Antibacterial carbonic anhydrase inhibitors: an update on the recent literature

References

• Gaynor M, Mankin AS. Macrolide antibiotics: binding site, mechanism of action, resistance [Research support, U.S. Gov’t, P.H.S. Review]. Curr Top Med Chem. 2003;3(9):949–961.
   PubMed Web of Science ®Google Scholar
• Khelaifia S, Drancourt M. Susceptibility of archaea to antimicrobial agents: applications to clinical microbiology. Clin Microbiol Infect. 2012 Sep;18(9):841–848.
   PubMed Web of Science ®Google Scholar
• Schleifer KH, Kandler O. Peptidoglycan types of bacterial cell walls and their taxonomic implications. Bacteriol Rev. 1972 Dec;36(4):407–477.
   PubMedGoogle Scholar
• Li Z, Velkov T. Polymyxins: mode of action. Adv Exp Med Biol. 2019;1145:37–54.
   PubMed Web of Science ®Google Scholar
• Capasso C, Supuran CT. Sulfa and trimethoprim-like drugs - antimetabolites acting as carbonic anhydrase, dihydropteroate synthase and dihydrofolate reductase inhibitors. J Enzyme Inhib Med Chem. 2014 Jun;29(3):379–387.
   PubMed Web of Science ®Google Scholar
• Roemer T, Krysan DJ. Antifungal drug development: challenges, unmet clinical needs, and new approaches. Cold Spring Harb Perspect Med. 2014 May 1;4(5):a019703-a019703.
   PubMed Web of Science ®Google Scholar
• Turk VE, Simic I, Likic R, et al. New drugs for bad bugs: what’s new and what’s in the pipeline? Clin Ther. 2016 Oct 06;38(10S):e9.
   PubMedGoogle Scholar
• Decker B, Masur H. Bad bugs, no drugs: are we part of the problem, or leaders in developing solutions? Crit Care Med. 2015 Jun;43(6):1153–1155.
   PubMed Web of Science ®Google Scholar
• Annunziato G, Angeli A, D’Alba F, et al. Discovery of new potential anti-infective compounds based on carbonic anhydrase inhibitors by rational target-focused repurposing approaches. ChemMedChem. 2016 Sep 06;11(17):1904–1914.
   PubMed Web of Science ®Google Scholar
• Ozensoy Guler O, Capasso C, Supuran CT. A magnificent enzyme superfamily: carbonic anhydrases, their purification and characterization. J Enzyme Inhib Med Chem. 2016 Oct;31(5):689–694.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, De Luca V, et al. Sulfonamide inhibition studies of the beta-carbonic anhydrase from the pathogenic bacterium vibrio cholerae. Bioorg Med Chem. 2016 Mar 1;24(5):1115–1120.
   PubMed Web of Science ®Google Scholar
• Del Prete S, De Luca V, De Simone G, et al. Cloning, expression and purification of the complete domain of the eta-carbonic anhydrase from plasmodium falciparum. J Enzyme Inhib Med Chem. 2016;15:1–6.
   Google Scholar
• Capasso C, Supuran CT. An overview of the carbonic anhydrases from two pathogens of the oral cavity: streptococcus mutans and porphyromonas gingivalis. Curr Top Med Chem. 2016;16(21):2359–2368.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Capasso C. An overview of the bacterial carbonic anhydrases. Metabolites. 2017 Nov 11;7:4.
   Web of Science ®Google Scholar
• Capasso C, Supuran CT. An overview of the alpha-, beta- and gamma-carbonic anhydrases from Bacteria: can bacterial carbonic anhydrases shed new light on evolution of bacteria? J Enzyme Inhib Med Chem. 2015 Apr;30(2):325–332.
   PubMed Web of Science ®Google Scholar
• Del Prete S, De Luca V, Nocentini A, et al. Anion inhibition studies of the beta-carbonic anhydrase from escherichia coli. Molecules. 2020 May 31;25:11.
   Web of Science ®Google Scholar
• Capasso C, Supuran CT. An overview of the selectivity and efficiency of the bacterial carbonic anhydrase inhibitors. Curr Med Chem. 2015;22(18):2130–2139.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Structure and function of carbonic anhydrases. Biochem J. 2016 Jul 15;473(14):2023–2032.
   PubMedGoogle Scholar
• Buzas GM, Supuran CT. The history and rationale of using carbonic anhydrase inhibitors in the treatment of peptic ulcers. In memoriam ioan Puscas (1932-2015). J Enzyme Inhib Med Chem. 2016 Aug;31(4):527–533.
   PubMed Web of Science ®Google Scholar
• Carta F, Supuran CT, Scozzafava A. Sulfonamides and their isosters as carbonic anhydrase inhibitors. Future Med Chem. 2014 6;Jun(10):1149–1165.
   Google Scholar
• Pinard MA, Lotlikar SR, Boone CD, et al. Structure and inhibition studies of a type II beta-carbonic anhydrase psCA3 from Pseudomonas aeruginosa. Bioorg Med Chem. 2015 Aug 1;23(15):4831–4838.
