Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II

References

• (a) Kolker AE. Visual prognosis in advanced glaucoma: a comparison of medical and surgical therapy for retention of vision in 101 eyes with advanced glaucoma. Trans Am Ophthalmol Soc 1977;75:539–45.
   PubMedGoogle Scholar
  (b) Werner EB, Drance SM, Schulzer M. Trabeculectomy and the progression of glaucomatous visual field loss. Arch Ophthalmol 1977;95:1374–7.
   PubMedGoogle Scholar
• Wiederholt M, Bielka S, Schweig F, et al. Regulation of outflow rate and resistance in the perfused anterior segment of the bovine eye. Exp Eye Res 1995;61:223–34.
   PubMed Web of Science ®Google Scholar
• Krupin T, Wax M, Moolchandani J. Aqueous production. Trans Ophthalmol Soc UK 1986;105:156–61.
   PubMedGoogle Scholar
• Mincione F, Scozzafava A, Supuran CT. The development of topically carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des 2008;14:649–54.
   PubMed Web of Science ®Google Scholar
• (a) 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
  (b) Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors and their therapeutic potential. Exp Opin Ther Pat 2000;10:575–600.
   Web of Science ®Google Scholar
• Bartlett JD, Jaanus SD. Clinical ocular pharmacology. Boston, MA: Butterworth, 1989:254–63.
   Google Scholar
• Supuran CT, Altamimi ASA, Carta F. Carbonic anhydrase inhibition and the management of glaucoma: a literature and patent review 2013–2019. Exp Opin Ther Pat 2019;29:781–92.
   PubMed Web of Science ®Google Scholar
• Supuran CT. The management of glaucoma and macular degeneration. Exp Opin Ther Pat 2019;29:745–7.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT, Berrino E. Rho-kinase inhibitors in the management of glaucoma. Exp Opin Ther Pat 2019;29:817–27.
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT, Bua S. Diagnostic markers for glaucoma: a patent and literature review (2013–2019). Exp Opin Ther Pat 2019;29:829–39.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT, Nocentini A. Adrenergic agonists and antagonists as antiglaucoma agents: a literature and patent review (2013–2019). Exp Opin Ther Pat 2019;29:805–15.
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT, Angeli A. Prostaglandin receptor agonists as antiglaucoma agents (a patent review 2013–2018). Exp Opin Ther Pat 2019;29:793–803.
   PubMed Web of Science ®Google Scholar
• (a) Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–89.
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors and their therapeutic potential. Exp Opin Ther Patents 2000;10:575–601.
   Web of Science ®Google Scholar
  (c) Supuran CT, Scozzafava A. Applications of carbonic anhydrase inhibitors and activators in therapy. Exp Opin Ther Patents 2002;12:217–42.
   Web of Science ®Google Scholar
• Casini A, Scozzafava A, Mincione F, et al. Carbonic anhydrase inhibitors: water-soluble 4-sulfamoylphenylthioureas as topical intraocular pressure-lowering agents with long-lasting effects. J Med Chem 2000;43:4884–92.
   PubMed Web of Science ®Google Scholar
• Maren TH. Role of carbonic anhydrase in aqueous humor and cerebrospinal fluid formation. In: Segal MB, ed. Barriers and fluids of the eye and brain. London: MacMillan Press; 1992:37–48.
   Google Scholar
• (a) Supuran CT. Carbonic anhydrase inhibitors and their potential in a range of therapeutic areas. Exp Opin Ther Pat 2018;28:709–12.
   PubMed Web of Science ®Google Scholar
  (b) Supuran CT. Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Exp Opin Drug Discov 2017;12:61–88.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Menabuoni L, Mincione F, et al. Carbonic anhydrase inhibitors. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring? J Med Chem 1999;42:2641–50.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Briganti F, Mincione G, et al. Carbonic anhydrase inhibitors: synthesis of water-soluble, amino acyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J Med Chem 1999;42:3690–700.
   PubMed Web of Science ®Google Scholar
• Borras J, Scozzafava A, Menabuoni L, et al. Carbonic anhydrase inhibitors: synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: is the tail more important than the ring? Bioorg Med Chem 1999;7:2397–406.
   PubMed Web of Science ®Google Scholar
• Renzi G, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: topical sulfonamide antiglaucoma agents incorporating secondary amine moieties. Bioorg Med Chem Lett 2000;10:673–6.
   PubMed Web of Science ®Google Scholar
• (a) Ilies M, Supuran CT, Scozzafava A, et al. Carbonic anhydrase inhibitors. Sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions. Bioorg Med Chem 2000;8:2145–55.
   PubMed Web of Science ®Google Scholar
  (b) Winum JY, Casini A, Mincione F, et al. Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-α-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg Med Chem Lett 2004;14:225–9.
   PubMed Web of Science ®Google Scholar
• Wei GF, Cui SS, Luan WJ, et al. Natural product-based design, synthesis and biological evaluation of Albiziabioside A derivatives that selectively induce HCT116 cell death. Eur J Med Chem 2016;113:92–101.
   PubMed Web of Science ®Google Scholar
• Krauss AHP, Impagnatiello F, Toris CB, et al. Ocular hypotensive activity of BOL-303259-X, a nitric oxide donating prostaglandin F2α agonist, in preclinical models. Exp Eye Res 2011;93:250–5.
   PubMed Web of Science ®Google Scholar
• Fabrizi F, Mincione F, Somma T, et al. A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J Enzyme Inhib Med Chem 2012;27:138–47.
   PubMed Web of Science ®Google Scholar
• Masini E, Carta F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors: a patent review. Exp Opin Ther Pat 2013;23:705–16.
   PubMed Web of Science ®Google Scholar
• Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–9.
   PubMed Web of Science ®Google Scholar
• Truppo E, Supuran CT, Sandomenico A, et al. Carbonic anhydrase VII is glutathionylated without loss of catalytic activity and affinity for sulfonamide inhibitors. Bioorg Med Chem Lett 2012;22:1560–4.
   PubMed Web of Science ®Google Scholar