins (e.g., ascorbic acid), or anti-inflammatory agents (e.g., ibuprofen).

[0089] The molecule of cosmetic interest may be chosen from amino acids, salicylic acid, betaine, caffeine, peptides used in cosmetology (for example tripeptide-1, palmitoyl tripeptide-1, palmitoyl tetrapeptide-7, palmitoyl hexapeptide-12, myristoyl hexapeptide-16, myristoyl pentapeptide-17, hexanoyl dipeptide-3 norleucine acetate, azelaoyl bis-dipeptide-10 and mixtures thereof) and mixtures thereof.

[0090] Among the antibiotics, mention may be made of: [3-lactams such as penicillins (for example piperacillin), carbapenems (for example meropenem), monobactams (for example aztreonam), cephalosporins (for example ceftriaxone), glycopeptides (for example teicoplanin and vancomycin), aminoglycosides (for example gentamicin and amikacin), oxazolidinones (for example li-nezolid) and mixtures thereof.

[0091] Antiviral agents include: abacavir, acyclovir (aciclovir), adefovir, amantadine, ampligen, amprenavir (agenerase), imifenovir (arbidol), atazanavir, atripla (efavirenz / lexamine marfovir tricyclovir), (Xofluza), bictarvy (Bictegravir / emtricitabine / tenofovir alafenamide), boceprevir, bulevirtide, lecidofovir, cobicistat (Tybost), combivir (Lamivudine / Zidovudine), daclatasvir (Daklinza), darunavir, delavirdine, delavirdine (Emtricita / Alafenamide), didanosine, docosanol, dolu-tegravir, doravirine (Pifeltro), edoxudine, efavirenz, elvitegravir, emtricitabine, enfuvirtide, ensitrelvir, entecavir, etravirine (Intelence), fam-cyclovir, fosamprene, foscarnavir, foscarnavir ganciclovir (Cytovene), ibacitabine, ibalizumab (Trogarzo), idoxuridine, imiquimod, inosine pranobex, indinavir, lamivudine, letermovir (Prevymis), lopinavir,loviride, maraviroc, methisazone, moroxydine, nelfinavir, nirmatrelvir / ritonavir (Paxlovid), nevirapine, nitazoxanide, norvir, oseltamivir (Tamiflu), pen-ciclovir, peramivir (Rapivab), pleconar, lactophyllo, lethalgrain, lethalgrain remdesivir, ribavirin, rilpivirine (Edurant), rimantadine, ritonavir, sa-quinavir, simeprevir (Olysio), sofosbuvir, stavudine, taribavirin (Viramidine), telaprevir, telbivudine (Tyzeka), tenofovir alafenamide, teproxinovir, disopravir trifluridine, trizivir, tromantadine, trunda, umifenovir, valaciclovir (Valtrex), valganciclovir (Valcyte), vicriviroc, vi-darabine, zalcitabine, zanamivir (Relenza), zidovudine and their mixtures. ,

[0092] In particular, the molecule of therapeutic or cosmetic interest can be chosen in the group consisting of acetylsalicylic acid, acyclovir, amitriptyline hydrochloride, amodiaquine hydrochloride, amoxicillin trihydrate, atenolol, bisoprolol fumarate, chloroquine hydrochloride or phosphate or sulfate, cimetidine, ciprofloxacin hydrochloride, codeine phosphate, diclofenac sodium or potassium, doxycycline hyclate, efavirenz, enalapril maleate, ethambutol dihydrochloride, fluconazole, folic acid, furosemide, ibuprofen, ketoprofen, isoniazid, lamivudine, levetiracetam, levofloxacin, metoclopramide hydrochloride, metronidazole, nifedipine, piroxicam, prednisolone, prednisone, primaquine diphosphate, proguanil hydrochloride, propranolol hydrochloride, pyrazinamide, quinidine sulfate, quinine sulfate, ranitidine hydrochloride, ribavirin, rifampicin, stavudine, verapamil hydrochloride, zidovudine,allopurinol, amiloride hydrochloride, amitriptyline hydrochloride, amlodipine, ascorbic acid, bisoprolol, calcium folinate, cetirizine, citalopram, escitalopram, clindamycin, cyclophosphamide, diazepam, diethylcarbamazine dihydrogen citrate, digoxin, donepezil, doxazosin, doxycycline hydrochloride, fluconazole, lamivudine, levodopa, levofloxacin, levo-norgestrel, lithium carbamate, loratadine, DL-methionine, mirtazapine, nicotinamide, norethisterone, ofloxacin, ondansetron, paracetamol (also called acetaminophen), phenobarbital, phenoxymethylpenicillin potassium, potassium iodide, pravastatin, promethazine hydrochloride, propylthiouracil, pyridoxine hydrochloride, quinapril, quinine sulfate, ramipril, riboflavin, salbutamol sulfate, abacavir, alendronic acid, amodiaquine, anastrazole, benznidazole,biperiden hydrochloride, captopril, carbidopa, cefaclor, chlorambucil, chloramphenicol, chlorphenamine hydrogen maleate, chlorpromazine hydrochloride, cimetidine, ciprofloxacin hydrochloride, clavulanic acid, clomiphene citrate, clomipramine hydrochloride, cloxacillin sodium, colchicine, cycloserine, didanosine, ergocalciferol, ergotamine tartrate, ethinylestradiol, ethionamide, ethosuximide, ferrous salts, flucytosine, gabapentin, glyceryl trinitrate, hydralazine hydrochloride, hydrochlorothiazide, isoniazid dinitrate isosorbide, letrozole, levamisole hydrochloride, levothyroxine sodium, lisinpril, losartan, medroxyprogesterone acetate, metformin hydrochloride, methotrexate sodium, methyldopa, sertraline, sildenafil, tamoxifen citrate, terbinafine, theophylline, tramadol, valproic acid, ven-lafaxine,warfarin sodium, zolpidem, morphine sulfate, bostigmine bromide, nifurtimox, penicillamine, pentamine, procarbazine hydrochloride, pyridostigmine bromide, risedronic acid, sulfadoxine, te- , razosine, thiamine hydrochloride, topiramate, zinc sulfate and mixtures thereof.

