Heptamethanindocyanine dye and its synthesis method and application

A technology of indole cyanine and dyes, applied in the direction of methine/polymethine dyes, organic dyes, chemical instruments and methods, etc., can solve the problems of limiting the application of anti-tumor therapy, not having direct killing of tumor cells, etc. Easy handling and high yield

Active Publication Date: 2011-12-07
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, such small chemical molecules themselves do not have the activity of directly killing tumor cells, which lim...

Method used

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  • Heptamethanindocyanine dye and its synthesis method and application
  • Heptamethanindocyanine dye and its synthesis method and application
  • Heptamethanindocyanine dye and its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0081] The preparation of embodiment 1 dialdehyde chlorocyclohexene (2-chloro-3-hydroxymethane-1-formyl cyclohexene)

[0082]

[0083] Control the internal temperature at 0-5°C, and slowly add 20ml (freshly evaporated to dry) POCl to the reactor containing 60ml (freshly evaporated to dry) DMF under stirring 3 After dropping, keep stirring at 0-5°C for another 30 minutes, then slowly rise to room temperature. 5ml of cyclohexanone was added, and the temperature was raised to 50°C for 6h. Stop the reaction, pour the reaction solution into water, and stir for 3 hours. A large number of yellow solids precipitated, filtered with suction, and the filter cake was washed with cold water until neutral. The crude product was refined with ethyl acetate to obtain 5.2 g of yellow granular crystals, with a yield of 65.3%. Store away from light and low temperature (4°C). Melting point: 130-131°C (literature melting point: 130-131°C) detection by thin layer chromatography: cyclohexane: e...

Embodiment 2

[0084] The preparation of embodiment 2N-hexanoic acid indole quaternary ammonium bromide (2,3,3-trimethyl-1-hexanoic acid-3H-indole bromide)

[0085]

[0086] Add 2,2,3-trimethyl-3H indole, 6-bromohexanoic acid and 1,2-o-dichlorobenzene (or DMF, or DMSO or toluene or ethylene glycol dimethyl ether) in the reactor, Reaction at 110°C for 12h. Check the reaction solution with fluorescence or bromocresol chloride, 6-bromohexanoic acid is fully involved in the reaction. Stop the reaction, cool to room temperature, and let stand for 10 hours. A large amount of yellow-brown solid precipitated out of the system, which was filtered with suction, and the filter cake was repeatedly washed with acetone until it became an off-white solid. The crude product does not need to be further purified, and can be directly carried out in the next step. Melting point range: 90-92°C; Thin-layer chromatography detection: methanol: chloroform (1:5), Rf value is about 0.3, inspected under 254nm ult...

Embodiment 3

[0087] The synthesis (29,34) of the heptamethine indocyanine dye of embodiment 3 double n-butyl ester or monobutyl ester side chain

[0088]

[0089] Add 2.780g indole quaternary ammonium salt 25 (7.809mmol) in the 500ml single port reaction flask, 0.645g condensing agent 29 (3.728mmol), use 250ml n-butanol alone, or with benzene (or toluene or hexanaphthene) mixed solution ( 7:3) was used as a solvent, a water separator and a condenser were installed, and under the protection of nitrogen, the reaction was refluxed at an external temperature of 120° C. for 5 hours, and the system turned from red to green. Stop the reaction, and distill under reduced pressure (0.098Mp, 60°C) to remove the solvent benzene and n-butanol to obtain 3.395g bright yellow solid (dark green), and obtain 3.395g bright yellow solid (dark green), through silica gel column chromatography Compound 29 (yield 60%) and compound 34 (yield 30%) were obtained respectively.

[0090] Structural analysis data of...

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Abstract

The invention relates to a heptamethine indocyanine dye containing N-fatty esters or N-fatty amide side chains, a synthetic method thereof and applications thereof in tumor targeting imaging and treatment. The heptamethine indocyanine dye which possesses or individually possesses near infrared absorption, fluorography and antineoplastic activity allows present research and development ideas and treatment levels of tumor targeting treatment medicaments to be greatly improved, and has great significances to aspects of early discovery, control and the like of various tumors.

Description

technical field [0001] The invention relates to the field of biology, in particular to a heptamethine indole cyanine dye and its synthesis method and application. Background technique [0002] Malignant tumor is a major disease that seriously endangers human health and life. It has become the first cause of death in my country. At present, there is still a lack of specific early diagnosis methods and ideal treatment measures for malignant tumors. Improving the level of tumor diagnosis and treatment is an important aspect of my country's economy and society. and the major needs of people's health. The introduction of the concept of tumor molecular targeted therapy and the successful application of targeted therapy drugs are major advances in the field of tumor therapy and an inevitable trend of future development. The current method of targeted therapy mainly uses the specific (or relatively specific) biomolecules possessed by tumor tissues or cells as targets, and chemically...

Claims

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Application Information

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IPC IPC(8): C09B23/08A61K49/00A61K31/405A61P35/00
Inventor 史春梦罗圣霖齐庆蓉粟永萍樊松张丽龙张超翁玲玲郑虎程天民
Owner ARMY MEDICAL UNIV
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