538
Views
460
CrossRef citations to date
0
Altmetric
Review

Carbonic anhydrase inhibitors and their therapeutic potential

&
Pages 575-600 | Published online: 25 Feb 2005

Bibliography

  • MAREN TH: The links among biochemistry, physiology and pharmacology in carbonic anhydrase mediated systems. In: Carbonic Anhydrase - From Biochemistry, and Genetics to Physiology and Clinical Medicine. Botré F, Gros G, Storey BT (Eds.), VCH, Weinheim (1990:186–207.
  • SUPURAN CT: Carbonic anhydrase inhibitors. In: Carbonic Anhydrase, and Modulation of Physiologic and Pathologic Processes in the Organism. Puscas I (Ed.) Helicon, Timisoara, Romania (1994):29–111.
  • HEWETT-EMMETT D: Evolution and distribution of the carbonic anhydrase gene families. In: Carbonic Anhydrase - New Horizons. Chegwidden WR, Edwards Y, Carter N (Eds.), Birkhauser, Basel (2000). In Press.
  • ••An excellent and comprehensive review of the CA genefamilies.
  • HEWETT-EMMETT D, TASHIAN RE: Functional diversity, conservation and convergence in the evolution of the a-, 13- and y-carbonic anhydrase gene families. Mol Phyl. Evol (1996) 5:50–77.
  • SMITH KS, JAKUBZICK C, WHITTAM TS, FERRY JG: Carbonic anhydrase is an ancient enzyme widespread in prokaryotes. Proc. Natl. Acad. Sci. USA (1999) 96:15184–15189.
  • CABISCOL E, LEVINE RL: Carbonic anhydrase IIIoxidative modification in vivo and loss of phosphatase activity during aging. J. Biol. Chem. (1995) 270:14742–14747.
  • PARKKILA AK, SCARIM AL, PARKKILA S, WAHEED A, CORBETT JA, SLY WS: Expression of carbonic anhydrase V in pancreatic beta cells suggests role for mitochondrial carbonic anhydrase in insulin secretion. J. Biol. Chem. (1998) 273:24620–24623.
  • BAIRD TT, WAHEED A, OKUYAMA T, SLY WS, FIERKE CA: Catalysis and inhibition of human carbonic anhydrase IV. Biochemistry (1997) 36:2669–2678.
  • PASTOREKOVA S, PARKKILA S, PARKKILA AK et al.: Carbonic anhydrase IX, MN/CA IX: analysis of stomach complementary DNA sequence and expres-sion in human and rat alimentary tracts. Gastroenter-ology (1997) 112:398–408.
  • LOVEJOY DA, HEWETT-EMMETT D, PORTER CA et al.: Evolutionary conserved, `acatalytic' carbonic anhydrase-related protein XI contains a sequence motif present in the neuropeptide sauvagine: the human CA-RP XI gene (CA11) is embedded between the secretor gene cluster and the DBP gene at 19q13.3. Genomics (1998) 54:484–493.
  • EARNHARDT JN, QIAN M, TU C, LAKKIS MM et al.: The catalytic properties of murine carbonic anhydrase VII. Biochemistry (1998) 30:10387–10845.
  • BELLINGHAM J, GREGORY-EVANS K, GREGORY-EVANS C,: Sequence and tissue expression of a novel human carbonic anhydrase-related protein, CARP-2, mapping to chromosome 19q13.3. Biochem. Biophys. Res. Commun. (1998) 253:364–367.
  • TURECI O, SAHIN U, VOLLMAR E et al.: Human carbonicanhydrase XII: cDNA cloning, expression and chromosomal localization of a carbonic anhydrase gene that is overexpressed in some renal cell cancers. Proc. Nail Acad. ScL USA (1998) 95.7608–7613.
  • MORI K, OGAWA Y, EBIHARA K et al: Isolation and characterization of CA XIV, a novel membrane-bound carbonic anhydrase from mouse kidney. J. Biol. Chem. (1999) 274:15701–15705.
