title: Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity.
abstract: A systematic analysis using 10 synthetic asimicin stereoisomers revealed that the stereochemistry of the bis-tetrahydrofuran core, including the tetrahydrofuran rings and the adjacent hydroxy functions, had significant effect on its cytotoxicity. Our findings set to rest the highly controversial perception that the stereochemistry of the tetrahydrofuran core has little effect on the activity, which is not true for its cytotoxic effect, and also reinforces the previous conclusion that asimicin is a highly potent anticancer compound.
authors.affiliation: The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. subhash@scripps.edu
authors.forename: Subhash C
authors.initials: SC
authors.lastname: Sinha
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Chen
authors.forename: Zheng-Zheng
authors.initials: ZZ
authors.lastname: Huang
authors.forename: Eiko
authors.initials: E
authors.lastname: Nakamaru-Ogiso
authors.forename: Halina
authors.initials: H
authors.lastname: Pietraszkiewicz
authors.forename: Matthew
authors.initials: M
authors.lastname: Edelstein
authors.forename: Frederick
authors.initials: F
authors.lastname: Valeriote
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity*; D006801:Humans; D051379:Mice; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D005663:Furans; C061022:bullatacin; C018674:tetrahydrofuran