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Small molecule peptide-based cholesteric organic gel molecules and preparation method thereof

An organogel, small molecular peptide technology, applied in the field of supramolecular chemistry, can solve the problems of low transition temperature and no thermal stability

Inactive Publication Date: 2010-11-03
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Present gel is all prepared by the method of sol-gel, and the gel that this method makes often sol-gel transition temperature is lower (<the boiling point of solvent), does not have higher thermal stability, this kind Disadvantages will limit further applications of these gels

Method used

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  • Small molecule peptide-based cholesteric organic gel molecules and preparation method thereof
  • Small molecule peptide-based cholesteric organic gel molecules and preparation method thereof
  • Small molecule peptide-based cholesteric organic gel molecules and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Gel Factor A (R=-CHCH 3 -CONH-(CH 2 ) m -, m=6, n=2) synthesis and gel preparation.

[0030]

[0031] Preparation of N-(R)-2-propionic acid-4-morpholinyl-1,8-naphthalene anhydride (2):

[0032] (1) The ethanol solution of L-alanine (251.2mg, 2.82mmol) and NaOH (113mg, 2.83mmol) was stirred at 40°C for 20 minutes, then added 4-morpholine-1,8-naphthalimide ( 800mg, 2.82mmol), N 2 Heated to reflux for 24 hours under protection, the reaction product was concentrated to remove ethanol, adjusted to pH=6-7 with dilute hydrochloric acid, the crude product was purified by column chromatography to obtain pure product, yield (469 mg, 47%). Melting point: 148-150°C.

[0033] 1 H NMR (400MHz, CDCl 3): δ1.68-1.69 (d, 3H, J = 7.2Hz), 3.26-3.28 (t, 4H, J = 4.4Hz), 4.01-4.04 (t, 4H, J = 4.4Hz), 5.78-5.83 ( m, 1H), 7.23-7.25(d, 1H, J=8Hz), 7.69-7.73(t, 1H, J=8Hz), 8.43-8.45(d, 1H, J=8Hz), 8.53-8.55(d, 1H, J=8Hz), 8.58-8.60(d, 1H, J=6.4Hz). 13 C (100MHz, CDCl 3 ): δ14.59, 48...

Embodiment 2

[0044] Gel factor B (R=-(CH 2 ) m -(NHCO)-CHCH 3 -, m=6, n=2) synthesis and gel preparation

[0045]

[0046] (1) Preparation of Cholesteryl N-alanine (5):

[0047] 3-Alanine (1g, 2mmol), lithium hydroxide hydrate ((2.5g, 60mmol) were put into a mixed solvent of 25mL water and 2mL tetrahydrofuran, and stirred at room temperature for 48 hours. The product was concentrated and adjusted to pH=2-3 with hydrochloric acid , to obtain a white solid (0.6 g, yield: 62%). Melting point: 112-114°C.

[0048] 1 H NMR (CDCl 3 ): δ0.68(s, 3H), 0.85-0.86(d, J=2Hz, 3H), 0.87-0.88(d, 3H, J=4.6Hz), 0.91-0.92(d, J=9.6Hz, 3H ), 0.95-1.61(m, 24H), 1.81-2.02(m, 5H), 2.20-2.61(m, 4H), 3.45-3.46(m, 2H), 4.80-4.53(m, 1H), 5.37-5.38 (m, 1H). 13 C(CDCl 3 ): δ8.68, 11.87, 18.73, 19.34, 21.05, 22.57, 22.83, 23.84, 24.30, 28.03, 28.20, 31.90, 34.36, 35.81, 36.20, 36.57, 37.00, 38.55, 39.553, 39.735, 40.8 51.80, 56.15, 56.71, 74.46, 122.51, 139.84, 156.04, 172.89. MALDI-TOF-MS calcd for C 31 h ...

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Abstract

The invention belongs to the technical field of super-molecular chemistry and particularly relates to small molecule peptide-based cholesteric organic gel molecules and a preparation method thereof. The cholesteric organic gel molecules can form gel in an organic solvent and the formed gel has thermal stability and water stability and can respond to ultrasound for realizing transformation of ultrasonically-induced gel into gel. The organic gel molecule comprises 1) an anhydride naphthalene part serving as a luminophor, 2) a middle small peptide serving as a functional group for forming intermolecular hydrogen bonds and 3) a sterides part which has biocompatibility and serves as a gelation factor and a hydrophobic group. The molecule can form high-quality gel which has rich micro-nanoscale macro morphologies, such as nuclear shells, solid balls, defect balls, nanofiber, micro-fiber and the like, and has regular shape and high repeatability in nearly ten organic solvents including acetonitrile, ethanol, benzene, toluene, acetone and the like through a sol-gel process. The organic fluorescent gel has a certain application value in the aspects of nano material preparation, medicinal carrier transportation, biological marking and the like.

Description

technical field [0001] The invention belongs to the technical field of supramolecular chemistry, and specifically relates to a cholesteric organogel molecule based on a small molecular peptide and a preparation method thereof. The cholesteric organogel molecule can form a gel in an organic solvent, and the formed The gel is thermally and water stable and responsive to ultrasound. Background technique [0002] Organogel (Organogel) forms a unique network structure through supramolecular interactions between gelling factors such as hydrogen bonds, static electricity, and hydrophobic interactions, thereby restricting the flow of solvents. This organogel can respond to environmental stimuli such as acid, alkali, light, and sound, so the organogel has broad application prospects in memory materials, biomarkers, and drug delivery and release. In addition, organogels generally have relatively regular micro-nano structures, which can provide molecular models and theoretical basis f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00C07K5/072C09K11/06
Inventor 易涛余旭东吴君臣兰海闯曹新华刘斌
Owner FUDAN UNIV
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