Carbonic anhydrase inhibitors

Medicinal Research Reviews

Volumn 23, Issue 2, 2003, Pages 146-189

  Supuran, Claudiu T ^a   Scozzafava, Andrea ^a   Casini, Angela ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Anticanceragent; Carbonic anhydrase; Diagnostic tool; Glaucoma; Isozymes; Sulfonamide; X ray

Indexed keywords

ACETAZOLAMIDE; ANTICONVULSIVE AGENT; ANTIGLAUCOMA AGENT; ANTINEOPLASTIC AGENT; AZO DYE; BRINZOLAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE III; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE V; CARBONATE DEHYDRATASE VI; CARBONATE DEHYDRATASE VII; CARBONATE DEHYDRATASE XIV; CARBONATE DEHYDRATASE XXII; DIAGNOSTIC AGENT; DICLOFENAMIDE; DORZOLAMIDE; ETHOXZOLAMIDE; HYDROXAMIC ACID; INDISULAM; METHAZOLAMIDE; SEZOLAMIDE; SULFANILAMIDE; SULFONAMIDE; TOPIRAMATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZONISAMIDE;

BIOSENSOR; CANCER INHIBITION; DEPRESSION; DRUG DESIGN; DRUG HYPERSENSITIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME LOCALIZATION; ENZYME MECHANISM; EPILEPSY; FATIGUE; GASTROINTESTINAL SYMPTOM; GLAUCOMA; HUMAN; LIBIDO DISORDER; MALAISE; METABOLIC ACIDOSIS; MYOPIA; NEPHROLITHIASIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; PARESTHESIA; POSITRON EMISSION TOMOGRAPHY; REVIEW; SIDE EFFECT; SKIN TINGLING; TUMOR; WEIGHT REDUCTION;

ANIMALS; CARBONIC ANHYDRASE INHIBITORS; CATALYSIS; DRUG DESIGN; HUMANS; MODELS, MOLECULAR;

EID: 0037369153     PISSN: 01986325     EISSN: None     Source Type: Journal    
DOI: 10.1002/med.10025     Document Type: Review

