Busse, Madleen, Trinh, Iman, Junk, Peter C., Ferrero, Richard L., and Andrews, Philip C. (2013) Synthesis and characterisation of bismuth(III) aminoarenesulfonate complexes and their powerful bactericidal activity against Helicobacter pylori. Chemistry: a European journal, 19 (17). pp. 5264-5275.

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Abstract

The synthesis and characterisation of nine new tris-substituted bismuth(III) aminoarenesulfonates of the general formula [Bi(O₃S-Rᴺ)₃] (Rᴺ=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 0.049gmL⁻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.

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