Method for preparing amphiphilic polymer and use thereof

Abstract

The present disclosure relates to the technical field of polymer materials, and in particular, the present disclosure relates to a method for preparing an amphiphilic polymer and a use thereof. The preparation method uses a hydrophobic polymer having good molecular chain flexibility as a hydrophobic chain to connect a hydrophilic amphoteric monomer molecule to at least one end of the hydrophobic polymer, so as to obtain an amphiphilic polymer with controllable molecular weight distribution of the polymer. The present disclosure uses a hydrophobic polymer having good molecular chain flexibility as a hydrophobic chain to improve membrane stability and reduce amphiphilic polymer molecular weight distribution to a certain extent, which increases interaction between amphiphilic polymers and membrane proteins, improves membrane protein stability in polymer biomimetic membranes, and lays a firmer foundation for the construction of biomimetic cell membranes.

Description

A method for preparing an amphiphilic polymer and its applications Technical Field

[0001] This disclosure relates to the field of polymer materials technology, and more specifically, to a method for preparing an amphiphilic polymer and its uses. Background Technology

[0002] In nature, the cell membrane plays a vital role in maintaining cellular stability, acting as a barrier against foreign substances, enabling selective transport of substances, and facilitating signal transduction. The cell membrane is typically composed of a complex series of phospholipids, membrane proteins, and other molecules. In the life sciences, constructing biomimetic membranes helps us fully understand the inherent properties, functions, and behaviors of cell membranes. Furthermore, their biocompatibility can be utilized to expand drug bioavailability, aid in medical imaging and diagnosis, and separate incompatible entities.

[0003] Initially, biomimetic membranes could be constructed using liposomes, which share a high degree of similarity with phospholipids on cell membranes. However, membrane structures formed by the self-assembly of liposomes are typically unstable, highly permeable, and prone to flow, making them difficult to use and customize. In recent years, amphiphilic block copolymers have attracted widespread attention due to their versatility, good extensibility, and high toughness, making it easier to form stable and functionalized polymer membrane materials. These block copolymers are usually composed of hydrophilic and hydrophobic blocks linked in a specific ratio or sequence. Common amphiphilic block copolymers include diblock copolymers (AB type), triblock copolymers (ABA type, BAB type, or ABC type), and multiblock copolymers. Hydrophilic blocks are formed by the polymerization of one or more strongly hydrophilic monomers, such as polyethylene glycol, polyoxazoline, polyacrylic acid, polyvinyl alcohol, and polyacrylamide; hydrophobic blocks are formed by the polymerization of one or more strongly hydrophobic monomers, such as polyolefins, polysiloxanes, polyesters, polyethers, and epoxy compounds. Among them, polydimethylsiloxane (PDMS) is widely used in the construction of polymer vesicles or biomimetic membranes due to its good chain flexibility, oxygen permeability and biological stability. The most representative polymer is a diblock or triblock copolymer composed of polydimethylsiloxane / poly(2-methyl-2-oxazoline) (PDMS / PMOXA) (i.e. PDMS-PMOXA, PMOXA-PDMS-PMOXA), which has been used to construct various membrane platform models, including polymer vesicles, free planar membranes, solid supported membranes, etc. Due to the high flexibility of PDMS blocks, membrane materials based on these polymers can successfully embed membrane proteins (F. Itel, et al., Dynamics of membrane proteins within synthetic polymer membranes with large hydrophobic mismatch, Nano Lett. 15(6)(2015) 3871–3878).

[0004] Therefore, the materials currently used to prepare vesicles or biomimetic membranes are mainly divided into phospholipid molecules and amphiphilic block copolymers. Phospholipid molecules are divided into natural phospholipids and synthetic phospholipids. Their structures are relatively fixed, usually composed of hydrophobic fatty acid chains and hydrophilic zwitterionic heads. Their physical and chemical properties are relatively limited, and simple chemical modifications or alterations can significantly affect their self-assembly performance. Vesicles or membrane materials formed by the self-assembly of phospholipid molecules are similar in structure to natural cell membranes, exhibiting good fluidity and permeability, but poor stability. Compared to phospholipid molecules, block copolymers have a high degree of tunability in physicochemical properties, allowing adjustment of the polymer's chemical structure, molecular weight, and hydrophilic / hydrophobic ratio according to actual needs. Vesicles or membrane materials formed by block copolymers have better membrane stability due to factors such as greater membrane thickness, weaker lateral fluidity, and molecular chain entanglement, but reduced membrane permeability. Furthermore, polymers all have a certain molecular weight distribution. Block copolymers formed by linking multiple polymers have a wider molecular weight distribution range, and an excessively wide molecular weight distribution is usually detrimental to the uniformity and stability of the assembly. Although modern polymerization techniques can control the molecular weight distribution of polymers to a relatively low level, the polydispersity of molecular weight still affects the self-assembly behavior of block copolymers, and even differences can occur when using different batches of the same copolymer. Furthermore, compared to monoblock polymers, block copolymers are composed of multiple different polymers linked together, making their molecular weight distribution even more difficult to control.

[0005] To further mimic the biological functions of cell membranes, it is often necessary to embed membrane protein molecules into artificially constructed vesicles or biomimetic membranes to achieve molecular recognition or transmembrane transport. Phospholipid membrane materials, firstly, are similar in size to cell membranes, thus exhibiting good compatibility with membrane proteins; secondly, the zwitterionic ions at the hydrophilic ends may interact electrostatically with the positive and negative charges on the membrane proteins, further enhancing the binding force between the membrane proteins and the phospholipid membrane materials. However, vesicles or monolayer biomimetic membrane materials formed by amphiphilic block copolymers have relatively large membrane thicknesses, resulting in a size mismatch with membrane proteins. Nevertheless, polymer chains possess a certain degree of compressibility, and block copolymers can adjust their chain segment conformations to reduce membrane thickness and match the size of membrane proteins. This places certain demands on the flexibility of the polymer chains; for example, polysiloxanes, due to their large bond angles and good flexibility, play an important role in the construction of biomimetic membranes. Furthermore, although some block copolymers can intercalate into membrane proteins, membrane proteins can only bind to the hydrophobic blocks through hydrophobic interactions, while the hydrophilic blocks are usually electrically neutral polymers that lack stable binding ability with membrane proteins.

