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A zinc phthalocyanine-chitooligosaccharide conjugate and its preparation method and application

A technology of zinc phthalocyanine and a conjugate, which is applied in the field of zinc phthalocyanine-chitosan oligosaccharide conjugate and its preparation, and achieves the effects of reducing dark toxicity, high reproducibility and simple preparation process

Active Publication Date: 2020-06-12
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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preparation example Construction

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

[0028] 1) With zinc phthalocyanine compound (1) or (2) Chitooligosaccharide is used as the raw material for the reaction (the molar ratio of phthalocyanine zinc compound to chitooligosaccharide repeating units is 1:10~30), dimethyl sulfoxide is used as the solvent, 1-hydroxybenzotriazole and 1- (3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is the condensation reagent (1-hydroxybenzotriazole, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide The molar ratio of diimine hydrochloride to zinc phthalocyanine compound is 1~20:1), reacted at room temperature 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 reaction solvent, raise the temperature to 65~80°C u...

Embodiment 1

[0036]20 mg (0.027 mmol) 1-[4-(2-carboxyethyl) phenoxy] phthalocyanine zinc, 5 mg (0.04 mmol) 5-aminovaleric acid, 10 mg (0.08 mmol) 1-hydroxybenzotriazole and 16 mg (0.08 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was dissolved in 2 mL of DMSO, reacted under nitrogen protection at room temperature for 12 h, stopped the reaction, concentrated to dryness, and passed 100 -200 mesh silica gel, wash off the first blue band with eluent (EA:DMF=10:1), then use eluent (EA:DMF=3:1, containing 1% acetic acid) to elute , to collect the second blue band. Concentrate it to dryness, dissolve it in DMF, pass it through a Bio-Beads S-X3 gel column, collect the first blue band, and spin dry to obtain 17.5 mg of blue powder, which is zinc phthalocyanine compound (1). The rate is 76.1%.

[0037] Product Characterization Data: 1 H NMR (400MHz, DMSO- d 6 , ppm) δ 11.27 (s, 1H, -OH), 9.18-8.84 (m, 6H, Pc-H α ), 8.73(d, J =9.5Hz, 1H, Pc-H α ), 8.20-7.90 (m, 7H, Pc-...

Embodiment 2

[0040] 10mg (0.014mmol) 1-[4-(2-carboxyethyl) phenoxy] phthalocyanine zinc, 2.45mg (0.02mmol) 5-aminovaleric acid, 5.7mg (0.042mmol) 1-hydroxybenzotri Azole and 8 mg (0.042 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were dissolved in 2 mL of DMSO, and reacted at room temperature for 12 hours under nitrogen protection, and 5.7 mg (0.042 mmol) 1-hydroxybenzotriazole, 8 mg (0.042 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.45 mg (0.02 mmol) 5-aminovaleric acid , continue to react at room temperature for 12 h under the protection of nitrogen, and TLC detection shows that the raw material phthalocyanine compound has completely disappeared. 10:1) to elute the impurities, and finally use EA / DMF (2:1, containing 1% acetic acid) to collect the blue band, concentrate to dryness, dissolve with DMF, pass through the Bio-Beads S-X3 gel column, and collect the first A blue band, 9.36mg of blue powder was obtained, which is the zinc phth...

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Abstract

The invention discloses a zinc phthalocyanine-chitosan oligosaccharide conjugate as well as a preparation method and application thereof. The zinc phthalocyanine-chitosan oligosaccharide conjugate refers to a conjugate of terminal carboxyl mono-substituted zinc phthalocyanine and chitosan oligosaccharide or quaternary ammonium derivatives thereof. The zinc phthalocyanine-chitosan oligosaccharide conjugate can be applied to photodynamic antibiosis, photodynamic cancer resistance, photodynamic diagnosis and photodynamic disinfection. The zinc phthalocyanine-chitosan oligosaccharide conjugate disclosed by the invention has zinc phthalocyanine and chitosan oligosaccharide or chitosan oligosaccharide ammonium salt double functional groups, and the synergy therapy effect can be achieved during photodynamic antibiosis; meanwhile, the chitosan oligosaccharide has excellent water solubility and biocompatibility, and can achieve the effects of effectively improving the amphiphilic property and biocompatibility of the zinc phthalocyanine, reducing the toxicity and improving the clinical application value of the zinc phthalocyanine.

Description

technical field [0001] The invention belongs to the field of medicine preparation, and in particular relates to a zinc 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 bacteri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A61K31/722A61K41/00A61K47/61A61P35/00A61P31/04A61P31/10A61P1/02A61P27/02A61P9/10A61P17/02A61P17/00A61P31/12A61L2/16
CPCA61K31/722A61K41/0071A61K47/61A61L2/16A61L2202/22A61L2202/24A61P1/02A61P9/10A61P17/00A61P17/02A61P27/02A61P31/04A61P31/10A61P31/12A61P35/00C08B37/003
Inventor 黄剑东唐凤翔李洪才高芳郑碧远王成宇薛琳莉
Owner FUZHOU UNIV
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