[0093] Preferably, the molecule of therapeutic or cosmetic interest is chosen from the group consisting of vitamins such as ascorbic acid, antimicrobial peptides such as temporins, antiviral agents and antibiotics.

[0094] Process for preparing particles according to the invention

[0095] The invention also relates to a process for preparing the particles as defined above, comprising mixing: - at least one compound of formula Chem. (I) as defined above; - at least one cyclodextrin, preferably α-cyclodextrin; and - possibly a molecule of therapeutic or cosmetic interest as defined above.

[0096] In a preferred embodiment, the compound of formula Chem. (I) and the cyclodextrin are introduced in a molar ratio of the compound of formula Chem. (I): cyclodextrin ranging from 1:1 to 1:20, preferably from 1:2 to 1:15, preferably from 1:5 to 1:10.

[0097] The mixture of at least one compound of formula Chem. (I), at least one cyclodextrin, and optionally a molecule of therapeutic or cosmetic interest can be carried out in water and / or a water-miscible solvent, preferably in a polar protic solvent such as water, ethanol or a mixture thereof, preferably water.

[0098] Said mixture can be carried out at room temperature, that is to say without a heating or cooling step. It may also be envisaged to carry out this mixture at another temperature, for example at a temperature ranging from 0°C to 70°C.

[0099] It can also be carried out for a period of 48 hours to 96 hours, preferably with stirring.

[0100] The process for preparing the particles according to the invention is therefore very simple since it can be carried out in a single step, by simply mixing the constituents of the particles. Furthermore, it can be carried out in a non-toxic solvent such as water.

[0101] The particles thus prepared can be used as they are, that is to say in suspension in the reaction medium such as water, or can be recovered or dried before use, for example by lyophilization. Cosmetic or pharmaceutical composition

[0102] The present invention also relates to a cosmetic or pharmaceutical composition comprising particles as defined above and at least one cosmetically or pharmaceutically acceptable excipient. Preferably, the composition according to the invention is in a form suitable for topical application.

[0103] The galenic forms used for topical application are in particular: lotions, milks, emulsions, serums, balms, masks, creams, dispersions, gels, mousses, shampoos, conditioners, and sprays.

[0104] The compositions according to the invention may contain surfactants, complexing agents, preservatives, antioxidants, stabilizing agents, emulsifiers, thickeners, gelling agents, humectants, emollients, trace elements, perfumes, colorants, UV filters and mixtures thereof.

[0105] Use of the particles and compositions according to the invention

[0106] The particles and compositions comprising at least one molecule of therapeutic or cosmetic interest can be used for the prolonged release of said molecule of therapeutic or cosmetic interest.

[0107] Particles not comprising a molecule of therapeutic or cosmetic interest can also be used as such as a medicament since the monosaccharide residue can act as an active ingredient. For example, the particles according to the invention comprising mannose can be used to compete with the mannose naturally present on the surface of cells and which serves for the adhesion of pathogenic microorganisms such as bacteria. Therefore, such particles could be used for their antibacterial properties. FIGURES

[0108] [Fig.l]: Chemical structure of a-CD.

[0109] [Fig.2]: Macroscopic appearance of formulations A, B, E, G and I at 10 mg / mL of ML before and after 3 days of stirring at 25°C.

[0110] [Fig.3A]: Images obtained in TEM and size distributions of suspensions A, B and C obtained by analysis of the TEM images and adjusted by a log-normal law. The average is called DMET.

[0111] [Fig.3B]: Images obtained in TEM and size distributions of suspensions D, E and F obtained by analysis of TEM images and adjusted by a log-normal law. The average is called DMET.

[0112] [Fig.3C]: Images obtained in TEM and size distributions of suspensions G, H and I obtained by analysis of TEM images and adjusted by a log-normal law. The average is called DMET.

[0113] [Fig.4]: Intensity size distribution of particles consisting of ML / a-CD (10 / 77 mg / mL).

[0114] [Fig.5]: Effect of initial a-CD concentration at ML concentration of 10 mg / mL on Dh (top right diagram), DMET (top left) and Zeta potential (bottom) of particles (n = 3).

[0115] [Fig.6]: SEM images of particles made of ML / a-CD (formulation F, 10 / 96 mg / mL).

[0116] [Fig.7]: Variation of dynamic viscosity as a function of shear rate of suspensions of particles consisting of ML / a-CD (formulation E, 10 / 80 mg / mL and formulation I, 10 / 140 mg / mL).

[0117] [Fig.8]: Macroscopic appearance of the 5 mg / mL formulations in ML after 3 days of magnetic stirring at 300 rpm and 25°C.

[0118] [Fig.9]: Images obtained in TEM and histograms of particle size distributions obtained by analysis of several images and adjusted by a log-normal law.

[0119] [Fig. 10]: Images obtained in SEM of the particle suspensions obtained with ML / a-CD by progressively increasing the concentration of a-CD: (A) 5 / 40 mg / mL, (B) 5 / 70 mg / mL, (C)5 / 80 mg / mL and (D) 5 / 113 mg / mL.

[0120] [Fig. 11]: Images obtained in AFM of the particle suspensions obtained with ML / a-CD 5 / 70 mg / mL.

[0121] [Fig. 12]: Intensity size distribution of particles obtained in suspensions formulated from a mixture of ML / a-CD in water. The concentration of a-CD is gradually increased: (A) 5 / 40 mg / mL, (B) 5 / 70 mg / mL, (C) 5 / 80 mg / mL and (D) 5 / 113 mg / mL.

