title: Synthesis of rotenoid derivatives with cytotoxic and topoisomerase II inhibitory activities.
abstract: 6-Deoxyclitoriacetal (1) and a series of 11 further derivatives of it (2-12) were synthesized and evaluated for their cytotoxic and topoisomerase IIα inhibitory activities. Compounds bearing epoxide (2), morpholine (6) and benzylamine (10) moieties showed promising in vitro cytotoxic activities against four cancer cell lines, with IC(50) values ranging from 0.38 to 0.73 μM. These three compounds also strongly inhibited topoisomerase II activity at 68.3-93.5% and showed a moderately high DNA intercalating property.
authors: Program of Biotechnology, Faculty of Science, Chulalongkorn University, 254 Phayathai Road, Bangkok 10330, Thailand.
authors: Supranee
authors: S
authors: Sangthong
authors: Kuakarun
authors: K
authors: Krusong
authors: Nattaya
authors: N
authors: Ngamrojanavanich
authors: Tirayut
authors: T
authors: Vilaivan
authors: Songchan
authors: S
authors: Puthong
authors: Supajittra
authors: S
authors: Chandchawan
authors: Nongnuj
authors: N
authors: Muangsin
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002417:Cattle; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004247:DNA / Q000187:drug effects; D004250:DNA Topoisomerases, Type II / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D012402:Rotenone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013696:Temperature
chemical_list: D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D012402:Rotenone; D004247:DNA; C427203:calf thymus DNA; D004250:DNA Topoisomerases, Type II