[0006] Some studies have attached zwitterionic segments to both ends of polysiloxanes, but these mainly involve attaching zwitterionic monomers containing propylene double bonds to the ends of PDMS via polymerization. This approach makes it difficult to accurately control the degree of polymerization of the zwitterionic monomers, which further increases the molecular weight distribution of the original polymer (Macromolecules 2003, 36, 10, 3475–3484). Other studies have replaced the alkyl chains of phospholipid molecules with oligodimethylsilanes for drug delivery. Structurally very similar to phospholipid molecules, containing only three siloxane repeating units, this does not substantially change the fact that phospholipid membranes are unstable (US2017 / 0355721 A1).

[0007] Therefore, given the problems of vesicles or biomimetic membranes assembled from phospholipid molecules being easily flowable and unstable, and the wide molecular weight distribution and weak compatibility between block copolymers and membrane proteins, there is an urgent need to develop a method for preparing amphiphilic polymers. Summary of the Invention

[0008] This disclosure aims to at least partially address one of the technical problems in the related art. To this end, one object of this disclosure is to provide a method for preparing an amphiphilic polymer and its uses. By using a hydrophobic polymer with good molecular chain flexibility as the hydrophobic chain, hydrophilic amphoteric monomer molecules are linked to at least one end of the hydrophobic polymer to obtain an amphiphilic polymer with controllable molecular weight distribution. Specifically, the hydrophobic polymer with good molecular chain flexibility as the hydrophobic chain can improve membrane stability. By precisely controlling the modification of hydrophilic amphoteric monomer molecules through Michael addition, the molecular weight distribution of the amphiphilic polymer can be controlled, increasing the interaction between the amphiphilic polymer and membrane proteins, improving the stability of membrane proteins on polymer-mimetic membranes, and laying a more solid foundation for the construction of biomimetic cell membranes.

[0009] Therefore, this disclosure provides a method for preparing amphiphilic polymers, wherein the method includes:

[0010] (1) Prepare a hydrophobic polymer, cap at least one end of the hydrophobic polymer, and modify the capped end with amino or thiol groups to obtain a hydrophobic polymer with primary or secondary amine groups or thiol groups at the end.

[0011] (2) The hydrophobic polymer obtained in step (1) is subjected to a Michael addition reaction with hydrophilic amphoteric monomer molecules to obtain the amphiphilic polymer;

[0012] The hydrophobic polymer includes at least one selected from polysiloxanes, epoxy compounds, polyolefins, and polyesters;

[0013] The hydrophilic amphoteric monomer molecules include those selected from hydrophilic amphoteric monomer molecules having methpropylene double bonds.

[0014] To mimic cell membranes and improve the stability of phospholipid assemblies, the inventors designed a method for preparing amphiphilic polymers. This method involves using a flexible hydrophobic polymer as the hydrophobic segment and attaching hydrophilic amphoteric monomer molecules (such as phosphocholine, sulfobetaine, carboxybetaine, etc.) to at least one end of the hydrophobic polymer, resulting in a phospholipid-like amphiphilic polymer. Unlike common block copolymers, the hydrophilic end provided in this disclosure is not a polymer, but rather one or more hydrophilic amphoteric monomer molecules attached to the end of the hydrophobic block via Michael addition. Compared to ordinary block copolymers, the molecular weight distribution of the resulting amphiphilic polymer depends on the molecular weight distribution of the hydrophobic polymer. The hydrophilic / hydrophobic balance of the amphiphilic polymer can be adjusted by regulating the length of the hydrophobic segment or the number of hydrophilic amphoteric monomer molecules. These polymers can self-assemble in solution systems or at water-oil interfaces to form polymer vesicles or biomimetic membrane structures, potentially providing novel alternative materials for applications such as biomimetic cell construction and drug delivery carriers.

[0015] According to embodiments of this disclosure, the molecular weight distribution of the prepared hydrophobic polymer is ≤1.15.

[0016] According to embodiments of this disclosure, the polysiloxane includes at least one selected from polydimethylsiloxane, polydiphenylsiloxane, polymethylphenylsiloxane, and copolymers thereof.

[0017] According to embodiments of this disclosure, at least one end of the hydrophobic polymer described in step (1) is capped using a capping agent.

[0018] According to embodiments of this disclosure, the capping agent comprises a product selected from dimethylchlorosilane.

[0019] According to embodiments of this disclosure, when the hydrophobic polymer is a polysiloxane, the polysiloxane obtained by the end-capping treatment has the following structural formula:

[0020] R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Replacement C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl;

[0021] The R a Independently selected from halogens, C1-C 10 Alkyl, C3-C 10 cycloalkyl, C1-C 10 Alkoxy;

[0022] n is any integer between 15 and 50.

[0023] According to embodiments of this disclosure, R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Substituted C1-C5 alkyl, C3-C5 cycloalkyl, 3-5 membered heterocyclic groups, C6-C 10 Aryl, 5-10 heteroaryl.

[0024] According to embodiments of this disclosure, R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Substituted C1 alkyl, C3 cycloalkyl, 3-membered heterocyclic, phenyl, 5-membered heteroaryl.

[0025] According to embodiments of this disclosure, R1 and R2 are each independently selected from methyl and phenyl.

[0026] According to embodiments of this disclosure, n is any integer from 20 to 30.

[0027] According to embodiments of this disclosure, at least one end of the polysiloxane is modified with an amino group to obtain a polysiloxane with a primary or secondary amine group at the end, having the structural formula as follows:

[0028] The R3 is independently selected from

[0029] x and y are each independent integers from 1 to 10;

[0030] R is independently selected from H, halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl;

[0031] R4 is independently selected from unsubstituted or substituted R4 groups. b Substituted H, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl;

[0032] The R b Independently selected from halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl;

[0033] R5 is independently selected from unsubstituted or substituted R5 groups. cThe substituted 3-10 nitrogen-containing cyclic group contains at least one secondary amine;

[0034] The R c Independently selected from halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl.

[0035] According to embodiments of this disclosure, the R4 is independently selected from unsubstituted or substituted groups R4. b Substituted H, C1-C5 alkyl, C3-C5 cycloalkyl, 3-5 membered heterocyclic group, C6-C 10 Aryl, 5-10 heteroaryl.

[0036] According to embodiments of this disclosure, the R4 is independently selected from unsubstituted or substituted groups R4. b Substituted H, C1 alkyl, C3 cycloalkyl, 3-membered heterocyclic group, phenyl, 5-membered heteroaryl.

