Chemoenzymatic synthesis and antitumor promoting activity of 6'- and 3-esters of 2-O-beta-D-glucosylglycerol.
Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.
Colombo
D
D
Dipartimento di Chimica e Biochimica Medica, Università di Milano, Italy. diego.colombo@unimi.it
Compostella
F
F
Ronchetti
F
F
Scala
A
A
Toma
L
L
Tokuda
H
H
Nishino
H
H
D016588:Anticarcinogenic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000956:Antigens, Viral / Q000187:drug effects / Q000276:immunology; D002460:Cell Line; D004952:Esters; D005989:Glycerides / Q000138:chemical synthesis* / Q000494:pharmacology*; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; C033305:Epstein-Barr virus early antigen; D004952:Esters; D005989:Glycerides; D006027:Glycosides