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Improved organic-inorganic hybrid solid having a modified outer surface

A solid, organic technology, applied in the field of preparation, can solve stability problems, biomedical application obstacles and other problems

Active Publication Date: 2015-06-17
CENT NAT DE LA RECHERCHE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these approaches to coverage have stability issues, especially in physiological environments, which represent an obstacle to the use of these MOF materials with modified external surfaces for in vivo biomedical applications (see Example 12)

Method used

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  • Improved organic-inorganic hybrid solid having a modified outer surface
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  • Improved organic-inorganic hybrid solid having a modified outer surface

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0440] Embodiment 1: Synthesis of nanoparticles of various MOFs

[0441] MIL-89 Nano Fe 3 OX[C 4 h 4 (CO 2 ) 2 ] 3 nH 2 O (X=F, Cl, OH)

[0442] From ferric acetate (1 mmol; synthesized according to the procedure described in C.T. Dziobkowski, T.J. Wrobleski, D.B. Brown, Inorg. Chem. 1982, 21, 671 [51]) and muconic acid (1 mmol; Fluka, 97%) in 5 mL of ethanol (Riedel-de 99.8%), with the addition of 0.25 mL of 2M sodium hydroxide (Alfa Aesar, 98%), MIL-89 nanometers were synthesized in an autoclave (Paar bomb) at 100° C. for 12 h. After cooling the vessel, the product was recovered by centrifugation at 5000 rpm for 10 minutes.

[0443] 200 mg of the solid was suspended in 100 mL of distilled water and stirred for 15 h to remove any solvent remaining in the pores. Then, the solid was recovered by centrifugation at 5000 rpm for 10 minutes.

[0444] The particle size measured by light scattering was 400 nm.

[0445] The nanoparticles show a round and slightly elongate...

Embodiment 2

[0480] Example 2: Synthesis of nanoparticles of iron trimesate MIL-100 functionalized with βCDP

[0481] With β-cyclodextrin phosphate (βCDP, Cyclolab, CY-2017.1, molecular formula: C 42 h 70 o 47 P 4 Na 4 ) modified organic-inorganic hybrid nanoparticles (nano-MOF) based on iron trimesate (MIL-100). This molecule has two essential features for effective surface modification of nano-MOFs: 1) it has a bulkier structure than the micropore windows of MIL-100, which should prevent it from being adsorbed in the pores, Thereby maintaining the porosity of the nanoparticles; 2) it is substituted by 4 phosphate groups, which should ensure a stable interaction with the nanoparticles by forming ionic covalent bonds with the iron atoms on the particle surface ( figure 2 ).

[0482] 2 mg of MIL-100 was modified by incubating with 500 μl of 2 mg / ml βCDP in water (weight ratio, nanoparticle:βCDP=1:0.5) for 24 h under stirring at room temperature. After incubation, the modified nanop...

Embodiment 3

[0510] Embodiment 3: synthetic branched chain PEG

[0511] At room temperature, under two-dimensional stirring, with 2 mL of 0.5 mg / mL star PEG (amino-dPEG TM (4)-[dPEG TM (12)-OMe] 3 , C 99 h 197 N 5 o 47 , 2209.63 g / mol, Iris Biotech, Germany) was incubated with an aqueous solution of 30 mg of MIL 100 nanoparticles for 2 minutes. At the end of the incubation, nanoparticles were recovered by centrifugation at 5600 xg for 10 min, followed by two washes with water. PEG was determined in the recovered supernatant after the first centrifugation by a colorimetric method (see Baleaux [33]). Only 1 wt% of PEG remained in the supernatant, suggesting that almost all PEG (99 wt%) interacted with the nanoparticles.

[0512] The porosity of the dried nanoparticles was analyzed by nitrogen adsorption at 77K. BET specific surface area from 1400m 2 / g changes to 1225m 2 / g, therefore, indicates that star PEG also penetrates the pores, as does linear PEG (see below). Furthermor...

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Abstract

The present invention concerns metal-organic hybrid solids having a modified outer surface. These solids can be used, for example, for the storage and vectoring of molecules of interest such as pharmaceutically active ingredients, compounds of interest in cosmetics and markers, for example contrast agents. These solids have good results in terms of active drug loading capacities, biocompatibility, stability and controlling the release of the active ingredients encapsulated.

Description

[0001] References to related applications [0002] This application claims priority from French patent application FR 12 / 55065 filed May 31, 2012, the content of which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to improved porous crystalline metal-organic framework (MOF) solids with modified external surfaces, and in particular to methods of making the same. [0004] For example, MOF solids of the invention can be used as contrast agents and / or for the delivery of pharmaceutical compounds. The solids of the invention can also be used for applications in the fields of storage, separation, catalysis, cosmetics or the food industry. The solid can also be used to guide and / or monitor pharmaceutical compounds in living organisms. The solid can also be used for detoxification. For example, the solid may be in the form of crystals, powders, granules or nanoparticles. [0005] Reference numbers in square brackets [X]...

Claims

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Application Information

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IPC IPC(8): C07F3/06C07F5/06C07F7/00A61K9/14C07F15/02A61K47/08C07F9/38G01N33/58A61P35/00
CPCA61K47/24A61K47/26A61K49/00C07F3/06C07F5/061C07F7/003C07F9/3873C07F15/025C08B37/0012C08B37/0021C08B37/003A61K2123/00A61P25/04A61P29/00A61P31/04A61P31/12A61P35/00A61K9/14A61K47/08G01N33/58
Inventor 鲁克桑德拉·格雷夫瓦伦丁娜·阿戈斯托尼萨米亚·达乌德-穆罕默德维奥莱塔·罗德里格斯-鲁伊斯米洛·马兰加拉斯洛·伊钦斯基帕特里西亚·霍卡雅达-科尔特斯克里斯蒂安·塞尔
Owner CENT NAT DE LA RECHERCHE SCI
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