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111. Fenesan I, Popescu R, Scozzafava A, Crucin V, Mateiciuc E, Bauer R, Ilies MA, Supuran CT. Carbonic anhydrase inhibitors. Phosphoryl-sulfonamides - A new class of high affinity inhibitors of isozymes I and II. J Enz Inhib 2000;15:297-310.
112. Scozzafava A, Banciu MD, Popescu A, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, and IV by sulfamide and sulfamic acid derivatives. J Enz Inhib 2000;15:443-453.
113. Supuran CT, Scozzafava A. Matrix metalloproteinase inhibitors. In: Smith HJ, Simons C, editors. Proteinase and peptidase inhibition: Recent potential targets for drug development. London: Taylor & Francis Publishing House; 2001. pp 35-52.
114. Scozzafava A, Supuran CT. Protease inhibitors. Synthesis of potent bacterial collagenase and matrix metalloproteinase inhibitors incorporating N-4-nitrobenzylsulfonylglycine hydroxamate moieties. J Med Chem 2000;43:1858-1865.
115. Scozzafava A, Supuran CT. Protease inhibitors. Synthesis of Clostridium histolyticum collagenase inhibitors incorporating sulfonyl-L-alanine hydroxamate moieties. Bioorg Med Chem Lett 2000;10:499-502.
116. Supuran CT, Scozzafava A. Protease inhibitors. Part 7. Inhibition of Clostridium histolyticum collagenase with sulfonylated derivatives of L-valine hydroxamate. Eur J Pharm Sci 2000;10:67-76.
117. Scolnick LR, Clements AM, Liao J, Crenshaw L, Hellberg M, May J, Dean TR, Christianson DW. Novel binding mode of hydroxamate inhibitors to human carbonic anhydrase II. J Am Chem Soc 1997;119:850-851.
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119. 99mTc-ECD consecutive SPECT method. J Cereb Blood Flow Metab 1997;17:1020-1032.
120. 11C]acetazolamide. Appl Radiat Isot 1988;39:671-675.
121. Salvadori PA, Supuran CT, Scozzafava A. unpublished results.
122. Masereel B, Rolin S, Abbate F, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: Anticonvulsant sulfonamides incorporating valproyl and other lipophilic moieties. J Med Chem 2002;45:312-320.
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124. (b) Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Novel compounds containing S-NH moieties in their molecule: Sulfenamido-sulfonamides, sulfenimido-sulfonamides and their interaction with isozymes I, II, and IV. J Enz Inhib 1998;13:419-442.
125. Gruneberg S, Wendt B, Klebe G. Subnanomolar inhibitors from computer screening: A model study using human carbonic anhydrase II. Angew Chem Int Ed 2001;40:389-393.
126. Kehayova PD, Bokinsky GE, Huber JD, Jain A. A caged hydrophobic inhibitor of carbonic anhydrase II. Org Lett 1999;1:187-188.
127. Scozzafava A, Mincione F, Menabuoni L, Supuran CT. Carbonic anhydrase inhibitors: Topically acting antiglaucoma sulfonamides incorporating phthaloyl and phthalimido moieties. Drug Des Dev 2001;17:337-348.
128. Scozzafava A, Saramet I, Banciu MD, Supuran CT. Carbonic anhydrase activity modulators: Synthesis of inhibitors and activators incorporating 2-subtituted-thiazol-4-yl-methyl scaffolds. J Enz Inhib 2001;16:351-358.
129. Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: Preparation of potent sulfonamides inhibitors incorporating bile acid tails. Bioorg Med Chem Lett 2002;12:1551-1557.
130. Chazalette C, Rivière-Baudet M, Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors: Allylsulfonamide, styrene sulfonamide, N-allyl sulfonamides and some of their metal (Si, Ge, B) derivatives. J Enz Inhib 2001;16:475-489.
131. Mincione F, Starnotti M, Menabuoni L, Scozzafava A, Casini A, Supuran CT. Carbonic anhydrase inhibitors: 4-Sulfamoyl-benzenecarboxamides and 4-chloro-3-sulfamoyl-benzenecarboxamides with strong topical antiglaucoma properties. Bioorg Med Chem Lett 2001;11:1787-1791.
132. Grzybowski BA, Ishchenko AV, Kim CY, Topalov G, Chapman R, Christianson DW, Whitesides GM, Shakhnovich EI. Combinatorial computational method gives new picomolar ligands for a known enzyme. Proc Natl Acad Sci USA 2002;99:1270-1273.
133. Alzuet G, Ferrer S, Borras J, Supuran CT. Complexes of heterocyclic sulfonamides - A class of dual carbonic anhydrase inhibitors. Roum Chem Quart Rev 1994;2:283-300.
134. Supuran CT. Carbonic anhydrase inhibitors. Part 13. Complex-type mechanism-based inhibitors. Rev Roum Chim 1992;37:849-855.
135. Supuran CT, Manole G, Andruh M. Carbonic anhydrase inhibitors. Part 11. Coordination compounds of heterocyclic sulfonamides with lanthanides are potent inhibitors of isozymes I and II. J Inorg Biochem 1993;49:97-103.
136. 3 complex. Carbonic anhydrase inhibitory properties. J Inorg Biochem 1996;62:31-39.
