BIOMEDICINAL AND GASTROPROTECTIVE ASPECTS OF ORGANOBISMUTH COMPOUNDS: RECENT APPROACHES AND FUTURE PERSPECTIVES
DOI:
https://doi.org/10.22159/ajpcr.2019.v12i5.32679Keywords:
Peptic ulcer, Helicobacter pylori, Organobismuth drugs, Eradication, GastroprotectiveAbstract
Objective: Peptic ulcer is a disease caused due to an imbalance of aggressive and defensive factors in the body. Helicobacter pylori infections and colonization are also associated strongly to the peptic ulcer disease. Bismuth-containing organic compounds have been attributed to a major influential role in the successful treatment of peptic ulcer by inhibiting gastric acid secretion and provide cytoprotective properties which result in ulcer healing. Hence, the objective of this review is to discuss recent approaches and future perspectives of organobismuth compounds in the treatment of peptic ulcer.
Results: A total of 112 papers were included in the review, among them 20 papers describe the pathophysiology of peptic ulcer, 10 papers discuss about diagnostic test for H pylori infection, 4 papers describe the drug regimen used in peptic ulcer treatment, 13 papers discuss about failure and alternative therapies for treatment of peptic ulcer, 8 papers describe the chemistry of bismuth, 20 papers discuss about mechanism of action of bismuth, 27 papers describe the newer bismuth complexes for H. pylori eradication, and 8 paper discuss about gastroprotective activity of bismuth-containing derivatives.
Conclusion: Organobismuth compounds/drugs are effective to eradicate H. pylori in conjunction with antibiotics. It also provides gastroprotective action and dramatic decrease of relapse rate which accounts for further exploration of organobismuth compounds to pave new ways for the design and synthesis of novel compounds in the effective treatment of peptic ulcer.
Downloads
References
Freston JW. The pathophysiological and pharmacological basis of peptic ulcer therapy. Toxicol Pathol 1988;16:260-6.
Kaur A, Singh R, Sharma R, Kumar S. Peptic ulcer: A review on etiology and pathogenesis. Int Res J Pharm 2012;3:34-3.
Zatorski H. Introduction to Gastrointestinal Diseases. Vol. 2. Switzerland: Springer; 2017. p. 7-20.
Rodríguez LA, Tolosa LB. Risk of upper gastrointestinal complications among users of traditional NSAIDs and COXIBs in the general population. Gastroenterology 2007;132:498-506.
Gabriel SE, Jaakkimainen L, Bombardier C. Risk for serious gastrointestinal complications related to use of nonsteroidal anti-inflammatory drugs. A meta-analysis. Ann Intern Med 1991;115:787-96.
Scharschmidt BF. Peptic ulcer disease. Pathophysiology and current medical management. West J Med 1987;146:724-33.
Mertz HR, Walsh JH. Peptic ulcer pathophysiology. Med Clin North Am 1991;75:799-814.
Rosenstock S, Jørgensen T, Bonnevie O, Andersen L. Risk factors for peptic ulcer disease: A population based prospective cohort study comprising 2416 Danish adults. Gut 2003;52:186-93.
Chou SP. An examination of the alcohol consumption and peptic ulcer association results of a national survey. Alcohol Clin Exp Res 1994;18:149-53.
Ashley MJ. Smoking and diseases of the gastrointestinal system: An epidemiological review with special reference to sex differences. Can J Gastroenterol 1997;11:345-52.Ashley MJ.
Monson RR. Cigarette smoking and body form in peptic ulcer. Gastroenterology 1970;58:337-44.
Peters MN, Richardson CT. Stressful life events, acid hypersecretion, and ulcer disease. Gastroenterology 1983;84:114-9.
Medalie JH, Stange KC, Zyzanski SJ, Goldbourt U. The importance of biopsychosocial factors in the development of duodenal ulcer in a cohort of middle-aged men. Am J Epidemiol 1992;136:1280-7.
Ray WA, Chung CP, Stein CM, Smalley WE, Hall K, Arbogast PG, et al. Risk of peptic ulcer hospitalizations in users of NSAIDs with gastroprotective cotherapy versus coxibs. Gastroenterology 2007; 133:790-8.
