title: Screening of bromotyramine analogues as antifouling compounds against marine bacteria.
abstract: Rapid and efficient synthesis of 23 analogues inspired by bromotyramine derivatives, marine natural products, by means of CuSO4-catalysed [3+2] alkyne-azide cycloaddition is described. The final target was then assayed for anti-biofilm activity against three Gram-negative marine bacteria, Pseudoalteromonas ulvae (TC14), Pseudoalteromonas lipolytica (TC8) and Paracoccus sp. (4M6). Most of the synthesised bromotyramine/triazole derivatives are more active than the parent natural products Moloka'iamine (A) and 3,5-dibromo-4-methoxy-β-phenethylamine (B) against biofilm formation by the three bacterial strains. Some of these compounds were shown to act as non-toxic inhibitors of biofilm development with EC50 < 200 μM without any effect on bacterial growth even at high concentrations (200 μM).
authors.affiliation: a MAPIEM , Université de Toulon , La Garde , France.
authors.forename: Sofyane
authors.initials: S
authors.lastname: Andjouh
authors.affiliation: a MAPIEM , Université de Toulon , La Garde , France.
authors.forename: Yves
authors.initials: Y
authors.lastname: Blache
mesh_terms: D001422:Bacterial Adhesion / Q000187:drug effects; D018441:Biofilms / Q000187:drug effects* / Q000254:growth & development; D057219:Biofouling / Q000517:prevention & control*; D001688:Biological Products / Q000302:isolation & purification / Q000494:pharmacology*; D010230:Paracoccus / Q000187:drug effects* / Q000254:growth & development / Q000502:physiology; D031161:Pseudoalteromonas / Q000187:drug effects* / Q000254:growth & development / Q000502:physiology; D014439:Tyramine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: C000622257:3,5-dibromo-4-methoxy-beta-phenethylamine; D001688:Biological Products; C000622258:moloka'iamine; D014439:Tyramine
keywords: Antifouling; bacterial biofilm; bromotyramine derivatives; click chemistry; triazole