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Phthalocyanine-chitosan oligosaccharide conjugates as well as preparation method and application thereof

A technology of chitosan oligosaccharide and conjugates, which is applied in the directions of pharmaceutical formulations, medical preparations without active ingredients, and medical preparations containing active ingredients, etc., to achieve the effects of easy operation, reduced dark toxicity, and simple preparation process

Active Publication Date: 2018-09-07
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Oligochitosan is an oligomer obtained from the degradation of chitosan. In addition to the excellent activity of chitosan, it also exhibits many excellent properties that chitosan does not have, such as good water solubility and antibacterial activity. There are few studies on oligochitosan as a drug delivery system with better properties

Method used

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Examples

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preparation example Construction

[0027] A kind of phthalocyanine-chitooligosaccharide conjugate, its preparation method comprises the following steps:

[0028] 1) With phthalocyanine compound (1) or (2) Chitooligosaccharide is used as the raw material for the reaction (the molar ratio of phthalocyanine compound to chitooligosaccharide repeating unit is 1:10~30), dimethyl sulfoxide is used as the solvent, 1-hydroxybenzotriazole, dicyclohexyl The mixture of carbodiimide and 4-dimethylaminopyridine is a condensation reagent (the molar ratio of 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, 4-dimethylaminopyridine and chitosan oligosaccharide repeating units is equal to 0.5~1.5mmol), heated to room temperature~35°C under ice-water bath and nitrogen protection, reacted for 16~24h, and then separated and purified by column chromatography and size exclusion chromatography to obtain or ;

[0029] 2) Dissolve the conjugate of formula (I) or (III) in a small amount of dimethyl sulfoxide, add isopropanol as a...

Embodiment 1

[0036] 14.5 mg 1-[4-(2-carboxyethyl)phenoxy]phthalocyanine (1, 0.02 mmol) and 54 mg 1-hydroxybenzotriazole (0.4 mmol) and 41.2 mg dicyclohexylcarbodiene Amine (DCC, 0.4 mmol) was placed in a 25 mL two-necked flask, 2 mL of dimethyl sulfoxide was added, and N 2 Stir in the dark, add 49 mg 4-dimethylaminopyridine (0.4 mmol) after 10 min, and slowly drop 60 mg chitosan oligosaccharide (MW=2kDa, 0.4 mmol repeating unit number) dissolved in 1 mL DMSO into the reaction solution reaction in an ice bath for 10 min, and then transferred to room temperature for 16 h in the dark. Pass through a 100-200 mesh silica gel column, first use DMF:EA=1:5 as the eluent to remove impurities, and then use DMF:CH 3 Elute with COOH=50:1 eluent, collect the corresponding effluent and spin dry, dissolve with a small amount of water, pass through Sephadex G-100 gel, collect the first blue band, concentrate, freeze-dry, 38 mg of blue network was obtained, which was the conjugate (I) of phthalocyanine (...

Embodiment 2

[0039] 30 mg of the phthalocyanine-chitooligosaccharide conjugate (I) obtained in Example 1 (0.194 mmol of free amino groups) was dissolved in a small amount of dimethyl sulfoxide, and added dropwise to 5 mL of isopropanol, under nitrogen protection Lower the temperature to 65°C, then add 59 mg (0.374 mmol) 2,3-epoxypropyltrimethylammonium chloride previously dissolved in 1 mL of isopropanol solution three times, with an interval of half an hour between each addition, React for 8 hours, stop the reaction, concentrate, pass through G-100 dextran gel, collect the first blue band, concentrate and freeze-dry to obtain 39.8 mg blue network solid, which is phthalocyanine (1) and average molecular weight It is a quaternized derivative (II) of a 2 kDa chitosan oligosaccharide conjugate (I). The degree of substitution of the quaternary ammonium radicals in the conjugate was determined to be 0.943 according to the H NMR spectrum (that is, 0.943 quaternary ammonium radicals were attached...

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Abstract

The invention discloses phthalocyanine-chitosan oligosaccharide conjugates as well as a preparation method and an application thereof, and belongs to the field of drug preparation. The phthalocyanine-chitosan oligosaccharide conjugates are monosubstituted carboxyl zinc phthalocyanine and chitosan oligosaccharide conjugates or quaternization derivatives of the conjugates, and can be applied to photodynamic bacterial resistance, photodynamic cancer resistance, photodynamic diagnosis and photodynamic disinfection. The phthalocyanine-chitosan oligosaccharide conjugates have double functional groups of phthalocyanine and chitosan oligosaccharide or chitosan oligosaccharide quaternary ammonium salt, thereby being capable of realizing a synergistic treatment effect while realizing photodynamic bacterial resistance; meanwhile, chitosan oligosaccharide has excellent water solubility and biocompatibility, accordingly, amphiphilic property and biocompatibility of phthalocyanine can be improved effectively, toxicity of phthalocyanine can be reduced, and clinical application value of phthalocyanine can be increased.

Description

technical field [0001] The invention belongs to the field of medicine preparation, and in particular relates to a phthalocyanine-chitooligosaccharide conjugate and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (or photodynamic therapy) is essentially the application of photosensitization reactions of photosensitizers (or photosensitizers) in the medical field. Its general action process is that the photosensitizer is injected into the body first, and after a period of time (the drug is relatively enriched in the target body), the target body is irradiated with light of a specific wavelength (the target in the body cavity can be introduced into the light source by means of optical fiber, etc.), so that The photosensitizer enriched in the target body is excited under light irradiation, which produces a series of photophysical and chemical reactions, and produces substances that can destroy the target body (such as bacterial in...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61P31/10A61P31/04A61K47/61A61K41/00
CPCA61K41/0071A61K47/61A61P31/04A61P31/10C08B37/003
Inventor 黄剑东唐凤翔孙雅郑碧远李洪才
Owner FUZHOU UNIV
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