title: Synthesis and characterisation of bismuth(III) aminoarenesulfonate complexes and their powerful bactericidal activity against Helicobacter pylori.
abstract: The synthesis and characterisation of nine new tris-substituted bismuth(III) aminoarenesulfonates of the general formula [Bi(O3S-R(N))3] (R(N) = o-aminophenyl 1, m-aminophenyl 2, 6-amino-3-methoxyphenyl 3, p-aminophenyl 4, 2-pyridyl 5, o-aminonaphthyl 6, 5-aminonaphthyl 7, 4-amino-3-hydroxynaphthyl 8 and 5-isoquinolinyl 9) is described. Two synthetic strategies, using Ag2O and [Bi(OtBu)3], were explored and compared. The possibility to access heteroleptic bismuth(III) complexes with the new silver(I) metathesis reaction is demonstrated with the synthesis of the heteroleptic bismuth(III) aminoarenesulfonate complexes [PhBi(O3S-P2)2(dmso)] 10, [Ph2Bi(O3S-P2)]∞ 11 and [PhBi(O3S-P2)2]∞ 12, of which the solid state structures 10 and 12 are presented (2P-SO3(-) = 2-pyridinesulfonate). These complexes offer remarkable in-vitro activity against three standard laboratory strains of Helicobacter pylori (H. pylori) as demonstrated by their exceptionally low minimum inhibitory concentration (MIC) values of 0.049 μg  mL(-1) for the strains 251 and B128, which places most MIC values in the nano-molar region. These results demonstrate the importance of the amino functionality in addition to the sulfonate group on the bactericidal properties against H. pylori.
authors.affiliation: School of Chemistry, Monash University, Clayton Campus, Clayton, VIC 3800, Australia.
authors.forename: Madleen
authors.initials: M
authors.lastname: Busse
authors.forename: Iman
authors.initials: I
authors.lastname: Trinh
authors.forename: Peter C
authors.initials: PC
authors.lastname: Junk
authors.forename: Richard L
authors.initials: RL
authors.lastname: Ferrero
authors.forename: Philip C
authors.initials: PC
authors.lastname: Andrews
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001729:Bismuth / Q000737:chemistry* / Q000494:pharmacology; D016481:Helicobacter Infections / Q000188:drug therapy / Q000382:microbiology; D016480:Helicobacter pylori / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D009942:Organometallic Compounds; D001729:Bismuth