[0122] [Fig. 13]: Effect of initial a-CD concentration at 5 mg / mL ML concentration on Dh (top right diagram), DMET (top left) and Zeta potential (bottom) of particles (n = 3).

[0123] [Fig. 14]: Release profile of ascorbic acid (AA) as a function of time. EXAMPLES 1 - Materials and methods

[0124] α-CD (C36H6o03o, M = 972.8 g / mol) and ascorbic acid (abbreviated AA, C6H8O6, M = 176.12 g / mol) were obtained from Sigma-Aldrich. Characterization of mannolipid (ML)

[0125] The study of the solubility of ML was carried out in water, methanol and methanol / chloroform mixture 1 / 1 v / v. In 10 mL glass vials, 10 mg of ML are added to 500 pL of solvent and left under magnetic stirring at 300 rpm at 25°C.

[0126] Fourier transform infrared spectroscopy analyses were carried out with a 4 cm1 resolution JASCO FT / IR-4100 spectrometer. An accumulation of 60 scans per measurement was carried out in order to obtain a spectrum located between 4000 and 400 cm1 analyzed by the Spectra Manager software. The sample to be analyzed is brought into contact with a crystal (diamond) before being crossed by the infrared beam.

[0127] Nuclear magnetic resonance (NMR) spectra were recorded with a 300 MHz Bruker UltraShield spectrometer. Physicochemical characterizations of particles

[0128] Particle size measurement was studied by dynamic light scattering (DLS) using a Zetasizer Nanoseries (Malvern, France). For this, 40 pL of each particle suspension was diluted in 960 pL of MillQ® water before detection. Each sample was analyzed three times at 25°C. Detection was done at 173°.

[0129] The Zeta potential of the particles was obtained on the same apparatus by diluting the particle suspensions as described previously; 40 pL are dispersed in 960 pL of a 1 mM NaCl solution. Each suspension was then placed in a Zeta potential measuring cell. For each sample, the Zeta potential corresponds to the average of three successive measurements.

[0130] Transmission electron microscopy (TEM) was used to determine the morphology and size of the particles obtained. The microscope used is a JEOL 1400 operating at 80 kV (Imagif, Gif sur Yvette, France). Each suspension (1 pL) is diluted in 49 pL of MilliQ® water, then 4 pL of this diluted suspension is deposited on a carbon-coated copper grid. After 5 min of drying, the grid is introduced into the microscope to visualize the sample. The size distribution was determined by analyzing at least 5 images of each sample using Image J software.

[0131] Scanning electron microscopy (SEM) images were obtained using a PEG electron microscope (Merlin model). The samples were diluted 1 / 100 (1 pL of the particle suspension in 99 pL of MillQ® water), then 25 pL of this dilution was placed on a metal pad and left to dry for 24 h before observation.

[0132] Atomic force microscopy (AFM) observations were performed using an Asylum MFP-3D microscope (Oxford Instruments, USA) allowing observations in air and in liquid media. AFM images were recorded in a non-contact mode with a silicon tip coated with an aluminum layer oscillating at a control frequency of 270 kHz. The suspension (1 pL) is diluted in 39 pL of MilliQ® water, then 2 pL of this diluted suspension is deposited on a mica plate and left to dry for 10 min.

[0133] Rheological characterizations of particle suspensions

[0134] The rheological tests are conducted with an AR-G2 rotary absolute rheometer (TA Instruments) equipped with a 40 mm diameter plane-plane cell and a Peltier effect device which allows temperature control (T = 20°C). The air gap angle is fixed at 1° and the surfaces are roughened to reduce the risk of wall slippage. The flow curves were obtained by applying a shear rate between 1 and 2000 s1.

[0135] Quantity of a-CD interacting with the alkyl chains of mannolipid (ML)

[0136] Formulations J to M (see Table 2) were centrifuged (Thermo Scientific Sorvall ST 16R Centrifuge) for 30 min at 3000 G in order to separate the assemblies from the supernatant. The supernatant, containing the excess a-CD, is recovered and filtered (0.2 pm hydrophilic syringe filter) in order to remove residual assemblies and aggregates larger than 0.2 pm. The filtrate obtained is subjected to a polarimetric assay (X = 589 nm, Perkin Elmer 341 polarimeter) to quantify the quantity of a-CD that has not interacted with the ML. Encapsulation of ascorbic acid

[0137] In order to estimate the encapsulation capacity of the particles according to the invention, vitamin C, also called ascorbic acid (AA), was tested as a hydrophilic model molecule. For this, three 2 mL solutions of AA at different concentrations (1 mg / mL, 2 mg / mL and 3 mg / mL) were prepared. Then, in a small vial protected from light, 5 mg of ML and 70 mg of a-CD were introduced, then the mass is made up to 1 g with the AA solution. The suspension is left stirring for 3 days at 25°C at 300 rpm. To determine the encapsulation efficiency (EE), the formulations were centrifuged at 3000 G for 30 min and the concentration of free (non-encapsulated) AA was determined at a wavelength equal to 265 nm using a spectrophotometer (Perkin-Elmer Lambda 25 controlled by UVWinlab software). Release of ascorbic acid

[0138] The release of AA from the particles was studied in phosphate buffer saline (PBS, pH = 7.4 ± 0.45) using the dialysis method. After removing the supernatant to determine the EE, the AA-loaded particles (ML / a-CD 5 / 70 mg / mL formulation with an initial AA concentration of 3 g / L) were lyophilized and then redispersed (m = 17 mg) in 2 mL of phosphate buffer and introduced into a dialysis bag (MWCO = 3500 Da) which will subsequently be immersed in a beaker containing 400 mL of PBS. The beaker is kept at 25°C and stirred with a magnetic bar. At regular time intervals, 2 mL of the PBS was withdrawn for UV analysis (X = 265 nm) to determine the concentration of released AA, and the same volume of fresh PBS was added to the release medium.