   PubMed Web of Science ®Google Scholar
• Ferraroni M, Del Prete S, Vullo D, et al. Crystal structure and kinetic studies of a tetrameric type II beta-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae. Acta Crystallogr D Biol Crystallogr. 2015 Dec 1;71(Pt 12):2449–2456.
   PubMedGoogle Scholar
• De Simone G, Monti SM, Alterio V, et al. Crystal structure of the most catalytically effective carbonic anhydrase enzyme known, SazCA from the thermophilic bacterium Sulfurihydrogenibium azorense. Bioorg Med Chem Lett. 2015 May 1;25(9):2002–2006.
   PubMed Web of Science ®Google Scholar
• Zolnowska B, Slawinski J, Pogorzelska A, et al. Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N’-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII. Eur J Med Chem. 2014 Jan;71:135–147.
   PubMed Web of Science ®Google Scholar
• De Luca L, Ferro S, Damiano FM, et al. Structure-based screening for the discovery of new carbonic anhydrase VII inhibitors. Eur J Med Chem. 2014 Jan;71:105–111.
   PubMed Web of Science ®Google Scholar
• Di Fiore A, Capasso C, De Luca V, et al. X-ray structure of the first `extremo-alpha-carbonic anhydrase’, a dimeric enzyme from the thermophilic bacterium Sulfurihydrogenibium yellowstonense YO3AOP1. Acta Crystallogr D Biol Crystallogr. 2013 Jun;69(Pt 6):1150–1159.
   PubMedGoogle Scholar
• Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem. 2012 Dec;27(6):759–772.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases–an overview. Curr Pharm Des. 2008;14(7):603–614.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Expert Opin Drug Discov. 2017 Jan;12(1):61–88.
   PubMed Web of Science ®Google Scholar
• Bhatt A, Mahon BP, Cruzeiro VW, et al. Structure-activity relationships of benzenesulfonamide-based inhibitors towards carbonic anhydrase isoform specificity. Chembiochem Eur J Chem Biol. 2017 Nov;18(18):213–222.
   PubMedGoogle Scholar
• Alterio V, Langella E, Viparelli F, et al. Structural and inhibition insights into carbonic anhydrase CDCA1 from the marine diatom Thalassiosira weissflogii. Biochimie. 2012 May;94(5):1232–1241.
   PubMed Web of Science ®Google Scholar
• Jensen EL, Clement R, Kosta A, et al. A new widespread subclass of carbonic anhydrase in marine phytoplankton. Isme J. 2019 Aug;13(8):2094–2106.
   PubMed Web of Science ®Google Scholar
• De Simone G, Di Fiore A, Capasso C, et al. The zinc coordination pattern in the eta-carbonic anhydrase from Plasmodium falciparum is different from all other carbonic anhydrase genetic families. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1385–1389.
   PubMed Web of Science ®Google Scholar
• Lomelino CL, Mahon BP, McKenna R, et al. Kinetic and X-ray crystallographic investigations on carbonic anhydrase isoforms I, II, IX and XII of a thioureido analog of SLC-0111. Bioorg Med Chem. 2016 Mar 1;24(5):976–981.
   PubMed Web of Science ®Google Scholar
• Fu X, Yu LJ, Mao-Teng L, et al. Evolution of structure in gamma-class carbonic anhydrase and structurally related proteins. Mol Phylogenet Evol. 2008 Apr;47(1):211–220.
   PubMed Web of Science ®Google Scholar
• D’Ambrosio K, Di Fiore A, Buonanno M, et al. Eta and Teta-carbonic anhydrases. London (UK): Elsevier; 2019. (Supuran CT, Nocentini A, editors. Carbonic Anhydrases. Biochemistry and Pharmacology of an Evergreen Pharmaceutical Target; Carbonic Anhydrases. Biochemistry and Pharmacology of an Evergreen Pharmaceutical Target)
   Google Scholar
• Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem. 2016;31(3):345–360.
   PubMed Web of Science ®Google Scholar
• Aspatwar A, Tolvanen ME, Ortutay C, et al. Carbonic anhydrase related proteins: molecular biology and evolution. Subcell Biochem. 2014;75:135–156.
   PubMedGoogle Scholar
• Supuran CT. Carbonic anhydrases as drug targets–an overview [Research support, Non-U.S. Gov’t review]. Curr Top Med Chem. 2007;7(9):825–833.
   PubMed Web of Science ®Google Scholar
• Perfetto R, Del Prete S, Vullo D, et al. Biochemical characterization of the native alpha-carbonic anhydrase purified from the mantle of the mediterranean mussel, mytilus galloprovincialis. J Enzyme Inhib Med Chem. 2017 Dec;32(1):632–639.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, Zoccola D, et al. Kinetic properties and affinities for sulfonamide inhibitors of an alpha-carbonic anhydrase (CruCA4) involved in coral biomineralization in the mediterranean red coral corallium rubrum. Bioorg Med Chem. 2017 Jul 01;25(13):3525–3530.