137. Supuran CT, Almajan GL. Carbonic anhydrase inhibitors. Part 34. Synthesis and biological activity of coordination compounds of 5-pivaloylamido-1,3,4-thiadiazole-2-sulfonamide with divalent metal ions. Main Group Met Chem 1995;18:347-351.
138. Supuran CT. Thienothiopyransulfonamides as complexing agents for the preparation of dual carbonic anhydrase inhibitors Metal Based Drugs 1995;2:327-330.
139. Supuran CT. Metal complexes of 1,3,4-thiadiazole-2,5-disulfonamide are strong dual carbonic anhydrase inhibitors, although the ligand possesses very weak such properties. Metal Based Drugs 1995;2:331-336.
140. Supuran CT, Scozzafava A. Synthesis of novel aromatic/heterocyclic sulfonamides and their metal complexes as inhibitors of carbonic anhydrase isozymes I, II, and IV. J Enz Inhib 1997;12:37-51.
141. Mincione G, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Part 46. Inhibition of carbonic anhydrase isozymes I, II, and IV with trifluoromethylsulfonamide derivatives and their Zn(II) and Cu(II) complexes. Metal Based Drugs 1997;4:27-34.
142. Borja P, Alzuet G, Server-Carriò J, Borras J, Supuran CT. Zinc complexes of carbonic anhydrase inhibitors. Crystal structure of
143. 4 complex. Inorg Chim Acta 1998;273:334-338.
144. Supuran CT, Scozzafava A, Saramet I, Banciu MD. Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, and IV with heterocyclic mercaptans, sulfenamides, sulfonamides and their metal complexes. J Enz Inhib 1998;13:177-194.
145. Supuran CT, Mincione F, Scozzafava A, Briganti F, Mincione G, Ilies MA. Carbonic anhydrase inhibitors. Part 52. Metal complexes of heterocyclic sulfonamides: A new class of strong topical intraocular pressure-lowering agents with potential use as antiglaucoma drugs. Eur J Med Chem 1998;33:247-254.
146. Supuran CT, Scozzafava A, Mincione F, Menabuoni L, Briganti F, Mincione G, Jitianu M. Carbonic anhydrase inhibitors. Part 60. The topical intraocular pressure-lowering properties of metal complexes of a heterocyclic sulfonamide: Influence of the metal ion upon biological activity. Eur J Med Chem 1999;34:585-594.
147. Briganti F, Tilli S, Mincione G, Mincione F, Menabuoni L, Supuran CT. Carbonic anhydrase inhibitors. Metal complexes of 5-(2-chlorophenyl)-1,3,4-thiadiazole-2-sulfonamide with topical intraocular pressure-lowering properties: The influence of metal ions upon the pharmacological activity. J Enz Inhib 2000;15:185-200.
148. Mastrolorenzo A, Scozzafava A, Supuran CT. Antifungal activity of Ag(I) and Zn(II) complexes of aminobenzolamide (5-sulfanilylamido-1,3,4-thiadiazole-2-sulfonamide) derivatives. J Enz Inhib 2000;15:517-531.
149. Ilies MA, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Part 91. Metal complexes of heterocyclic sulfonamides as potential pharmacological agents in the treatment of gastric acid secretion imbalances. Metal Based Drugs 2000;7:57-62.
150. Ul-Hassan M, Scozzafava A, Chohan ZH, Supuran CT. Carbonic anhydrase inhibitors: Metal complexes of a sulfanilamide derived Schiff base and their interaction with isozymes I, II, and IV. J Enz Inhib 2001;16:499-505.
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153. Thompson RB, Maliwal BP, Feliccia VL, Fierke CA, McCall K. Determination of picomolar concentrations of metal ions using fluorescence anisotropy: Biosensing with a reagentless enzyme transducer. Anal Chem 1998;70:4717-4723.
154. Thompson RB, Maliwal BP, Whetsell WO, Maliwal BP, Fierke CA, Frederickson CJ. Fluorescence microscopy of stimulated Zn(II) release from organotypic cultures of mammalian hippocampus using a carbonic anhydrase-based biosensor system. J Neurosci Meth 2000;96:35-45.
155. Chirica LC, Elleby B, Jonsson BH, Lindskog S. The complete sequence, expression in Escherichia coli, purification and some properties of carbonic anhydrase from Neisseria gonorrhoeae. Eur J Biochem 1997;244:755-760.
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157. Nafi BM, Miles RJ, Butler LO, Carter ND, Kelly C, Jeffery S. Expression of carbonic anhydrase in neisseriae and other heterotrophic bacteria. J Med Microbiol 1990;32:1-7.
158. Smith KS, Ferry JG. Prokaryotic carbonic anhydrases. FEMS Microbiol Rev 2000;24:335-366.
159. Supuran CT, Scozzafava A, Mastrolorenzo A. Bacterial proteases: Current therapeutic use and future prospects for the development of new antibiotics. Exp Opin Ther Patents 2001;11:221-259.
160. Krungkrai SR, Suraveratum N, Rochanakij S, Krungkrai J. Characterisation of carbonic anhydrase in Plasmodium falciparum. Int J Parasitol 2001;31:661-668.