[0037] According to embodiments of this disclosure, the R4 is independently selected from H and C1 alkyl groups.

[0038] According to embodiments of this disclosure, R5 is independently selected from unsubstituted or substituted groups R. c The substituted 5-8 member nitrogen-containing cyclic group contains at least one secondary amine.

[0039] According to embodiments of this disclosure, R5 is independently selected from unsubstituted or substituted groups R. c Substituted pyrazoles, imidazoles, triazoles, tetrazolium, piperidine, and piperazine.

[0040] According to embodiments of this disclosure, R5 is independently selected from piperidine and piperazine.

[0041] According to embodiments of this disclosure, the hydrophilic amphoteric monomer molecule includes at least one independently selected from methacryloyloxyethyl phosphoric acid choline, methacryloyloxyethyl sulfobetaine, and methacryloyloxyethyl carboxybetaine.

[0042] This disclosure also provides an amphiphilic polymer obtained by the method described above. The amphiphilic polymer obtained by the method has a hydrophobic segment with good flexibility and a hydrophilic amphoteric monomer molecule attached to at least one end of the hydrophobic segment. The hydrophilic / hydrophobic balance of the polymer can be adjusted by regulating the length of the hydrophobic segment or the number of hydrophilic amphoteric monomer molecules, thereby solving problems such as the wide molecular weight distribution of conventional block copolymers and the instability of films assembled from phospholipid molecules.

[0043] This disclosure further provides the use of the above-described method or the above-described amphiphilic polymer in the preparation of vesicles or biomimetic membranes. The above-described method and the amphiphilic polymer obtained by the method utilize a hydrophobic polymer with good molecular chain flexibility as the hydrophobic chain, at least one segment of which is linked to a hydrophilic amphiphilic monomer molecule. By adjusting the length of the hydrophobic segment or the number of hydrophilic amphiphilic monomer molecules, the molecular weight distribution of the amphiphilic polymer can be controlled relatively precisely. Using it in the preparation of vesicles or biomimetic membranes can not only improve membrane stability but also increase the interaction between the amphiphilic polymer and membrane proteins, improving the stability of membrane proteins on the polymer biomimetic membrane, thus laying a more solid foundation for the construction of biomimetic cell membranes.

[0044] This disclosure also provides a vesicle comprising the aforementioned amphiphilic polymer. The aforementioned amphiphilic polymer is a hydrophobic polymer with good molecular chain flexibility, serving as the hydrophobic chain. At least one segment of the hydrophobic polymer is connected to a hydrophilic amphoteric monomer molecule. By adjusting the length of the hydrophobic segment or the number of hydrophilic amphoteric monomer molecules, the molecular weight distribution of the amphiphilic polymer can be controlled relatively precisely. Using it in vesicle preparation not only improves membrane stability but also increases the interaction between the amphiphilic polymer and membrane proteins, enhancing the stability of membrane proteins on the vesicle and laying a more solid foundation for vesicle construction.

[0045] This disclosure also provides a biomimetic membrane comprising the aforementioned amphiphilic polymer. The amphiphilic polymer, with its hydrophobic chain exhibiting good molecular chain flexibility, has at least one segment linked to a hydrophilic amphoteric monomer molecule. By adjusting the length of the hydrophobic segment or the number of hydrophilic monomer molecules, the molecular weight distribution of the amphiphilic polymer can be precisely controlled. Using it in the preparation of biomimetic membranes not only improves membrane stability but also enhances the interaction between the amphiphilic polymer and membrane proteins, thereby increasing the stability of membrane proteins on the polymer biomimetic membrane and laying a more solid foundation for the construction of biomimetic cell membranes.

[0046] The advantages of this disclosure over the prior art are:

[0047] This disclosure provides a method for preparing phospholipid-like amphiphilic polymers. The method utilizes hydrophobic polymers with good molecular chain flexibility as hydrophobic chains to improve the stability of assembled membranes. By modifying at least one end of the polymer with an amino or thiol group, the modification of hydrophilic amphoteric monomer molecules can be accurately controlled by Michael addition reaction, which reduces the molecular weight distribution of the amphiphilic polymer to a certain extent. At the same time, this method also increases the interaction between the amphiphilic polymer and membrane proteins, thereby improving the stability of membrane proteins on polymer biomimetic membranes.

[0048] Additional aspects and advantages of this disclosure will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of this disclosure. Attached Figure Description

[0049] The above and / or additional aspects and advantages of this disclosure will become apparent and readily understood from the description of the embodiments taken in conjunction with the following drawings, in which:

[0050] Figure 1 shows a schematic diagram of the amino-terminal modification of the Si-H end-capped polysiloxane of this disclosure;

[0051] Figure 2 shows a schematic diagram of the Michael addition reaction between the amino-terminated polysiloxane of this disclosure and a hydrophilic amphoteric monomer molecule with a methpropylene double bond.

[0052] Figure 3 shows the 1H NMR spectrum of the piperidine-modified polydimethylsiloxane in Example 3 of this disclosure;

[0053] Figure 4 shows the 1H NMR spectra of polydimethylsiloxane after each of the two end modifications of the polydimethylsiloxane in Example 12 of this disclosure was modified with a hydrophilic monomer molecule of phosphocholine.

[0054] Detailed description of the invention

[0055] The embodiments of this disclosure are described in detail below. The embodiments described below are exemplary and are only used to explain this disclosure, and should not be construed as limiting this disclosure.

[0056] Furthermore, the terms "first" and "second" are used for descriptive purposes only and should not be construed as indicating or implying relative importance or implicitly specifying the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include at least one of that feature. In the description of this disclosure, "a plurality of" means at least two, such as two, three, etc., unless otherwise explicitly specified.

[0057] The term "C1-C" 10"Alkyl" should be understood to refer to a straight-chain or branched saturated monovalent hydrocarbon group having 1-10 carbon atoms. Such alkyl groups are, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl, or 1,2-dimethylbutyl, etc. "C1-C5 alkyl" should be understood to refer to a straight-chain or branched saturated monovalent hydrocarbon group having 1-5 carbon atoms. Other related terms follow the same principle.

[0058] The term "C3-C" 10 "Cycloalkyl" should be understood as indicating a saturated monovalent monocyclic or bicyclic hydrocarbon ring with 3-10 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, or cyclodecyl, or a bicyclic hydrocarbon ring such as decahydronaphthalene. "C3-C5 cycloalkyl" should be understood as indicating a saturated monovalent monocyclic or bicyclic hydrocarbon ring with 3-5 carbon atoms. Other related terms follow the same principle.

