Structural and solution studies of phenylbismuth(III) sulfonate complexes and their activity against Helicobacter pylori

Andrews, Philip C., Busse, Madleen, Deacon, Glen B., Ferrero, Richard L., Junk, Peter C., Huynh, Katie K., Kumar, Ish, and MacLellan, Jonathan G. (2010) Structural and solution studies of phenylbismuth(III) sulfonate complexes and their activity against Helicobacter pylori. Dalton Transactions, 39 (40). pp. 9633-9641.

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View at Publisher Website: http://dx.doi.org/10.1039/c0dt00629g
 
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Abstract

Three bis-phenylbismuth sulfonates [Ph2Bi(O3SR)]∞ (R = p-tolyl 1, mesityl 2 or S-(+)-10-camphoryl 3) have been synthesised and characterised. Their tendency for ligand redistribution in solution, and activity against the bacterium Helicobacter pylori have been investigated. The structures of 2 and 3 have been authenticated by X-ray diffraction crystallography. They are structurally very similar with polymeric helical chain structures composed of four coordinate Bi atoms which bridge between two sulfonate O atoms with near linear O–Bi–O bond angles. The two phenyl rings are cis to one another and trans to the stereochemically active lone pair. Upon dissolution of the pure compounds 1, 2 and 3, a ligand redistribution reaction occurs in which the mono-phenylbismuth bis-sulfonates, the bismuth tris-sulfonates and triphenylbismuth are formed. Two further complexes of general formula [PhBi(O3SR)2]∞ (where R = p-tolyl 4, and mesityl 5) were thus obtained and their crystal structures determined. The presence of the single sulfonato ligand in compounds 1, 2 and 3 resulted in a dramatic increase in bacteriocidial activity towards H. pylori (MIC values of ≥6.25 µg mL−1) relative to BiPh3 (>64 µg mL−1) and the sulfonic acids, which were essentially inactive.

Item ID: 29671
Item Type: Article (Research - C1)
ISSN: 1477-9234
Keywords: crystal-structure; x-ray; molecular-structure; bismuth compounds; target sites; carboxylates; chemistry; agents; triphenylbismuth; susceptibility
Date Deposited: 02 Oct 2013 10:34
FoR Codes: 03 CHEMICAL SCIENCES > 0302 Inorganic Chemistry > 030204 Main Group Metal Chemistry @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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