[0139] Regarding lyophilization, 500 pL of the particle suspension was placed in a vial and then frozen at -20°C for 12 h. Then the sample was placed in the lyophilizer chamber for 24 h at -55°C under a pressure of 0.5 mbar. 2 - Synthesis of mannolipid

[0140] Synthesis and characterization of the 3-azidopropvl-2.3.4.6-tetra-O-acetvl-aD-mannopvranoside

[0141] This compound is synthesized from mannose pentaacetate (CAS RN 4163-65-9) and 3-chloropropanol in two steps as described in the literature (Ma et al. 2016).

[0142] 'H NMR (300 MHz, CDC13): ô 5.34 - 5.13 (m, 4H), 4.75 (d, J = 1.7 Hz, 1H), 4.21 (dd, J = 12.2, 5.4 Hz, 1H), 4.05 (dd, J = 12.2, 2.5 Hz, 1H), 3.90 (ddd, J = 8.3, 5.4, 2.4 Hz, 1H), 3.80 - 3.70 (m, 1H), 3.46 (dt, J = 9.9, 5.9 Hz, 1H), 3.37 (t, J = 6.5 Hz, 2H), 2.09 (s, 3H, CH3 Ac), 2.04 (s, 3H, CH3 Ac), 1.98 (s, 3H, CH3 Ac), 1.93 (s, 3H, CH3 Ac), 1.89-1.76 (m, 2H).

[0143] 13C NMR (75 MHz, CDC13) : at 170.7 (CO Ac), 170.2 (CO Ac), 170.0 (CO Ac), 169.8 (CO Ac), 97.8, 69.6 (CMan), 69.2 (CMan), 6.8, 6.6 (CMan), CMan (CMan), 65.0, 62.6, 48.2, 28.8, 21.0 (CH3 Ac), 20.8 (CH3 Ac), 20.8 (CH3 Ac), 20.8 (CH3 Ac).

[0144] Synthesis and Characterization of Tetraacetylated Mannolipid O Ac A»O / v O AcO -i.--' ■ A. with rf THEIR

[0145] Triphenylphosphine (543 mg, 2.074 mmol, 1.3 equiv.) was added to a solution of 3-azidopropyl-2,3,4,6-tetra-O-acetyl-aD-mannopyranoside (688 mg, 1.595 mmol, 1 equiv.) and stearoyl chloride (773 mg, 2.552 mmol, 1.6 equiv.) in anhydrous dichloromethane (DCM) (2 mL). The mixture was stirred overnight and N,N-diisopropylethylamine (330 mL, 1.914 mmol, 1.2 equiv.) was added. Stirring was stopped 15 minutes after the addition of N,N-diisopropylethylamine (DIEA) by diluting with dichloromethane (13 mL) and washing with 1M hydrochloric acid solution (2x5 mL) and saturated sodium bicarbonate solution (5 mL). The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was then roughly purified by flash chromatography (CyHex / AcOEt 60:40) to obtain 1 gram of tetraacetylated mannolipid as the major compound.

[0146] Rf: 0.23 (CyHex / AcOEt 60:40).

[0147] RMN 'H (300 MHz, CDC13) : ô 5,97 (t, J = 5,1 Hz, 1H, NH amide), 5,24 - 5,19 (m, 2H), 5,16 (app s, 1H), 4,74 (s, 1H), 4,22 (dd, J = 12,2, 5,1 Hz, 1H), 4.02 (dd, J = 12.2, 2.0 Hz, 1H), 3.91 (br s, 1H), 3.78 - 3.64 (m, 1H), 3.44 (dt, J = 10.0, 5.9 Hz, 1H), 3.36 - 3.22 (m, 2H), 2.15 - 2.06 (m, 5H, NHCOCH2, CH3 Ac), 2.03 (s, 3H, CH3 Ac), 1.98 (s, 3H, CH3 Ac), 1.92 (s, 3H, CH3 Ac), 1.83-1.71 (m, 2H), 1.60 - 1.49 (m, 2H, NHCOCH2CH2), 1.18 (br s, 28H, 14xCH2), 0.80 (t, J = 6.4 Hz, 3H).

[0148] 13C RMN (75 MHz, CDC13) : ô 173.4 (CO amide), 170.6 (CO Ac), 170.0 (CO Ac), 169.9 (CO Ac), 169.6 (CO Ac), 97.6, 69.4, 69.1, 68.5, 66.5, 66.1, 62.5 37.0. Synthesis and characterization of mannolipid (ML)

[0150] To a solution of the tetraacetylated mannolipid in anhydrous methanol (30 mL) at 0 °C, sodium (30 mg) was added. The solution was stirred for 5 hours while allowing the temperature to rise to room temperature and then the mixture was neutralized using a cation exchange resin such as Amberlyst® IR 120 H+. The resin was then removed by filtration and the filtrate was then concentrated in vacuo. The crude product was then purified by silica gel column chromatography (DCM / EtOH 85:15) to obtain the pure product (390 mg, 49%, yields of both steps) in the form of a white powder.

[0151] Rf: 0.26 (DCM / EtOH 85:15).

[0152] ESLHRMS m / z [M+H]+ calculated for C27H54NO7: 504.3895, found: 504.3890.

[0153] 'H NMR (300 MHz, MeOD / CDCl3 90:10 v:v): ô 4.75 (s, 1H), 3.93 - 3.21 (m, 10H), 2.22 (t, J = 7.3 Hz, 2H), 1.87 - 1.76 (m, 2H), 1.62 (br s, 2H), 1.29 (br s, 28H, 14xCH2), 0.98 - 0.84 (m, 3H, CH3).

