메뉴 건너뛰기




Volumn 10, Issue 1, 2000, Pages 29-41

Carbonic anhydrase activators: Part 24. High affinity isozymes I, II and IV activators, derivatives of 4-(4-chlorophenylsulfonylureido-amino acyl)ethyl-1H-imidazole

Author keywords

4 Chlorophenylsulfonyl isocyanate; Amino acid; Carbonic anhydrase; Enzyme activators; Histamine; Sulfonylureas

Indexed keywords

AMINO ACID; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; ENZYME ACTIVATOR; HISTAMINE; SULFONAMIDE; SULFONYLUREA DERIVATIVE;

EID: 0034047082     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0928-0987(99)00086-X     Document Type: Article
Times cited : (34)

References (35)
  • 1
    • 0027400041 scopus 로고
    • Use of affinity capillary electrophoresis to determine kinetic and equilibrium constants for binding of arylsulfonamides to bovine carbonic anhydrase
    • Avila L.Z., Chu Y.H., Blossey E.C., Whitesides G.M. Use of affinity capillary electrophoresis to determine kinetic and equilibrium constants for binding of arylsulfonamides to bovine carbonic anhydrase. J. Med. Chem. 36:1993;126-133.
    • (1993) J. Med. Chem. , vol.36 , pp. 126-133
    • Avila, L.Z.1    Chu, Y.H.2    Blossey, E.C.3    Whitesides, G.M.4
  • 3
    • 0025354634 scopus 로고
    • Fine tuning of the catalytic properties of carbonic anhydrase. Studies of a Thr200-His variant of human isoenzyme II
    • Behravan G., Jonsson B.H., Lindskog S. Fine tuning of the catalytic properties of carbonic anhydrase. Studies of a Thr200-His variant of human isoenzyme II. Eur. J. Biochem. 190:1990;351-357.
    • (1990) Eur. J. Biochem. , vol.190 , pp. 351-357
    • Behravan, G.1    Jonsson, B.H.2    Lindskog, S.3
  • 4
    • 0030772018 scopus 로고    scopus 로고
    • Carbonic anhydrase activators: X-ray crystallographic and spectroscopic investigations for the interaction of isozymes I and II with histamine
    • Briganti F., Mangani S., Orioli P., Scozzafava A., Vernaglione G., Supuran C.T. Carbonic anhydrase activators: X-ray crystallographic and spectroscopic investigations for the interaction of isozymes I and II with histamine. Biochemistry. 36:1997;10384-10392.
    • (1997) Biochemistry , vol.36 , pp. 10384-10392
    • Briganti, F.1    Mangani, S.2    Orioli, P.3    Scozzafava, A.4    Vernaglione, G.5    Supuran, C.T.6
  • 5
    • 0001610142 scopus 로고    scopus 로고
    • A ternary complex of carbonic anhydrase: X-ray crystallographic structure of the adduct of human carbonic anhydrase II with the activator phenylalanine and the inhibitor azide
    • Briganti F., Iaconi V., Mangani S., Orioli P., Scozzafava A., Vernaglione G., Supuran C.T. A ternary complex of carbonic anhydrase: X-ray crystallographic structure of the adduct of human carbonic anhydrase II with the activator phenylalanine and the inhibitor azide. Inorg. Chim. Acta. 275/276:1998;295-300.
    • (1998) Inorg. Chim. Acta , vol.275-276 , pp. 295-300
    • Briganti, F.1    Iaconi, V.2    Mangani, S.3    Orioli, P.4    Scozzafava, A.5    Vernaglione, G.6    Supuran, C.T.7
  • 6
    • 0033584160 scopus 로고    scopus 로고
    • Novel carbonic anhydrase isozymes I, II and IV activators incorporating sulfonyl-histamino moieties
    • Briganti F., Scozzafava A., Supuran C.T. Novel carbonic anhydrase isozymes I, II and IV activators incorporating sulfonyl-histamino moieties. Bioorg. Med. Chem. Lett. 9:1999;2043-2048.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 2043-2048
    • Briganti, F.1    Scozzafava, A.2    Supuran, C.T.3
  • 7
    • 0028142654 scopus 로고
    • Carbonic anhydrase activators. 3. Structure-activity correlations for a series of isozyme II activators
