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Phenothiazinium photoantimicrobials with basic side chains

Paper ID Volume ID Publish Year Pages File Format Full-Text
30024 44454 2015 6 PDF Available
Title
Phenothiazinium photoantimicrobials with basic side chains
Abstract

•Novel cationic side chain phenothiazinium derivatives synthesised.•Polycationic on ionisation – up to 5 positive charges.•Highly active photoantimicrobials compared to methylene blue.

Derivatives of the standard cationic photosensitiser, methylene blue, were synthesised, having extra amino (basic) functionality in the auxochromic side-chain. The resulting analogues were profiled for photodynamic activity in vitro, and screened against standard Gram-positive and Gram-negative bacteria for photobactericidal activity. The substitution pattern of the derivatives was such that ionisation of the amino groups in situ, via protonation, provided a range of charge distribution and degree of charge across the molecular framework.While most examples exhibited greater activity than the lead compound, in addition to similar activity to the known, but more powerful, phenothiazinium photoantimicrobial, dimethyl methylene blue, this was also associated with relatively high dark toxicity, inferring that these compounds were targeting crucial structures before illumination.One derivative having an asymmetrical structure, with separation between a lipophilic and a hydrophilic region exhibited a combination of very high phototoxicity coupled with very low dark effects, against both the standard screen and an additional one containing further, relevant pathogen species, including Candida albicans. It is suggested that the great activity of this analogue is due to efficient membrane targeting.

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Phenothiazinium photoantimicrobials with basic side chains
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 150, September 2015, Pages 38–43
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