title: Antineoplastic agents. 380. Isolation and X-ray crystal structure determination of isoaaptamine from the Republic of Singapore Hymeniacidon sp. and conversion to the phosphate prodrug hystatin 1.
abstract: By use of bioassay (murine P388 lymphocytic leukemia cell line) guided isolation procedures, extracts of the Republic of Singapore marine sponge Hymeniacidon sp. were found to contain demethyloxyaaptamine (1) and aaptamine (3) as prominent cancer cell growth inhibitory constituents accompanied by the trace, albeit more active, component isoaaptamine (4). The isolation, X-ray structure elucidation, and antineoplastic and antimicrobial activities of isoaaptamine (4) have been summarized. Because of instability, isoaaptamine (4) was converted to a stable sodium phosphate prodrug designated hystatin 1 (7).
authors.affiliation: Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona 85287-2404, USA.
authors.forename: George R
authors.initials: GR
authors.lastname: Pettit
authors.forename: Holger
authors.initials: H
authors.lastname: Hoffmann
authors.forename: James
authors.initials: J
authors.lastname: McNulty
authors.forename: Kerianne C
authors.initials: KC
authors.lastname: Higgs
authors.forename: Alison
authors.initials: A
authors.lastname: Murphy
authors.forename: David J
authors.initials: DJ
authors.lastname: Molloy
authors.forename: Delbert L
authors.initials: DL
authors.lastname: Herald
authors.forename: Michael D
authors.initials: MD
authors.lastname: Williams
authors.forename: Robin K
authors.initials: RK
authors.lastname: Pettit
authors.forename: Dennis L
authors.initials: DL
authors.lastname: Doubek
authors.forename: John N A
authors.initials: JN
authors.lastname: Hooper
authors.forename: Leslie
authors.initials: L
authors.lastname: Albright
authors.forename: Jean M
authors.initials: JM
authors.lastname: Schmidt
authors.forename: Jean-Charles
authors.initials: JC
authors.lastname: Chapuis
authors.forename: Larry P
authors.initials: LP
authors.lastname: Tackett
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D007941:Leukemia P388; D015394:Molecular Structure; D009287:Naphthyridines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009792:Oceans and Seas; D010710:Phosphates; D011161:Porifera / Q000737:chemistry*; D011355:Prodrugs / Q000737:chemistry / Q000494:pharmacology; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D009287:Naphthyridines; D010710:Phosphates; D011355:Prodrugs; C485042:demethyloxyaaptamine; C485041:hystatin 1; C417553:isoaaptamine; C018279:sodium phosphate