    • Clare B.W., Supuran C.T. Carbonic anhydrase activators. 3. Structure-activity correlations for a series of isozyme II activators. J. Pharm. Sci. 83:1994;768-779.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 768-779
    • Clare, B.W.1    Supuran, C.T.2
  • 8
    • 0028998264 scopus 로고
    • Increasing binding constants of ligands to carbonic anhydrase by using 'greasy tails'
    • Gao J.M., Qiao S., Whitesides G.M. Increasing binding constants of ligands to carbonic anhydrase by using 'greasy tails'. J. Med. Chem. 38:1995;2292-2301.
    • (1995) J. Med. Chem. , vol.38 , pp. 2292-2301
    • Gao, J.M.1    Qiao, S.2    Whitesides, G.M.3
  • 10
    • 0001867527 scopus 로고    scopus 로고
    • Evolution and distribution of the carbonic anhydrase gene families
    • In: Chegwidden, W.R. (Ed.), Birkhauser, New York (in press)
    • 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).
    • (1999) Carbonic Anhydrase - New Horizons
    • Hewett-Emmett, D.1
  • 11
    • 0030664701 scopus 로고    scopus 로고
    • 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
    • Ilies M.A., Banciu M.D., Ilies M., Chiraleu F., Briganti F., Scozzafava A., Supuran C.T. 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. 32:1997;911-918.
    • (1997) Eur. J. Med. Chem. , vol.32 , pp. 911-918
    • Ilies, M.A.1    Banciu, M.D.2    Ilies, M.3    Chiraleu, F.4    Briganti, F.5    Scozzafava, A.6    Supuran, C.T.7
  • 12
    • 0017378545 scopus 로고
    • Carbon-13 nuclear magnetic resonance probe of active site ionization of human carbonic anhydrase B
    • Khalifah R.G., Strader D.J., Bryant S.H., Gibson S.M. Carbon-13 nuclear magnetic resonance probe of active site ionization of human carbonic anhydrase B. Biochemistry. 16:1977;2241-2247.
    • (1977) Biochemistry , vol.16 , pp. 2241-2247
    • Khalifah, R.G.1    Strader, D.J.2    Bryant, S.H.3    Gibson, S.M.4
  • 13
    • 0030849266 scopus 로고    scopus 로고
    • Structure and mechanism of carbonic anhydrase
    • Lindskog S. Structure and mechanism of carbonic anhydrase. Pharmacol. Ther. 74:1997;1-20.
    • (1997) Pharmacol. Ther. , vol.74 , pp. 1-20
    • Lindskog, S.1
  • 14
    • 0001113609 scopus 로고
    • The catalytic mechanism of carbonic anhydrase
    • Lindskog S., Coleman J.E. The catalytic mechanism of carbonic anhydrase. Proc. Natl. Acad Sci. USA. 70:1964;2505-2508.
    • (1964) Proc. Natl. Acad Sci. USA , vol.70 , pp. 2505-2508
    • Lindskog, S.1    Coleman, J.E.2
  • 16
    • 0027443910 scopus 로고
    • Chemical properties of carbonic anhydrase IV, the membrane-bound enzyme
    • Maren T.H., Wynns G.C., Wistrand P.J. Chemical properties of carbonic anhydrase IV, the membrane-bound enzyme. Mol. Pharmacol. 44:1993;901-905.
    • (1993) Mol. Pharmacol. , vol.44 , pp. 901-905
    • Maren, T.H.1    Wynns, G.C.2    Wistrand, P.J.3
  • 17
    • 0014062860 scopus 로고
    • The catalytic versatility of erythrocyte carbonic anhydrase. III. Kinetic studies of the enzyme-catalyzed hydrolysis of p-nitrophenyl acetate
    • Pocker Y., Stone J.T. The catalytic versatility of erythrocyte carbonic anhydrase. III. Kinetic studies of the enzyme-catalyzed hydrolysis of p-nitrophenyl acetate. Biochemistry. 6:1967;668-678.
    • (1967) Biochemistry , vol.6 , pp. 668-678
    • Pocker, Y.1    Stone, J.T.2
  • 19
    • 0029965708 scopus 로고    scopus 로고
    • Acetazolamide in the treatment of seizures
    • Reiss W.G., Oles K.S. Acetazolamide in the treatment of seizures. Ann. Pharmacother. 30:1996;514-519.
    • (1996) Ann. Pharmacother. , vol.30 , pp. 514-519
    • Reiss, W.G.1    Oles, K.S.2
  • 20
    • 0342748046 scopus 로고    scopus 로고
