Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy

Bioorg Med Chem. 2002 Jan;10(1):57-69. doi: 10.1016/s0968-0896(01)00255-3.

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.

MeSH terms

  • Cell Survival / drug effects
  • Glycosylation
  • Humans
  • Photochemotherapy*
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry
  • Porphyrins / pharmacology*
  • Spectrum Analysis
  • Sulfhydryl Compounds / chemistry*
  • Tumor Cells, Cultured

Substances

  • Porphyrins
  • Sulfhydryl Compounds