Goh KL. Helicobacter pylori and peptic ulcer disease a causal link. Med J Malaysia 1997;52:161-8.
de Martel C, Parsonnet J. Helicobacter pylori infection and gender: A meta-analysis of population-based prevalence surveys. Dig Dis Sci 2006;51:2292-301.
Granström M, Tindberg Y, Blennow M. Seroepidemiology of helicobacter pylori infection in a cohort of children monitored from 6 months to 11 years of age. J Clin Microbiol 1997;35:468-70.
Das J, Nazir MF. Helicobacter pylori infection in children; diagnosis and treatment a review. Bangladesh J Child Health 2005;29:22-30.
O’Connor HJ. The role of Helicobacter pylori in peptic ulcer disease. Scand J Gastroenterol Suppl 1994;201:11-5.
Joshi YK. Helicobacter pylori infection: Current status. J Indian Acad Clin Med 2000;5:148-55.
McNulty CA, Dent JC, Uff JS, Gear MW, Wilkinson SP. Detection of Campylobacter pylori by the biopsy urease test: An assessment in 1445 patients. Gut 1989;30:1058-62.
Goodwin CS, Blincow ED, Warren JR, Waters TE, Sanderson CR, Easton L, et al. Evaluation of cultural techniques for isolating Campylobacter pyloridis from endoscopic biopsies of gastric mucosa. J Clin Pathol 1985;38:1127-31.
Jones DM, Lessells AM, Eldridge J. Campylobacter like organisms on the gastric mucosa: Culture, histological, and serological studies. J Clin Pathol 1984;37:1002-6.
Moter A, Göbel UB. Fluorescence in situ hybridization (FISH) for direct visualization of microorganisms. J Microbiol Methods 2000;41:85-112.
Shahamat M, Alavi M, Watts JE, Gonzalez JM, Sowers KR, Maeder DW, et al. Development of two PCR-based techniques for detecting helical and coccoid forms of Helicobacter pylori. J Clin Microbiol 2004;42:3613-9.
Gulcan EM, Varol A, Kutlu T, Cullu F, Erkan T, Adal E, et al. Helicobacter pylori stool antigen test. Indian J Pediatr 2005;72:675-8.
Rathbone BJ, Wyatt JI, Worsley BW, Shires SE, Trejdosiewicz LK, Heatley RV, et al. Systemic and local antibody responses to gastric Campylobacter pyloridis in non-ulcer dyspepsia. Gut 1986;27:642-7.
Graham DY, Klein PD, Evans DJ Jr., Evans DG, Alpert LC, Opekun AR, et al. Campylobacter pylori detected noninvasively by the 13C-urea breath test. Lancet 1987;1:1174-7.
O’Brien B, Goeree R, Mohamed AH, Hunt R. Cost-effectiveness of Helicobacter pylori eradication for the long-term management of duodenal ulcer in Canada. Arch Intern Med 1995;155:1958-64.
Veldhuyzen van Zanten SJ, Sherman PM, Hunt RH. Helicobacter pylori: New developments and treatments. CMAJ 1997;156:1565-74.
Nakajima S, Graham DY, Hattori T, Bamba T. Strategy for treatment of Helicobacter pylori infection in adults. I. Updated indications for test and eradication therapy suggested in 2000. Curr Pharm Des 2000;6:1503-14.
Cassel-Beraud AM, Le Jan J, Mouden JC, Andriantsoa M, Andriantsiferana R. Preliminary study of the prevalence of Helicobacter pylori in Tananarive, Madagascar and the antibacterial activity in vitro of 13 Malagasy medicinal plants on this germ. Arch Inst Pasteur Madagascar 1991;59:9-23.
Chenoll E, Casinos B, Bataller E, Astals P, Echevarría J, Iglesias JR, et al. Novel probiotic Bifidobacterium bifidum CECT 7366 strain active against the pathogenic bacterium Helicobacter pylori. Appl Environ Microbiol 2011;77:1335-43.
Chen L, Li Y, Li J, Xu X, Lai R, Zou Q, et al. An antimicrobial peptide with antimicrobial activity against Helicobacter pylori. Peptides 2007;28:1527-31.
