Remarkable in vitro bactericidal activity of bismuth(iii) sulfonates against Helicobacter pylori

Andrews, Philip C.; Busse, Madleen; Deacon, Glen B.; Ferrero, Richard L.; Junk, Peter Courtney; MacLellan, Jonathan G.; Vom, Amelia

doi:10.1039/c2dt31360j

Cited by 39 publications

(44 citation statements)

References 54 publications

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“…These activity results are comparable with the bismuth(III) sulfonate 70 and amino arenesulfonate 35 complexes. The inclusion of the nitrogen atom in the heterocycle showed no effects, as the tris-substituted bismuth(III) derived from L-proline, 2, displayed results that were comparable with exocyclic bismuth(III) compounds.…”

Section: General Observationssupporting

confidence: 64%

Bismuth(iii) complexes derived from α-amino acids: the impact of hydrolysis and oxido-cluster formation on their activity against Helicobacter pylori

et al. 2014

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Eight bismuth(III) complexes derived from a variety of α-amino acids covering a range of physico-chemical properties (L-phenylalanine (Phe), L-proline (Pro), L-methionine (Met), L-cysteine (Cys), D,L-serine (Ser), L-tyrosine (Tyr), l-aspartic acid (Asp) and L-glutamic acid (Glu)) have been synthesised, characterised, and evaluated for their activity against Helicobacter pylori. The optimal synthetic procedure utilises [Bi(O(t)Bu)3], giving the complexes [BiL3] (L = Phe 1, Pro 2, Met 3, Ser 5, Tyr 6) and [Bi2L3] (L = Cys 4, Asp 7, Glu 8) cleanly and in good yield. However, the synthesis is sensitive to both temperature and moisture. The solubility and stability of the bismuth(III) complexes was investigated using ESI-MS. Almost all compounds (except for [Bi(Phe)3] and [Bi(Pro)3]) were found to be partially or completely soluble in aqueous solution giving a pH 2.5-5.0, indicating the presence of free α-amino acid and hydrolysis of the bismuth(III) complexes to polynuclear bismuth oxido-clusters. The results of the bactericidal studies against Helicobacter pylori demonstrate that this hydrolysis process impacts significantly on the observed Minimum Inhibitory Concentration (MICs) which are increased substantially, often by many orders of magnitude, when the complexes are initially prepared in water rather than DMSO.

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Section: General Observationssupporting

confidence: 64%

Bismuth(iii) complexes derived from α-amino acids: the impact of hydrolysis and oxido-cluster formation on their activity against Helicobacter pylori

et al. 2014

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“…Our initial approach was to attempt to replicate our previous successful synthesis of hetero‐10 and homoleptic3 bismuth(III) sulfonates using [Bi(Ph) 3 ] through both solvent‐free (SF) and solvent‐mediated (SM) methods. An important driving force in both approaches is the elimination of benzene, with the ease of this protolysis reaction correlating loosely to the p K a value of the acid 11.…”

Section: Resultsmentioning

confidence: 99%

“…In particular, they form part of triple or quadruple therapies in the treatment and eradication of Helicobacter pylori, the bacterium responsible for gastritis, peptic‐ulcer disease and gastric cancer 2. We demonstrated recently that bismuth arenesulfonates show in vitro activity against H. pylori orders of magnitude greater than that observed for carboxylates, and thus had the potential to offer greater efficacy in significantly lower concentrations 3. Importantly, sulfonic acids are considered relatively benign, showing little or no mutagenic or carcinogenic activity towards mammalian cells 4.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterisation of Bismuth(III) Aminoarenesulfonate Complexes and Their Powerful Bactericidal Activity against Helicobacter pylori

Busse

Trinh

Junk

et al. 2013

Chemistry A European J

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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.

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“…pylori relative to BiPh 3 and the essentially ineffective sulfonic acids . The same or higher bactericidal activities have been determined for heteroleptic 5‐sulfosalicylates, homoleptic arenesulfonates, and aminoarenesulfonates . These bismuth sulfonates are more effective against H .…”

Section: Introductionmentioning

confidence: 62%

Homo‐ and Heteroleptic Coordination Polymers and Oxido Clusters of Bismuth(III) Vinylsulfonates

Wrobel

Rüffer

Korb

et al. 2018

Chemistry A European J

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The synthesis and characterization of six homo- and heteroleptic coordination polymers and oxido clusters of bismuth(III) vinylsulfonates are reported. The solvent-mediated reaction of BiPh and vinylsulfonic acid in ethanol produces [{Ph Bi(O SCH=CH )} ] (1), which crystallizes as a one-dimensional coordination polymer as a result of bridging sulfonato ligands accompanied by intermolecular Bi⋅⋅⋅ π(arene) London dispersion interactions. In solution, compound 1 equilibrates to give [{PhBi(O SCH=CH ) } ] (2) and BiPh . Compound 2 is obtained as a single product by the reaction of BiPh with vinylsulfonic acid in acetonitrile and crystallizes as a one-dimensional coordination polymer. The homoleptic vinylsulfonate [{Bi(O SCH=CH ) } ] (3) was isolated as a two-dimensional coordination polymer, which is quite moisture sensitive, but did not provide a distinct polynuclear bismuth oxido cluster upon hydrolysis. However, by treatment of [Bi O (OH) (NO ) ]⋅H O or [Bi O (OMc) (dmso) (H O) ]⋅2 DMSO⋅5 H O (OMc=methacrylate) with vinylsulfonic acid, such a cluster, namely, [Bi O (OH)(O SCH=CH ) (dmso) ](O SCH=CH )⋅3 DMSO (4), is available as the main product. Starting from the hexanuclear bismuth oxido nitrate, another cluster, [Bi O (NO ) (O SCH=CH ) (dmso) ](O SCH=CH ) ⋅2 DMSO (5), was observed as a co-crystallizing side product, which upon further hydrolysis afforded [Bi O (NO ) (OH) (O SCH=CH ) (dmso) (H O) ](O SCH=CH ) ⋅2 H O (6).

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Remarkable in vitro bactericidal activity of bismuth(iii) sulfonates against Helicobacter pylori

Cited by 39 publications

References 54 publications

Bismuth(iii) complexes derived from α-amino acids: the impact of hydrolysis and oxido-cluster formation on their activity against Helicobacter pylori

Bismuth(iii) complexes derived from α-amino acids: the impact of hydrolysis and oxido-cluster formation on their activity against Helicobacter pylori

Synthesis and Characterisation of Bismuth(III) Aminoarenesulfonate Complexes and Their Powerful Bactericidal Activity against Helicobacter pylori

Homo‐ and Heteroleptic Coordination Polymers and Oxido Clusters of Bismuth(III) Vinylsulfonates

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