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

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

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