title: Ammosamide D, an oxidatively ring opened ammosamide analog from a marine-derived Streptomyces variabilis.
abstract: Ammosamide D (1), an oxidized analog of the ammosamide family, was isolated from a marine-derived Streptomyces variabilis. Pyrroloquinoline containing alkaloids are a growing class of natural products, with 1 being the first example of an oxidized analog resulting in a 5,6-dioxo-5,6-dihydroquinoline ring system. Attempts at chemical conversion of ammosamide B to ammosamide D revealed that a strong chemical oxidant is required. Ammosamide D has modest cytotoxicity to the MIA PaCa-2 pancreatic cancer cell line.
authors.affiliation: Department of Biochemistry, Division of Chemistry, University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390, United States.
authors.forename: Ende
authors.initials: E
authors.lastname: Pan
authors.forename: Matthew
authors.initials: M
authors.lastname: Jamison
authors.forename: Muhammed
authors.initials: M
authors.lastname: Yousufuddin
authors.forename: John B
authors.initials: JB
authors.lastname: MacMillan
mesh_terms: D000577:Amides / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006574:Heterocyclic Compounds, 2-Ring; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry; D006801:Humans; D008386:Marine Biology; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry*; D058570:TOR Serine-Threonine Kinases / Q000037:antagonists & inhibitors
chemical_list: D000577:Amides; D001688:Biological Products; D006574:Heterocyclic Compounds, 2-Ring; D006575:Heterocyclic Compounds, 3-Ring; C534622:ammosamide A; C534623:ammosamide B; C573446:ammosamide D; D058570:TOR Serine-Threonine Kinases