   PubMed Web of Science ®Google Scholar
• Capasso C, Supuran CT. Bacterial, fungal and protozoan carbonic anhydrases as drug targets. Expert Opin Ther Targets. 2015;19(12):1689–1704.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Capasso C. The eta-class carbonic anhydrases as drug targets for antimalarial agents. Expert Opin Ther Targets. 2015 Apr;19(4):551–563.
   PubMed Web of Science ®Google Scholar
• Capasso C, Supuran CT. Anti-infective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin Ther Pat. 2013;23(6):693–704.
   PubMed Web of Science ®Google Scholar
• Manchado E, Huang CH, Tasdemir N, et al. A pipeline for drug target identification and validation. Cold Spring Harb Symp Quant Biol. 2016;81:257–267.
   PubMedGoogle Scholar
• Capasso C, Supuran CT. Inhibition of bacterial carbonic anhydrases as a novel approach to escape drug resistance. Curr Top Med Chem. 2017;17(11):1237–1248.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibition and the management of neuropathic pain. Expert Rev Neurother. 2016 Aug;16(8):961–968.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Drug interaction considerations in the therapeutic use of carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol. 2016;12(4):423–431.
   PubMed Web of Science ®Google Scholar
• Otten H. Domagk and the development of the sulphonamides. J Antimicrob Chemother. 1986 Jun;17(6):689–696.
   PubMed Web of Science ®Google Scholar
• Achari A, Somers DO, Champness JN, et al. Crystal structure of the anti-bacterial sulfonamide drug target dihydropteroate synthase. Nat Struct Biol. 1997 Jun;4(6):490–497.
   PubMedGoogle Scholar
• Vullo D, Del Prete S, Fisher GM, et al. Sulfonamide inhibition studies of the eta-class carbonic anhydrase from the malaria pathogen plasmodium falciparum. Bioorg Med Chem. 2015 Feb 1;23(3):526–531.
   PubMed Web of Science ®Google Scholar
• Vullo D, De Luca V, Del Prete S, et al. Sulfonamide inhibition studies of the gamma-carbonic anhydrase from the antarctic bacterium pseudoalteromonas haloplanktis. Bioorg Med Chem Lett. 2015 Sep 1;25(17):3550–3555.
   PubMed Web of Science ®Google Scholar
• Vullo D, De Luca V, Del Prete S, et al. Sulfonamide inhibition studies of the gamma-carbonic anhydrase from the antarctic cyanobacterium nostoc commune. Bioorg Med Chem. 2015 Apr 15;23(8):1728–1734.
   PubMed Web of Science ®Google Scholar
• Dedeoglu N, DeLuca V, Isik S, et al. Sulfonamide inhibition study of the beta-class carbonic anhydrase from the caries producing pathogen Streptococcus mutans. Bioorg Med Chem Lett. 2015 Apr;17(25):2291–2297.
   Google Scholar
• Alafeefy AM, Ceruso M, Al-Tamimi AM, et al. Inhibition studies of quinazoline-sulfonamide derivatives against the gamma-CA (PgiCA) from the pathogenic bacterium, Porphyromonas gingivalis. J Enzyme Inhib Med Chem. 2015;30(4):592–596.
   PubMed Web of Science ®Google Scholar
• Alafeefy AM, Abdel-Aziz HA, Vullo D, et al. Inhibition of human carbonic anhydrase isozymes I, II, IX and XII with a new series of sulfonamides incorporating aroylhydrazone-, [1,2,4]triazolo[3,4-b][1,3,4]thiadiazinyl- or 2-(cyanophenylmethylene)-1,3,4-thiadiazol-3(2H)-yl moieties. J Enzyme Inhib Med Chem. 2015 Feb;30(1):52–56.
   PubMed Web of Science ®Google Scholar
• Diaz JR, Fernandez Baldo M, Echeverria G, et al. A substituted sulfonamide and its Co (II), Cu (II), and Zn (II) complexes as potential antifungal agents. J Enzyme Inhib Med Chem. 2016;31(sup2):51–62.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, De Luca V, et al. Comparison of the sulfonamide inhibition profiles of the alpha-, beta- and gamma-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae. Bioorg Med Chem Lett. 2016 Apr 15;26(8):1941–1946.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, De Luca V, et al. Cloning, expression, purification and sulfonamide inhibition profile of the complete domain of the eta-carbonic anhydrase from Plasmodium falciparum. Bioorg Med Chem Lett. 2016 Sep 1;26(17):4184–4190.
   PubMed Web of Science ®Google Scholar
• Abdel Gawad NM, Amin NH, Elsaadi MT, et al. Synthesis of 4-(thiazol-2-ylamino)-benzenesulfonamides with carbonic anhydrase I, II and IX inhibitory activity and cytotoxic effects against breast cancer cell lines. Bioorg Med Chem. 2016 Jul 01;24(13):3043–3051.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Legionella pneumophila carbonic anhydrases: underexplored antibacterial drug targets. Pathogens. 2016;5:44.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Vullo D, Minakuchi T, et al. Sulfonamide inhibition studies of two beta-carbonic anhydrases from the bacterial pathogen legionella pneumophila. Bioorg Med Chem. 2014 Jun 1;22(11):2939–2946.
