Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy.
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.
Sylvain
I
I
Université de Limoges, Laboratoire de Chimie des Substances Naturelles, 123 Avenue Albert Thomas, F-87060, Limoges, France.
Zerrouki
R
R
Granet
R
R
Huang
Y M
YM
Lagorce
J-F
JF
Guilloton
M
M
Blais
J-C
JC
Krausz
P
P
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
D011166:Porphyrins; D013438:Sulfhydryl Compounds