Lee JH, Shim JS, Lee JS, Kim JK, Yang IS, Chung MS, et al. Inhibition of pathogenic bacterial adhesion by acidic polysaccharide from green tea (Camellia sinensis). J Agric Food Chem 2006;54:8717-23.
Kabir S. The current status of Helicobacter pylori vaccines: A review. Helicobacter 2007;12:89-102.
Malfertheiner P, Megraud F, O’Morain C, Bazzoli F, El-Omar E, Graham D, et al. Current concepts in the management of Helicobacter pylori infection: The Maastricht III consensus report. Gut 2007;56:772-81.
Fock KM, Katelaris P, Sugano K, Ang TL, Hunt R, Talley NJ, et al. Second Asia-Pacific consensus guidelines for Helicobacter pylori infection. J Gastroenterol Hepatol 2009;24:1587-600.
Lambert JR, Midolo P. The actions of bismuth in the treatment of Helicobacter pylori infection. Aliment Pharmacol Ther 1997; 11 Suppl 1:27-33.
Mégraud F. The challenge of Helicobacter pylori resistance to antibiotics: The comeback of bismuth-based quadruple therapy. Therap Adv Gastroenterol 2012;5:103-9.
Konturek SJ, Radecki T, Piastucki I, Drozdowicz D. Studies on the gastroprotective and ulcer-healing effects of colloidal bismuth subcitrate. Digestion 1987;37 Suppl 2:8-15.
Tanaka S, Guth PH, Paulsen G, Kaunitz JD. Gastroprotective effect of ranitidine bismuth citrate is associated with increased mucus bismuth concentration in rats. Gut 1996;39:164-71.
Stables R, Campbell CJ, Clayton NM, Clitherow JW, Grinham CJ, McColm AA, et al. Gastric anti-secretory, mucosal protective, anti-pepsin and anti-helicobacter properties of ranitidine bismuth citrate. Aliment Pharmacol Ther 1993;7:237-46.
Konturek S, Brzozowski T, Drozdowicz D, Bielanski W. Campylobacter pylori. New York: Springer; 1988. p. 184-92.
Sun H, Szeto KY. Binding of bismuth to serum proteins: Implication for targets of bi (III) in blood plasma. J Inorg Biochem 2003;94:114-20.
Tooth B. The Hydrothermal Chemistry of Bismuth and the Liquid Bismuth Collector Model, Thesis. Adelaide: University Adelaide; 2013.
Silver AF, Ash AG, Stone AG, Strontium AG, Sulfur BG, Talc BG, et al. Mineral Commodity Summaries. United States: Geological Survey; 2011.
Ojebuoboh FK. Bismuth Production, properties, and applications. JOM 1992;44:46-9.
Naumov AV. World market of bismuth: A review. Russ J Non Ferrous Metals 2007;48:10-6.
Habashi F. Encyclopedia of Metalloproteins New York: Springer; 2013. p. 283-4.
Cotton FA, Wilkinson G, Murillo CA, Bochmann M. Advanced Organic Chemistry. New York: John Wiley and Sons; 1999.
Busev AI, Tiptsova VG, Ivanov VM. Hand Book of the Analtical Chemistry of Rare Elements. Ann Arbor: Ann Arbor Hunphrey Science Publishers; 1970.
Ulvenlund S, Bengtsson LA. Univalent bismuth a subvalent main group metal ion stable in aqueous solution. Acta Chem Scan Col 1994;48:635-9.
Wang Y, Hu L, Xu F, Quan Q, Lai YT, Xia W, et al. Integrative approach for the analysis of the proteome-wide response to bismuth drugs in Helicobacter pylori. Chem Sci 2017;8:4626-33.
Slomiany BL, Kasinathan C, Slomiany A. Lipolytic activity of Campylobacter pylori: Effect of colloidal bismuth subcitrate (De-nol) Am J Gastroenterol 1989;84:1273-7.
Nilius M, Ströhle A, Bode G, Malfertheiner P. Coccoid like forms (CLF) of Helicobacter pylori. Enzyme activity and antigenicity. Zentralbl Bakteriol 1993;280:259-72.
