Bilateral biotin-phthalocyanine zinc conjugate as well as preparation and application thereof

A biotin, zinc phthalocyanine technology, applied in the fields of drug combination, organic chemistry, organic chemistry methods, etc., can solve the problems of poor tumor selectivity, uncertain structure, insufficient targeting, etc., and achieve strong tissue penetration and production. The effect of low cost, easy separation and purification

Inactive Publication Date: 2016-03-23
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the shortcomings of the traditional first and second generation photosensitizers, such as: unknown components, uncertain structure, poor selectivity to tumors, insufficient targeting, etc.

Method used

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  • Bilateral biotin-phthalocyanine zinc conjugate as well as preparation and application thereof
  • Bilateral biotin-phthalocyanine zinc conjugate as well as preparation and application thereof
  • Bilateral biotin-phthalocyanine zinc conjugate as well as preparation and application thereof

Examples

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Embodiment 1

[0027] (1) Disperse sodium hydride (18mg, 0.44mmol) evenly in anhydrous THF, then slowly add the THF solution of compound (Ⅳ) (195mg, 0.20mmol) into the above reaction solution, stir for a while and then add propargyl bromide (34μL, 0.44mmol), react overnight at 60°C under nitrogen protection, TLC detects that the reaction is complete, add a small amount of water after the reaction solution is cooled to room temperature, stir for a while, remove THF by rotary evaporation under reduced pressure, extract with dichloromethane and water, Combine the organic phases and wash with anhydrous Na 2 SO 4 Dry, remove the solvent by rotary evaporation under reduced pressure, use dichloromethane-methanol (30:1, v / v) as the eluent, and purify by silica gel column chromatography to obtain blue-green solid compound (II): , (215mg, 98%); 1 HNMR (400MHz, CDCl 3 and a small amount of C 5 D. 5 N):δ9.36-9.40(m,4H,Pc-H α ),9.29(d, J =6.8Hz,2H,Pc-H α ),8.08-8.15(m,6H,Pc-H β ),7.45(s,2H,Pc-H...

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Abstract

The invention discloses a bilateral biotin-phthalocyanine zinc conjugate as well as preparation and application thereof. According to the conjugate disclosed by the invention, a biotin-cell growth-promoting factor (which is a critical micronutrient for cells to maintain normal functions, growth and reproduction) is used as a tumor target and is covalently connected onto a phthalocyanine zinc photosensitizer capable of being used for a photodynamic therapy, thus obtaining a third-generation anti-cancer photosensitizer for targeted therapy. Meanwhile, according to the conjugate, the biotin instead of a phthalocyanine zinc derivative acts a research object, human breast cancer cell MCF-7 and human embryo lung inoblast HELF act as subject cell lines respectively, a research regarding the in-vitro anti-cancer activity of the biotin is developed, and a prodrug suitable for a molecular targeted therapy is screened out, and a foundation is laid for applying the biotin instead of the phthalocyanine zinc derivative to the targeted therapy of cancers. The compound, namely the conjugate disclosed by the invention, is relatively simple in synthesis method, easily available in raw materials, low in cost, fewer in side reactions, relatively high in yield, easy to purify and beneficial for industrial production.

Description

technical field [0001] The invention belongs to the field of anticancer drug design and synthesis, and in particular relates to a bilateral biotin-phthalocyanine zinc conjugate and its preparation and application. Background technique [0002] Cancer has gradually become the number one killer of human health, and it seriously threatens people's health. Photodynamic therapy (Photodynamic Therapy, PDT) is a new cancer treatment technology after the three traditional tumor treatment methods such as surgery, chemotherapy and radiotherapy. It is an important new interdisciplinary and research field of laser, medicine, biology and chemistry. Photodynamic therapy is a series of photophysical and photochemical reactions after the photosensitizer enriched in the diseased tissue is excited by a certain wavelength of light, so that the oxygen molecules in the tissue are converted into cytotoxic reactive oxygen species (Reactive Oxygen Species, ROS), thereby Achieving the destruction o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00A61P35/00
CPCC07B2200/13C07D519/00
Inventor 刘见永侯雪妮叶发荣薛金萍
Owner FUZHOU UNIV
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