[0059] The term "3-10 membered heterocyclic group" should be understood to refer to a saturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1-5, preferably 1-3, heteroatoms selected from N, O, and S. Specifically, the heterocyclic group may include, but is not limited to: 4-membered rings, such as azirmonobutylene or oxobutylene; 5-membered rings, such as tetrahydrofuranyl, dioxacyclopentenyl, pyrrolyl, imidazoalkyl, pyrazolyl, or pyrrololinyl; or 6-membered rings, such as tetrahydropyranyl, piperidinyl, morpholinyl, dithiaalkyl, thiomorpholinyl, piperazinyl, or trithiaalkyl; or 7-membered rings, such as diazacycloheptyl. Optionally, the heterocyclic group may be benzofused. The heterocyclic group may be bicyclic, such as, but not limited to, a 5,5-membered ring, like a hexahydrocyclopentano[c]pyrrolo-2(1H)-yl ring, or a 5,6-membered bicyclic ring, like a hexahydropyrrolo[1,2-a]pyrazinolo-2(1H)-yl ring. The nitrogen-containing ring may be partially unsaturated, meaning it may contain one or more double bonds, such as, but not limited to, 2,5-dihydro-1H-pyrrolo, 4H-[1,3,4]thiadiazinyl, 4,5-dihydrooxazolyl, or 4H-[1,4]thiazinyl, or it may be benzofused, such as, but not limited to, dihydroisoquinolinyl. Other related terms follow the same pattern.

[0060] The term "C6-C" 20"Aryl" should be understood to preferably represent a monovalent aromatic or partially aromatic monocyclic, bicyclic, or tricyclic hydrocarbon ring having 6-20 carbon atoms. In particular, a ring with 6 carbon atoms ("C6 aryl"), such as phenyl; or a ring with 9 carbon atoms ("C9 aryl"), such as indenyl or indenyl; or a ring with 10 carbon atoms ("C9 aryl"). 10 Aryl groups, such as tetrahydronaphthyl, dihydronaphthyl, or naphthyl, or rings with 13 carbon atoms (“C”). 13 Aryl groups, such as fluorene groups, or rings with 14 carbon atoms (“C”). 14 Aryl), for example, anthracene. The term "C6-C" is used. 10 "Aryl" should preferably be understood to refer to a monocyclic, bicyclic, or tricyclic hydrocarbon ring having 6-10 carbon atoms and possessing monovalent aromaticity or partial aromaticity. Other related terms follow the same principle.

[0061] The term "5-20-membered heteroaryl" should be understood to include monovalent monocyclic, bicyclic, or tricyclic aromatic ring systems having 5-20 ring atoms and containing 1-5 heteroatoms independently selected from N, O, and S, such as "5-14-membered heteroaryl". The term "5-14-membered heteroaryl" should also be understood to include monovalent monocyclic, bicyclic, or tricyclic aromatic ring systems having 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14 ring atoms, particularly 5, 6, 9, or 10 carbon atoms, and containing 1-5, preferably 1-3, heteroatoms each independently selected from N, O, and S, and in each case, may be benzofused. Specifically, the heteroaryl group is selected from thienyl, furanyl, pyrroleyl, oxazolyl, thiazolyl, imidazoleyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia-4H-pyrazolyl, and their benzo[derivatives], such as benzofuranyl, benzothienyl, benzooxazolyl, benzoisooxazolyl, benzoimidazolyl, benzotriazolyl, indazole, indolyl, isindolyl, etc.; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and their benzo[derivatives], such as quinolinyl, quinazolinyl, isoquinolinyl, etc.; or acrylinyl, inazinyl, purinyl, and their benzo[derivatives]; or terpenolyl, phthalazinyl, quinazolinyl, quinoxolinyl, naphridinyl, pteridinyl, carbazolyl, acridineyl, phenazinyl, phenothiazinyl, phenothiazinyl, etc.

[0062] The term "C1-C" 10 "Alkoxy" should be understood as a straight-chain or branched alkyl group having 1-10 carbon atoms, which are connected at any carbon atom of the alkyl group via oxygen bonds. Examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, etc.

[0063] The term "3-10 nitrogen-containing cyclic group" should be understood to include monovalent monocyclic, bicyclic, or tricyclic aromatic ring systems that have 3-10 ring atoms and contain 1-5 nitrogen atoms.

[0064] According to embodiments of this disclosure, one aspect of this disclosure provides a method for preparing an amphiphilic polymer, the method comprising:

[0065] (1) Prepare a hydrophobic polymer, and perform end capping treatment on at least one end of the hydrophobic polymer, and modify the end after end capping treatment with amino or thiol groups to obtain a hydrophobic polymer with primary or secondary amine groups or thiol groups at the end.

[0066] According to specific embodiments of this disclosure, the hydrophobic polymer includes those selected from polysiloxanes, epoxy compounds, polyolefins, and polyesters. It possesses good molecular chain flexibility, and using it as a hydrophobic segment can improve the stability of the assembled film. The polysiloxanes include, but are not limited to, polydimethylsiloxane, polydiphenylsiloxane, polymethylphenylsiloxane, and their copolymers. The epoxy compounds include, but are not limited to, ethylene oxide, propylene oxide, and butane oxide. The polyolefins include, but are not limited to, polyethylene, polypropylene, and poly-1-butene. The polyesters include, but are not limited to, PET (polyethylene terephthalate), PLA (polylactic acid), and PCL (polycaprolactone).

[0067] Hydrophobic polymers can be prepared by anionic polymerization or organic base-catalyzed ring-opening polymerization to obtain hydrophobic polymers with narrow molecular weight distributions. Taking polysiloxanes as an example, polysiloxanes with narrow molecular weight distributions (≤1.15) can be obtained by anionic polymerization or organic base-catalyzed ring-opening polymerization.

[0068] Then, at least one end of the hydrophobic polymer is capped using a capping agent such as dimethylchlorosilane.

[0069] When the hydrophobic polymer is a polysiloxane, end-capping treatment can yield a polysiloxane with at least one Si-H end, exhibiting a degree of polymerization between 15 and 50, preferably 20-30. The structural formula of the polysiloxane obtained by the end-capping treatment is as follows:

[0070] R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Replacement C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl;

[0071] The R a Independently selected from halogens, C1-C 10 Alkyl, C3-C10 cycloalkyl, C1-C 10 Alkoxy;

[0072] n is any integer from 15 to 50, preferably any integer from 20 to 30.