Midolo PD, Norton A, Itzstein Von M, Lambert JR. Novel bismuth compounds have in vitro activity against Helicobacter pylori. FEMS Microbiol Lett 1997;157:229-32.
Sox TE, Olson CA. Binding and killing of bacteria by bismuth subsalicylate. Antimicrob Agents Chemother 1989;33:2075-82.
Armstrong JA, Wee SH, Goodwin CS, Wilson DH. Response of Campylobacter pyloridis to antibiotics, bismuth and an acid-reducing agent in vitro an ultrastructural study. J Med Microbiol 1987;24:343-50.
Domenico P, Landolphi DR, Cunha BA. Reduction of capsular polysaccharide and potentiation of aminoglycoside inhibition in gram-negative bacteria by bismuth subsalicylate. J Antimicrob Chemother 1991;28:801-10.
Lee SP. A potential mechanism of action of colloidal bismuth subcitrate: Diffusion barrier to hydrochloric acid. Scand J Gastroenterol Suppl 1982;80:17-21.
Konturek SJ, Radecki T, Piastucki I, Drozdowicz D. Advances in the understanding of the mechanism of cytoprotective action by colloidal bismuth subcitrate. Scand J Gastroenterol Suppl 1986;122:6-10.
Zhang L, Mulrooney SB, Leung AF, Zeng Y, Ko BB, Hausinger RP, et al. Inhibition of urease by bismuth(III): Implications for the mechanism of action of bismuth drugs. Biometals 2006;19:503-11.
Habala L, Devínsky F, Egger A. REVIEW: Metal complexes as urease inhibitors. J Coord Chem 2018;71:1-49.
Jin L, Szeto KY, Zhang L, Du W, Sun H. Inhibition of alcohol dehydrogenase by bismuth. J Inorg Biochem 2004;98:1331-7.
Chen Z, Zhou Q, Ge R. Inhibition of fumarase by bismuth(III): Implications for the tricarboxylic acid cycle as a potential target of bismuth drugs in Helicobacter pylori. Biometals 2012;25:95-102.
Cun S, Li H, Ge R, Lin MC, Sun H. 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 2008;283:15142-51.
He X, Liao X, Li H, Xia W, Sun H. Bismuth-induced inactivation of ferric uptake regulator from Helicobacter pylori. Inorg Chem 2017;56:15041-8.
Bland MV, Ismail S, Heinemann JA, Keenan JI. The action of bismuth against Helicobacter pylori mimics but is not caused by intracellular iron deprivation. Antimicrob Agents Chemother 2004;48:1983-8.
Lemire JA, Harrison JJ, Turner RJ. Antimicrobial activity of metals: Mechanisms, molecular targets and applications. Nat Rev Microbiol 2013;11:371-84.
Herrmann WA, Herdtweck E, Pajdla L. Metal complexes in biology and medicine, VI synthesis and structure of (Penicillaminato-O,S,N) bismuth(III) Chloride. Chem Ber 1993;126:895-8.
Shaw CF, Savas MM. In: Stillman MJ, Shaw CF, Suzuki KT, editors. Metallothioneins: Synthesis, Structure and Properties of Metallothioneins, Phytochelatins, and Metalthiolate Complexes. New York: VCH; 1992. p. 144-62.
Li H, Sadler PJ, Sun H. Rationalization of the strength of metal binding to human serum transferrin. Eur J Biochem 1996;242:387-93.
Diemer R, Dittes U, Nuber B, Seifried V, Opferkuch W, Keppler BK, et al. Synthesis, characterization and molecular structures of some bismuth(III) complexes with thiosemicarbazones and dithiocarbazonic acid methylester derivatives with activity against Helicobacter pylori. Met Based Drugs 1995;2:271-92.
Domagk G, Behnisch R, Mietzsch F, Schmidt H. Uber eine neue, gegen tuberkelbazillen in vitro wirksame verbindungsklasse. Naturwiss 1946;33:315.
Easmon J, Heinisch G, Holzer W, Rosenwirth B. Pyridazines. 63. Novel thiosemicarbazones derived from formyl and acyldiazines: Synthesis, effects on cell proliferation, and synergism with antiviral agents. J Med Chem 1992;35:3288-96.
