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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


Sajida Ahmed

Eric Davoust

H. Savoie


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.


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.

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
Print ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 45
Issue 31
Pages 6045-6047
Keywords Porphyrins; Photobiology
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