[0073] According to specific embodiments of this disclosure, R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Substituted C1-C5, C3-C5 cycloalkyl, 3-5 membered heterocyclic groups, C6-C 10 Aryl, 5-10 heteroaryl.

[0074] According to specific embodiments of this disclosure, R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Substituted C1 alkyl, C3 cycloalkyl, 3-membered heterocyclic, phenyl, 5-membered heteroaryl.

[0075] According to a preferred embodiment of this disclosure, R1 and R2 are each independently selected from methyl and phenyl.

[0076] Then, for the end-capped hydrophobic polymers, taking the aforementioned polysiloxane as an example, the Si-H end-capped polysiloxane is converted into a polysiloxane with a primary or secondary amine group or a thiol group at the end through a carbon chain linker, namely R3. The amino modification can be achieved by hydrosilylation of Si-H with a small molecule containing a double bond and an amino group at the end, such as 3-buten-1-amine, or by hydrosilylation of Si-H with a small molecule containing a double bond and a hydroxyl group at the end, such as 3-buten-1-ol or N-hydroxyethylacrylamide, followed by conversion to an amino group. The aim is to prepare polysiloxanes with an amino group at the end, wherein the amino group contains at least one active hydrogen atom to facilitate subsequent Michael addition reactions with hydrophilic amphoteric monomer molecules containing propylene double bonds. The modification of the thiol group is similar to that of the primary or secondary amine group and can be achieved through click chemistry reactions between the thiol group and the terminal olefin.

[0077] The R3 is independently selected from

[0078] x and y are each independent integers from 1 to 10;

[0079] R is independently selected from H, halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl.

[0080] Modifying at least one end of the polysiloxane with an amino group yields a polysiloxane with a primary or secondary amine group at the end, with the structural formula as follows:

[0081] R4 is independently selected from unsubstituted or substituted R4 groups. b Substituted H, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl;

[0082] The R b Independently selected from halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl;

[0083] R5 is independently selected from unsubstituted or substituted R5 groups. c The substituted 3-10 nitrogen-containing cyclic group contains at least one secondary amine;

[0084] The R c Independently selected from halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl.

[0085] According to specific embodiments of this disclosure, R4 is independently selected from unsubstituted or substituted groups R. b Substituted H, C1-C5 alkyl, C3-C5 cycloalkyl, 3-5 membered heterocyclic group, C6-C 10 Aryl, 5-10 heteroaryl.

[0086] According to specific embodiments of this disclosure, R4 is independently selected from unsubstituted or substituted groups R. b Substituted H, C1 alkyl, C3 cycloalkyl, 3-membered heterocyclic group, phenyl, 5-membered heteroaryl.

[0087] According to specific embodiments of this disclosure, R4 is independently selected from H and C1 alkyl groups.

[0088] According to specific embodiments of this disclosure, R5 is independently selected from unsubstituted or substituted groups R. c The substituted 5-8 member nitrogen-containing cyclic group contains at least one secondary amine.

[0089] According to specific embodiments of this disclosure, R5 is independently selected from unsubstituted or substituted groups R. c Substituted pyrazoles, imidazoles, triazoles, tetrazolium, piperidine, and piperazine.

[0090] According to specific embodiments of this disclosure, R5 is independently selected from piperidine and piperazine.

[0091] The specific reaction process is shown in Figure 1 (only the reaction process on the polymer side is shown here), where the terminal amino group of the polysiloxane can be... It can also be an amino ring, such as pyrazole, imidazole, triazole, tetrazolium, piperidine, piperazine, etc.

[0092] (2) The hydrophobic polymer obtained in step (1) is subjected to Michael addition reaction with hydrophilic amphoteric monomer molecules to obtain the amphiphilic polymer.

[0093] The specific process is shown in Figure 2 (only the reaction process on the polymer side is shown here).

[0094] The hydrophilic amphoteric monomer molecules include those selected from amphoteric monomer molecules containing methacrylic double bonds, including but not limited to methacryloyloxyethyl phosphorocholine, methacryloyloxyethyl sulfobetaine, and methacryloyloxyethyl carboxybetaine. Hydrophobic polymers with amino or thiol groups (containing active hydrogen) at the end can be linked to hydrophilic amphoteric monomer molecules containing propylene double bonds, such as methacryloyloxyethyl phosphorocholine, methacryloyloxyethyl sulfobetaine, and methacryloyloxyethyl carboxybetaine, under weakly basic conditions via Michael addition reaction. The number of hydrophilic amphoteric monomer molecules modified depends on the number of active hydrogens on the amino or thiol group at the end of the hydrophobic polymer. That is, when the hydrophobic polymer is terminal to a primary amine (i.e., containing two active hydrogens), no more than two hydrophilic amphoteric monomer molecules can be modified; when the hydrophobic polymer is terminal to a secondary amine (i.e., containing one active hydrogen), one hydrophilic amphoteric monomer molecule can be modified; when the hydrophobic polymer is terminal to a thiol group (i.e., containing one active hydrogen), one hydrophilic amphoteric monomer molecule can be modified. This allows for precise control over the amount of hydrophilic amphiphilic monomers used for modification, without further expanding the molecular weight distribution of the polymer. The resulting amphiphilic polymer's molecular weight distribution depends on the molecular weight distribution of the hydrophobic polymer, thus solving the problem of wide molecular weight distribution and unstable assembled films associated with conventional block copolymers.

[0095] According to specific embodiments of this disclosure, the method may further include purification, drying, and concentration of the obtained amphiphilic polymer. The purification process can be achieved through conventional separation and purification methods such as extraction; the drying process can be achieved by adding conventional drying agents such as anhydrous magnesium sulfate; and the concentration process can be achieved through conventional concentration methods such as rotary evaporation.

[0096] According to specific embodiments of this disclosure, the above-described preparation method and the amphiphilic polymer obtained by the above-described preparation method can be used to prepare vesicles or biomimetic membranes. This not only improves the stability of the membrane, but also increases the interaction between the amphiphilic polymer and membrane proteins, thereby improving the stability of membrane proteins on the polymer biomimetic membrane. This can lay a more solid foundation for the construction of biomimetic cell membranes.

