A new approach to antiglaucoma drugs: Carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 1, 2012, Pages 138-147

  Fabrizi, Francesca ^a   Mincione, Francesco ^b   Somma, Teresa ^a   Scozzafava, Gabriele ^c   Galassi, Fernando ^a   Masini, Emanuela ^a   Impagnatiello, Francesco ^d   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b Ospedale di Pescia   (Italy)

^c Dipartimento di Economia Ingegneria   (Italy)

^d NicOx Research Institute   (Italy)

Author keywords

Carbomer; Carbonic anhydrase; Dorzolamide; Glaucoma; Intraocular pressure; NO donor; Sulfonamide

Indexed keywords

ANTIGLAUCOMA AGENT; CARBONATE DEHYDRATASE INHIBITOR; CYCLIC AMP; CYCLIC GMP; DORZOLAMIDE; INTERLEUKIN 1BETA; ISOSORBIDE MONONITRATE; NCX 250; NITRATE; NITRIC OXIDE; NITRIC OXIDE DONOR; NITRITE; PROSTAGLANDIN E2; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; GLAUCOMA; HEMODYNAMICS; INTRAOCULAR PRESSURE; MALE; NONHUMAN; OPTIC NERVE; PRIORITY JOURNAL; RABBIT; VASCULARIZATION;

ACRYLIC RESINS; ANIMALS; CARBONIC ANHYDRASES; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; GLAUCOMA; ISOSORBIDE DINITRATE; MALE; MOLECULAR STRUCTURE; NITRATES; NITRIC OXIDE; RABBITS; SULFONAMIDES; THIOPHENES; TIME FACTORS;

ANIMALIA; ORYCTOLAGUS CUNICULUS;

EID: 84855408335     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.597749     Document Type: Article

References (27)

1. Quigley HA, Nickells RW, Kerrigan LA, Pease ME, Thibault DJ, Zack DJ. Retinal ganglion cell death in experimental glaucoma and after axotomy occurs by apoptosis. Invest Ophthalmol Vis Sci 1995;36:774-786.
2. Mincione F, Scozzafava A, Supuran CT. (2009). Antiglaucoma carbonic anhydrase inhibitors as ophthalomologic drugs. In: Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications;, Supuran CT; Winum JY Eds., Wiley, Hoboken (NJ), pp 139-154.
3. Galassi F, Masini E, Giambene B, Fabrizi F, Uliva C, Bolla M et al. A topical nitric oxide-releasing dexamethasone derivative: effects on intraocular pressure and ocular haemodynamics in a rabbit glaucoma model. Br J Ophthalmol 2006;90:1414-1419. (Pubitemid 44702072)
4. Impagnatiello F, Borghi V, Gale DC, Batugo M, Guzzetta M, Brambilla S et al. A dual acting compound with latanoprost amide and nitric oxide releasing properties, shows ocular hypotensive effects in rabbits and dogs. Exp Eye Res 2011 (Epub ahead of print).
5. Krauss AH, Impagnatiello F, Toris CB, Gale DC, Prasanna G, Borghi V et al. Ocular hypotensive activity of BOL-303259-X, a nitric oxide donating Prostaglandin F2a agonist, in preclinical models. Exp Eye Res (In Press).
6. Steele RM, Benedini F, Biondi S, Borghi V, Carzaniga L, Impagnatiello F et al. Nitric oxide-donating carbonic anhydrase inhibitors for the treatment of open-angle glaucoma. Bioorg Med Chem Lett 2009;19:6565-6570.
7. Mincione F, Benedini F, Biondi S, Cecchi A, Temperini C, Formicola G et al. Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action. Bioorg Med Chem Lett 2011;21:3216-3221.
8. Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem 2004;19:199-229. (Pubitemid 39004275)
9. Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146-189. (Pubitemid 36241096)
10. Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-181. (Pubitemid 351194064)
11. Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467-3474.
12. Mincione F, Scozzafava A, Supuran CT. The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents. Curr Top Med Chem 2007;7:849-854. (Pubitemid 46825081)
13. Xu Y, Chen Z, Song J. [A study of experimental carbomer glaucoma and other experimental glaucoma in rabbits]. Zhonghua Yan Ke Za Zhi 2002;38:172-175.
14. Perrino E, Uliva C, Lanzi C, Soldato PD, Masini E, Sparatore A. New prostaglandin derivative for glaucoma treatment. Bioorg Med Chem Lett 2009;19:1639-1642.
15. de Leval X, Ilies M, Casini A, Dogné JM, Scozzafava A, Masini E et al. Carbonic anhydrase inhibitors: synthesis and topical intraocular pressure lowering effects of fluorine-containing inhibitors devoid of enhanced reactivity. j Med Chem 2004;47:2796-2804. (Pubitemid 38656732)
16. Scozzafava A, Menabuoni L, Mincione F, Supuran CT. Carbonic anhydrase inhibitors. A general approach for the preparation of water-soluble sulfonamides incorporating polyaminopolycarboxylate tails and of their metal complexes possessing longlasting, topical intraocular pressure-lowering properties. J Med Chem 2002;45:1466-1476. (Pubitemid 34246110)
17. Sharon R. Draize test-motivations for change. Food Chem Toxicol 1985; 23:139-143.
18. Masini E, Nistri S, Vannacci A, Bani Sacchi T, Novelli A, Bani D. Relaxin inhibits the activation of human neutrophils: involvement of the nitric oxide pathway. Endocrinology 2004;145:1106-1112. (Pubitemid 38280989)
19. Bani D, Masini E, Bello MG, Bigazzi M, Sacchi TB. Relaxin activates the L-arginine-nitric oxide pathway in human breast cancer cells. Cancer Res 1995;55:5272-5275.
20. Harper JF, Brooker G. Femtomole sensitive radioimmunoassay for cyclic AMP and cyclic GMP after 2'0 acetylation by acetic anhydride in aqueous solution. J Cyclic Nucleotide Res 1975;1:207-218.
21. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of proteindye binding. Anal Biochem 1976;72:248-254.
22. 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;246:2561-2573.
23. Davies NM, Farr SJ, Hadgraft J, Kellaway IW. Evaluation of mucoadhesive polymers in ocular drug delivery. I. Viscous solutions. Pharm Res 1991;8:1039-1043.
24. Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastoreková S et al. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? Bioorg Med Chem Lett 2005;15:963-969. (Pubitemid 40458631)
25. Liao SY, Ivanov S, Ivanova A, Ghosh S, Cote MA, Keefe K et al. Expression of cell surface transmembrane carbonic anhydrase genes CA9 and CA12 in the human eye: overexpression of CA12 (CAXII) in glaucoma. J Med Genet 2003;40:257-261. (Pubitemid 36506438)
26. Thyelefors B, Negrel AD. The global impact of glaucoma, Bulletin of the World Health Organization, 1994.
27. Koleva D. Medical costs of glaucoma and ocular hypertension in italian referral centres: a prospective study, Ophthalmologica 2007; 221:340-347. (Pubitemid 47339658)