Synthesis and antiangiogenic activity of thioacetal artemisinin derivatives

• Published in: Bioorganic & medicinal chemistry Vol. 12; no. 14; pp. 3783 - 3790
• Main Authors: Oh, Sangtae, Jeong, In Howa, Ahn, Chan Mug, Shin, Woon-Seob, Lee, Seokjoon
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15.07.2004; Elsevier Science
• Subjects: Acetals - chemistry; Angiogenesis; Angiogenesis Inhibitors - chemical synthesis; Angiogenesis Inhibitors - chemistry; Angiogenesis Inhibitors - pharmacology; Animals; Antiangiogenesis; Antineoplastic agents; Artemisinin; Artemisinins - chemical synthesis; Artemisinins - chemistry; Artemisinins - pharmacology; Biological and medical sciences; Cell Division - drug effects; Cell Line; Chick Embryo; Endothelium, Vascular - cytology; Endothelium, Vascular - drug effects; Gas Chromatography-Mass Spectrometry; General aspects; Humans; Magnetic Resonance Spectroscopy; Medical sciences; Pharmacology. Drug treatments; Sesquiterpenes - chemical synthesis; Sesquiterpenes - chemistry; Sesquiterpenes - pharmacology; Spectrophotometry, Infrared; Thioacetal artemisinin; Angiogenesis; Antiangiogenesis; Artemisinin; Thioacetal artemisinin; Antineoplastic agent; Endoperoxide; Human; Cell proliferation; Endothelial cell; Thioacetal; Tetracyclic compound; Oxygen heterocycle; In vitro; Vascularization; Peracetal; Structure activity relation; Blood vessel; Inhibition; Neovascularization; Antiangiogenic agent; Chemical synthesis; Umbilical vein; Organic peroxide
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2004.05.013

Graphic Various thioacetal artemisinin derivatives can inhibit the angiogenesis and might be angiogenesis inhibitors. In particular, 10α-phenylthiodihydroartemisinins ( 5), 10β-benzenesulfonyl-9- epi-dihydroartemisinin ( 11) and 10α-mercaptodihydroartemisinin ( 13) exhibit strong growth inhibition activity against HUVEC proliferation. Compound 11 have a good inhibitiory activity upon HUVEC tube formation, and 5 and 11 show a strong inhibitory effect on angiogenesis using CAM assay at 5 μg/egg by 90%.