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Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro

Ahmed, Sajida; Davoust, Eric; Savoie, H.; Boa, Andrew N; Boyle, Ross W

Authors

Sajida Ahmed

Eric Davoust

H. Savoie

Ross W Boyle



Abstract

A convenient and flexible synthesis of meso-tetraaryl porphyrins substituted with three thioglycosyl units, and also bearing one pyridyl substituent is reported. Quaternisation of the pyridine nitrogen with alkyl iodides gives access to a range of water soluble glycosyl cationic porphyrins. Screening for photodynamic activity against human colorectal adenocarcinoma cells (HT-29) indicates that all the glycosyl cationic porphyrins made in this way are active photosensitisers, but direct comparison with a cationic porphyrin bearing no sugar residues indicates an important role for these groups in reducing generalised 'dark' toxicity.

Citation

Ahmed, S., Davoust, E., Savoie, H., Boa, A. N., & Boyle, R. W. (2004). Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 45(31), 6045-6047. https://doi.org/10.1016/j.tetlet.2004.06.021

Journal Article Type Article
Acceptance Date Jun 3, 2004
Online Publication Date Jul 2, 2004
Publication Date Jul 26, 2004
Deposit Date Jul 5, 2018
Journal TETRAHEDRON LETTERS
Print ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 45
Issue 31
Pages 6045-6047
DOI https://doi.org/10.1016/j.tetlet.2004.06.021
Keywords Porphyrins; Photobiology
Public URL https://hull-repository.worktribe.com/output/396026
Publisher URL https://www.sciencedirect.com/science/article/pii/S0040403904012572?via%3Dihub