  • CHEGWIDDEN WR, DODGSON SJ, SPENCER IM: The role of carbonic anhydrase in metabolism and cell growth in animals. In: Carbonic Anhydrase - New Horizons. Chegwidden, WR, Edwards Y, Carter N (Eds.), Birkhauser, Basel (2000). In Press.
  • SUPURAN CT, CONROY CW, MAREN TH: Is cyanate a carbonic anhydrase substrate? Proteins StrucL FuncL Genet. (1997) 27:272–278.
  • BRIGANTI F, MANGANI S, SCOZZAFAVA A, VERNAGLIONE G, SUPURAN CT: Carbonic anhydrase catalyzes cyanamide hydration to urea: is it mimicking the physiological reaction? J. Biol. Inorg. Chem. (1999) 4:528–536.
  • BEYER KH, BAER JE: Physiological basis for the actionof newer diuretic drugs. PharmacoL Rev. (1961) 13:517–562.
  • PUSCAS I, SUPURAN CT: Farmacologia clinica da ulcerapeptica. In: Aparelho Digestivo. Coelho J (Ed.), MEDSI, Rio de Janeiro (1996):1704–1734.
  • WISTRAND PJ, LINDQVIST A: Design of carbonic anhydrase inhibitors and the relationship between the pharmacodynamics and pharmacokinetics of acetazolamide. In: Carbonic Anhydrase - From Biochem-istry, and Genetics to Physiology and Clinical Medicine. Botre F, Gros G, Storey BT (Eds.), VCH, Weinheim (1990:352–378.
  • REISS WG, OLES KS: Acetazolamide in the treatment ofseizures. Ann. Pharmacother. (1996) 30:514–519.
  • LARSON EB, ROACH RC, SCHOENE RB, HORNBEIN TF:Acute mountain sickness and acetazolamide. Clinical efficacy and effect on ventilation.J. Am. Med. Ass. (1982) 248:328–332.
  • LILJAS A, HAKANSSON K, JONSSON BH, XUE Y: Inhibi-tion and catalysis of carbonic anhydrase. Recent crystallographic analyses. Eur. J. Biochem. (1994) 219:1–10.
  • CAPPALONGA AM, ALEXANDER RS, CHRISTIANSON DW:Mapping protein-peptide affinity: binding of peptidyl-sulfonamide inhibitors to human carbonic anhydrase II. J. Am. Chem. Soc. (1994) 116:5063–5068.
  • SMITH GM, ALEXANDER RS, CHRISTIANSON DW et al.: Positions of His-64 and a bound water in human carbonic anhydrase II upon binding three structurally related inhibitors. Protein Sci. (1994) 3:118–125.
  • STAMS T, CHEN Y, BORIACK-SJODIN PA et al: Structures of murine carbonic anhydrase IV and human carbonic anhydrase II complexed with brinzolamide: Molecular basis of isozyme-drug discrimination. Protein Sci. (1998) 7:556–563.
  • BRIGANTI F, MANGANI S, ORIOLI P, SCOZZAFAVA A, VERNAGLIONE G, SUPURAN CT: Carbonic anhydrase activators: X-ray crystallographic and spectroscopic investigations for the interaction of isozymes I and II with histamine. Biochemistry (1997) 36:10384–10392.
  • SCOZZAFAVA A, MENABUONI L, MINCIONE F, BRIGANTI F, MINCIONE G, SUPURAN CT: 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. (1999) 42:2641–2650.
  • BORRAS J, SCOZZAFAVA A, MENABUONI L et al.: Carbonic anhydrase inhibitors: synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: is the tail more important than the ring? Bioorg. Med. Chem. (1999) 7:2397–2406.
  • SCOZZAFAVA A, BRIGANTI F, MINCIONE G, MENABUONI L, MINCIONE F, SUPURAN CT: Carbonic anhydrase inhibitors: synthesis of water-soluble, amino acyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J. Med. Chem. (1999) 42:3690–3700.