   PubMed Web of Science ®Google Scholar
• Vullo D, Sai Kumar RS, Scozzafava A, et al. Anion inhibition studies of a beta-carbonic anhydrase from clostridium perfringens [Research support, Non-U.S. Gov’t]. Bioorg Med Chem Lett. 2013 Dec 15;23(24):6706–6710.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Minakuchi T, Maresca A, et al. The beta-carbonic anhydrases from Mycobacterium tuberculosis as drug targets. Curr Pharm Des. 2010;16(29):3300–3309.
   PubMed Web of Science ®Google Scholar
• Carta F, Maresca A, Covarrubias AS, et al. Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from mycobacterium tuberculosis, Rv3588c. Bioorg Med Chem Lett. 2009 Dec 1;19(23):6649–6654.
   PubMed Web of Science ®Google Scholar
• Nguyen K, Ahlawat R. Famotidine. Treasure Island (FL): StatPearls; 2020.
   Google Scholar
• Komiya T, Huang CH. Updates in the clinical development of epacadostat and other indoleamine 2,3-dioxygenase 1 inhibitors (IDO1) for human cancers. Front Oncol. 2018;8:423.
   PubMed Web of Science ®Google Scholar
• De Simone G, Supuran CT. (In)organic anions as carbonic anhydrase inhibitors. J Inorg Biochem. 2012 Jun;111:117–129.
   PubMed Web of Science ®Google Scholar
• Carta F, Aggarwal M, Maresca A, et al. Dithiocarbamates strongly inhibit carbonic anhydrases and show antiglaucoma action in vivo. J Med Chem. 2012 Feb 23;55(4):1721–1730.
   PubMed Web of Science ®Google Scholar
• Carta F, Aggarwal M, Maresca A, et al. Dithiocarbamates: a new class of carbonic anhydrase inhibitors. Crystallographic and kinetic investigations. Chem Comm. 2012 Feb 11;48(13):1868–1870.
   PubMed Web of Science ®Google Scholar
• Monti SM, Maresca A, Viparelli F, et al. Dithiocarbamates are strong inhibitors of the beta-class fungal carbonic anhydrases from cryptococcus neoformans, Candida albicans and Candida glabrata. Bioorg Med Chem Lett. 2012 Jan 15;22(2):859–862.
   PubMed Web of Science ®Google Scholar
• Maresca A, Carta F, Vullo D, et al. Dithiocarbamates strongly inhibit the beta-class carbonic anhydrases from mycobacterium tuberculosis. J Enzyme Inhib Med Chem. 2013 Apr;28(2):407–411.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Mastrolorenzo A, Supuran CT. Arylsulfonyl-N,N-dialkyl-dithiocarbamates as tumor cell growth inhibitors: novel agents targeting beta-tubulin? J Enzym Inhib. 2001 Jan;16(1):55–63.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Mastrolorenzo A, Supuran CT. Arylsulfonyl-N,N-diethyl-dithiocarbamates: a novel class of antitumor agents. Bioorg Med Chem Lett. 2000 Aug 21;10(16):1887–1891.
   PubMed Web of Science ®Google Scholar
• Innocenti A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of transmembrane isoforms IX, XII, and XIV with less investigated anions including trithiocarbonate and dithiocarbamate.Bioorg Med Chem Lett. 2010 Mar 1;20(5):1548–1550.
   Google Scholar
• McKenna R, Supuran CT. Carbonic anhydrase inhibitors drug design. Subcell Biochem. 2014;75:291–323.
   PubMedGoogle Scholar
• Adak AK, Leonov AP, Ding N, et al. Bishydrazide glycoconjugates for lectin recognition and capture of bacterial pathogens [Research Support, N.I.H., ExtramuralResearch support, U.S. Gov’t, Non-P.H.S.]. Bioconjug Chem. 2010 Nov 17;21(11):2065–2075.
   PubMed Web of Science ®Google Scholar
• Lomelino CL, Supuran CT, Non-Classical MR. Inhibition of Carbonic Anhydrase. Int J Mol Sci. 2016 Jul 16;17(7):1150.
   PubMed Web of Science ®Google Scholar
• Kusian B, Sultemeyer D, Bowien B. Carbonic anhydrase is essential for growth of ralstonia eutropha at ambient CO(2) concentrations. J Bacteriol. 2002 Sep;184(18):5018–5026.
   PubMed Web of Science ®Google Scholar
• Cronk JD, Endrizzi JA, Cronk MR, et al. Crystal structure of E. coli beta-carbonic anhydrase, an enzyme with an unusual pH-dependent activity. Protein Sci. 2001 May;10(5):911–922.
   PubMed Web of Science ®Google Scholar
• Merlin C, Masters M, McAteer S, et al. Why is carbonic anhydrase essential to escherichia coli? J Bacteriol. 2003 Nov;185(21):6415–6424.
