Synthesis and Characterisation of Bismuth(III) Aminoarenesulfonate Complexes and Their Powerful Bactericidal Activity against Helicobacter pylori |
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Authors: | Dr Madleen Busse Iman Trinh Prof Peter C Junk Assoc Prof Richard L Ferrero Prof Philip C Andrews |
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Institution: | 1. School of Chemistry, Monash University, Clayton Campus, Clayton, VIC 3800 (Australia), Fax: (+61)?3?9905?4597;2. School of Pharmacy and Molecular Sciences, James Cook University, Townsville, QLD 4811 (Australia);3. Monash Institute of Medical Research, Centre for Innate Immunity and Infectious Diseases, Monash University, 27‐31 Wright Street, Clayton, VIC 3168 (Australia) |
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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 0.049 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. |
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Keywords: | aminoarene sulfonates biological activity bismuth helicobacter pylori ligand effects |
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