title: A new cytotoxic brominated acetylenic hydrocarbon from the marine sponge Haliclona sp. with a selective effect against human breast cancer.
abstract: Three acetylenic brominated derivatives were isolated from a Red Sea sponge, Haliclona sp. One of them, 18-bromooctadeca-9(E),17(E)-dien-7,15-diynoic acid (3), is a known metabolite, and the other two are new compounds, (1E,5E,12E,19E)-1,22-dibromodocosa-1,5,12,19-tetraen-3,14,21-triyne (1) and methyl 18-bromooctadeca-9(E),17(E)-dien-7,15-diynoate (2) which was isolated for the first time as a natural metabolite. Structures of all compounds were determined based on extensive spectroscopic measurements [1D (1H, 13C and DEPT) and 2D (HSQC, HMBC and NOESY) NMR, MS, UV, and IR]. All compounds, except 3, were evaluated for their cytotoxicity employing four cancer cell lines, i.e. MCF-7 (human breast cancer), HepG2 (human hepatocellular carcinoma), WI-38 (skin carcinoma), and Vero (African green monkey kidney). Compounds 1 and 2 had potent selective antitumour activity towards MCF-7 cells with IC50 values of 32.5 and 50.8 microM, respectively.
authors: Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, PO Box 80207, Jeddah 21589, Saudi Arabia.
authors: Walied M
authors: WM
authors: Alarif
authors: Ahmed
authors: A
authors: Abdel-Lateff
authors: Sultan S
authors: SS
authors: Al-Lihaibi
authors: Seif-Eldin N
authors: SE
authors: Ayyad
authors: Farid A
authors: FA
authors: Badria
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D001943:Breast Neoplasms / Q000473:pathology*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000302:isolation & purification* / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D008386:Marine Biology; D011161:Porifera / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000970:Antineoplastic Agents; D006842:Hydrocarbons, Brominated; D000114:Acetylene