[0154] 13C NMR (75 MHz, MeOD / CDCl3 90:10 v: v): ô 175.3 (CO amide), 100.2, 73.2 (C Man), 71.3 (CMan), 70.7 (CMan), 67.2 (CMan), 64.6, 61.6, 36.5, 35.7, 31.7, 29.5 - 28.9 (13xCH2), 25.8, 22.4, 13.3. 3 - Preparation of the particles according to the invention

[0155] In 10 mL glass bottles were successively introduced the mannolipid whose synthesis is described above (ML), alpha-cyclodextrin (a-CD) and MilliQ® water. The suspensions are left under magnetic stirring at 300 rpm for 72 h at 25°C.

[0156] Several particle syntheses were carried out at different concentrations of a-CD and ML (see Table 2).

[0157] [Table 2]: Formulation ML (mg) a-CD (mg) MilliQ® Water ML / a-CD (mg / mL) Immoles a-CD / ML QSP1 g (g) A 10 0 0.989 10 / 0 0.0 B 10 40 0.950 10 / 40 2.1 C 10 57 0.931 10 / 57 3.0 D 10 77 0.911 10 / 77 4.0 E 10 80 0.910 10 / 80 4.1 F 10 96 0.892 10 / 96 5.0 G 10 110 0.880 10 / 110 5.7 H 10 134 0.854 10 / 134 6.9 I 10 140 0.850 10 / 140 7.2 J 5 40 0.955 5 / 40 4.1K 5 70 0.925 5 / 70 7.2 L 5 80 0.915 5 / 80 8.3 M 5 113 0.882 5 / 113 11.7

[0158] Ra cD / ML is the ratio between the number of moles of a-CD and ML.

[0159] Compositions of the prepared particle suspensions 4 - Characterization of a-CD / ML particles 4.1. 10 mg / mL ML formulations (A to I)

[0160] - Macroscopic aspect:

[0161] Without a-CD, ML is insoluble in water before stirring. After 72 h of stirring, a white suspension is obtained. After a few hours without stirring, a precipitate forms, which may be the sedimentation of water-insoluble ML aggregates. By adding a-CD, whitish and opaque suspensions were obtained by the interaction of the alkyl chains (Cp) of ML with a-CD (see [Fig.2]).

[0162] - Morphology, size and load:

[0163] The formulations were first observed in TEM. Without a-CD (10 / 0), the image in [Fig.3A] shows objects of indefinite shape and aggregates larger than 2 pm, very polydisperse. The size of these aggregates can reach 3.4 pm. This may be due to the low solubility of ML in water. In the presence of a-CD (formulation B, 40 mg / mL), the TEM image shows objects of size varying from 50 to 350 nm. The morphology of the particles is a rather rounded shape.

[0164] As the concentration of a-CD increases, the particles become more contrasted and the shape of the particles becomes more visible. In the presence of a-CD at concentrations above 80 mg / mL, TEM images of the particles formed in The different formulations highlight small spherical particles grouped around larger particles. We can see in Figures 3B and 3C that the increase in the initial amount of a-CD and therefore the Ra_cD / ci7 ratio leads to an increase in the average particle diameter analyzed by TEM (DMET). The higher the concentration of a-CD, the greater the number of a-CD molecules interacting with the ML. As a result, the alkyl chains of the ML become saturated with a-CDs leading to larger, organized and well-defined structures.

[0165] The hydrodynamic diameter of the particles suspended in water was subsequently measured by dynamic light scattering (DLS). [Fig.4] highlights the intensity distribution of the particle diameters in formulation D (10 / 77 mg / mL). This figure shows that the particles have a diameter of approximately 608 ± 7 nm with a polydispersity index (PDI) of 0.245.

[0166] The results of the measurements of the variation of hydrodynamic diameters as a function of the concentration of a-CD are shown in [Fig.5]. The particle sizes measured by TEM are much smaller than those obtained by DLS. This discrepancy between the DLS and TEM values ​​becomes even more marked for concentrations of a-CD higher than 57 mg / mL for which the formulations are more opaque and viscous.

[0167] Furthermore, it can be seen that the average particle diameter in the 10 / 77 mg / mL formulation (DMET = 216 ± 30 nm) is much smaller than that measured by DLS (Dh = 608 ± 7 nm). As can be seen from the TEM images, the particles are stuck to each other and assembled into aggregates. As a result, their scattering intensity is stronger than that of individual particles and the hydrodynamic diameter value obtained is only the measurement of the diameter of several aggregated particles.

[0168] Regarding the Zeta potential of the particles, we can see that the latter have a negative Zeta potential. We can also observe an increase in the Zeta potential with the concentrations of a-CD. The latter starts at -14.22 ± 0.22 mV in the absence of a-CD and then reaches a value of -0.12 ± 0.25 mV in the formulation I 10 / 140 mg / mL. This result is attributed to the threading of the alkyl chains of the ML into the cavities of CDs, which leads to a masking of their negative charge and therefore an increase in the charge of the particles. It should be noted that although the general trend is towards an increase in Zeta potential with increasing a-CD concentrations, the potentials obtained remain close in suspensions whose a-CD concentration varies from 57 to 134 mg / mL with an average value of -2.83 ± 1.10 mV and an average deviation of -0.89 mV.

[0169] The SEM images of formulation F shown in [Fig.6] highlight spherical particles. We observed that some particles had a structure with a core and a crown. This could be the result of two successive processes. First, the a-CDs will thread along the alkyl chain of the ML to form inclusion complexes which then self-assemble into a bilayer. Indeed, the ML molecules have a polar head (mannose) and an apolar hydrocarbon chain. The polar parts would remain in contact with the external aqueous medium while the interior of the bilayer is composed of alkyl chains included in the hydrophobic cavities of the a-CD molecules.

