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.