    • Carbonic anhydrase activators. Part 21. Novel activators of isozymes I, II and IV incorporating carboxamido- And ureido histamine moieties
    • (in press)
    • Scozzafava, A., Supuran, C.T., 1999a. Carbonic anhydrase activators. Part 21. Novel activators of isozymes I, II and IV incorporating carboxamido- and ureido histamine moieties. Eur. J. Med. Chem. (in press).
    • (1999) Eur. J. Med. Chem.
    • Scozzafava, A.1    Supuran, C.T.2
  • 21
    • 0032840903 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Part 66. Arylsulfonylureido and arylureido-substituted aromatic and heterocyclic sulfonamides: Towards selective inhibitors of carbonic anhydrase isozyme I
    • Scozzafava A., Supuran C.T. Carbonic anhydrase inhibitors. Part 66. Arylsulfonylureido and arylureido-substituted aromatic and heterocyclic sulfonamides: towards selective inhibitors of carbonic anhydrase isozyme I. J. Enzyme Inhib. 14:1999;343-363.
    • (1999) J. Enzyme Inhib. , vol.14 , pp. 343-363
    • Scozzafava, A.1    Supuran, C.T.2
  • 22
    • 0033566151 scopus 로고    scopus 로고
    • 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?
    • Scozzafava A., Menabuoni L., Mincione F., Briganti F., Mincione G., Supuran C.T. 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. 42:1999;2641-2650.
    • (1999) J. Med. Chem. , vol.42 , pp. 2641-2650
    • Scozzafava, A.1    Menabuoni, L.2    Mincione, F.3    Briganti, F.4    Mincione, G.5    Supuran, C.T.6
  • 23
    • 0033539043 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route
    • Scozzafava A., Briganti F., Mincione G., Menabuoni L., Mincione F., Supuran C.T. Carbonic anhydrase inhibitors. Synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J. Med. Chem. 42:1999;3690-3700.
    • (1999) J. Med. Chem. , vol.42 , pp. 3690-3700
    • Scozzafava, A.1    Briganti, F.2    Mincione, G.3    Menabuoni, L.4    Mincione, F.5    Supuran, C.T.6
  • 24
    • 0002057911 scopus 로고
    • Carbonic anhydrase II deficiency syndrome: Clinical delineation, interpretation and implications
    • S.J. Dodgson, R.E. Tashian, G. Gros, & N.D. Carter. New York: Plenum Press
    • Sly W.S. Carbonic anhydrase II deficiency syndrome: clinical delineation, interpretation and implications. Dodgson S.J., Tashian R.E., Gros G., Carter N.D. The Carbonic Anhydrases. 1991;183-196 Plenum Press, New York.
    • (1991) The Carbonic Anhydrases , pp. 183-196
    • Sly, W.S.1
  • 25
    • 0029057703 scopus 로고
    • Human carbonic anhydrases and carbonic anhydrase deficiencies
    • Sly W.S., Hu P.Y. Human carbonic anhydrases and carbonic anhydrase deficiencies. Annu. Rev. Biochem. 64:1995;375-401.
    • (1995) Annu. Rev. Biochem. , vol.64 , pp. 375-401
    • Sly, W.S.1    Hu, P.Y.2
  • 28
    • 0027745222 scopus 로고
    • Carbonic anhydrase activators. VII. Isozyme II activation by bis-azolylmethanes, -ethanes and related azoles
    • Supuran C.T., Balaban A.T., Cabildo P., Claramunt R.M., Lavandera J.L., Elguero J. Carbonic anhydrase activators. VII. Isozyme II activation by bis-azolylmethanes, -ethanes and related azoles. Biol. Pharm. Bull. 16:1993;1236-1239.
    • (1993) Biol. Pharm. Bull. , vol.16 , pp. 1236-1239
    • Supuran, C.T.1    Balaban, A.T.2    Cabildo, P.3    Claramunt, R.M.4    Lavandera, J.L.5    Elguero, J.6
  • 29
    • 0029849446 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Synthesis and inhibitory properties of 1,3,4-thiadiazole-2,5-bissulfonamide
    • Supuran C.T., Conroy C.W., Maren T.H. Carbonic anhydrase inhibitors: synthesis and inhibitory properties of 1,3,4-thiadiazole-2,5-bissulfonamide. Eur. J. Med. Chem. 31:1996;843-846.
    • (1996) Eur. J. Med. Chem. , vol.31 , pp. 843-846