[0170] - Rheological properties:

[0171] The rheological properties were determined by measuring the dynamic viscosity as a function of the shear rate of formulations at 10 / 80 mg / mL and 10 / 140 mg / mL ([Fig.7]). We note that the viscosity decreases with the shear rate. The particle suspensions therefore have a shear-thinning behavior. This phenomenon could result from the breakdown of interactions between the particles on the one hand and the interruption of the non-covalent bonding points within the inclusion complexes under the effect of the applied stress on the other hand. In addition, we note that the viscosity value increases with the increase in the a-CD concentration. This behavior can be explained by the increase in particle size (increase in the volume fraction occupied by the particles), which opposes the flow. 4.2. 5 mg / mL ML formulations (J to M)

[0172] - Macroscopic aspect:

[0173] After 3 days of stirring, the suspensions obtained are white ([Fig.8]) and much less viscous than those obtained with a ML concentration of 10 mg / mL.

[0174] - Morphology, size and load:

[0175] In order to characterize the morphology and size of the particles formed, a TEM study of these formulations was conducted. The observed images are dominated by the presence of spherical particles aggregated with each other ([Fig.9]). In addition, it is observed that the increase in the concentration of a-CD is accompanied by an increase in the particle size. This result is in agreement with what was observed with the particles obtained at a ML concentration of 10 mg / mL.

[0176] The particles were also characterized by SEM and AFM. As shown in [Fig. 10] obtained by SEM, the particles obtained are spherical. The AFM images of the particle suspension obtained with ML / a-CD 5 / 70 mg / mL in [Fig. 11] show the presence of spherical nanoparticles with a diameter of approximately 130 nm close to that measured by TEM.

[0177] DLS measurements were used to determine the hydrodynamic diameters of the particles in solution. [Fig.l2].A shows particles of about 100 nm accompanied by particles of size equal to 628 nm. The first peak could correspond to well-dispersed individual particles while the second would be attributed to aggregated particles. On the other hand, the intensity distributions of the particle diameters obtained at 70, 80 and 113 mg / mL of a-CD, present a single peak around 920 ± 32 nm, 1114 + 45 nm and 1174 + 125 nm respectively.

[0178] As for the particles obtained with an ML concentration of 10 mg / mL, the values ​​of the hydrodynamic diameters are clearly higher than those obtained by MET, SEM and AFM microscopy ([Fig. 13]).

[0179] The measurements of the Zeta potential of the particles presented in [Fig. 13] show that it is negative in the absence of a-CD. The Zeta potential increases significantly when going from a concentration of 40 mg / mL of a-CD (-10.60 + 1.91 mV) to 70 mg / mL (-2.54 + 0.2 mV). From an a-CD concentration of 70 mg / mL, the Zeta potential hardly varies any more.

[0180] A polarimetric assay of the supernatants obtained after centrifugation and filtration was carried out. Table 3 lists the results of the initial concentrations of a-CD ([a-CD]0) as well as the residual concentrations of a-CD ([a-CD]R). The values ​​of [a-CD]R were obtained from the measurements of the rotation angles made on the supernatants. The concentration of a-CD interacting with the alkyl chains of the ML ([a-CD]interaction) is then deduced by subtraction between the initial concentrations and those found in the filtrate.

[0181] [Table 3]: [ML] (mg / mL) [a-CD]0 (mg / mL) Rotation angle (°) [a-CD]R (mg / mL) [Q CD] interaction (mg / mL) Ratio (ll(alkyl chain)) / (ll(ct-CD)interaction) 5 40 0.57 12.30 27.69 1 / 1.42 5 70 1.82 39.33 30.67 1 / 1.57 5 80 2.26 48.84 31.16 1 / 1.6 5 113 3.74 80.83 34.16 1 / 1.75

[0182] n(alkyl chain): number of moles of Cl7 chains which would be likely to interact with the a-CD; n(a_CDjinteraction: number of moles of a-CD which would interact with the alkyl chains s(Cl 7) carried by the ML

[0183] Summary of the results of the a-CD assays in the supernatants of the suspensions

[0184] Increasing the initial concentration of a-CD results in an increase in the stoichiometry of the interaction between the C17 alkyl chain and a-CD. The higher the The higher the concentration of a-CD, the more molecules interact with the alkyl chain of the ML and saturate more with a-CD, which may explain the increase in particle size observed during TEM analysis.

[0185] 5 - Encapsulation and release of ascorbic acid (AA)

[0186] The encapsulation of AA within the particles is essentially based on its in non-covalent interaction (hydrophobic interactions, hydrogen bonds, Van der Waals forces) with the particles. Table 4 lists the encapsulation efficiencies of the particles formed with ML / a-CD (5 / 70 mg / mL).

[0187] [Table 4]: [ AA] initiated (mg / mL) [AA] encapsulated (mg / mL) EE (%) 1 0.39 39 2 0.57 29 3 0.96 32

[0188] EE: Encapsulation efficiency (%) = [AA]encapsulated / [AA]initial 100

[0189] Particle encapsulation efficiency as a function of the initial AA concentration

[0190] The concentration of encapsulated AA increases from 0.39 to 0.96 mg / mL when the initial concentration varies from 1 to 3 mg / mL. These results show that it is possible to encapsulate a hydrophilic molecule in the particles.