  • SCOZZAFAVA A, BRIGANTI F, ILIES MA, SUPURAN CT: Carbonic anhydrase inhibitors, synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus the cytosolic isozymes. J. Med. Chem. (2000) 43:292–300.
  • VIDGREN J, SVENSSON A, LILJAS A. Refined structure of the aminobenzolamide complex of human carbonic anhydrase II at 1.9 A and sulphonamide modelling of bovine carbonic anhydrase III. Int. J. Biol. Macromol (1993) 15:97–100.
  • FRIEDENWALD JS. The formation of the intraocular fluid. Am. J. Ophthalmol (1949) 32:9–27.
  • KINSEY VE. Comparative chemistry of aqueous humor in posterior and anterior chambers of rabbit eye. Arch. Ophthalmol (1953) 50:401–417.
  • KINSEY VE, BARANY E. The rate flow of aqueous humor. II. Derivation of rate of flow and its physiologic signifi-cance. Am. J. Ophthalmol (1949) 32:189–202.
  • WISTRAND PJ. Carbonic anhydrase in the anterior uvea of the rabbit. Acta Physic)]. Scand. (1951) 24:144–148.
  • BECKER B. The mechanism of the fall in intraocularpressure by the carbonic anhydrase inhibitor Diamox. Am. J. Ophthalmol (1955) 39:177–183.
  • KINSEY VE, REDDY DVN. Turnover of total carbon dioxide in aqueous humors and the effect thereon of acetazolamide. Arch. Ophthalmol (1959) 62:78–83.
  • SUGRUE MF: The pharmacology of antiglaucoma drugs. Pharmac. Ther. (1989) 43:91–138.
  • BARTLETT JD, JAANUS SD: Clinical ocular pharma-cology. Butterworth, Boston (1989)254–263.
  • MAREN, TH: Role of carbonic anhydrase in aqueous humor and cerebrospinal fluid formation. In: Barriers, and Fluids of the Eye and Brain. Segal, MB (Ed.), MacMillan Press, London. (1992):37–48.
  • MAREN TH: The development of topical carbonic anhydrase inhibitors. J. Glaucoma (1995) 4:49–62.
  • MAREN TH: Carbonic anhydrase: chemistry, physiology and inhibition. Physiol. Rev. (1967) 47:595–781.
  • ••Although outdated, this comprehensive review on thechemistry, physiology and pharmacology of CA and sulphonamide inhibitors, remains one of the best available works in this area and maintained its importance (it is also a citation classic).
  • MAREN TH, JANKOWSKA L, SANYAL G, EDELHAUSER HF: The, transcorneal permeability of sulfonamide carbonic anhydrase innhibitors and their effect on aqueous humor secretion. Exp. Eye Res. (1983) 36:457–480.
  • ••This pioneering paper (which has been rejected by twojournals prior to its publication) explains the reasons why the classical CAIs do not function via the topical route as TOP lowering drugs and constitutes the theoretical basis for the development of topical CAIs.
  • SUGRUE MF: Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Progr. Ret. Eye Res. (2000) 19:87–112.
  • SILVER LH: Dose-response evaluation of the ocular hypotensive effect of brinzolamide ophthalmic suspension (Azopt). Brinzolamide dose-response study group. Surv. Ophthalmol. (2000) 44 (Suppl. 2):147–153.
  • AALTO-KORTE K: Contact allergy to dorzolamide eyedrops. Contact Dermatitis (1998) 39:206.
  • CARLSEN J, DURCAN J, SWARTZ M, CRANDALL A: Nephrolithiasis with dorzolamide. Arch. Ophthalmol (1999) 117:1087–1088.
  • THOE SCHWARTZENBERG GW, TROPE GE: Anorexia, depression and dementia induced by dorzolamide eyedrops (Trusopt). Can. J. Ophthalmol (1999) 34:93–94.
