Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy.
Several glycosyl derivatives of squamocin (1) have been synthesized by glycosylation under Lewis acid catalysis with two different 1-O-acetyl sugars. Separation of these compounds has been achieved by HPLC and centrifugal partition chromatography (CPC). A detailed NMR, ESIMS, and LSIMS study allowed complete structural elucidations. The cytotoxic activity of the glycosyl derivatives was investigated and compared with that of squamocin and dihydrosquamocin against human epidermoid carcinoma cells (KB), African green monkey (Cercopithecus aethiops) kidney epithelial cells (VERO), and mouse lymphocytic leukemia cells (L1210). The antiproliferative effects of some derivatives were studied on cell cycles in mouse lymphocytic leukemia cells (L1210).
Queiroz
E F
EF
Laboratoire de Pharmacognosie, UPRES-A 8076 CNRS (BioCIS), and Laboratoire de Cancérologie, Faculté de Pharmacie, Université de Paris-Sud, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France.
Roblot
F
F
Duret
P
P
Figadère
B
B
Gouyette
A
A
Laprévote
O
O
Serani
L
L
Hocquemiller
R
R
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002453:Cell Cycle / Q000187:drug effects; D002522:Chlorocebus aethiops; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006031:Glycosylation; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D014407:Tumor Cells, Cultured; D014709:Vero Cells
D000970:Antineoplastic Agents; D005663:Furans; D007783:Lactones; C112079:isomurisolenin