[0097] Where specific techniques or conditions are not specified in the examples, they shall be performed in accordance with the techniques or conditions described in the literature in this field or in accordance with the product instructions. Reagents or instruments whose manufacturers are not specified are all commercially available conventional products.

[0098] Example 1

[0099] A method for preparing polydimethylsiloxane (PDMS) with amino groups (primary amines) at both ends of the polymer is shown below:

[0100] (1) Weigh 0.1 mol of hexamethylcyclotetrasiloxane monomer into a 250 mL flask with a side arm. After purging with argon three times, add 60 mL of tetrahydrofuran (THF) and stir to dissolve. Accurately weigh 0.01 mol of deionized water as an initiator, dissolve it in 10 mL of tetrahydrofuran, and add it to the flask. Then add a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst. Stir at 30 °C for 24 h. Add excess pyridine and excess dimethylchlorosilane for end capping. Stir at room temperature for 3 h. Remove THF by rotary evaporation. Add 40 mL of acetonitrile for washing. After removing the supernatant, add acetonitrile and wash repeatedly 4-5 times. Dry the lower liquid by rotary evaporation and remove the low molecular weight polymer under reduced pressure at 130 °C to obtain PDMS with Si-H end capping.

[0101] (2) Weigh 5.00 g of the above polymer and add it to a 100 mL flask with a side arm. After removing water under reduced pressure at 120 °C for 30 min, add 20 mL of anhydrous toluene to dissolve polymer P1. Then, add 0.5-1.0 g of 3-buten-1-amine and a catalytic amount of Karstedt's catalyst (in Xylene, Pt ~ 2%) to the flask in sequence, and reflux and stir overnight at 110 °C. After the reaction is complete, remove the toluene by rotary evaporation, add 40 mL of dichloromethane to dissolve the polymer, add an appropriate amount of activated carbon, stir thoroughly, filter, and evaporate the filtrate to obtain PDMS with amino groups at both ends of the polymer, denoted as P1.

[0102] Example 2

[0103] A method for preparing polydimethylsiloxane (PDMS) with an amino group (primary amine) at one end of the polymer is shown below:

[0104] (1) Weigh 0.1 mol of hexamethylcyclotetrasiloxane monomer into a 250 mL flask with a side arm. After purging with argon three times, add 60 mL of tetrahydrofuran (THF) and stir to dissolve. Accurately weigh 0.01 mol of tert-butyldimethylsilanol as an initiator, dissolve it in 10 mL of tetrahydrofuran, and add it to the flask. Then add a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst. Stir at 30 °C for 24 h. Add excess pyridine and dimethylchlorosilane for end capping. Stir at room temperature for 3 h. Remove THF by rotary evaporation. Add 40 mL of acetonitrile for washing. After removing the supernatant, add acetonitrile and wash repeatedly 4-5 times. Dry the lower liquid by rotary evaporation and remove the low molecular weight polymer under reduced pressure at 130 °C to obtain PDMS with one end capped by tert-butyl and the other end capped by Si-H.

[0105] (2) Accurately weigh 5.00 g of the above polymer and add it to a 100 mL flask with a side arm. After removing water under reduced pressure at 120 °C for 30 min, add 20 mL of anhydrous toluene to dissolve polymer P1. Then, add 0.5-1.0 g of 3-buten-1-amine and a catalytic amount of Karstedt's catalyst (in Xylene, Pt ~ 2%) to the flask sequentially, and reflux and stir overnight at 110 °C. After the reaction is complete, remove the toluene by rotary evaporation, add 40 mL of dichloromethane to dissolve the polymer, add an appropriate amount of activated carbon, stir thoroughly, filter, and evaporate the filtrate to obtain PDMS with an amino group at one end, denoted as P2.

[0106] Example 3

[0107] A method for preparing polydimethylsiloxane (PDMS) with amino (secondary amine) groups at both ends of the polymer is shown below:

[0108] (1) Weigh 0.1 mol of hexamethylcyclotetrasiloxane monomer into a 250 mL flask with a side arm. After purging with argon three times, add 60 mL of tetrahydrofuran (THF) and stir to dissolve. Accurately weigh 0.01 mol of water as an initiator, dissolve it in 10 mL of tetrahydrofuran, and add it to the flask. Then add a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst. Stir at 30 °C for 24 h. Add excess pyridine and dimethylchlorosilane for end capping. Stir at room temperature for 3 h. Remove THF by rotary evaporation. Add 40 mL of acetonitrile for washing. After removing the supernatant, add acetonitrile and wash repeatedly 4-5 times. Dry the lower liquid by rotary evaporation and remove the low molecular weight polymer under reduced pressure at 130 °C to obtain PDMS with one end capped by tert-butyl and the other end capped by Si-H.

[0109] (2) Accurately weigh 5.00 g of the above polymer and add it to a 100 mL flask with a side arm. After removing water under reduced pressure at 120 °C for 30 min, add 20 mL of anhydrous toluene to dissolve polymer P1. Then, add 0.8-1.5 g of allyl piperazine and a catalytic amount of Karstedt's catalyst (in Xylene, Pt ~ 2%) to the flask in sequence, and reflux and stir overnight at 110 °C. After the reaction is complete, remove the toluene by rotary evaporation, add 40 mL of dichloromethane to dissolve the polymer, add an appropriate amount of activated carbon, stir thoroughly, filter, and evaporate the filtrate to dryness to obtain PDMS with piperazine (secondary amine) at one end of the polymer, denoted as P3. Its 1H NMR spectrum is shown in Figure 3.

[0110] Examples 4-10

[0111] A method for preparing polysiloxane (PDMS) with amino groups at one or both ends of a polymer is described. The preparation method is similar to that in Example 1 or 2, except that the cyclotrisiloxane monomers used are different, the initiators are different, the degree of polymerization is different, and the types of terminal amino groups are different, which are referred to as P3-P10 in sequence, as shown in Table 1.

[0112] Table 1. Degree of polymerization results of different types of polysiloxanes prepared.

[0113] The above-mentioned polymers containing amino groups at their ends can also be obtained by first preparing carbon hydroxyl-terminated polysiloxanes and then modifying them by amylation.