    • Supuran, C.T.1    Conroy, C.W.2    Maren, T.H.3
  • 30
    • 0029824776 scopus 로고    scopus 로고
    • Carbonic anhydrase activators. XV. A kinetic study of the interaction of bovine isozyme with pyrazoles, bis- And tris-azolyl methanes
    • Supuran C.T., Claramunt R.M., Lavandera J.L., Elguero J. Carbonic anhydrase activators. XV. A kinetic study of the interaction of bovine isozyme with pyrazoles, bis- and tris-azolyl methanes. Biol. Pharm. Bull. 19:1996;1417-1422.
    • (1996) Biol. Pharm. Bull. , vol.19 , pp. 1417-1422
    • Supuran, C.T.1    Claramunt, R.M.2    Lavandera, J.L.3    Elguero, J.4
  • 31
    • 0029788683 scopus 로고    scopus 로고
    • Carbonic anhydrase activators. Part 14. Synthesis of mono and bis pyridinium salt derivatives of 2-amino-5-(2-aminoethyl)- And 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole and their interaction with isozyme II
    • Supuran C.T., Barboiu M., Luca C., Pop E., Brewster M.E., Dinculescu A. Carbonic anhydrase activators. Part 14. Synthesis of mono and bis pyridinium salt derivatives of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole and their interaction with isozyme II. Eur. J. Med. Chem. 31:1996;597-606.
    • (1996) Eur. J. Med. Chem. , vol.31 , pp. 597-606
    • Supuran, C.T.1    Barboiu, M.2    Luca, C.3    Pop, E.4    Brewster, M.E.5    Dinculescu, A.6
  • 32
    • 0032122565 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Part 53. Synthesis of substituted-pyridinium derivatives of aromatic sulfonamides: The first non-polymeric membrane-impermeable inhibitors with selectivity for isozyme IV
    • Supuran C.T., Scozzafava A., Ilies M.A., Iorga B., Cristea T., Briganti F., Chiraleu F., Banciu M.D. Carbonic anhydrase inhibitors. Part 53. Synthesis of substituted-pyridinium derivatives of aromatic sulfonamides: the first non-polymeric membrane-impermeable inhibitors with selectivity for isozyme IV. Eur. J. Med. Chem. 33:1998;577-595.
    • (1998) Eur. J. Med. Chem. , vol.33 , pp. 577-595
    • Supuran, C.T.1    Scozzafava, A.2    Ilies, M.A.3    Iorga, B.4    Cristea, T.5    Briganti, F.6    Chiraleu, F.7    Banciu, M.D.8
  • 33
    • 0031776867 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Part 52. Metal complexes of heterocyclic sulfonamides - A new class of strong topical intraocular pressure-lowering agents in rabbits
    • Supuran C.T., Mincione F., Scozzafava A., Briganti F., Mincione G., Ilies M.A. 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. 33:1998;247-254.
    • (1998) Eur. J. Med. Chem. , vol.33 , pp. 247-254
    • Supuran, C.T.1    Mincione, F.2    Scozzafava, A.3    Briganti, F.4    Mincione, G.5    Ilies, M.A.6
  • 34
    • 0032791653 scopus 로고    scopus 로고
    • 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
    • Supuran C.T., Scozzafava A., Menabuoni L., Mincione F., Briganti F., Mincione G. 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. 8:1999;317-328.
    • (1999) Eur. J. Pharm. Sci. , vol.8 , pp. 317-328
    • Supuran, C.T.1    Scozzafava, A.2    Menabuoni, L.3    Mincione, F.4    Briganti, F.5    Mincione, G.6
  • 35
    • 0016722749 scopus 로고
    • The catalytic mechanism of carbonic anhydrase. Hydrogen-isotope effects on the kinetic parameters of the human C isoenzyme
    • Steiner H., Jonsson B.H., Lindskog S. The catalytic mechanism of carbonic anhydrase. Hydrogen-isotope effects on the kinetic parameters of the human C isoenzyme. Eur. J. Biochem. 59:1975;253-259.
    • (1975) Eur. J. Biochem. , vol.59 , pp. 253-259
    • Steiner, H.1    Jonsson, B.H.2    Lindskog, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.