[0191] The release of AA from particles containing 3 mg / mL of AA was then studied in a phosphate buffer saline medium (PBS - pH 7.4 ± 0.45), thus mimicking the blood environment. It is useful to remember that the particles are more particularly intended for topical application (cutaneous and / or mucous membranes) and that this protocol is widely used in the literature for the study of the release of active substances intended for topical routes (Jing Li et al. 2011). The release profile ([Fig. 14]) shows several stages. A first region characterized by a slow initial release lasting 5 hours (less than 30%) and a second region characterized by a rapid release. The latter is probably linked to a rapid diffusion of AA molecules adsorbed on the surface of the particles by weak bonds while the slow release at the beginning is probably due to a diffusion of AA trapped in the core of the particles.In view of these results, we can conclude that the particles made it possible to obtain, on the one hand, a controlled release of AA since the quantity released at the beginning remains low and, on the other hand, a faster release after 5 hours, resulting in an increase in the release rate where a cumulative concentration of 81% is reached after 30 hours. Bibliographic references:

[0192] Ahmed Z. et al. New insights on the structure of hexagonally faceted platelets from hydrophobically modified chitosan and a-cyclodextrin. International Journal of Pharmaceutics. 2018, 548(1), 23-33.

[0193] Crini G., Fenyvesi E., Szente L. Outstanding contribution of Professor Jôzsef Szejtli to cyclodextrin applications in foods, cosmetics, drugs, chromatography and bio-technology: a review. Environmental Chemistry Letters. 2021, 19(3), 2619-2641.

[0194] Del Valle, E. M. M.. Cyclodextrins and their uses: a review. Process biochemistry. 2004, 39(9), 1033-1046.

[0195] Diaz-Salmeron R., et al. Hierarchical supramolecular platelets from hydrophobically-modified polysaccharides and a-cyclodextrin: Effect of hydrophobization and a-cyclodextrin concentration on platelet formation. International Journal of Phar-maceutics. 2018, 548(1), 227-236.

[0196] Greene’s Protective Groups In Organic Synthesis », 4ème édition, 2007, John Wiley & Sons, Hoboken, New Jersey

[0197] Jing Li J., Zhao F., Li J. Polyrotaxanes for applications in life science and bio-technology. Applied Microbiology and Biotechnology. 2011, 90, 427-443.

[0198] Ma J. et al. Glycosylated platinum(IV) prodrugs demonstrated significant therapeutic efficacy in cancer cells and minimized side-effects. Dalton Transactions, 2016, 45, 11830-11838.

[0199] Mathapa B. G., Paunov V. N. Self-assembly of cyclodextrin-oil inclusion complexes at the oil-water interface: a route to surfactant-free émulsions. Journal of Materials Chemistry A. 2013, 1, 10836-10846.

[0200] Mirchandani Y., Patravale V. B., Brijesh S. Solid lipid nanoparticles for hydrophilic drugs. Journal of Controlled Release. 2021, 335, 457-464.

[0201] Rekharsky M. V., Inoue Y. Complexation thermodynamics of cyclodextrins. Chemical reviews. 1998,98(5), 1875-1918.

[0202] Salatin et al. An Alternative Approach for Improved Entrapment Efficiency of Hydrophilic Drug Substance in PLGA Nanoparticles by Interfacial Polymer Déposition Following Solvent Displacement. Jundishapur Journal ofNatural Pharmaceutical Products. 2018, 13(4):el2873.

[0203] WO 2013 / 150193

[0204] Zhang L., Su T., He B., Gu Z. Self-assembly Polyrotaxanes Nanoparticles as Carriers for Anticancer Drug Methotrexate Delivery. Nano-Micro Letters. 2014, 6, 108-115.

Claims

Claims

1. Particles comprising: at least one compound of the following formula: [Chem. (I)] in which - n represents 0 or 1; - M represents a residue of a monosaccharide, preferably of an aldohexose, of which an OH group, preferably the OH group in the anomeric position, is replaced by the group -X-(AY)nZ and of which one or more -OH groups are optionally replaced by a group -OSO3H and / or of which a group -CH2 -OH is optionally replaced by a group -COOH; X represents -O-, -S-, -NRr, -OC(O)-, -SC(O)-, -N(R!)C(O)-, -OC(S)-, -SC(S)-, or -N(R!)C(S)-, the first atom of the groups being linked to M; - A represents a spacer, the spacer being a (Ci-C2o)alkyl chain, in particular (Ci-Ci5)alkyl, in particular (Ci-Ci0 )alkyl, and preferably (Ci-C8)alkyl, optionally interrupted one or more times by one or more units chosen from the group consisting of -O-, -S-, -NR2-, -C(O)-, and -C(S)-, and / or optionally substituted with one or more groups chosen from the group consisting of a halogen atom, -NO2, -CN, -OR3, -SR4, and -NR5R6; - Y represents -O-, -S-, -NR7-, -C(O)-, -C(S)-, -OC(O)-, -C(O)O-, -SC(O)-, -C(O)S-, -N(R7)C(O)-, -C(O)N(R7)-, -OC(S)-, -C(S)O-, -SC(S)-, -C(S)S-, -N(R7)C(S)-, or -C(S)N(R7)-; - R1 to R7 represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group; and - Z represents a saturated or unsaturated hydrocarbon chain, in particular saturated, linear or branched, preferably linear, comprising from 4 to 40 carbon atoms, preferably 12 to 24 carbon atoms; - at least one cyclodextrin, preferably α-cyclodextrin.

2. Particles according to claim 1, characterized in that M represents a residue of D-mannose, D-galactose or D-glucose of which one or more -OH groups are optionally replaced by an -OSO3H group or of which one -CH2-OH group is optionally replaced by a -COOH group; preferably represents a residue of D-mannose.

3. Particles according to any one of claims 1 to 2, characterized in that X represents -0-, -NRr, -OC(O)-, or -N(Ri)C(O)-; in particular -0- or -NHC0-.