[0114] Example 11

[0115] A polymer with two phosphocholine amphoteric monomer molecules modified at each end is prepared as follows:

[0116] Taking the polymer with primary amine terminals obtained in Example 1 as an example, 5.00 g of the P1 polymer from Example 1 was placed in a 100 mL flask with a side arm. The mixture was dehydrated under reduced pressure at 120 °C for 30 min, and then purged with argon gas three times. After cooling to room temperature, 20 mL of anhydrous chloroform was added to dissolve it. 3.00-5.00 g of methacryloxyethyl phosphocholine was weighed and dissolved in 20 mL of anhydrous chloroform, then added to the above reaction flask. A small amount of triethylamine was added, and the mixture was stirred at 60 °C for 48 h. After the reaction was complete, the liquid in the reaction flask was transferred to a 250 mL separatory funnel and repeatedly extracted and washed with 200 mL of water to remove excess methacryloxyethyl phosphocholine. The organic phase was preserved, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain a PDMS amphiphilic polymer with two phosphocholine derivatives modified at both ends.

[0117] Example 12

[0118] A polymer with one phosphorocholine amphoteric monomer molecule modified at each end is prepared as follows:

[0119] Taking the polymer with a secondary amine terminus obtained in Example 3 as an example, 5.00 g of the P3 polymer from Example 3 was placed in a 100 mL flask with a side arm. The mixture was dehydrated under reduced pressure at 120 °C for 30 min, and then purged with argon gas three times. After cooling to room temperature, 20 mL of anhydrous chloroform was added to dissolve it. 3.00-5.00 g of methacryloyloxyethyl phosphocholine was weighed and dissolved in 20 mL of anhydrous chloroform, then added to the above reaction flask. A small amount of triethylamine was added, and the mixture was stirred at 60 °C for 48 h. After the reaction was complete, the liquid in the reaction flask was transferred to a 250 mL separatory funnel and repeatedly extracted and washed with 200 mL of water to remove excess methacryloyloxyethyl phosphocholine. The organic phase was preserved, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain a PDMS amphiphilic polymer with one phosphocholine terminus at each end. Its 1H NMR spectrum is shown in Figure 4.

[0120] Example 13

[0121] A polymer with two phosphocholine amphoteric monomer molecules modified at one end is prepared as follows:

[0122] Taking the polymer with a primary amine at one end obtained in Example 2 as an example, 5.00 g of the P2 polymer from Example 2 was placed in a 100 mL flask with a side arm. The mixture was dehydrated under reduced pressure at 120 °C for 30 min, and then purged with argon gas three times. After cooling to room temperature, 20 mL of anhydrous chloroform was added to dissolve it. 3.00-5.00 g of methacryloxyethyl phosphocholine was weighed and dissolved in 20 mL of anhydrous chloroform, then added to the above reaction flask. A small amount of triethylamine was added, and the mixture was stirred at 60 °C for 48 h. After the reaction was complete, the liquid in the reaction flask was transferred to a 250 mL separatory funnel and repeatedly extracted and washed with 200 mL of water to remove excess methacryloxyethyl phosphocholine. The organic phase was preserved, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain a PDMS amphiphilic polymer with two phosphocholine-modified ends.

[0123] Example 14

[0124] A polymer with one end modified with a phosphorocholine amphoteric monomer molecule is prepared by the following method:

[0125] Taking the polymer with a secondary amine terminus obtained in Example 6 as an example, 5.00 g of the P6 polymer from Example 6 was placed in a 100 mL flask with a side arm. The mixture was dehydrated under reduced pressure at 120 °C for 30 min, and then purged with argon gas three times. After cooling to room temperature, 20 mL of anhydrous chloroform was added to dissolve it. 1.00-3.00 g of methacryloxyethyl phosphocholine was weighed and dissolved in 20 mL of anhydrous chloroform, then added to the above reaction flask. A small amount of triethylamine was added, and the mixture was stirred at 60 °C for 48 h. After the reaction was complete, the liquid in the reaction flask was transferred to a 250 mL separatory funnel and repeatedly extracted and washed with 200 mL of water to remove excess methacryloxyethyl phosphocholine. The organic phase was preserved, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain a PDMS amphiphilic polymer with one phosphocholine terminus modified at one end.

[0126] Example 15

[0127] A polymer with two sulfobetaine amphoteric monomer molecules modified at both ends is prepared as follows:

[0128] Taking the polymer with primary amine terminals obtained in Example 1 as an example, 5.00 g of the P1 polymer from Example 1 was placed in a 100 mL flask with a side arm. The mixture was dehydrated under reduced pressure at 120 °C for 30 min, and then purged with argon gas three times. After cooling to room temperature, 20 mL of anhydrous chloroform was added to dissolve it. 3.00-5.00 g of methacryloyloxyethyl sulfobetaine was weighed and dissolved in 20 mL of anhydrous chloroform, then added to the above reaction flask. A small amount of triethylamine was added, and the mixture was stirred at 60 °C for 48 h. After the reaction was complete, the liquid in the reaction flask was transferred to a 250 mL separatory funnel and repeatedly extracted and washed with 200 mL of water to remove excess methacryloyloxyethyl sulfobetaine. The organic phase was preserved, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain a PDMS amphiphilic polymer with two sulfobetaines modified at each end.

[0129] Example 16

[0130] A polymer with one sulfobetaine amphoteric monomer molecule modified at each end is prepared as follows:

[0131] Taking the polymer with a secondary amine terminal obtained in Example 3 as an example, 5.00 g of the P3 polymer from Example 3 was placed in a 100 mL flask with a side arm. The mixture was dehydrated under reduced pressure at 120 °C for 30 min, and then purged with argon gas three times. After cooling to room temperature, 20 mL of anhydrous chloroform was added to dissolve it. 3.00-5.00 g of methacryloyloxyethyl sulfobetaine was weighed and dissolved in 20 mL of anhydrous chloroform, then added to the above reaction flask. A small amount of triethylamine was added, and the mixture was stirred at 60 °C for 48 h. After the reaction was complete, the liquid in the reaction flask was transferred to a 250 mL separatory funnel and repeatedly extracted and washed with 200 mL of water to remove excess methacryloyloxyethyl sulfobetaine. The organic phase was preserved, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain a PDMS amphiphilic polymer with one sulfobetaine modified at each end.

