A. Scozzafava, C.T. Supuran / European Journal of Pharmaceutical Sciences 10 (2000) 29–41
41
anhydrase: X-ray crystallographic structure of the adduct of human
carbonic anhydrase II with the activator phenylalanine and the
inhibitor azide. Inorg. Chim. Acta 275/276, 295–300.
Briganti, F., Scozzafava, A., Supuran, C.T., 1999. Novel carbonic
anhydrase isozymes I, II and IV activators incorporating sulfonyl-
histamino moieties. Bioorg. Med. Chem. Lett. 9, 2043–2048.
Clare, B.W., Supuran, C.T., 1994. Carbonic anhydrase activators. 3.
Structure–activity correlations for a series of isozyme II activators. J.
Pharm. Sci. 83, 768–779.
Gao, J.M., Qiao, S., Whitesides, G.M., 1995. Increasing binding constants
of ligands to carbonic anhydrase by using ‘greasy tails’. J. Med. Chem.
38, 2292–2301.
Gao, J.M., Cheng, X.H., Chen, R.D., Sigal, G.B., Bruce, J.E., Schwartz,
B.L., Hofstadler, S.A., Anderson, G.A., Smith, R.D., Whitesides, G.M.,
1996. Screening derivatized peptide libraries for tight binding in-
hibitors to carbonic anhydrase II by electrospray ionization–mass
spectroscopy. J. Med. Chem. 39, 1949–1955.
Hewett-Emmett, D., 1999. Evolution and distribution of the carbonic
anhydrase gene families. In: Chegwidden, W.R. (Ed.), Carbonic
Anhydrase — New Horizons. Birkhauser, New York (in press).
Ilies, M.A., Banciu, M.D., Ilies, M., Chiraleu, F., Briganti, F., Scozzafava,
A., Supuran, C.T., 1997. Carbonic anhydrase activators. Part 17.
Synthesis and activation studies of a series of 1-(1,2,4-triazole-1H-3-
yl)-2,4,6-trisubstituted-pyridinium salts against isozymes I, II and IV.
Eur. J. Med. Chem. 32, 911–918.
Khalifah, R.G., Strader, D.J., Bryant, S.H., Gibson, S.M., 1977. Carbon-
13 nuclear magnetic resonance probe of active site ionization of
human carbonic anhydrase B. Biochemistry 16, 2241–2247.
Lindskog, S., 1997. Structure and mechanism of carbonic anhydrase.
Pharmacol. Ther. 74, 1–20.
Supuran, C.T., 1999a. Carbonic anhydrase inhibitors. Synthesis of
water-soluble, topically effective intraocular pressure lowering aro-
matic/heterocyclic sulfonamides containing cationic or anionic moi-
eties. Is the tail more important than the ring? J. Med. Chem. 42,
2641–2650.
Scozzafava, A., Briganti, F., Mincione, G., Menabuoni, L., Mincione, F.,
Supuran, C.T., 1999b. Carbonic anhydrase inhibitors. Synthesis of
water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-
lasting intraocular pressure-lowering properties via the topical route. J.
Med. Chem. 42, 3690–3700.
Sly, W.S., 1991. Carbonic anhydrase II deficiency syndrome: clinical
delineation, interpretation and implications. In: Dodgson, S.J., Tashian,
R.E., Gros, G., Carter, N.D. (Eds.), The Carbonic Anhydrases, Plenum
Press, New York, pp. 183–196.
Sly, W.S., Hu, P.Y., 1995. Human carbonic anhydrases and carbonic
anhydrase deficiencies. Annu. Rev. Biochem. 64, 375–401.
Supuran, C.T., 1994. Carbonic anhydrase inhibitors. In: Puscas, I. (Ed.),
Carbonic Anhydrase and Modulation of Physiologic and Pathologic
Processes in the Organism, Helicon, Timisoara, pp. 29–111.
Supuran, C.T., Puscas, I., 1994. Carbonic anhydrase activators. In:
Puscas, I. (Ed.), Carbonic Anhydrase and Modulation of Physiologic
and Pathologic Processes in the Organism, Helicon, Timisoara, pp.
113–146.
Supuran, C.T., Balaban, A.T., Cabildo, P., Claramunt, R.M., Lavandera,
J.L., Elguero, J., 1993. Carbonic anhydrase activators. VII. Isozyme II
activation by bis-azolylmethanes, -ethanes and related azoles. Biol.
Pharm. Bull. 16, 1236–1239.