  • KONOWAL A, MORRISON JC, BROWN SV et al.: Irreversible corneal decompensation in patients treated with topical dorzolamide. Am. J. Ophthalmol (1999) 127:403–406.
  • MENABUONI L, SCOZZAFAVA A, MINCIONE F, BRIGANTIF, MINCIONE G, SUPURAN CT: Carbonic anhydrase inhibitors, water-soluble, topically effective intrao-cular pressure lowering agents derived from isonico-tinic acid and aromatic/heterocyclic sulfonamides: Is the, tail more important than the ring ? J. Enz. Inhib. (1999) 14:457–474.
  • SUPURAN CT, SCOZZAFAVA A, MENABUONI L, MINCIONE F, BRIGANTI F, MINCIONE G: Carbonic anhydrase inhibitors. Part 70. Synthesis and ocular pharmacology of a new class of water-soluble, topically effective intraocular pressure lowering agents derived from nicotinic acid and aromatic/heterocyclic sulfonamides. Eur. J. Med. Chem. (1999) 34:799–808.
  • BARBOIU M, SUPURAN CT, MENABUONI L, SCOZZAFAVAA, MINCIONE F, BRIGANTI F, MINCIONE G: Carbonic anhydrase inhibitors. Synthesis of topically effective intraocular pressure lowering agents derived from 5- (co-aminoalkylcarboxamido)-1,3,4-thiadiazole-2-sulfonamide. J. Enz. Inhib. (1999) 15:23–46.
  • MINCIONE G, MENABUONI L, BRIGANTI F, SCOZZAFAVAA, MINCIONE F, SUPURAN CT: Carbonic anhydrase inhibitors. Part 79. Synthesis and ocular pharma-cology of topically acting sulfonamides incorporating GABA moieties in their molecule, with long-lasting intraocular pressure lowering properties. Eur. J. Pharm. Sci. (1999) 9:185–199.
  • WAYMAN L, LARSSON LI, MAUS T, ALM A, BRUBAKER R: Comparison of dorzolamide and timolol as suppres-sors of aqueous humor flow in humans. Arch. Ophthalmol (1997) 115:1368–1371.
  • ALM A: Prostaglandin derivates as ocular hypotensive agents. Progr. Retinal Eye Res. (1998) 17:291–312.
  • LARSSON LI, ALM A. Aqueous humor flow in human eyes treated with dorzolamide and different doses of acetazolamide. Arch. Ophthalmol (1998) 116:19–24.
  • COX SN, HAY E, BIRD AC: Treatment of chronic macular edema with acetazolamide. Arch. Ophthalmol (1988) 106:1190–1195.
  • GROVER S, FISHMAN GA, FISCELLA RG, ADELMAN AE:Efficacy of dorzolamide hydrochloride in the manage-ment of chronic cystoid macular edema in patients with retinitis pigmentosa. Retina (1997) 17:222–231.
  • SPONSEL WE, HARRISON J, ELLIOTT WR, TRIGO Y, KAVANAGH J, HARRIS A: Dorzolamide hydrochloride and visual function in normal eyes. Am. J. Ophthalmol (1997) 123:759–766.
  • BARNES GE, LI B, DEAN T, CHANDLER ML: Increasedoptic nerve head blood flow after 1 week of twice daily brinzolamide treatment in Dutch-belted rabbits. Surv. Ophthalmol (2000) 44 (Suppl. 2):131–140.
  • ORZALESI N, PIERROTTET C, PORTA A, ASCHERO M: Long-term treatment of retinitis pigmentosa with acetazolamide. A pilot study. Graefes Arch. Clin. Exp. Ophthalmol (1993) 231:254–256.
  • GONZALEZ C. Serous retinal detachment. Value of acetazolamide. J. Fr. Ophtalmol (1992) 15:529–536.
