Bismuth(III) saccharinate and thiosaccharinate complexes and the effect of ligand substitution on their activity against helicobacter pylori

Andrews, Philip C., Ferrero, Richard L., Forsyth, Craig M., Junk, Peter C., Maclellan, Jonathan G., and Peiris, Roshani M. (2011) Bismuth(III) saccharinate and thiosaccharinate complexes and the effect of ligand substitution on their activity against helicobacter pylori. Organometallics, 30 (22). pp. 6283-6291.

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Abstract

Five bismuth(III) saccharinate and thiosaccharinate complexes, [Ph2Bi(sac)]∞1, [Bi(sac)3]n2, [Ph2Bi(tsac)]∞4, [PhBi(tsac)2]n5, [Bi(tsac)3]n6 (sacH = saccharin, tsacH = thiosaccharin), have been synthesized and fully characterized. The tendency for ligand redistribution in [Ph2Bi(sac)]∞ has been investigated in solution by NMR spectroscopy. The structures of [Ph2Bi(sac)]∞1 and [Ph2Bi(tsac)]∞4 have been confirmed by X-ray crystallography. In Ph2Bi(sac) the sac ligand is bound to a four-coordinate bismuth center via its imino nitrogen atom with an accompanying long-range Bi–O interaction. However, in the structure of [Ph2Bi(tsac)]∞ the ligand is σ-bound through the exocyclic sulfur atom, giving a thiolate complex, confirming the more thiophilic nature of bismuth(III). Both complexes consist of polymeric chain structures with formally four-coordinated bismuth atoms. The complexes were assessed for their activity against H. pylori. The activity is both ligand dependent and sensitive to the degree of ligand substitution. The saccharinate complexes, 1 and 2, show activity comparable with standard tris-carboxylato bismuth(III) compounds, 6.25 μg/mL, while the activity of the thiolato complexes, 4–6, increases dramatically on increasing the number of thiolate groups from one to three (range 50–6.25 μg/mL). Saccharin, thiosaccharin, and BiPh3 were found to be inactive.

Item ID: 29663
Item Type: Article (Refereed Research - C1)
Keywords: carbonic-anhydrase inhibitors; molecular-structure; spectroscopic characterization; antitumor-activity; crystal-structures; oxo-clusters; target sites; solvent-free; chemistry; infection
ISSN: 1520-6041
Funders: Australian Research Council (ARC), Bayer Schering Pharma , Monash University
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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