Cyclic and branched acyl chain galactoglycerolipids and their effect on anti-tumor-promoting activity.
Fifteen new galactoglycerolipid analogues, in which one or two branched, alicyclic or aromatic acyl chains are linked to 2-O-beta-D-galactosylglycerol (6'-position or 1,6' positions), were prepared and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. All compounds were active in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the branched compounds resulting in the most active glycoglycerolipid analogues of the series. The branched 2-O-[6-O-(3-methylbutanoyl)-beta-D-galactopyranosyl]-sn-glycerol (1a) and the structurally related alicyclic 2-O-[6-O-(2-cyclohexylethanoyl)-beta-D-galactopyranosyl]-sn-glycerol (1d), when tested in an in vivo two-stage carcinogenesis test, exhibited inhibitory effects on mouse skin tumor promotion.
Colombo
Diego
D
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133 Milano, MI, Italy. diego.colombo@unimi.it
Franchini
Laura
L
Toma
Lucio
L
Ronchetti
Fiamma
F
Tanaka
Reiko
R
Takayasu
Junko
J
Nishino
Hoyoku
H
Tokuda
Harukuni
H
D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006017:Glycolipids / Q000737:chemistry / Q000494:pharmacology*; D004854:Herpesvirus 4, Human / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008958:Models, Molecular
D016588:Anticarcinogenic Agents; D000998:Antiviral Agents; D006017:Glycolipids