Klayman DL, Scovill JP, Bartosevich JF, Bruce J 2-acetylpyridine thiosemicarbazones 5. 1-[1-(2-pyridyl)ethyl]-3-thiosemicarbazides as potential antimalarial agents. J Med Chem 1983;26:35-9.
Antonini I, Claudi F, Cristalli G, Franchetti P, Grifantini M, Martelli S, et al. Synthesis of 4-amino-1-beta-D-ribofuranosyl-1H-pyrrolo[2,3-b] pyridine (1-deazatubercidin) as a potential antitumor agent. J Med Chem 1982;25:1258-61.
Dittes U, Vogel E, Keppler BK. Overview on bismuth (III) and bismuth (V) tropolanato complexes with activity against H. pylori. Coord Chem Rev 1997;163:345-64.
Shaikh AR, Giridhar R, Megraud F, Yadav MR. Metalloantibiotics: Synthesis, characterization and antimicrobial evaluation of bismuth-fluoroquinolone complexes against Helicobacter pylori. Acta Pharm 2009;59:259-71.
Sharma PC, Jain A, Jain S. Fluoroquinolone antibacterials: A review on chemistry, microbiology and therapeutic prospects. Acta Pol Pharm 2009;66:587-604.
Andrews PC, Deacon GB, Ferrero RL, Junk PC, Karrar A, Kumar I, et al. Bismuth(III) 5-sulfosalicylate complexes: Structure, solubility and activity against Helicobacter pylori. Dalton Trans 2009;32:6377-84.
Andrews PC, Ferrero RL, Junk PC, Kumar I, Luu Q, Nguyen K, et al. Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori. Dalton Trans 2010;39:2861-8.
Andrews PC, Deacon GB, Jackson WR, Maguire M, Scott NM, Skelton BW, et al. Solvent free synthesis of bismuth thiolates and carboxylates. J Chem Soc Dalton Trans 2002;24:4634-8.
Andrews PC, Deacon GB, Forsyth CM, Junk PC, Kumar I, Maguire M, et al. Towards a structural understanding of the anti-ulcer and anti-gastritis drug bismuth subsalicylate. Angew Chem Int Ed Engl 2006;45:5638-42.
Andrews PC, Ferrero RL, Craig M, Forsyth CM, Junk PC, Jonathan G, et al. Bismuth(III) saccharinate and thiosaccharinate complexes and the effect of ligand substitution on their activity against Helicobacter pylori. Organometallics 2011;30:6283-91.
Raad AT, Boghaei DM, Khavasi HR. Saccharin complexes of zinc(II) with phenanthroline and 2,9-dimethyl-1,10-phenanthroline: Synthesis and characterization. J Coord Chem 2010;63:273-83.
Frija LM, Alegria EC, Sutradhar M, Cristiano ML, Ismael A, Kopilovich M, et al. Copper(II) and cobalt(II) tetrazole-saccharinate complexes as effective catalysts for oxidation of secondary alcohols. J Mol Catal A 2016;425:283-90.
Ali M, McWhinnie WR. Organobismuth (III) and organobismuth (V) carboxylates and their evaluation as paint driers. Appl Organomet Chem 1993;7:137-41.
Ogawa K, Terada T, Muranaka Y, Hamakawa T, Fujii S. Studies on hypolipidemic agents. V. Synthesis and esterase-inhibitory activity of 2-(1, 4- and 4,4-dialkylcyclohexyl)-2-oxoethyl are nesulfonates. Chem Pharm Bull (Tokyo) 1987;35:4130-6.
Ogawa K, Terada T, Muranaka Y, Hamakawa T, Ohta S, Okamoto M, et al. Studies on hypolipidemic agents. IV. Syntheses and biological activities of trans and cis-2-(4-alkylcyclohexyl)-2-oxoethyl are nesulfonates. Chem Pharm Bull (Tokyo) 1987;35:3276-83.
Ogawa K, Terada T, Muranaka Y, Hamakawa T, Fujii S. Studies on hypolipidemic agents. III. Synthesis and esterase-inhibitory activity of omega-cycloalkyl-2-oxoalkyl are nesulfonates. Chem Pharm Bull (Tokyo) 1987;35:2426-36.
