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Fatty chain end group diamine substituted hypocrellin derivative and its preparing method and use

A technology of chain end-group diamine and oleocanthin, applied in the field of photosensitizers, can solve the problems of reduced singlet oxygen quantum yield, disadvantages, disadvantages, etc., and achieve the effects of low dark toxicity, good potential performance and complete structure

Inactive Publication Date: 2005-10-19
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But their biggest shortcoming is that they have no obvious absorption in the phototherapy window (600-900 nanometers)
However, we found that the singlet oxygen quantum yield of previous aminated derivatives (including 2-substituted amino derivatives) was lower than that of the parent, so this is very unfavorable for their application in PDT
In addition, since the environment of tumor cells is acidic (low pH) (Cancer Res., 1989, 49, 6449), derivatives of the molecules themselves which are weakly basic highlight their specific affinity for tumor cells The superiority in the PDT process, and the acidic derivatives of the molecule itself, such as amino acid substituted derivatives, sulfonic acid substituted derivatives, are at a disadvantage in the screening of photosensitizers

Method used

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  • Fatty chain end group diamine substituted hypocrellin derivative and its preparing method and use
  • Fatty chain end group diamine substituted hypocrellin derivative and its preparing method and use
  • Fatty chain end group diamine substituted hypocrellin derivative and its preparing method and use

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Experimental program
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Effect test

Embodiment 1

[0026] Hypocretin B (HB) 100 mg (0.19×10 -3 mol), 50 times (molar ratio) excess 1,3-propylenediamine and 50 milliliters of tetrahydrofuran were put into a 100 milliliter three-necked round-bottomed flask, electromagnetically stirred, and reacted under argon protection for 6 hours. The solvent was evaporated under reduced pressure, the residue was extracted with chloroform for 3 to 5 times, the chloroform solution was washed with water until the water layer was colorless, the chloroform solution was concentrated under reduced pressure, separated by silica gel plate chromatography, and the developing solution was petroleum ether: ethyl acetate: ethanol , volume ratio=2:2:1. The green product components were collected and further chromatographically purified by this method to obtain the Schiff base compound of propylenediamine at position 17 and hypocrellin B.

[0027] Identification of this compound:

[0028] UV spectrum λ max : 490nm, 590nm, 635nm;

[0029] Infrared spectru...

Embodiment 2

[0036] Hypocretin B (HB) 100 mg (0.19×10 -3 mol), 50 times (molar ratio) excess 1,3-propanediamine and 100 milliliters of pyridine were put into a 250 milliliter three-necked round-bottomed flask, electromagnetically stirred, and reacted under argon protection for 13 hours. The solvent was evaporated under reduced pressure, the residue was extracted several times with chloroform, the chloroform solution was washed with water until the water layer was colorless, the chloroform solution was concentrated under reduced pressure, and separated by silica gel plate chromatography, the developing solution was petroleum ether: ethyl acetate: ethanol, volume Ratio = 2:2:1. The green product components were collected and further chromatographically purified by this method to obtain the Schiff base compound of propylenediamine at position 17 and hypocrellin B.

[0037] Identification of this compound:

[0038] UV spectrum λ max : 490nm, 590nm, 635nm;

[0039] Infrared spectrum ν max ...

Embodiment 3

[0046] Hypocretin B (HB) 100 mg (0.19×10 -3 mol), 50 times (molar ratio) excess 1,3-propylenediamine and 50 milliliters of dioxane were put into a 100 milliliter three-neck round bottom flask, electromagnetically stirred, and reacted under argon protection for 21 hours. The solvent was evaporated under reduced pressure, the residue was extracted several times with chloroform, the chloroform solution was washed with water until the water layer was colorless, the chloroform solution was concentrated under reduced pressure, and separated by silica gel plate chromatography, the developing solution was petroleum ether: ethyl acetate: ethanol, volume Ratio = 2:2:1. The green product components were collected and further chromatographically purified by this method to obtain the Schiff base compound of propylenediamine at position 17 and hypocrellin B.

[0047] Identification of this compound:

[0048] UV spectrum λ max : 490nm, 590nm, 635nm;

[0049] Infrared spectrum ν max : 33...

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Abstract

The present invention discloses fatty chain end group diamine substituted hypocrellin derivatives, including 2-site amino substituted hypocrellin A, 2-site amino substituted hypocrellin B, and Schiff base formed with hypocrellin A or hypocrellin B with diamine in the site-17. Compared with hypocrellin A and hypocrellin B, the products of the present invention has stronger absorption in phototherapeutic window of 600-900 nm, can produce active oxygen in photosensitive condition, and has powerful photodynamic effect and low dark toxicity. The present invention also discloses the preparation process and the use in preparing medicine for treating cancer and AIDS.

Description

technical field [0001] The invention relates to a photosensitizer with photodynamic activity, a preparation method and an application thereof. Background technique [0002] Photodynamic therapy (PDT phototherapy for short) is an emerging interdisciplinary subject, which uses light to irradiate biological tissues stained by photosensitizers to produce photochemical effects, thereby producing therapeutic effects on some diseases. Its advantage lies in its high efficiency and safety. Under light irradiation, it can continuously generate hundreds of highly reactive reactive oxygen molecules, thereby killing target molecules of the corresponding order of magnitude. Compared with traditional chemical drugs, it can only kill one target Molecules are remarkably efficient. On the other hand, photochemotherapy has two-way selectivity of drug localization and light localization, which avoids or reduces damage to normal cells, greatly reduces toxic and side effects, and increases safet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/18A61P35/00C07D319/14
Inventor 赵井泉赵跃伟谢杰
Owner INST OF CHEM CHINESE ACAD OF SCI
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