Synthesis and biological testing of thioalkane- and thioarene-spaced bis-beta-D-glucopyranosides.
A three-step synthesis of bis-beta-D-glucopyranosides containing thioalkane or thioarene spacers of different length and flexibility is described. The key-step reaction allows an easy modulation of final saccharidic products so that a library of molecules with different glycosidic residues and spacers can be obtained. Two of the new thioarene-spaced bis-beta-D-glucopyranosides endow with a specific cytotoxic potential. A more detailed investigation of one of the two compounds ascertains that this effect is attributable to induction of cell death by apoptosis.
Aversa
Maria C
MC
Dipartimento di Chimica Organica e Biologica, Università degli Studi di Messina, Messina, Italy.
Barattucci
Anna
A
Bonaccorsi
Paola
P
Marino-Merlo
Francesca
F
Mastino
Antonio
A
Sciortino
Maria T
MT
D017209:Apoptosis / Q000187:drug effects; D016923:Cell Death / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013434:Sulfenic Acids / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D005960:Glucosides; D013434:Sulfenic Acids; D013438:Sulfhydryl Compounds