Bismuth(III) 5-sulfosalicylate complexes: structure, solubility and activity against Helicobacter pylori.
Treatment of 5-sulfosalicylic acid (H(3)Ssal) with BiPh(3) results in the formation of the first dianionic carboxylate-sulfonate bismuth complex, [PhBi(HSsal)H(2)O](infinity) 1a, and its ethanol analogue [PhBi(HSsal)EtOH](infinity) 1b (space group P2(1)/c), while Bi(OAc)(3) gives the mixed monoanionic and dianionic complex, {[Bi(HSsal)(H(2)Ssal)(H(2)O)(3)](2) x 2 H(2)O}(infinity) 2 (space group P1). The three complexes are all polymeric in the solid state as determined by single crystal X-ray diffraction, with extended frameworks constructed from dimeric [Bi(HSsal)](2), 1a and 1b, or from [Bi(HSsal)(H(2)Ssal)](2) units, 2. The heteroleptic bismuth complexes 1a and 2 display remarkable aqueous solubility, 10 and 2.5 mg ml(-1) respectively, resulting in a clear solution of pH 1.5. In contrast, 1b is essentially insoluble in aqueous environments. All three complexes show significant activity against the bacterium Helicobacter pylori of <6.25 microg ml(-1).
Andrews
Philip C
PC
School of Chemistry, Monash University, Clayton, Melbourne, Vic. 3800, Australia. phil.andrews@sci.monash.edu.au
Deacon
Glen B
GB
Ferrero
Richard L
RL
Junk
Peter C
PC
Karrar
Abdulgader
A
Kumar
Ish
I
MacLellan
Jonathan G
JG
D001729:Bismuth / Q000737:chemistry*; D018360:Crystallography, X-Ray; D016480:Helicobacter pylori / Q000187:drug effects*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D012459:Salicylates / Q000737:chemistry* / Q000494:pharmacology; D012995:Solubility; D013696:Temperature
D009942:Organometallic Compounds; D012459:Salicylates; D001729:Bismuth