Development of Praziquantel sulphonamide derivatives as antischistosomal drugs

References

• McManus DP, Dunne DW, Sacko M, et al. Schistosomiasis. Nat Rev Dis Primers 2018;4:1479.
   Web of Science ®Google Scholar
• Caffrey CR. Schistosomiasis and its treatment. Future Med Chem 2015;7:675–6.
   PubMed Web of Science ®Google Scholar
• Lago EM, Xavier RP, Teixeira TR, et al. Antischistosomal agents: state of art and perspectives. Future Med Chem 2018;10:89–120.
   PubMed Web of Science ®Google Scholar
• World Health Organization. Ending the neglect to attain the Sustainable Development Goals − a road map for neglected tropical diseases 2021 − 2030. World Health Organization: Geneva; 2020.
   Google Scholar
• Barsoum RS, Esmat G, El-Baz T. Human schistosomiasis: clinical perspective: review. J Adv Res 2013;4:433–44.
   PubMedGoogle Scholar
• Monti L, Cornec AS, Oukoloff K, et al. Congeners derived from microtubule-active phenylpyrimidines produce a potent and long-lasting paralysis of schistosoma mansoni in vitro. ACS Infect Dis 2021;7:1089–103.
   PubMed Web of Science ®Google Scholar
• Meyer T, Sekljic H, Fuchs S, et al. Taste, a new incentive to switch to (R)-praziquantel in schistosomiasis treatment. PLoS Negl Trop Dis 2009;3:e357.
   PubMed Web of Science ®Google Scholar
• Andrews P, Thomas H, Pohlke R, Seubert J. Praziquantel. Med Res Rev 1983;3:147–200.
   PubMed Web of Science ®Google Scholar
• Gray DJ, McManus DP, Li Y, et al. Schistosomiasis elimination: lessons from the past guide the future. Lancet Infect Dis 2010;10:733–6.
   PubMed Web of Science ®Google Scholar
• Sabah AA, Fletcher C, Webbe G, Doenhoff MJ. Schistosoma mansoni: chemotherapy of infections of different ages. Exp Parasitol 1986;61:294–303.
   PubMed Web of Science ®Google Scholar
• Wang W, Wang L, Liang YS. Susceptibility or resistance of praziquantel in human schistosomiasis: a review. Parasitol Res 2012;111:1871–7.
   PubMed Web of Science ®Google Scholar
• Doenhoff MJ, Cioli D, Utzinger J. Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis 2008;21:659–67.
   PubMed Web of Science ®Google Scholar
• Melman SD, Steinauer ML, Cunningham C, et al. Reduced susceptibility to praziquantel among naturally occurring Kenyan isolates of Schistosoma mansoni. PLoS Negl Trop Dis 2009;3:e504.
   PubMed Web of Science ®Google Scholar
• Da'dara AA, Angeli A, Ferraroni M, et al. Crystal structure and chemical inhibition of essential schistosome host-interactive virulence factor carbonic anhydrase SmCA. Commun Biol 2019;2:333.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Capasso C. An overview of the bacterial carbonic anhydrases. Metabolites 2017;7:56.
   PubMed Web of Science ®Google Scholar
• Mishra CB, Tiwari M, Supuran CT. Progress in the development of human carbonic anhydrase inhibitors and their pharmacological applications: where are we today? Med Res Rev 2020;40:2485–565.
   PubMed Web of Science ®Google Scholar
• Angeli A, Ferraroni M, Da’dara AA, et al. Structural insights into Schistosoma mansoni carbonic anhydrase (SmCA) inhibition by selenoureido-substituted benzenesulfonamides. J Med Chem 2021;64:10418–28.
   PubMed Web of Science ®Google Scholar
• Angeli A, Pinteala M, Maier SS, et al. Sulfonamide inhibition studies of an α-carbonic anhydrase from Schistosoma mansoni, a platyhelminth parasite responsible for schistosomiasis. Int J Mol Sci 2020;21:1842.
   PubMed Web of Science ®Google Scholar
• Thomas CM, Timson DJ. The mechanism of action of praziquantel: can new drugs exploit similar mechanisms? Curr Med Chem 2020;27:676–96.
   PubMed Web of Science ®Google Scholar
• Park SK, Friedrich L, Yahya NA, et al. Mechanism of praziquantel action at a parasitic flatworm ion channel. Sci Transl Med 2021;13:eabj5832.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Tanini D, Carradori S, Capperucci A, et al. Chalcogenides-incorporating carbonic anhydrase inhibitors concomitantly reverted oxaliplatin-induced neuropathy and enhanced antiproliferative action. Eur J Med Chem 2021;225:113793.
   PubMed Web of Science ®Google Scholar
• Xiao SH, Catto BA, Webster LT, Jr. Effects of praziquantel on different developmental stages of Schistosoma mansoni in vitro and in vivo. J Infect Dis 1985;151:1130–7.
   PubMed Web of Science ®Google Scholar
• Angeli A, Etxebeste-Mitxeltorena M, Sanmartín C, et al. Tellurides bearing sulfonamides as novel inhibitors of leishmanial carbonic anhydrase with potent antileishmanial activity. J Med Chem 2020;63:4306–14.
   PubMed Web of Science ®Google Scholar
• Llanos MA, Sbaraglini ML, Villalba ML, et al. A structure-based approach towards the identification of novel antichagasic compounds: Trypanosoma cruzi carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2020;35:21–30.
   PubMed Web of Science ®Google Scholar
• Angeli A, Di Cesare Mannelli L, Lucarini E, et al. Design, synthesis and X-ray crystallography of selenides bearing benzenesulfonamide moiety with neuropathic pain modulating effects. Eur J Med Chem 2018;154:210–9.
   PubMed Web of Science ®Google Scholar
• Gul HI, Yamali C, Bulbuller M, et al. Anticancer effects of new dibenzenesulfonamides by inducing apoptosis and autophagy pathways and their carbonic anhydrase inhibitory effects on hCA I, hCA II, hCA IX, hCA XII isoenzymes. Bioorg Chem 2018;78:290–7.
   PubMed Web of Science ®Google Scholar
• Leslie AGW, Powell HR, Procesing diffraction data with mosflm. In: Read RJ, Sussman JL, eds. Evolving methods for macromolecular crystallography, vol 245. Dordrecht: NATO Science series, Springer; 2007:41–51.
   Google Scholar
• Murshudov GN, Vagin AA, Dodson EJ. Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr D Biol Crystallogr 1997;53:240–55.
   PubMed Web of Science ®Google Scholar
• Emsley P, Lohkamp B, Scott W, Cowtan K. Features and development of Coot. Acta Crystallogr D Biol Crystallogr 2010;66:486–501.
   PubMed Web of Science ®Google Scholar
• Lovell SC, Davis IW, Arendall WB, III, et al. Structure validation by Cα geometry: ϕ,ψ and Cβ deviation. Proteins 2003;50:437–50.
   PubMed Web of Science ®Google Scholar
• Pettersen EF, Goddard TD, Huang CC, et al. UCSF Chimera-a visualization system for exploratory research and analysis. J Comput Chem 2004;25:1605–12.
   PubMed Web of Science ®Google Scholar
• Lombardo FC, Pasche V, Panic G, et al. Life cycle maintenance and drug-sensitivity assays for early drug discovery in Schistosoma mansoni. Nat Protoc 2019;14:461–81.
   PubMed Web of Science ®Google Scholar