title: Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy.
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.
authors.affiliation: Université de Limoges, Laboratoire de Chimie des Substances Naturelles, 123 Avenue Albert Thomas, F-87060, Limoges, France.
authors.forename: I
authors.initials: I
authors.lastname: Sylvain
authors.forename: R
authors.initials: R
authors.lastname: Zerrouki
authors.forename: R
authors.initials: R
authors.lastname: Granet
authors.forename: Y M
authors.initials: YM
authors.lastname: Huang
authors.forename: J-F
authors.initials: JF
authors.lastname: Lagorce
authors.forename: M
authors.initials: M
authors.lastname: Guilloton
authors.forename: J-C
authors.initials: JC
authors.lastname: Blais
authors.forename: P
authors.initials: P
authors.lastname: Krausz
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D006031:Glycosylation; D006801:Humans; D010778:Photochemotherapy; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013057:Spectrum Analysis; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014407:Tumor Cells, Cultured
chemical_list: D011166:Porphyrins; D013438:Sulfhydryl Compounds