  • BARNISH IT, CROSS PE, DICKINSON RP, GADSBY B, PARRY MJ, RANDALL MJ, SINCLAIR IW: Cerebrovasodila-tion through selective inhibition of the enzyme carbonic anhydrase. 2. Imidazo[2,1-b]thiadiazole and imidazo,[2,1-b]thiazolesulfonamides. J. Med. Chem. (1980) 23:117–121.
  • LASSEN NA, FRIBERG L, KASTRUP J, RIZZI D, JENSEN JJ:Effects of acetazolamide on cerebral blood flow and brain tissue oxygenation. Postgrad. Med. 1 (1987) 63:185-187.
  • CHUFAN EE, PEDREGOSA JC, BALDINI ON, BRUNO-BLANCH L: Anticonvulsant activity of analogues of acetazolamide. Farmaco (1999) 54:838–841.
  • SCARROW AM, SEGAL R, MEDSGER TA, WASKO MC: Communicating hydrocephalus secondary to diffuse meningeal spread of Wegener's granulomatosis: case report and literature review. Neurosurgery (1998) 43:1470–1473.
  • BATTISTINI S, STENIRRI S, PIATTI M et al.: A newCACNA1A gene mutation in acetazolamide-responsive familial hemiplegic migraine and ataxia. Neurology (1999) 13:38–43.
  • COWEN MA, GREEN M, BERTOLLO DN, ABBOTT K: A treatment for tardive dyskinesia and some other extrapyramidal symptoms. J. Clin. Psychopharmacol (1997) 17:190–193.
  • CLARKE C: High altitude cerebral oedema. Int. J. Sports Med. (1988) 9:170–174.
  • WILNER A, RAYMOND K, POLLARD R: Topiramate and metabolic acidosis. Epilepsia (1999) 40:792–795.
  • GRIGGS RC, MOXLEY RT, RIGGS JE, ENGEL WK: Effects of acetazolamide on myotonia. Ann. Neurol. (1978) 3:531–537.
  • LINKS TP, SMIT AJ, MOLENAAR WM, ZWARTS MJ, OOSTERHUIS HJ: Familial hypokalemic periodic paralysis. Clinical, diagnostic and therapeutic aspects. Neurol. Sci. (1994) 122:33–43.
  • UITTI RJ: Medical treatment of essential tremor andParkinson's disease. Geriatrics (1998) 53:46–48.
  • BERNHARD WN, SCHALIK LM, DELANEY PA, BERNHARDTM, BARNAS GM: Acetazolamide plus low-dose dexamethasone is better than acetazolamide alone to ameliorate symptoms of acute mountain sickness. Aviat. Space Environ. Med. (1998) 69:883–886.
  • BRADWELL AR, WRIGHT AD, WINTERBORN M, IMRAY C:Acetazolamide and high altitude disease. Int. J. Sports Med. (1992) 13 (Suppl. 0:63–64.
  • SUPURAN CT, POPESCU A, BANCIU MD: Carbonic anhydrase inhibitors. Part 10. New derivatives of 1,3, 4-thiadiazole-2-sulfonamide and 4-methyl-2-sulfonamido-_2-1,3,4-thiadiazoline. Rev. Roum. Chim. (1992) 37:289–297.
  • PORCELLI MJ, GUGELCHUK GM: A trek to the top: a review of acute mountain sickness. J. Am. Osteopath. Assoc. (1995) 95:718–720.
  • LONNERHOLM G, SELKING O, WISTRAND PJ: Amount and distribution of carbonic anhydrases CA land CA II in the gastrointestinal tract. Gastroenterology (1985) 88:1151–1161.
  • SLY WS, HU PY: Human carbonic anhydrases and carbonic anhydrase defficiencies. Ann. Rev. Biochem. (1995) 64:375–401.
