title: Subereamolline A as a potent breast cancer migration, invasion and proliferation inhibitor and bioactive dibrominated alkaloids from the Red Sea sponge Pseudoceratina arabica.
abstract: A new collection of several Red Sea sponges was investigated for the discovery of potential breast cancer migration inhibitors. Extracts of the Verongid sponges Pseudoceratina arabica and Suberea mollis were selected. Bioassay-directed fractionation of both sponges, using the wound-healing assay, resulted into the isolation of several new and known brominated alkaloids. Active fractions of the sponge Pseudoceratina arabica afforded five new alkaloids, ceratinines A-E (2-6), together with the known alkaloids moloka'iamine (1), hydroxymoloka'iamine (7) and moloka'iakitamide (8). The active fraction of the sponge Suberea mollis afforded the three known alkaloids subereamolline A (9), aerothionin (10) and homoaerothionin (11). Ceratinine B (3) possesses an unprecedented 5,7-dibrominated dihydroindole moiety with an epoxy ring on the side chain of a fully substituted aromatic moiety. Ceratinines D (5) and E (6) possess a terminal formamide moiety at the ethylamine side chain. Subereamolline A (9) potently inhibited the migration and invasion of the highly metastatic human breast cancer cells MDA-MB-231 at the nanomolar doses. Subereamolline A and related brominated alkaloids are novel scaffolds appropriate for further future use for the control of metastatic breast cancer.
authors.affiliation: Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia.
authors.forename: Lamiaa A
authors.initials: LA
authors.lastname: Shaala
authors.forename: Diaa T A
authors.initials: DT
authors.lastname: Youssef
authors.forename: Mansour
authors.initials: M
authors.lastname: Sulaiman
authors.forename: Fathy A
authors.initials: FA
authors.lastname: Behery
authors.forename: Ahmed I
authors.initials: AI
authors.lastname: Foudah
authors.forename: Khalid A El
authors.initials: KA
authors.lastname: Sayed
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D001943:Breast Neoplasms / Q000188:drug therapy* / Q000473:pathology; D045744:Cell Line, Tumor; D002465:Cell Movement / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D005260:Female; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000302:isolation & purification / Q000494:pharmacology; D019156:Indian Ocean; D009361:Neoplasm Invasiveness / Q000517:prevention & control; D009362:Neoplasm Metastasis; D011161:Porifera / Q000737:chemistry*; D013141:Spiro Compounds / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000470:Alkaloids; D006842:Hydrocarbons, Brominated; D013141:Spiro Compounds; C580973:subereamolline A