   PubMed Web of Science ®Google Scholar
• Ueda K, Nishida H, Beppu T. Dispensabilities of carbonic anhydrase in proteobacteria. Int J Evol Biol. 2012;2012:324549.
   PubMedGoogle Scholar
• Modak JK, Tikhomirova A, Gorrell RJ, et al. Anti-helicobacter pylori activity of ethoxzolamide. J Enzyme Inhib Med Chem. 2019 Dec;34(1):1660–1667.
   PubMed Web of Science ®Google Scholar
• Ronci M, Del Prete S, Puca V, et al. Identification and characterization of the alpha-CA in the outer membrane vesicles produced by helicobacter pylori. J Enzyme Inhib Med Chem. 2019 Dec;34(1):189–195.
   PubMed Web of Science ®Google Scholar
• Buzas GM. [Helicobacter pylori – 2010]. Orv Hetil. 2010 Dec 5;151(49):2003–2010.
   PubMedGoogle Scholar
• Abuaita BH, Withey JH. Bicarbonate induces vibrio cholerae virulence gene expression by enhancing ToxT activity. Infect Immun. 2009 Sep;77(9):4111–4120.
   PubMed Web of Science ®Google Scholar
• Kohler S, Ouahrani-Bettache S, Winum JY. Brucella suis carbonic anhydrases and their inhibitors: towards alternative antibiotics? J Enzyme Inhib Med Chem. 2017 Dec;32(1):683–687.
   PubMed Web of Science ®Google Scholar
• Singh S, Supuran CT. 3D-QSAR CoMFA studies on sulfonamide inhibitors of the Rv3588c beta-carbonic anhydrase from mycobacterium tuberculosis and design of not yet synthesized new molecules. J Enzyme Inhib Med Chem. 2014 Jun;29(3):449–455.
   PubMed Web of Science ®Google Scholar
• Ceruso M, Vullo D, Scozzafava A, et al. Sulfonamides incorporating fluorine and 1,3,5-triazine moieties are effective inhibitors of three beta-class carbonic anhydrases from mycobacterium tuberculosis. J Enzyme Inhib Med Chem. 2014 Oct;29(5):686–689.
   PubMed Web of Science ®Google Scholar
• Rollenhagen C, Bumann D. Salmonella enterica highly expressed genes are disease specific. Infect Immun. 2006;74(3):1649–1660.
   PubMed Web of Science ®Google Scholar
• Lotlikar SR, Kayastha BB, Vullo D, et al. Pseudomonas aeruginosa β-carbonic anhydrase, psCA1, is required for calcium deposition and contributes to virulence. Cell calcium. 2019;84–101.
   Web of Science ®Google Scholar
• Del Prete S, De Luca V, Scozzafava A, et al. Biochemical properties of a new alpha-carbonic anhydrase from the human pathogenic bacterium, Vibrio cholerae. J Enzyme Inhib Med Chem. 2014 Feb;29(1):23–27.
   PubMed Web of Science ®Google Scholar
• Vullo D, Del Prete S, Di Fonzo P, et al. Comparison of the sulfonamide inhibition profiles of the beta- and gamma-carbonic anhydrases from the pathogenic bacterium burkholderia pseudomallei. Molecules. 2017 Mar 7;22(3). DOI:10.3390/molecules22030421
   Web of Science ®Google Scholar
• Del Prete S, Vullo D, Di Fonzo P, et al. Anion inhibition profiles of the gamma-carbonic anhydrase from the pathogenic bacterium burkholderia pseudomallei responsible of melioidosis and highly drug resistant to common antibiotics. Bioorg Med Chem. 2017 Jan 15;25(2):575–580.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Minakuchi T, Vullo D, et al. Inhibition studies of the beta-carbonic anhydrases from the bacterial pathogen salmonella enterica serovar typhimurium with sulfonamides and sulfamates. Bioorg Med Chem. 2011 Aug 15;19(16):5023–5030.
   PubMed Web of Science ®Google Scholar
• Vullo D, Nishimori I, Minakuchi T, et al. Inhibition studies with anions and small molecules of two novel beta-carbonic anhydrases from the bacterial pathogen salmonella enterica serovar typhimurium. Bioorg Med Chem Lett. 2011 Jun 15;21(12):3591–3595.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, De Luca V, et al. Biochemical characterization of recombinant beta-carbonic anhydrase (PgiCAb) identified in the genome of the oral pathogenic bacterium porphyromonas gingivalis. J Enzyme Inhib Med Chem. 2015 Jun;30(3):366–370.
   PubMed Web of Science ®Google Scholar
• Del Prete S, De Luca V, Vullo D, et al. Biochemical characterization of the gamma-carbonic anhydrase from the oral pathogen porphyromonas gingivalis, PgiCA. J Enzyme Inhib Med Chem. 2014 Aug;29(4):532–537.
   PubMed Web of Science ®Google Scholar
• He J, Li Y, Cao Y, et al. The oral microbiome diversity and its relation to human diseases. Folia Microbiol (Praha). 2015 Jan;60(1):69–80.
   PubMed Web of Science ®Google Scholar
• Wade WG. The oral microbiome in health and disease. Pharmacol. Res. 2013 Mar;69(1):137–143.