  • SAARNIO J, PARKKILA S, PARKKILA AK, WAHEED A, KARTTUNEN T, SLY WS: Cell-specific expression of mitochondrial carbonic anhydrase in the human and rat gastrointestinal tract. J. Histochem. Cytochem. (1999) 47:517–524.
  • HENKIN RI, MARTIN BM, AGARWAL RP: Decreased parotid saliva gustin/carbonic anhydrase VI secretion: an enzyme disorder manifested by gustatory and olfactory dysfunction. Am. J. Med. Sci (1999) 318:380–391.
  • JANOWITZ HD, COLCHER H, HOLLANDER F: Inhibitionof gastric acid secretion in dogs by carbonic anhydrase inhibitor 2-acetylamino-1,3,4-thiadiazole-2-sulfonamide. Am. J. Physiol. (1952) 171:325–330.
  • SWENSON ER: Distribution and functions of carbonicanhydrase in the gastrointestinal tract. In: The Carbonic Anhydrases. Dodgson SJ, Tashian RE, Gros G, Carter ND (Eds.), Plenum Press, New York and London (1990:265–287.
  • VINCE JW, REITHMEYER RAF: Carbonic anhydrase II binds to the carboxyl terminus of human band 3, the erythrocyte C1-/HCO3- exchanger. J. Biol. Chem. (1998) 273:28430–28437.
  • ILIES MA, SCOZZAFAVA A, SUPURAN CT: Carbonic anhydrase inhibitors. Part 91. Metal complexes of heterocyclic sulfonamides as potential pharmacol-ogical agents in the treatment of gastric acid secretion imbalances. Metal Based Drugs (2000) 7:57–62.
  • MILOV DE, JOU WS, SHIREMAN RB, CHUN PW: The effectof bile salts on carbonic anhydrase. Hepatology (1992) 15:288–296.
  • JACKSON EK: Diuretics. In: Goodman and Gilman 's ThePharmacological Basis of Therapeutics, 9th Ed. Hardman JG, Limbird LE, Molinoff PB, Ruddon RW, Gilman AG (Eds.), McGraw-Hill, New York (1996):685–713.
  • SUPURAN CT, CONROY CW, MAREN TH: Carbonic anhydrase inhibitors: synthesis and inhibitory properties of 1,3,4-thiadiazole-2,5-bissulfonamide. Eur. J. Med. Chem. (1996) 31:843–846.
  • LONNERHOLM G, WISTRAND PJ, BARANY E: Carbonic anhydrases isoenzymes in the rat kidney. Effects of chronic acetazolamide treatment. Acta Physiol. Scand. (1986) 126:51–60.
  • SUPURAN CT, MANOLE G: Carbonic Anhydrase Inhibitors: Synthesis, reactions and therapeutic applications. Roumanian Academy Publishing House, Bucharest (1999):11–178.
  • MAREN TH: Benzolamide. a renal carbonic anhydrase inhibitor. In: Orphan Drugs. Karch FE (Ed.), Marcel Dekker, New York and Basel (1982):89–115.
  • TINKER JP, COULSON R, WEINER IM: Dextran-bound inhibitors of carbonic anhydrase. J. Pharmacol Exptl. Ther. (1981) 218:600–607.
  • SUPURAN CT, SCOZZAFAVA A, ILIES MA et al.: 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. (1998) 33:577–594.
  • GAY CV: The role of carbonic anhydrase in bone-resorbing cells. In: Carbonic Anhydrase - From Biochemistry, and Genetics to Physiology and Clinical Medicine. Botré F, Gros G, Storey BT (Eds.), VCH, Weinheim (1990:419–422.
  • PIERCE WW, WAITE LC: Bone-targeted carbonic anhydrase inhibitors: effect of a proinhibitor on bone resorption in vitro. Proc. Soc. Exp. Biol. Med. (1987) 186:96–102.
  • TEICHER BA, LIU SD, LIU JT, HOLDEN SA, HERMAN TS: A carbonic anhydrase inhibitor as a potential modulator of cancer therapies. AntiCancer Res. (1993) 13:1549–1556.
