Synthesis, Spectroscopy, and Cytotoxicity of Glycosylated Acetogenin Derivatives as Promising Molecules for Cancer Therapy

• Published in: Journal of medicinal chemistry Vol. 43; no. 8; pp. 1604 - 1610
• Main Authors: Queiroz, Emerson F, Roblot, François, Duret, Philippe, Figadère, Bruno, Gouyette, Alain, Laprévote, Olivier, Serani, Laurent, Hocquemiller, Reynald
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.04.2000; Amer Chemical Soc
• Subjects: Animals; Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biological and medical sciences; Cell Cycle - drug effects; Cercopithecus aethiops; Chemistry, Medicinal; Drug Screening Assays, Antitumor; Furans - chemical synthesis; Furans - chemistry; Furans - pharmacology; General aspects; Glycosylation; Humans; Lactones - chemical synthesis; Lactones - chemistry; Lactones - pharmacology; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; Mice; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; Tumor Cells, Cultured; Vero Cells; BIS-TETRAHYDROFURAN ACETOGENIN; ENZYME PRODRUG THERAPY; SEEDS; SQUAMOCIN; RECENT PROGRESS; ROOTS; SPINESCENS; ANNONACEOUS ACETOGENINS; Antineoplastic agent; Furan derivatives; Monkey; Cytotoxicity; L1210-Leukemia; Oxygen heterocycle; Kidney; Structure activity relation; Cell cycle; Primates; Glycoside; Chemical synthesis; Tumor cell; Human; Rodentia; Glucoside; Lactone; In vitro; Vertebrata; Polyketides; Mammalia; Cell line; Mouse; Animal; KB cell line
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm990568m

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).