Poly-substituted near-infrared hypocrellin derivative, preparation method and applications thereof

A technology of hypocretin and its derivatives, which is applied in the field of multi-substituted near-infrared hypocretin derivatives and their preparation, and can solve the problems of increased molar extinction coefficient and red shift

Active Publication Date: 2018-04-20
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the past ten years, there have been many chemical modifications for hypocrellin, and its absorption wavelength has been red-shifted to 600-700nm, and the molar extinction coefficient has been significantly increased. However, no bamboo with a maximum absorption wavelength greater than 700nm has been developed so far. Rhodobacter derivatives

Method used

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  • Poly-substituted near-infrared hypocrellin derivative, preparation method and applications thereof
  • Poly-substituted near-infrared hypocrellin derivative, preparation method and applications thereof
  • Poly-substituted near-infrared hypocrellin derivative, preparation method and applications thereof

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Experimental program
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Effect test

Embodiment 1

[0052] Hypocretin B (HB) and deacetylated hypocrellin B used in the present invention can be extracted and prepared by the following method, and can also be obtained through commercial purchase.

[0053] Extraction of Hypocretin A (HA): HA is extracted from natural Hypocrethin, reference (Organic Chemistry, 1989, 9, 252-254). 100g bamboo red fungus is pulverized with a pulverizer, placed in a Soxhlet extractor, continuously extracted for one day with 1000mL acetone as a solvent until the extract is nearly colorless, the extract is filtered to remove a small amount of insoluble solid insolubles, then spin-dried to remove acetone, and use 500mL dichloromethane was dissolved, washed with 4×400mL distilled water, the organic layer was separated and spin-dried, the solid residue was washed with 5×100mL petroleum ether, the solid was spontaneously ignited and dried in air, and then recrystallized twice with chloroform-petroleum ether to obtain The crystal is the target product HA, a...

Embodiment 2

[0057]

[0058] The preparation method of compound 1 refers to the literature: Photoreactions of hypocrellin B with thiolcompounds, Journal of Photochemistry and Photobiology B: Biology, 1998, 44, 45-52; Synthesis of a new water-soluble phototherapeutic sensitizer from hypocrellin B with enhanced red of absorption, Synthesis a new water-soluble phototherapeutic sensitizer, Dyes and Pigments, 1999, 4, 93-100. Put 10 groups of 5 mL of hypocretin B HB (0.2 mM) and mercaptoethylamine hydrochloride (0.01 mM) in ethanol / water buffer solution (1 / 3, pH=10) in 10 photochemical reactors at room temperature Illuminate with a 450W high-pressure sodium lamp for 20 minutes (filter the light below 470nm with a glass long-pass filter). After the reaction was completed, it was acidified with 10% hydrochloric acid, extracted with chloroform, and the chloroform phase was washed with water and spin-dried to obtain a crude product. The obtained crude product is further separated by silica gel ...

Embodiment 3

[0065]

[0066] The preparation method of compound 2 refers to the literature: Photoreactions of hypocrellin B with thiolcompounds, Journal of Photochemistry and Photobiology B: Biology, 1998, 44, 45-52; Synthesis of a new water-soluble phototherapeutic sensitizer, Dyes and Pigments, 1999, 4, 93 -100. Put 10 groups of 5mL hypocretin B HB (0.5mM) and cysteine ​​hydrochloride (0.05mM) in methanol / water buffer solution (1 / 3, pH=11) into 10 photochemical reactors, Illuminate with a 450W high-pressure sodium lamp for 20 minutes at room temperature (filter light below 470nm with a glass long-pass filter). After the reaction was completed, it was acidified with 10% hydrochloric acid, extracted with chloroform, and the chloroform phase was washed with water and spin-dried to obtain a crude product. The obtained crude product was further separated by silica gel plate chromatography, and the developer was chloroform:methanol (volume ratio 98:1), to obtain 4 and 5 substituted, 8 and ...

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Abstract

The invention discloses a poly-substituted near-infrared hypocrellin derivative, a preparation method and applications thereof, wherein the poly-substituted near-infrared hypocrellin derivative is represented by the following formula (I) or formula (II). According to the present invention, the sites 2 (3 or 15), 4 and 5 (or 8 and 9) are simultaneously substituted to modify hypocrellin so as to obtain the novel hypocrellin derivative with absorption of more than 700 nm, wherein the molar extinction coefficient is 10000-40000 M<-1>cm<-1>; the derivative can efficiently produce singlet state oxygen and other reactive oxygen species under near-infrared light irradiation, and has good photodynamic effect; and by further adjusting the hydrophilicity and the hydrophobicity of the hypocrellin precursor through the substituents, the poly-substituted near-infrared hypocrellin derivative can meet different clinical medication requirements. The formulas (I) and (II) are defined in the specification.

Description

technical field [0001] The invention relates to the technical field of photosensitizer medicine for photodynamic therapy. More specifically, it relates to a multi-substituted near-infrared hypocretin derivative and its preparation method and application. Background technique [0002] Photodynamic therapy (PDT for short) is a new treatment technology formed in the late 1970s, which combines the advantages of modern laser technology, light guide technology, optical information processing technology, biophotochemical technology and modern medical technology. . PDT contains three variable parameters: photosensitizer, light source and molecular oxygen, all of which are indispensable. Photosensitizers can absorb the energy of light of a specific wavelength and transfer it to the surrounding oxygen molecules, producing a large number of reactive oxygen species (reactive oxygen species, ROS), including singlet oxygen, oxygen radicals, hydroxyl radicals, hydrogen peroxide, etc., th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/14C07D513/06C07D513/16A61K41/00A61P35/00
CPCA61K41/0057C07D279/14C07D513/06C07D513/16
Inventor 汪鹏飞刘卫敏吴加胜顾瑛葛介超张洪艳
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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