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Fullerene multi-nitrogen heterocyclic water-soluble derivatives as well as preparation method and application thereof

A fullerene and water-soluble technology, applied in drug delivery, emulsion delivery, organic chemistry, etc., can solve the problems of easy cross-interference, large steric hindrance effect, unfavorable coupling reaction, etc., to achieve rich variety and improve Solubility effect

Inactive Publication Date: 2011-04-06
HANGZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The above-mentioned water-soluble derivatives of fullerene are used as nano-biological materials for coupling biomacromolecules or various markers in the field of nano-biological labeling and detection technology. Fullerene alcohols are not easy to undergo covalent coupling due to the modification of hydroxyl groups on the surface of the carbon cage. Linkage reaction; the end of the side chain of the fullerene malonate derivative is a carboxyl functional group, although it can undergo amidation coupling reaction, but the side chain is too short, the active group is too close to the surface of the carbon cage, because the steric hindrance effect is too large It is not conducive to the coupling reaction; amino acid derivatives of fullerenes have two functional groups, amino and carboxyl, and are prone to cross-interference during amidation coupling reactions

Method used

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  • Fullerene multi-nitrogen heterocyclic water-soluble derivatives as well as preparation method and application thereof
  • Fullerene multi-nitrogen heterocyclic water-soluble derivatives as well as preparation method and application thereof
  • Fullerene multi-nitrogen heterocyclic water-soluble derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: C 60 Multiple addition product C with 2-azidoethylamine 60 (NCH 2 CH 2 NH 2 ) x (Compound 1) Preparation

[0045] Weigh 0.10mmol of C 60 Dissolve in 15ml of chlorobenzene, under inert gas protection at normal temperature, stir with a magnet, slowly add 2-azidoethylamine solution (5.0mmol of 2-azidoethylamine dissolved in 5ml of chlorobenzene) dropwise within 30 minutes, After the dropwise addition was completed, the temperature was slowly raised to 80° C., and the reaction was heated for 3 days, and the temperature was raised to reflux for 1 day, and the reaction was stopped. During heating, bright purple C 60 The solution gradually turned orange-red and continued to darken to brown. After the reaction liquid was cooled to room temperature, the solvent was distilled off under reduced pressure, and the residue was washed with toluene, diethyl ether, and methanol successively to obtain a brownish black solid, namely compound 1, with a yield of 58%.

[...

Embodiment 2

[0053] Example 2: C 60 Multiple addition product C with 2-azidoacetic acid 60 (NCH 2 COOH) x (Compound 2) and C 60 (NCH 2 COONa) x (Compound 3) Preparation

[0054] Weigh 0.10mmol of C 60 Dissolve in 15ml of chlorobenzene, under the protection of inert gas at normal temperature, stir with a magnet, slowly add 2-azidoacetic acid solution (2.0mmol of 2-azidoacetic acid dissolved in 5ml of chlorobenzene) dropwise within 30 minutes, dropwise After completion, the temperature was slowly raised to 50° C., the reaction was heated for 24 hours, and the temperature was continuously raised to reflux for 5 hours. The solvent was removed, and the residue was washed successively with toluene, diethyl ether, and methanol to obtain a tan solid, namely compound 2, with a yield of 95%.

[0055] Weigh 10mg of compound 2 solid powder, dissolve it in an appropriate amount of 1mol / L NaOH, mix well, control the pH value at 12-13, and separate with Sephadex G-15 chromatographic column, neutr...

Embodiment 3

[0058] Example 3: C 60 Multiple addition product C with 3-azidopropionic acid 60 (NCH 2 CH 2 COOH) x (Compound 4) and C 60 (NCH 2 CH 2 COONa) x (Compound 5) Preparation

[0059] Weigh 0.10mmol of C 60 Dissolve in 15ml of chlorobenzene, under the protection of inert gas at normal temperature, stir with a magnet, slowly add 3-azidopropionic acid solution (2.0mmol 3-azidopropionic acid dissolved in 5ml of chlorobenzene) dropwise within 30 minutes, drop After the addition was completed, the temperature was raised slowly to 60° C., and the reaction was heated for 24 hours, and the temperature was continued to rise and reflux for 10 hours. The solvent was removed, and the residue was washed successively with toluene and ethyl acetate to obtain a brownish-yellow solid, namely compound 4, with a yield of 92%.

[0060] The preparation method of Compound 5 was the same as that of Compound 3 in Example 2, except that Compound 2 was replaced by Compound 4 to obtain purified Comp...

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Abstract

The invention discloses fullerene multi-nitrogen heterocyclic water-soluble derivatives as well as a preparation method and an application thereof. The fullerene multi-nitrogen heterocyclic water-soluble derivatives are fullerene imino derivatives which prepared from fullerene C2n and nitrine organic compound by a cycloaddition reaction. The structural formula of the derivatives is C2n[N(CH2)mCH2NH2]x or C2n[N(CH2)m-1CH2COOM]x, wherein n=30-50, m=1-5, x= 8-24, and M is H, NH4, Na or K. The derivatives of the invention have good aqueous phase dissolubility, have perssad-NH2 or -COOH with reactivity at side chain end which are suitable for coupling and bonding various markers or large biological molecules, thereby being applied to nano-biomarkers and detecting techniques.

Description

technical field [0001] The invention belongs to the field of nano-biological materials, and relates to a class of fullerene polyaza bridge water-soluble derivatives and a preparation method and application thereof. The fullerene polyaza bridge water-soluble derivatives can be coupled to biological macromolecules and Various markers are used as water-soluble nano-biological materials for nano-biological labeling and detection. Background technique [0002] Fullerene is a general term for a class of caged carbon clusters with molecular sizes on the order of nanometers. Take the "star molecule" C 60 The typical representative fullerene-based carbon nanomaterials have attracted much attention from scientific and technological workers because of their unique structures and novel properties. Due to the strong hydrophobicity of fullerene molecules, they can only be dissolved in organic solvents that are harmful to organisms, have poor biocompatibility with organisms, are not easi...

Claims

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Application Information

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IPC IPC(8): C07D203/26C07D471/08A61K49/18A61K49/06
Inventor 何睿陈亮文焦艳华陈灿玉梁媛媛李霞黄志坚
Owner HANGZHOU NORMAL UNIVERSITY
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