Structural and solution studies of phenylbismuth(III) sulfonate complexes and their activity against Helicobacter pylori.
Three bis-phenylbismuth sulfonates [Ph(2)Bi(O(3)SR)](∞) (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(O(3)SR)(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 BiPh(3) (>64 μg mL(-1)) and the sulfonic acids, which were essentially inactive.
Andrews
Philip C
PC
School of Chemistry, Monash University, Clayton, Melbourne, VIC 3800, Australia. phil.andrews@monash.edu
Busse
Madleen
M
Deacon
Glen B
GB
Ferrero
Richard L
RL
Junk
Peter C
PC
Huynh
Katie K
KK
Kumar
Ish
I
Maclellan
Jonathan G
JG
D001729:Bismuth / Q000737:chemistry*; D056831:Coordination Complexes / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D016480:Helicobacter pylori / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D013451:Sulfonic Acids / Q000737:chemistry*
D056831:Coordination Complexes; D013451:Sulfonic Acids; D001729:Bismuth