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The substituted amino group type dependent sensitivity enhancing of cationic phthalocyanine derivatives for photodynamic activity

Paper ID Volume ID Publish Year Pages File Format Full-Text
26441 43952 2016 14 PDF Available
Title
The substituted amino group type dependent sensitivity enhancing of cationic phthalocyanine derivatives for photodynamic activity
Abstract

•Two kinds of amino groups modified phthalocyanines were synthesized.•The synthesized phthalocyanine has good water solubility.•Phthalocyanine hydrochloride has high activity which has no extensive applicability.•The substituted amino group type effects photodynamic activity.

Many reports indicated that the cellular uptaken and photodynamic anti-cancer activity of amino group modified phthalocyanine (Pc) could be greatly improved in the acid environment around cancer cells because such Pc could transfer to their hydrochloride protonated form and inhibit the intramolecular photoinduced electron transfer (PET) effect. However, no more researches are carried out to indicate whether this law has the extensive applicability in all kinds of amino modified Phthalocyanines (Pcs). So, here, four amino groups modified Pcs and their hydrochloride or quaternized cationic derivatives, with two kinds of amino groups (phenylamine and benzylamine) substituted were synthesized. Their solubility in aqueous system, cancer cell uptaken ability and photodynamic activities were also systematically compared. Our research results indicated that above law had the extensive applicability in benzylamine amino groups modified Pcs. But for phenylamine amino groups modified ones, the cancer cell uptaken ability and anti-cancer activity of hydrochloride derivatives were obviously decreased comparing with the unmodified Pc because its nitrogen atom was closer to the Pc ring, which would induce its nitrogen atom and the ring to form p–π conjugation system, furthermore, the relatively free state of lone pair electrons of surrounding nitrogen atom leaded to PET strengthening.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideTwo kinds of amino groups (phenylamine and benzylamine) modified Pcs and their hydrochloride or quaternized derivatives were designed and synthesized. The substituted amino group type dependent sensitivity enhancing of cationic phthalocyanine derivatives for photodynamic activity was showed.

Keywords
Photodynamic therapy; Phthalocyanine; Phenylamine; Benzylamine; Hydrochloride; Quaternization
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The substituted amino group type dependent sensitivity enhancing of cationic phthalocyanine derivatives for photodynamic activity
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 315, 15 January 2016, Pages 107–120
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us