   PubMed Web of Science ®Google Scholar
• Lif Holgerson P, Ohman C, Ronnlund A, et al. Maturation of oral microbiota in children with or without dental caries. PloS One. 2015;10(5):e0128534.
   PubMed Web of Science ®Google Scholar
• Georgios A, Vassiliki T, Sotirios K. Acidogenicity and acidurance of dental plaque and saliva sediment from adults in relation to caries activity and chlorhexidine exposure. J Oral Microbiol. 2015;7:26197.
   PubMed Web of Science ®Google Scholar
• Dedeoglu N, DeLuca V, Isik S, et al. Sulfonamide inhibition study of the beta-class carbonic anhydrase from the caries producing pathogen streptococcus mutans. Bioorg Med Chem Lett. 2015 Jun 1;25(11):2291–2297.
   PubMed Web of Science ®Google Scholar
• Dedeoglu N, De Luca V, Isik S, et al. Cloning, characterization and anion inhibition study of a beta-class carbonic anhydrase from the caries producing pathogen Streptococcus mutans. Bioorg Med Chem. 2015 Jul 1;23(13):2995–3001.
   PubMed Web of Science ®Google Scholar
• Celli J, Zahrt TC. Mechanisms of Francisella tularensis intracellular pathogenesis. Cold Spring Harb Perspect Med. 2013 Apr 01;3(4):a010314.
   PubMed Web of Science ®Google Scholar
• Kinkead LC, Allen LA. Multifaceted effects of Francisella tularensis on human neutrophil function and lifespan. Immunol Rev. 2016 Sep;273(1):266–281.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, Osman SM, et al. Anion inhibitors of the beta-carbonic anhydrase from the pathogenic bacterium responsible of tularemia, Francisella tularensis. Bioorg Med Chem. 2017 Sep 1;25(17):4800–4804.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Perfetto R, Rossi M, et al. A one-step procedure for immobilising the thermostable carbonic anhydrase (SspCA) on the surface membrane of Escherichia coli. J Enzyme Inhib Med Chem. 2017 Dec;32(1):1120–1128.
   PubMed Web of Science ®Google Scholar
• Cordes LG, Wilkinson HW, Gorman GW, et al. Atypical legionella-like organisms: fastidious water-associated bacteria pathogenic for man. Lancet. 1979 Nov 3;2(8149):927–930.
   PubMed Web of Science ®Google Scholar
• Escoll P, Rolando M, Gomez-Valero L, et al. From amoeba to macrophages: exploring the molecular mechanisms of legionella pneumophila infection in both hosts. Curr Top Microbiol Immunol. 2013;376:1–34.
   PubMed Web of Science ®Google Scholar
• Backert S, Neddermann M, Maubach G, et al. Pathogenesis of Helicobacter pylori infection. Helicobacter. 2016 Sep;21(Suppl 1):19–25.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Onishi S, Takeuchi H, et al. The alpha and beta classes carbonic anhydrases from helicobacter pylori as novel drug targets. Curr Pharm Des. 2008;14(7):622–630.
   PubMed Web of Science ®Google Scholar
• Joseph P, Turtaut F, Ouahrani-Bettache S, et al. Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from brucella suis. J Med Chem. 2010 Mar 11;53(5):2277–2285.
   PubMed Web of Science ®Google Scholar
• Joseph P, Ouahrani-Bettache S, Montero JL, et al. A new beta-carbonic anhydrase from Brucella suis, its cloning, characterization, and inhibition with sulfonamides and sulfamates, leading to impaired pathogen growth. Bioorg Med Chem. 2011 Feb 1;19(3):1172–1178.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Isik S, Vullo D, et al. DNA cloning, characterization, and inhibition studies of an alpha-carbonic anhydrase from the pathogenic bacterium vibrio cholerae. J Med Chem. 2012 Dec 13;55(23):10742–10748.
   PubMed Web of Science ®Google Scholar
• Alafeefy AM, Ceruso M, Al-Tamimi AM, et al. Quinazoline-sulfonamides with potent inhibitory activity against the alpha-carbonic anhydrase from vibrio cholerae. Bioorg Med Chem. 2014 Oct 1;22(19):5133–5140.
   PubMed Web of Science ®Google Scholar
• Ceruso M, Del Prete S, Alothman Z, et al. Sulfonamides with potent inhibitory action and selectivity against the alpha-carbonic anhydrase from vibrio cholerae. ACS Med Chem Lett. 2014 Jul 10;5(7):826–830.
   PubMed Web of Science ®Google Scholar
• Angeli A, Abbas G, Del Prete S, et al. Acyl selenoureido benzensulfonamides show potent inhibitory activity against carbonic anhydrases from the pathogenic bacterium vibrio cholerae. Bioorg Chem. 2017 Dec;75:170–172.
   PubMed Web of Science ®Google Scholar
• De Vita D, Angeli A, Pandolfi F, et al. Inhibition of the alpha-carbonic anhydrase from vibrio cholerae with amides and sulfonamides incorporating imidazole moieties. J Enzyme Inhib Med Chem. 2017 Dec;32(1):798–804.