[0132] Example 17

[0133] A polymer with two carboxybetaine amphoteric monomer molecules modified at both ends is prepared as follows:

[0134] Taking the polymer with a primary amine terminus obtained in Example 1 as an example, 5.00 g of the P1 polymer from Example 1 was placed in a 100 mL flask with a side arm. The mixture was dehydrated under reduced pressure at 120 °C for 30 min, and then purged with argon gas three times. After cooling to room temperature, 20 mL of anhydrous chloroform was added to dissolve it. 3.00-5.00 g of methacryloyloxyethyl carboxybetaine was weighed and dissolved in 20 mL of anhydrous chloroform, then added to the above reaction flask. A small amount of triethylamine was added, and the mixture was stirred at 60 °C for 48 h. After the reaction was complete, the liquid in the reaction flask was transferred to a 250 mL separatory funnel and repeatedly extracted and washed with 200 mL of water to remove excess methacryloyloxyethyl carboxybetaine. The organic phase was preserved, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain a PDMS amphiphilic polymer with one sulfobetaine modified at each end.

[0135] In the description of this specification, the references to terms such as "one embodiment," "some embodiments," "example," "specific example," or "some examples," etc., indicate that a specific feature, structure, material, or characteristic described in connection with that embodiment or example is included in at least one embodiment or example of this disclosure. In this specification, the illustrative expressions of the above terms do not necessarily refer to the same embodiment or example. Furthermore, the specific features, structures, materials, or characteristics described may be combined in any suitable manner in one or more embodiments or examples. Moreover, without contradiction, those skilled in the art can combine and integrate the different embodiments or examples described in this specification, as well as the features of different embodiments or examples.

[0136] Although embodiments of the present disclosure have been shown and described above, it is to be understood that the above embodiments are exemplary and should not be construed as limiting the present disclosure. Those skilled in the art can make changes, modifications, substitutions and variations to the above embodiments within the scope of the present disclosure.

Claims

1. A method for preparing an amphiphilic polymer, wherein, The method includes: (1) Prepare a hydrophobic polymer, cap at least one end of the hydrophobic polymer, and modify the capped end with amino or thiol groups to obtain a hydrophobic polymer with primary or secondary amine groups or thiol groups at the end. (2) The hydrophobic polymer obtained in step (1) is subjected to a Michael addition reaction with hydrophilic amphoteric monomer molecules to obtain the amphiphilic polymer; The hydrophobic polymer includes at least one selected from polysiloxanes, epoxy compounds, polyolefins, and polyesters; The hydrophilic amphoteric monomer molecules include those selected from hydrophilic amphoteric monomer molecules having methpropylene double bonds.

2. The method according to claim 1, wherein, The molecular weight distribution of the prepared hydrophobic polymer is ≤1.

15.

3. The method according to claim 1, wherein, The polysiloxane includes at least one selected from polydimethylsiloxane, polydiphenylsiloxane, polymethylphenylsiloxane, and copolymers thereof.

4. The method according to claim 1, wherein, At least one end of the hydrophobic polymer described in step (1) is capped using a capping agent.

5. The method according to claim 4, wherein, The capping agent includes those selected from dimethylchlorosilane.

6. The method according to claim 1, wherein, When the hydrophobic polymer is a polysiloxane, the structural formula of the polysiloxane obtained by the end-capping treatment is: R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Replacement C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl; The R a Independently selected from halogens, C1-C 10 Alkyl, C3-C 10 cycloalkyl, C1-C 10 Alkoxy; n is any integer between 15 and 50.

7. The method according to claim 6, wherein, R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Substituted C1-C5 alkyl, C3-C5 cycloalkyl, 3-5 membered heterocyclic groups, C6-C 10 Aryl, 5-10 heteroaryl.

8. The method according to claim 6, wherein, R1 and R2 are each independently selected from unsubstituted or substituted groups R1 and R2. a Substituted C1 alkyl, C3 cycloalkyl, 3-membered heterocyclic, phenyl, 5-membered heteroaryl.

9. The method according to claim 6, wherein, R1 and R2 are each independently selected from methyl and phenyl.

10. The method according to claim 6, wherein, The n is any integer between 20 and 30.

11. The method according to any one of claims 6-10, wherein, Modifying at least one end of the polysiloxane with an amino group yields a polysiloxane with a primary or secondary amine group at the end, with the structural formula as follows: The R3 is independently selected from x and y are each independent integers from 1 to 10. R is independently selected from H, halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl; R4 is independently selected from unsubstituted or substituted R4 groups. b Substituted H, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl; The R b Independently selected from halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl; R5 is independently selected from unsubstituted or substituted R5 groups. c The substituted 3-10 nitrogen-containing cyclic group contains at least one secondary amine; The R c Independently selected from halogens, C1-C 10 Alkyl, C3-C 10 Cycloalkyl, 3-10 membered heterocyclic, C6-C 20 Aryl, 5-20 heteroaryl.

12. The method according to claim 11, wherein, The R4 is independently selected from unsubstituted or substituted R4 groups. b Substituted H, C1-C5 alkyl, C3-C5 cycloalkyl, 3-5 membered heterocyclic group, C6-C 10 Aryl, 5-10 heteroaryl.

13. The method according to claim 11, wherein, The R4 is independently selected from unsubstituted or substituted R4 groups. b Substituted H, C1 alkyl, C3 cycloalkyl, 3-membered heterocyclic, phenyl, 5-membered heteroaryl.

14. The method according to claim 11, wherein, The R4 is independently selected from H and C1 alkyl groups.

15. The method according to claim 11, wherein, The R5 is independently selected from unsubstituted or substituted R5 groups. c The substituted 5-8 member nitrogen-containing cyclic group contains at least one secondary amine.

16. The method according to claim 11, wherein, The R5 is independently selected from unsubstituted or substituted R5 groups. c Substituted pyrazoles, imidazoles, triazoles, tetrazolium, piperidine, and piperazine.

17. The method according to claim 11, wherein, R5 is independently selected from piperidine and piperazine.

18. The method according to claim 1, wherein, The hydrophilic amphoteric monomer molecule includes at least one independently selected from methacryloyloxyethyl phosphorocholine, methacryloyloxyethyl sulfobetaine, and methacryloyloxyethyl carboxybetaine.

19. An amphiphilic polymer, wherein, The amphiphilic polymer is obtained by the method described in any one of claims 1-18.

20. Use of the method according to any one of claims 1-18 or the amphiphilic polymer according to claim 19 in the preparation of vesicles or biomimetic membranes.

21. A vesicle, wherein, The vesicles comprise the amphiphilic polymer of claim 19.

22. A biomimetic membrane, wherein, The biomimetic membrane comprises the amphiphilic polymer of claim 19.

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