2,250
Views
19
CrossRef citations to date
0
Altmetric
Research Paper

Design, synthesis, in vitro inhibition and toxicological evaluation of human carbonic anhydrases I, II and IX inhibitors in 5-nitroimidazole series

ORCID Icon, , , , ORCID Icon, ORCID Icon, , ORCID Icon & ORCID Icon show all
Pages 109-117 | Received 27 Sep 2019, Accepted 22 Oct 2019, Published online: 05 Nov 2019

References

  • Aspatwar A, Haapanen S, Parkkila S. An update on the metabolic roles of carbonic anhydrases in the model Alga Chlamydomonas reinhardtii. Metabolites 2018;8:22.
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
  • Aspatwar A, Tolvanen ME, Ortutay C, Parkkila S. Carbonic anhydrase related proteins: molecular biology and evolution. Subcell Biochem 2014;75:135–56.
  • Alterio V, Di Fiore A, D'Ambrosio K, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev 2012;112:4421–68.
  • Gilmour KM. Perspectives on carbonic anhydrase. Comp Biochem Physiol A Mol Integr Physiol 2010;157:193–7.
  • Aggarwal M, Boone CD, Kondeti B, McKenna R. Structural annotation of human carbonic anhydrases. J Enzyme Inhib Med Chem 2013;28:267–77.
  • Sethi KK, Vullo D, Verma SM, et al. Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I II VII IX and XII with benzene sulfonamides incorporating 4567-tetrabromophthalimide moiety. Bioorg Med Chem 2013;21:5973–82.
  • Mboge MY, Mahon BP, Lamas N, et al. Structure activity study of carbonic anhydrase IX: selective inhibition with ureido-substituted benzenesulfonamides. Eur J Med Chem 2017;132:184–91.
  • Falsini M, Squarcialupi L, Catarzi D, et al. 3-Hydroxy-1H-quinazoline-24-dione as a new scaffold to develop potent and selective inhibitors of the tumor-associated carbonic anhydrases IX and XII. J Med Chem 2017;60:6428–39.
  • Liu K, Zhu HL. Nitroimidazoles as anti-tumor agents. Anticancer Agents Med Chem 2011;11:687–91.
  • Overgaard J, Overgaard M, Nielsen OS, et al. A comparative investigation of nimorazole and misonidazole as hypoxic radiosensitizers in a C3H mammary carcinoma in vivo. Br J Cancer 1982;46:904–11.
  • Supuran CT. Carbonic anhydrase inhibitors and activators for novel therapeutic applications. Future Med Chem 2011;3:1165–80.
  • Gourmelon A, Delrue N. Validation in support of internationally harmonised OECD Test Guidelines for assessing the safety of chemicals. Adv Exp Med Biol 2016;856:9–32.
  • Aspatwar A, Becker HM, Parvathaneni NK, et al. Nitroimidazole-based inhibitors DTP338 and DTP348 are safe for zebrafish embryos and efficiently inhibit the activity of human CA IX in Xenopus oocytes. J Enzyme Inhib Med Chem 2018;33:1064–73.
  • Aspatwar A, Hammaren M, Koskinen S, et al. beta-CA-specific inhibitor dithiocarbamate Fc14-584B: a novel antimycobacterial agent with potential to treat drug-resistant tuberculosis. J Enzyme Inhib Med Chem 2017;32:832–40.
  • Kazokaite J, Aspatwar A, Kairys V, et al. Fluorinated benzenesulfonamide anticancer inhibitors of carbonic anhydrase IX exhibit lower toxic effects on zebrafish embryonic development than ethoxzolamide. Drug Chem Toxicol 2017;40:309–19.
  • Rami M, Dubois L, Parvathaneni NK, et al. Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates. J Med Chem 2013;56:8512–20.
  • De Simone G, Langella E, Esposito D, et al. Insights into the binding mode of sulphamates and sulphamides to hCA II: crystallographic studies and binding free energy calculations. J Enzyme Inhib Med Chem 2017;32:1002–11.
  • Dubois LJ, Niemans R, van Kuijk SJ, et al. New ways to image and target tumour hypoxia and its molecular responses. Radiother Oncol 2015;116:352–7.
  • Supuran CT, Winum JY. Carbonic anhydrase IX inhibitors in cancer therapy: an update. Future Med Chem 2015;7:1407–14.
  • Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73.
  • Aspatwar A, Hammaren MM, Parikka M, Parkkila S. Rapid evaluation of toxicity of chemical compounds using zebrafish embryos. J Vis Exp 2019;150:e59315.
  • Ritz C, Baty F, Streibig JC, Gerhard D. Dose-response analysis using R. PLoS One 2015;10:e0146021.
  • Dubois L, Peeters SG, van Kuijk SJ, et al. Targeting carbonic anhydrase IX by nitroimidazole based sulfamides enhances the therapeutic effect of tumor irradiation: a new concept of dual targeting drugs. Radiother Oncol 2013;108:523–8.
  • Ernst IM, Palani K, Esatbeyoglu T, et al. Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin iberin and cheirolin. Pharmacol Res 2013;70:155–62.
  • Bonnet M, Hong CR, Gu Y, et al. Novel nitroimidazole alkylsulfonamides as hypoxic cell radiosensitisers. Bioorg Med Chem 2014;22:2123–32.