   PubMed Web of Science ®Google Scholar
• Angeli A, Abbas G, Del Prete S, et al. Selenides bearing benzenesulfonamide show potent inhibition activity against carbonic anhydrases from pathogenic bacteria vibrio cholerae and burkholderia pseudomallei. Bioorg Chem. 2018 Sep;79:319–322.
   PubMed Web of Science ®Google Scholar
• Bua S, Berrino E, Del Prete S, et al. Synthesis of novel benzenesulfamide derivatives with inhibitory activity against human cytosolic carbonic anhydrase I and II and vibrio cholerae alpha- and beta-class enzymes. J Enzyme Inhib Med Chem. 2018 Dec;33(1):1125–1136.
   PubMed Web of Science ®Google Scholar
• Bua S, Osman SM, Del Prete S, et al. Click-tailed benzenesulfonamides as potent bacterial carbonic anhydrase inhibitors for targeting mycobacterium tuberculosis and vibrio cholerae. Bioorg Chem. 2019 May;86:183–186.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, Di Fonzo P, et al. Sulfonamide inhibition profile of the gamma-carbonic anhydrase identified in the genome of the pathogenic bacterium burkholderia pseudomallei the etiological agent responsible of melioidosis. Bioorg Med Chem Lett. 2017 Feb 1;27(3):490–495.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, Di Fonzo P, et al. Comparison of the anion inhibition profiles of the beta- and gamma-carbonic anhydrases from the pathogenic bacterium burkholderia pseudomallei. Bioorg Med Chem. 2017 Mar 15;25(6):2010–2015.
   PubMed Web of Science ®Google Scholar
• Maresca A, Carta F, Vullo D, et al. Carbonic anhydrase inhibitors. Inhibition of the Rv1284 and Rv3273 beta-carbonic anhydrases from mycobacterium tuberculosis with diazenylbenzenesulfonamides. Bioorg Med Chem Lett. 2009 Sep 1;19(17):4929–4932.
   PubMed Web of Science ®Google Scholar
• Minakuchi T, Nishimori I, Vullo D, et al. Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from mycobacterium tuberculosis with sulfonamides and a sulfamate. J Med Chem. 2009 Apr 23;52(8):2226–2232.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Minakuchi T, Vullo D, et al. Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from mycobacterium tuberculosis. J Med Chem. 2009 May 14;52(9):3116–3120.
   PubMed Web of Science ®Google Scholar
• Wani TV, Bua S, Khude PS, et al. Evaluation of sulphonamide derivatives acting as inhibitors of human carbonic anhydrase isoforms I, II and mycobacterium tuberculosis beta-class enzyme Rv3273. J Enzyme Inhib Med Chem. 2018 Dec;33(1):962–971.
   PubMed Web of Science ®Google Scholar
• Maresca A, Vullo D, Scozzafava A, et al. Inhibition of the beta-class carbonic anhydrases from mycobacterium tuberculosis with carboxylic acids. J Enzyme Inhib Med Chem. 2013 Apr;28(2):392–396.
   PubMed Web of Science ®Google Scholar
• Prete SD, Vullo D, Osman SM, et al. Sulfonamide inhibition study of the carbonic anhydrases from the bacterial pathogen porphyromonas gingivalis: the beta-class (PgiCAb) versus the gamma-class (PgiCA) enzymes. Bioorg Med Chem. 2014 Sep 1;22(17):4537–4543.
   PubMed Web of Science ®Google Scholar
• Ceruso M, Del Prete S, AlOthman Z, et al. Synthesis of sulfonamides with effective inhibitory action against porphyromonas gingivalis gamma-carbonic anhydrase. Bioorg Med Chem Lett. 2014 Aug 15;24(16):4006–4010.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Vullo D, Minakuchi T, et al. Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from helicobacter pylori. Bioorg Med Chem Lett. 2006 Apr 15;16(8):2182–2188.
   PubMed Web of Science ®Google Scholar
• Modak JK, Liu YC, Machuca MA, et al. Structural basis for the inhibition of helicobacter pylori alpha-carbonic anhydrase by sulfonamides. PLoS One. 2015;10(5):e0127149.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Minakuchi T, Kohsaki T, et al. Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors. Bioorg Med Chem Lett. 2007 Jul 1;17(13):3585–3594.
   PubMed Web of Science ®Google Scholar
• Lotlikar SR, Kayastha BB, Vullo D, et al. Pseudomonas aeruginosa beta-carbonic anhydrase, psCA1, is required for calcium deposition and contributes to virulence. Cell Calcium. 2019 Dec;84:102080.
   PubMed Web of Science ®Google Scholar
• Vullo D, Nishimori I, Scozzafava A, et al. Inhibition studies of a beta-carbonic anhydrase from Brucella suis with a series of water soluble glycosyl sulfanilamides. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2178–2182.