Supuran, C.T., Conroy, C.W., Maren, T.H., 1996a. Carbonic anhydrase
inhibitors: synthesis and inhibitory properties of 1,3,4-thiadiazole-2,5-
bissulfonamide. Eur. J. Med. Chem. 31, 843–846.
Lindskog, S., Coleman, J.E., 1964. The catalytic mechanism of carbonic
anhydrase. Proc. Natl. Acad Sci. USA 70, 2505–2508.
Lindskog, S., Behravan, G., Engstrand, C., Forsman, C., Jonsson, B.H.,
Liang, Z., Ren, X., Xue, Y., 1991. Structure–function relations in
human carbonic anhydrase II as studied by site-directed mutagenesis.
Supuran, C.T., Claramunt, R.M., Lavandera, J.L., Elguero, J., 1996b.
Carbonic anhydrase activators. XV. A kinetic study of the interaction
of bovine isozyme with pyrazoles, bis- and tris-azolyl methanes. Biol.
Pharm. Bull. 19, 1417–1422.
Supuran, C.T., Barboiu, M., Luca, C., Pop, E., Brewster, M.E., Din-
culescu, A., 1996c. Carbonic anhydrase activators. Part 14. Synthesis
of mono and bis pyridinium salt derivatives of 2-amino-5-(2-amino-
ethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole and their
interaction with isozyme II. Eur. J. Med. Chem. 31, 597–606.
Supuran, C.T., Scozzafava, A., Ilies, M.A., Iorga, B., Cristea, T., Briganti,
F., Chiraleu, F., Banciu, M.D., 1998a. Carbonic anhydrase inhibitors.
Part 53. Synthesis of substituted-pyridinium derivatives of aromatic
sulfonamides: the first non-polymeric membrane-impermeable in-
hibitors with selectivity for isozyme IV. Eur. J. Med. Chem. 33,
577–595.
Supuran, C.T., Mincione, F., Scozzafava, A., Briganti, F., Mincione, G.,
Ilies, M.A., 1998b. Carbonic anhydrase inhibitors. Part 52. Metal
complexes of heterocyclic sulfonamides — A new class of strong
topical intraocular pressure-lowering agents in rabbits. Eur. J. Med.
Chem. 33, 247–254.
`
In: Botre, F., Gros, G., Storey, B.T. (Eds.), Carbonic Anhydrase —
From Biochemistry and Genetics To Physiology and Clinical Medi-
cine, VCH, Weinheim, pp. 1–13.
Maren, T.H., Wynns, G.C., Wistrand, P.J., 1993. Chemical properties of
carbonic anhydrase IV, the membrane-bound enzyme. Mol. Pharmacol.
44, 901–905.
Pocker, Y., Stone, J.T., 1967. The catalytic versatility of erythrocyte
carbonic anhydrase. III. Kinetic studies of the enzyme-catalyzed
hydrolysis of p-nitrophenyl acetate. Biochemistry 6, 668–678.
Raisz, L.G., Simmons, H.A., Thompson, W.J., Shepard, K.L., Anderson,
P.S., Rodan, G.A., 1988. Effects of a potent carbonic anhydrase
inhibitor on bone resorption in organ culture. Endocrinology 122,
1083–1086.
Reiss, W.G., Oles, K.S., 1996. Acetazolamide in the treatment of seizures.
Ann. Pharmacother. 30, 514–519.
Scozzafava, A., Supuran, C.T., 1999a. Carbonic anhydrase activators. Part
21. Novel activators of isozymes I, II and IV incorporating carbox-
amido- and ureido histamine moieties. Eur. J. Med. Chem. (in press).
Scozzafava, A., Supuran, C.T., 1999b. Carbonic anhydrase inhibitors.
Part 66. Arylsulfonylureido and arylureido-substituted aromatic and
heterocyclic sulfonamides: towards selective inhibitors of carbonic
anhydrase isozyme I. J. Enzyme Inhib. 14, 343–363.
Supuran, C.T., Scozzafava, A., Menabuoni, L., Mincione, F., Briganti, F.,
Mincione, G., 1999. Carbonic anhydrase inhibitors. Part 71. Synthesis
and ocular pharmacology of a new class of water-soluble, topically
effective intraocular pressure lowering sulfonamides incorporating
picolinoyl moieties. Eur. J. Pharm. Sci. 8, 317–328.
Steiner, H., Jonsson, B.H., Lindskog, S., 1975. The catalytic mechanism
of carbonic anhydrase. Hydrogen-isotope effects on the kinetic param-
eters of the human C isoenzyme. Eur. J. Biochem. 59, 253–259.
Scozzafava, A., Menabuoni, L., Mincione, F., Briganti, F., Mincione, G.,