Synthesis and anti-tumor-promoting activity of glycoglycerolipid analogues lacking the glycerol backbone.
Glycoglycerolipid analogues lacking the glycerol backbone were prepared through a lipase catalyzed transesterification of beta-D-galactosylethylene glycol. The inhibitory effect of the resultant isomeric hexanoates at the primary alcoholic positions, beta-D-galactosylethylene glycol itself and nonyl beta-D-galactopyranoside, was tested on Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), as a primary screening test for inhibitors of tumor promotion. All the compounds assayed were found to be less active than the reference 2-O-beta-D-galactopyranosylglycerol derivatives, of which they are simplified models, indicating that the anti-tumor-promoting activity is very closely related to the presence of a free hydroxymethylene group on the glycerol-like aglycone moiety.
Colombo
Diego
D
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133 Milan, Italy. diego.colombo@unimi.it
Ronchetti
Fiamma
F
Scala
Antonio
A
Toma
Lucio
L
Tokuda
Harukuni
H
Nishino
Hoyoku
H
D016588:Anticarcinogenic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000956:Antigens, Viral / Q000378:metabolism; D002175:Candida / Q000378:metabolism; D002273:Carcinogens / Q000037:antagonists & inhibitors / Q000633:toxicity; D004354:Drug Screening Assays, Antitumor; D005990:Glycerol / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008049:Lipase / Q000378:metabolism; D011549:Pseudomonas / Q000201:enzymology; D013755:Tetradecanoylphorbol Acetate / Q000037:antagonists & inhibitors / Q000633:toxicity
D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; D002273:Carcinogens; C033305:Epstein-Barr virus early antigen; D006017:Glycolipids; C015903:glycerolglycolipids; D008049:Lipase; D013755:Tetradecanoylphorbol Acetate; D005990:Glycerol