   PubMed Web of Science ®Google Scholar
• Ombouma J, Vullo D, Kohler S, et al. N-glycosyl-N-hydroxysulfamides as potent inhibitors of Brucella suis carbonic anhydrases. J Enzyme Inhib Med Chem. 2015 Dec;30(6):1010–1012.
   PubMed Web of Science ®Google Scholar
• Monti SM, Meccariello A, Ceruso M, et al. Inhibition studies of Brucella suis beta-carbonic anhydrases with a series of 4-substituted pyridine-3-sulphonamides. J Enzyme Inhib Med Chem. 2018 Dec;33(1):255–259.
   PubMed Web of Science ®Google Scholar
• Del Prete S, De Luca V, Bua S, et al. The effect of substituted benzene-sulfonamides and clinically licensed drugs on the catalytic activity of CynT2, a carbonic anhydrase crucial for escherichia coli life cycle. Int J Mol Sci. 2020 Jun 11;21:11.
   Web of Science ®Google Scholar
• Del Prete S, Bua S, Supuran CT, et al. Escherichia coli γ-carbonic anhydrase: characterisation and effects of simple aromatic/heterocyclic sulphonamide inhibitors. J Enzyme Inhib Med Chem. 2020;35(1):1545–1554.
   PubMed Web of Science ®Google Scholar
• Vullo D, Isik S, Del Prete S, et al. Anion inhibition studies of the alpha-carbonic anhydrase from the pathogenic bacterium vibrio cholerae. Bioorg Med Chem Lett. 2013 Mar 15;23(6):1636–1638.
   PubMed Web of Science ®Google Scholar
• Vullo D, Del Prete S, De Luca V, et al. Anion inhibition studies of the beta-carbonic anhydrase from the pathogenic bacterium vibrio cholerae. Bioorg Med Chem Lett. 2016 Mar 1;26(5):1406–1410.
   PubMed Web of Science ®Google Scholar
• Vullo D, Del Prete S, Osman SM, et al. Anion inhibition study of the beta-class carbonic anhydrase (PgiCAb) from the oral pathogen porphyromonas gingivalis. Bioorg Med Chem Lett. 2014 Sep 15;24(18):4402–4406.
   PubMed Web of Science ®Google Scholar
• Del Prete S, Vullo D, De Luca V, et al. A highly catalytically active gamma-carbonic anhydrase from the pathogenic anaerobe porphyromonas gingivalis and its inhibition profile with anions and small molecules. Bioorg Med Chem Lett. 2013 Jul 15;23(14):4067–4071.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Vullo D, Minakuchi T, et al. Anion inhibition studies of two new beta-carbonic anhydrases from the bacterial pathogen legionella pneumophila. Bioorg Med Chem Lett. 2014;24(4):1127–1132.
   PubMed Web of Science ®Google Scholar
• Aspatwar A, Hammaren M, Parikka M, et al. In vitro inhibition of mycobacterium tuberculosis beta-carbonic anhydrase 3 with mono- and dithiocarbamates and evaluation of their toxicity using zebrafish developing embryos. J Enzyme Inhib Med Chem. 2020;35(1):65–71.
   PubMed Web of Science ®Google Scholar
• Aspatwar A, Kairys V, Rala S, et al. Mycobacterium tuberculosis beta-carbonic anhydrases: novel targets for developing antituberculosis drugs. Int J Mol Sci. 2019;20(20):5153.
   Web of Science ®Google Scholar
• Shahidzadeh R, Opekun A, Shiotani A, et al. Effect of the carbonic anhydrase inhibitor, acetazolamide, on helicobacter pylori infection in vivo: a pilot study. Helicobacter. 2005 Apr;10(2):136–138.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov. 2008;7(2):168–181.
   PubMed Web of Science ®Google Scholar
• Rahman MM, Tikhomirova A, Modak JK, et al. Antibacterial activity of ethoxzolamide against helicobacter pylori strains SS1 and 26695. Gut Pathog. 2020;12:20.
   PubMed Web of Science ®Google Scholar
• Kaur J, Cao X, Abutaleb NS, et al. Optimization of acetazolamide-based scaffold as potent inhibitors of vancomycin-resistant enterococcus. J Med Chem. 2020. in press. DOI:10.1021/acs.jmedchem.0c00734
   Web of Science ®Google Scholar
• Masereel B, Rolin S, Abbate F. Carbonic anhydrase inhibitors: anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties. J Med Chem. 2002;45(2):312–320.
   PubMed Web of Science ®Google Scholar
• Thiry A, Dogné JM, Supuran CT, et al. Carbonic anhydrase inhibitors as anticonvulsant agents. Curr Top Med Chem. 2007;7(9):855–864.
   PubMed Web of Science ®Google Scholar
• Thiry A, Dogné JM, Supuran CT, et al. Anticonvulsant sulfonamides/sulfamates/sulfamides with carbonic anhydrase inhibitory activity: drug design and mechanism of action. Curr Pharm Des. 2008;14(7):661–671.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Bacterial carbonic anhydrases as drug targets: toward novel antibiotics? Front Pharmacol. 2011;2:34.
   PubMed Web of Science ®Google Scholar