Recent advances in bioinorganic chemistry of bismuth

Sun, 2004, Bismuth in medicine, Met Ions Biol Syst, 41, 333 2011 Marshall, 1984, Unidentified curved bacilli in the stomach of patients with gastritis and peptic ulceration, Lancet, 1, 1311, 10.1016/S0140-6736(84)91816-6 Chen, 2006, Fabrication of bismuth subcarbonate nanotube arrays from bismuth citrate, Chem Commun (Camb), 2265, 10.1039/b601764a Chen, 2010, Bismuth subcarbonate nanoparticles fabricated by water-in-oil microemulsion-assisted hydrothermal process exhibit anti-Helicobacter pylori properties, Mat Res Bull, 45, 654, 10.1016/j.materresbull.2009.12.035 Yang, 2007, Biocoordination chemistry of bismuth: recent advances, Coord Chem Rev, 251, 2354, 10.1016/j.ccr.2007.03.003 Andre, 2011, Mechanosynthesis of the metallodrug bismuth subsalicylate from Bi2O3 and structure of bismuth salicylate without auxiliary organic ligands, Angew Chem Int Ed, 50, 7858, 10.1002/anie.201103171 Andrews, 2006, Towards a structural understanding of the anti-ulcer and anti-gastritis drug bismuth subsalicylate, Angew Chem Int Ed, 45, 5638, 10.1002/anie.200600469 Tsang, 2011, Tracking bismuth antiulcer drug uptake in single Helicobacter pylori cells, J Am Chem Soc, 133, 7355, 10.1021/ja2013278 Sun, 2009, Identification and characterization of metallodrug binding proteins by (metallo)proteomics, Metallomics, 1, 25, 10.1039/B813121J Ge, 2007, Bioinorganic chemistry of bismuth and antimony: target sites of metallodrugs, Acc Chem Res, 40, 267, 10.1021/ar600001b Yang, 2011, Bismuth: environmental pollution and health effects, 414 Li, 2003, Structure of colloidal bismuth subcitrate (CBS) in dilute HCl: unique assembly of bismuth citrate dinuclear units ([Bi(cit)2Bi]2−), J Am Chem Soc, 125, 12408, 10.1021/ja037019x Yang, 2010, Polymeric architectures of bismuth citrate based on dimeric building blocks, Sci Chin-Chem, 53, 2152, 10.1007/s11426-010-4113-x Mehring, 2007, From molecules to bismuth oxide-based materials: potential homo- and heterometallic precursors and model compounds, Coord Chem Rev, 251, 974, 10.1016/j.ccr.2006.06.005 Andrews, 2009, Synthesis, ethanolysis, and hydrolysis of bismuth(III) ortho-nitrobenzoate complexes en route to a pearl necklace-like polymer of Bi10 oxo-clusters, Organometallics, 28, 3999, 10.1021/om9002158 Andrews, 2010, Structural and solution studies of phenylbismuth(III) sulfonate complexes and their activity against Helicobacter pylori, Dalton Trans, 39, 9633, 10.1039/c0dt00629g Andrews, 2010, Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori, Dalton Trans, 39, 2861, 10.1039/c000164c Murafuji, 2011, Bismuth heterocycles based on a diphenyl sulfone scaffold: synthesis and substituent effect on the antifungal activity against Saccharomyces cerevisiae, Eur J Med Chem, 46, 519, 10.1016/j.ejmech.2010.11.031 Yagura, 2008, Heterocyclic organobismuth(III) induces apoptosis of human promyelocytic leukemic cells through activation of caspases and mitochondrial perturbation, Biochem Pharmacol, 76, 974, 10.1016/j.bcp.2008.07.038 Yang, 2007, Bismuth complexes inhibit the SARS coronavirus, Angew Chem Int Ed, 46, 6464, 10.1002/anie.200701021 Yang, 2007, Inhibition of SARS coronavirus helicase by bismuth complexes, Chem Commun (Camb), 4413, 10.1039/b709515e Tiekink, 2007, Cytotoxicity, qualitative structure-activity relationship (QSAR), and anti-tumor activity of bismuth dithiocarbamate complexes, J Inorg Biochem, 101, 809, 10.1016/j.jinorgbio.2007.01.010 Tiekink, 2002, Antimony and bismuth compounds in oncology, Crit Rev Oncol Hematol, 42, 217, 10.1016/S1040-8428(01)00217-7 Andrews, 2009, Bismuth(III) 5-sulfosalicylate complexes: structure, solubility and activity against Helicobacter pylori, Dalton Trans, 6377, 10.1039/b900774a Yagura, 2005, Antibacterial properties of some cyclic organobismuth(III) compounds, Antimicrob Agents Chemother, 49, 2729, 10.1128/AAC.49.7.2729-2734.2005 Andrews, 2011, Anti-Leishmanial activity of homo- and heteroleptic bismuth(III) carboxylates, J Inorg Biochem, 105, 454, 10.1016/j.jinorgbio.2010.08.007 Friebolin, 2005, Antitumoral activity of non-platinum xanthate complexes, J Med Chem, 48, 7925, 10.1021/jm040899l Iuchi, 2009, Heterocyclic organobismuth(III) compound targets tubulin to induce G2/M arrest in HeLa