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Retina

Vasodilation of Pre-contracted Porcine Retinal Arteries by Carbonic Anhydrase Inhibitors with Enhanced Lipophilicity

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Pages 1615-1621 | Received 10 Jul 2022, Accepted 14 Sep 2022, Published online: 11 Oct 2022

References

  • Supuran CT. Structure and function of carbonic anhydrases. Biochem J. 2016;473(14):2023–2032. doi:10.1042/BCJ20160115.
  • Alterio V, Di Fiore A, D'Ambrosio K, Supuran CT, De Simone G. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev. 2012;112(8):4421–4468. doi:10.1021/cr200176r.
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov. 2008;7(2):168–181. doi:10.1038/nrd2467.
  • Sugrue MF. Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Prog Retin Eye Res. 2000;19(1):87–112. doi:10.1016/S1350-9462(99)00006-3.
  • Wolfensberger TJ. The role of carbonic anhydrase inhibitors in the management of macular edema. Doc Ophthalmol. 1999;97(3-4):387–397.
  • Harris A, Arend O, Kagemann L, Garrett M, Chung HS, Martin B. Dorzolamide, visual function and ocular hemodynamics in normal-tension glaucoma. J Ocul Pharmacol Ther. 1999;15(3):189–197. doi:10.1089/jop.1999.15.189.
  • Martinez A, Gonzalez F, Capeans C, Perez R, Sanchez-Salorio M. Dorzolamide effect on ocular blood flow. Invest Ophthalmol Vis Sci. 1999;40(6):1270–1275.
  • Stefansson E, Jensen PK, Eysteinsson T, Bang K, Kiilgaard JF, Dollerup J, Scherfig E, la Cour M. Optic nerve oxygen tension in pigs and the effect of carbonic anhydrase inhibitors. Invest Ophthalmol Vis Sci. 1999;40(11):2756–2761.
  • Stefansson E, Pedersen DB, Jensen PK, la Cour M, Kiilgaard JF, Bang K, Eysteinsson T. Optic nerve oxygenation. Prog Retin Eye Res. 2005;24(3):307–332. doi:10.1016/j.preteyeres.2004.09.001.
  • Josefsson A, Sigurdsson SB, Bang K, Eysteinsson T. Dorzolamide induces vasodilatation in isolated pre-contracted bovine retinal arteries. Exp Eye Res. 2004;78(2):215–221. doi:10.1016/j.exer.2003.11.010.
  • Kehler AK, Holmgaard K, Hessellund A, Aalkjaer C, Bek T. Variable involvement of the perivascular retinal tissue in carbonic anhydrase inhibitor induced relaxation of porcine retinal arterioles in vitro. Invest Ophthalmol Vis Sci. 2007;48(10):4688–4693. doi:10.1167/iovs.07-0048.
  • El-Galaly A, Aalkjaer C, Kringelholt SK, Misfeldt MW, Bek T. Dorzolamide-induced relaxation of porcine retinal arterioles in vitro depends on nitric oxide but not on acidosis in vascular smooth muscle cells. Exp Eye Res. 2014;128(:67–72. doi:10.1016/j.exer.2014.09.006.
  • Eysteinsson T, Gudmundsdottir H, Hardarson AO, Berrino E, Selleri S, Supuran CT, Carta F. Carbonic anhydrase inhibitors of different structures dilate pre-contracted porcine retinal arteries. Int J Mol Sci. 2019;20(3):467. doi:10.3390/ijms20030467.
  • Tsikas D, Gambaryan S. Nitrous anhydrase activity of carbonic anhydrase II: cysteine is required for nitric oxide (NO) dependent phosphorylation of VASP in human platelets. J Enzyme Inhib Med Chem. 2021;36(1):525–534. doi:10.1080/14756366.2021.1874946.
  • Tsikas D. Comment on the article structure and mechanism of copper-carbonic anhydrase II: a nitrite reductase. IUCrJ. 2021;8(Pt 2):327–328. doi:10.1107/S2052252520016644.
  • Angeli A, Carta F, Bartolucci G, Supuran CT. Synthesis of novel acyl selenoureido benzensulfonamides as carbonic anhydrase I, II, VII and IX inhibitors. Bioorg Med Chem. 2017;25(13):3567–3573. doi:10.1016/j.bmc.2017.05.014.
  • Angeli A, Tanini D, Peat TS, Di Cesare Mannelli L, Bartolucci G, Capperucci A, Ghelardini C, Supuran CT, Carta F. Discovery of new selenoureido analogues of 4-(4-fluorophenylureido)benzenesulfonamide as carbonic anhydrase inhibitors. ACS Med Chem Lett. 2017;8(9):963–968. doi:10.1021/acsmedchemlett.7b00280.
  • Angeli A, di Cesare Mannelli L, Trallori E, Peat TS, Ghelardini C, Carta F, Supuran CT. Design, synthesis, and X-ray of selenides as new class of agents for prevention of diabetic cerebrovascular pathology. ACS Med Chem Lett. 2018;9(5):462–467. doi:10.1021/acsmedchemlett.8b00076.
  • Angeli A, di Cesare Mannelli L, Lucarini E, Peat TS, Ghelardini C, Supuran CT. Design, synthesis and X-ray crystallography of selenides bearing benzenesulfonamide moiety with neuropathic pain modulating effects. Eur J Med Chem. 2018;154:210–219. doi:10.1016/j.ejmech.2018.05.026.
  • Angeli A, Tanini D, Capperucci A, Malevolti G, Turco F, Ferraroni M, Supuran CT. Synthesis of different thio-scaffolds bearing sulfonamide with subnanomolar carbonic anhydrase ii and ix inhibitory properties and X-ray investigations for their inhibitory mechanism. Bioorg Chem. 2018;81:642–648. doi:10.1016/j.bioorg.2018.09.028.
  • 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(8):2561–2573. doi:10.1016/S0021-9258(18)62326-9.
  • Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT. New chemotypes acting as isozyme-selective carbonic anhydrase inhibitors with low affinity for the offtarget cytosolic isoform II. Bioorg Med Chem Lett. 2012;22(6):2182–2185. doi:10.1016/j.bmcl.2012.01.129.
  • Carta F, Maresca A, Scozzafava A, Supuran CT. 5- and 6-membered (thio)lactones are prodrug type carbonic anhydrase inhibitors. Bioorg Med Chem Lett. 2012;22(1):267–270. doi:10.1016/j.bmcl.2011.11.018.
  • Daina A, Michielin O, Zoete V. Swissadme: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 2017;7:42717. doi:10.1038/srep42717.
  • Leeson PD, Springthorpe B. The influence of drug-like concepts on decision-making in medicinal chemistry. Nat Rev Drug Discov. 2007;6(11):881–890. doi:10.1038/nrd2445.
  • Rassam SM, Patel V, Kohner EM. The effect of acetazolamide on the retinal circulation. Eye. 1993;7 (5):697–702. doi:10.1038/eye.1993.159.
  • la Cour M, Kiilgaard JF, Eysteinsson T, Wiencke AK, Bang K, Dollerup J, Jensen PK, Stefánsson E. Optic nerve oxygen tension: effects of intraocular pressure and dorzolamide. Br J Ophthalmol. 2000;84(9):1045–1049. doi:10.1136/bjo.84.9.1045.

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