Synthesis of amide derivatives of chlorin e6 and investigation of their biological activity

In this work there is a synthesis of new photosensitizers which is based on amide derivatives of chlorin е6 . For the disclosure of an extra ring of the initial compound - pheophorbide a 1, we used primary aliphatic amines with 4-12 carbon atoms in the alkyl chain. The reaction is carried out under...

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Bibliographic Details
Published in:	Journal of photochemistry and photobiology. B, Biology Vol. 153; pp. 76 - 81
Main Authors:	Gushchina, O.I., Larkina, E.A., Nikolskaya, T.A., Mironov, A.F.
Format:	Journal Article
Language:	English
Published:	Switzerland Elsevier B.V 01-12-2015
Subjects:	Amides - chemistry Apoptosis - drug effects Apoptosis - radiation effects Cell Line, Tumor Chlorin e6 Humans In vitro study K562 Cells Light Microscopy, Fluorescence PDT Pheophorbide a Photosensitizer Photosensitizing Agents - chemical synthesis Photosensitizing Agents - chemistry Photosensitizing Agents - pharmacology Porphyrins - chemical synthesis Porphyrins - chemistry Porphyrins - pharmacology Chlorin e6 PDT Pheophorbide a Photosensitizer In vitro study Chlorin e
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Summary:	In this work there is a synthesis of new photosensitizers which is based on amide derivatives of chlorin е6 . For the disclosure of an extra ring of the initial compound - pheophorbide a 1, we used primary aliphatic amines with 4-12 carbon atoms in the alkyl chain. The reaction is carried out under mild conditions in chloroform with heating to 40ºС. The structure of all compounds obtained was confirmed by means of electronic, IR, 1Н-NMR spectroscopy and mass-spectrometry. The photoactivity and the dark toxicity of the compounds 2b-2h were investigated on two cancer cell lines: P-388 and K-562. The biological investigations revealed a good photoactivity and low dark toxicity of all compounds 2b-2f. The amide derivatives of chlorin е6 with 6 and 7 carbon atoms in the alkyl part showed the best results in our research. Thus, in this paper we propose a reliable scheme of synthesis of chlorin's photosensitizers which are promising agents for PDT. [Display omitted] •The optimal temperature for alkylamide of chlorin e6 synthesis is 40°C.•30-fold alkylamine molar excess is enough for good yield of alkylamide of chlorin e6.•Сhlorins with 6 and 7 carbon atoms in the alkyl part have the best photoactivity.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1011-1344 1873-2682
DOI:	10.1016/j.jphotobiol.2015.09.007