Suzuki H, Matano Y. Organobismuth Chemistry. New York: Elsevier; 2001. p. 159-61.
Garner CD, Hughes B. Inorganic compounds containing the trifluoroacetate group. IV. Preparation and properties of arsenic tris (trifluoroacetate), [As(O2CCF3)], and related compounds. Inorg Chem 1975;14:1722-4.
Busse M, Border E, Junk PC, Richard L, Ferrero RL, Andrews PC. Bismuth(III) complexes derived from α-amino acids: The impact of hydrolysis and oxido-cluster formation on their activity against Helicobacter pylori. Dalton Trans 2014;43:17980-90.
Sadler PJ, Muncie C, Shipman MA. Biological Inorganic Chemistry Structure and Reactivity. California: University Science Books; 2007.
Sun H, Li H, Mason AB, Woodworth RC, Sadler PJ. Competitive binding of bismuth to transferrin and albumin in aqueous solution and in blood plasma. J Biol Chem 2001;276:8829-35.
Li H, Sun H. Recent advances in bioinorganic chemistry of bismuth. Curr Opin Chem Biol 2012;16:74-83.
Ge R, Chen Z, Zhou Q. The actions of bismuth in the treatment of Helicobacter pylori infections: An update. Metallomics 2012;4:239-43.
Andrews PC, Blair VL, Ferrero RL, Junk PC, Kedzierski L, Peiris RM, et al. Bismuth(III) β-thioxoketonates as antibiotics against Helicobacter pylori and as anti-leishmanial agents. Dalton Trans 2014;43:1279-91.
Pathak A, Blair VL, Ferrero RL, Mehring M, Andrews PC. Bismuth(III) benzohydroxamates: Powerful anti-bacterial activity against Helicobacter pylori and hydrolysis to a unique bi34 oxido-cluster [Bi34O22(BHA)22(H-BHA)14(DMSO)6]. Chem Commun (Camb) 2014;50:15232-4.
Pathak A, Blair VL, Ferrero RL, Junk PC, Tabor RF, Andrews PC, et al. Synthesis and structural characterisation of bismuth(III) hydroxamates and their activity against Helicobacter pylori. Dalton Trans 2015;44:16903-13.
D’Souza RS, Dhume VG. Gastric cytoprotection. Indian J Physiol Pharmacol 1991;35:88-98.
Konturek SJ, Radecki T, Piastucki I, Brzozowski T, Drozdowicz D. Gastrocytoprotection by colloidal bismuth subcitrate (De-nol) and sucralfate. Role of endogenous prostaglandins. Gut 1987;28:201-5.
Tytgat GN. Colloidal bismuth subcitrate in peptic ulcer a review. Digestion 1987;37 Suppl 2:31-41.
Wagstaff AJ, Benfield P, Monk JP. Colloidal bismuth subcitrate. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in peptic ulcer disease. Drugs 1988;36:132-57.
Tanaka S, Guth PH, Carryl OR, Kaunitz JD. Cytoprotective effect of bismuth subsalicylate in indomethacin-treated rats is associated with enhanced mucus bismuth concentration. Aliment Pharmacol Ther 1997;11:605-12.
Gorbach SL. Bismuth therapy in gastrointestinal diseases. Gastroenterology 1990;99:863-75.
Tay HP, Chaparala RC, Harmon JW, Huesken J, Saini N, Hakki FZ, et al. Bismuth subsalicylate reduces peptic injury of the oesophagus in rabbits. Gut 1990;31:11-6.
Kotzampassi K, Paramythiotis D, Voudouris A, Milias K, Eleftheriadis E. The influence of ranitidine bismuth citrate on rat gastric mucosal microcirculation and adherent mucus gel layer. Ann Gastroenterol 2000;13:118-21.
Pudlo M, Demougeot C, Girard-Thernier C. Arginase inhibitors: A rational approach over one century. Med Res Rev 2017;37:475-513.
Debraekeleer A, Remaut H. Future perspective for potential Helicobacter pylori eradication therapies. Future Microbiol 2018; 13:671-87.
Published
How to Cite
Issue
Section
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.