  • PUSCAS I, COLTAU M, FARCAU D, PUSCAS C, SUPURAN CT: Carbonic anhydrase and cancer. In: Carbonic Anhydrase, and Modulation of Physiologic and Pathologic Processes in the Organism. Puscas I (Ed.), Helicon, Timisoara, Roumania (1994)551–557.
  • CHEGWIDDEN WR, SPENCER IM: Sulphonamide inhibi-tors of carbonic anhydrase inhibit the growth of human lymphoma cells in culture. Inflammopharmacol (1995) 3:231–239.
  • SUPURAN CT, BRIGANTI F, TILLI S, CHEGWIDDEN WR, SCOZZAFAVA A: Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents ?./. Med. Chem. (2000) 43: (In press).
  • PARKKILA S, RAJANIEMI H, PARKKILA AK et al.: Carbonic anhydrase inhibitor suppresses invasion of renal cancer cells in vitro. Proc. Natl. Acad. Sci. USA (2000) 97:2220–2224.
  • NOGRADI A: The role of carbonic anhydrase in tumours. Am. J. Path. (1998) 153:1–4.
  • TAKI K, HIRAHARA K, TOMITA S, TOTOKI T: Acetazolamide-induced increase in blood flow to rabbit organs is confirmed using colored microspheres. Heart Vessels (1998) 13:63–67.
  • GAMBHIR S, INAO S, TADOKORO M et al.: Comparison of vasodilatory effect of carbon dioxide inhalation and intravenous acetazolamide on brain vasculature using positron emission tomography. Neurol. Res. (1997) 19:139–144.
  • GROSSMANN WM, KOEBERLE B: The dose-response relationship of acetazolamide on the cerebral blood flow in normal subjects. Cerebrovasc. Dis. (2000) 10:65–69.
  • BERTHEZENE Y, NIGHOGHOSSIAN N, MEYER R et al.: Can cerebrovascular reactivity be assessed by dynamic susceptibility contrast-enhanced MRI ? Neuroradiology (1998) 40:1–5.
  • DETRE JA, SAMUELS OB, ALSOP DC, GONZALEZ-AT JB, KASNER SE, RAPS EC: Noninvasive magnetic resonance imaging evaluation of cerebral blood flow with acetazolamide, challenge in patients with cerebrovas-cular stenosis. J. Magn. Reson. Imaging (1999) 10:870–875.
  • HIRANO T, MINEMATSU K, HASEGAWA Y, TANAKA Y, HAYASHIDA K, YAMAGUCHI T: Acetazolamide reactivity on 123I-IMP single photon emission computed tomography inpatients with major cerebral artery occlusive disease: correlation with positron emission tomography parameters. J. Cereb. Blood Flow Metab. (1994) 14:763–770.
  • HAYASHIDA K, TANAKA Y, HIROSE Y et al.: Vasoreactive effect of acetazolamide as a function of time with sequential PET 150-water measurement. Nucl. Med. Commun. (1996) 17:1047–1051.
  • TAKEUCHI R, MATSUDA H, YONEKURA Y, SAKAHARA H, KONISHI J: Noninvasive quantitative measurements of cerebral blood flow using technetium-99m-L,L-ECD SPECT activated with acetazolamide: quantification analysis by equal-volume-split 99mTc-ECD consecutive SPECT method. J. Cereb. Blood Flow Metab. (1997) 17:1020–1032.
  • LE BARS D, LUTHRA SK, PIKE VW, SWENSON ER: The radiosynthesis of a 11C-labelled carbonic anhydrase inhibitor - [carbonyl-11C]acetazolamide. Appl. RadiaL Isot. (1988) 39:671–675.
  • SALVADORI PA, SUPURAN CT, PETRONI D et al.: Carbonic anhydrase inhibitors: radiosynthesis of tight-binding 18F-labelled sulfonamide carbonic anhydrase inhibitors. Appl. RadiaL Isot. (2000) (In press).