4. Particles according to any one of claims 1 to 3, characterized in that: n represents 0 and X represents -N(Ri)C(0)-, N(Ri) being linked to M; or n is equal to 1, A represents a chain -(CH2)m- with m representing 1, 2, 3, 4, 5 or 6, in particular 3, and Y represents -0C(0)-, -C(0)0-, -N(R7)C(0)- or -C(0)N(R7)-, preferably -N(R7)C(0)- such as -NHC(O)-, the first atom of the groups being linked to A; or n is 1, X is -0-, A is a -(CH2)m- chain with m being 1, 2, 3, 4, 5, 6, 7 or 8, including 2 or 3 and Y is -N(R7)C(0)- or -C(0)N(R7)-; or n is 1, X is -0-, A is -(CH2)-(CH2)-O-(CH2 )-(CH2)- and Y is -N(R7)C(0)-, where N(R7) is bonded to A.

5. Particles according to claim 1, characterized in that they comprise: - at least one compound of the following formula: [Chem. (II)] HO^o HO^y / C HO™ "NH - at least one α-cyclodextrin.

6. Particles according to any one of claims 1 to 5, characterized in that they have a hydrodynamic diameter ranging from 10 nm to 10 pm, preferably from 40 nm to 4 pm, preferentially from 200 nm to 2 pm and / or a number average diameter DMET ranging from 10 nm to 10 pm, in particular from 20 nm to 1 pm, in particular from 50 nm to 300 nm.

7. Particles according to any one of claims 1 to 6, characterized in that they further comprise at least one molecule of therapeutic or cosmetic interest, preferably a molecule chosen from the group consisting of vitamins such as ascorbic acid, antimicrobial peptides such as temporins, antiviral agents, antibiotics.

8. Process for preparing particles according to any one of claims 1 to 7 comprising the mixture: - of at least one compound of formula Chem. (I) as defined in any one of claims 1 to 7; - of at least one cyclodextrin, preferably α-cyclodextrin; and - optionally of a molecule of therapeutic or cosmetic interest.

9. Method according to claim 8, characterized in that the compound of formula Chem. (I) and the cyclodextrin are introduced in a molar ratio compound of formula Chem. (I):cyclodextrin ranging from 1:1 to 1:20, preferably from 1:2 to 1:15, preferentially from 1:5 to 1:

10.

10. A method according to claim 8 or 9, characterized in that the mixing is carried out in water and / or a water-miscible solvent, preferably in a polar protic solvent such as water, ethanol or a mixture thereof, preferably water.

11. Compound of the following formula: [Chem. (I)] — XAY to™ Z in which n represents 0 or 1; - M represents a residue of a monosaccharide, preferably of an aldohexose, of which an OH group, preferably the OH group in the anomeric position, is replaced by the group -X-(AY)nZ and of which one or more -OH groups are optionally replaced by a group -OSO3H and / or of which a group -CH2-OH is optionally replaced by a group -COOH; X represents -0-, -S-, -NRr, -0C(0)-, -SC(O)-, -N(Ri)C(0)-, -OC(S)-, -SC(S)-, or -N(Ri)C(S)-, the first atom of the groups being linked to M; - A represents a spacer, the spacer being a (Ci-C2o)alkyl chain, in particular (C1-C15)alkyl, in particular (Ci-Cio)alkyl, and preferably (CrC8)alkyl, optionally interrupted one or more times by one or more units chosen from the group consisting of -O-, -S-, -NR2-, -C(O)-, and -C(S)-, and / or optionally substituted with one or more groups chosen from the group consisting of a halogen atom, -NO2, -CN, -0R3, -SR4, and -NR5R6;Y represents -0-, -S-, -NR7-, -C(0)-, -C(S)-, -0C(0)-, -C(0)0-, -SC(O)-, -C(O)S-, -N(R7)C(0)-, -C(0)N(R7)-, -OC(S)-, -C(S)O-, -SC(S)-, -C(S)S-, -N(R7)C(S)-, or -C(S)N(R 7)-; - R1 to R7 represent, independently of each other, a hydrogen atom or a (C1-C6)alkyl group; and - Z represents a saturated or unsaturated hydrocarbon chain, in particular saturated, linear or branched, preferably linear, comprising from 4 to 40 carbon atoms, preferably 12 to 24 carbon atoms.;

12. Compound according to claim 11, characterized in that M represents a residue of D-mannose, D-galactose or D-glucose of which one or more -OH groups are optionally replaced by an -OSO3H group or of which one -CH2-0H group is optionally replaced by a -COOH group; preferably represents a residue of D-mannose.

13. Compound according to claim 11 or 12, characterized in that X represents -0-, -NRr, -0C(0)-, or -N(Ri)C(0)-; in particular -0- or - NHCO-.

14. Compound according to any one of claims 11 to 13, characterized in that: n represents 0 and X represents -N(Ri)C(O)-, N(Ri) being linked to M; or n is equal to 1, A represents a -(CH2)m- chain with m representing 1, 2, 3, 4, 5 or 6, in particular 3 and Y represents -OC(O)-, -C(O)O-, -N(R7)C(O)- or -C(O)N(R7)-, preferably -N(R7)C(O)- such as -NHC(O)-, the first atom of the groups being linked to A; or n is 1, X is -O-, A is a chain -(CH2)m- with m being 1, 2, 3, 4, 5, 6, 7 or 8, including 2 or 3 and Y is -N(R7)C(O)- or -C(O)N(R7)-; or n is 1, X represents -O-, A represents -(CH2)-(CH2)-O-(CH2 )-(CH2)- and Y represents -N(R7)C(O)-, with N(R7) being linked to A.

15. Compound according to claim 11, of the following formula: [Chem. (II)]

16.

17.

18. Cosmetic or pharmaceutical composition comprising particles according to any one of claims 1 to 7 and at least one cosmetically or pharmaceutically acceptable excipient, preferably in a form suitable for topical application. Use of particles according to claim 7 for the prolonged release of the molecule of cosmetic interest. Particles according to any one of claims 1 to 7, for use as a medicament, preferably as a prolonged-release medicament.

Images