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  • Title: Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy.
    Author: Sylvain I, Zerrouki R, Granet R, Huang YM, Lagorce JF, Guilloton M, Blais JC, Krausz P.
    Journal: Bioorg Med Chem; 2002 Jan; 10(1):57-69. PubMed ID: 11738607.
    Abstract:
    The aim of this work is the synthesis of a new family of glycosylated porphyrins in which the sugar moieties are linked to the tetrapyrrole ring by a thioglycosidic bond. Two series have been designed. The first one corresponds to meso-aryl porphyrin derivatives. The second one has been obtained from protoporphyrin IX derivatization. Aryl-porphyrins were prepared from tristolyl o- and p-hydroxyporphyrins followed by bromoallylation and thioglycosylation with peracetylated S-glucose, mannose and galactose and deprotection. The other series has been synthesized from protoporphyrin IX dimethylester with a regioselective glycosylation of terminal alkenyl carbon. The UV-visible, NMR and MALDI mass spectra are presented. Photocytotoxicities of the synthesized compounds against K562 chronic leukaemia cell line has been evaluated.
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