cells, J Pharmacol Sci, 109, 573, 10.1254/jphs.09020FP Tanner, 2003, The severe acute respiratory syndrome (SARS) coronavirus NTPase/helicase belongs to a distinct class of 5′ to 3′ viral helicases, J Biol Chem, 278, 39578, 10.1074/jbc.C300328200 Li, 1996, Unexpectedly strong binding of a large metal ion (Bi3+) to human serum transferrin, J Biol Chem, 271, 9483, 10.1074/jbc.271.16.9483 Sun, 2001, Competitive binding of bismuth to transferrin and albumin in aqueous solution and in blood plasma, J Biol Chem, 276, 8829, 10.1074/jbc.M004779200 Zhang, 2001, Interactions of bismuth with human lactoferrin and recognition of the Bi(III)-lactoferrin complex by intestinal cells, Biochemistry, 40, 13281, 10.1021/bi010579t Sun, 2003, Binding of bismuth to serum proteins: implication for targets of Bi(III) in blood plasma, J Inorg Biochem, 94, 114, 10.1016/S0162-0134(02)00649-9 Sun, 1999, Interactions of bismuth complexes with metallothionein(II), J Biol Chem, 274, 29094, 10.1074/jbc.274.41.29094 Senkovich, 2010, Unique host iron utilization mechanisms of Helicobacter pylori revealed with iron-deficient chemically defined media, Infect Immun, 78, 1841, 10.1128/IAI.01258-09 Jin, 2004, Inhibition of alcohol dehydrogenase by bismuth, J Inorg Biochem, 98, 1331, 10.1016/j.jinorgbio.2004.03.016 Mounicou, 2009, Metallomics: the concept and methodology, Chem Soc Rev, 38, 1119, 10.1039/b713633c Cvetkovic, 2010, Microbial metalloproteomes are largely uncharacterized, Nature, 466, 779, 10.1038/nature09265 Sun, 2010, Metallomics: an integrated science for metals in biology and medicine, Ann Rep Prog Chem Sec A Inorg Chem, 106, 20, 10.1039/b920672h Ge, 2007, A proteomic approach for the identification of bismuth-binding proteins in Helicobacter pylori, J Biol Inorg Chem, 12, 831, 10.1007/s00775-007-0237-7 Zhang, 2006, Inhibition of urease by bismuth(III): implications for the mechanism of action of bismuth drugs, Biometals, 19, 503, 10.1007/s10534-005-5449-0 Murafuji, 2006, Inhibition of jack bean urease by organobismuth compounds, Bioorg Med Chem Lett, 16, 1510, 10.1016/j.bmcl.2005.12.034 Ge, 2006, Expression and characterization of a histidine-rich protein, Hpn: potential for Ni2+ storage in Helicobacter pylori, Biochem J, 393, 285, 10.1042/BJ20051160 Zeng, 2008, Binding of Ni2+ to a histidine- and glutamine-rich protein, Hpn-like, J Biol Inorg Chem, 13, 1121, 10.1007/s00775-008-0397-0 Seshadri, 2007, Roles of His-rich hpn and hpn-like proteins in Helicobacter pylori nickel physiology, J Bacteriol, 189, 4120, 10.1128/JB.01245-06 Ge, 2006, Thermodynamic and kinetic aspects of metal binding to the histidine-rich protein, Hpn, J Am Chem Soc, 128, 11330, 10.1021/ja062589t Kozlowski, 2011, The -Cys-Cys- motif in Helicobacter pylori's Hpn and HspA proteins is an essential anchoring site for metal ions, Dalton Trans, 40, 5604, 10.1039/c1dt10187k Zeng, 2011, Metal-binding properties of an Hpn-like histidine-rich protein, Chemistry, 17, 5852, 10.1002/chem.201100279 Wegner, 2011, Metal-binding properties of Hpn from Helicobacter pylori and implications for the therapeutic activity of bismuth, Chem Sci, 2, 451, 10.1039/C0SC00411A Cun, 2008, A histidine-rich and cysteine-rich metal-binding domain at the C terminus of heat shock protein A from Helicobacter pylori: implication for nickel homeostasis and bismuth susceptibility, J Biol Chem, 283, 15142, 10.1074/jbc.M800591200 Cun, 2010, A zinc-binding site by negative selection induces metallodrug susceptibility in an essential chaperonin, Proc Natl Acad Sci USA, 107, 4943, 10.1073/pnas.0913970107 Chen, 2012, Inhibition of fumarase by bismuth (III): implications for the tricarboxylic acid cycle as a potential target of bismuth drugs in Helicobacter pylori, Biometals, 25, 95, 10.1007/s10534-011-9485-7 Kozlowski, 2010, The C terminus of HspA-a potential target for native Ni(II) and Bi(III) anti-ulcer drugs, Dalton Trans, 39, 5814, 10.1039/c0dt00013b Kondo, 2004, Citrate enhances the protective effect of orally administered bismuth subnitrate against the nephrotoxicity of cis-diamminedichloroplatinum, Cancer Chemother Pharmacol, 53, 33 Tsang, 2012, Probing of bismuth antiulcer drug targets in H. pylori by laser ablation-inductively coupled plasma mass spectrometry, Metallomics, 10.1039/c2mt00169a