  • BERGMANN SR: Cardiac positron emission tomography. Semin. Nucl. Med. (1998) 28:320–340.
  • SALVATORI M: Advances in pulmonary nuclear medicine. Rays (1997) 22:51–72.
  • FREY KA, MINOSHIMA S, KUHL DE: Neurochemical imaging of Alzheimer's disease and other degenerative dementia. Q. J. Nucl. Med. (1998) 42:166–178.
  • SWENSON ER: The role of lung carbonic anhydrase in ventilation-perfusion matching. In: Carbonic Anhydrase - From Biochemistry, and Genetics to Physiology and Clinical Medicine. Botrè F., Gros G., Storey B.T.( Eds.), VCH, Weinheim, Germany (1991):393–403.
  • SUPURAN CT, ILIES MA, SCOZZAFAVA A: Carbonic anhydrase inhibitors. Part 29. Interaction of isozymes I, II and IV with benzolamide-like derivatives. Eur. J. Med. Chem. (1998) 33:739–751.
  • LEINER M: Das Ferment Kohlensdureanhydrase im Tierkörper. Naturwiss. (1940) 28:316–317.
  • KIESE M: Die Aktivierung der Kohlensdureanhydrase. Naturwiss. (1941) 29:116–117
  • LEINER M, LEINER G: Die Aktivatoren der Kohlensdure-anhydrase. Naturwiss. (1941) 29:195–197.
  • LEINER M, LEINER G: Die Messmethoden zur Untersuchung der katalytischen Wirksamkeit der Kohlensdureanhydrase. Biochem. Z (1941) 311:119–145.
  • BRIGANTI F, IACONI V, MANGANI S et al.: A ternary complex of carbonic anhydrase: X-ray crystallo-graphic structure of the adduct of human carbonic anhydrase, II with the activator phenylalanine and the inhibitor azide. Inorg. Chim. Acta (1998) 275–276:295–300.
  • SUPURAN CT, PUSCAS I: Carbonic anhydrase activators. In: Carbonic anhydrase, and modulation of physiologic and pathologic processes in the organism. Puscas I (Ed.), Helicon, Timisoara (1994):113–145.
  • CLARE BW, SUPURAN CT: Carbonic anhydrase activa-tors. 3. Structure-activity correlations for a series of isozyme II activators. J. Pharm. Sci. (1994) 83:768–773.
  • ILIES MA, BANCIU MD, ILIES M et al.: Carbonic anhydrase activators. Part 17. Synthesis and activation study of a series of 1-(1,2,4-triazole-(1H)-3-y0-2,4,6-trisubstituted-pyridinium salts against isozymes I,, II and IV. Eur. J. Med. Chem. (1997) 32:911–918.
  • SUPURAN CT, BARBOIU M, LUCA C, POP E, BREWSTER ME, DINCULESCU A: Carbonic anhydrase activators. Part 14. Synthesis of mono- and bis- pyridinium salt derivatives of 2-amino-5-(2-aminoethy0- and 2-amino-5-(3-aminopropy0-1,3,4-thiadiazole and their interaction with isozyme II. Eur. J. Med. Chem. (1996) 31:597–606.
  • SUPURAN CT, CLARAMUNT RM, LAVANDERA JL, ELGUERO J: Carbonic anhydrase activators. Part 15. A kinetic study of the interaction of bovine isozyme II with pyrazoles, bis- and tris-azolylmethanes. Pharm. Bull. (1996) 19:1417–1422.
  • SUPURAN CT, BALABAN AT, CABILDO P, CLARAMUNT RM, LAVANDERA JL, ELGUERO J: Carbonic anhydrase activators. Part 7. Isozyme II activation with bis-azolylmethanes, -ethanes and related azoles. Pharm. Bull. (1993) 16:1236–1239.
  • BRIGANTI F, SCOZZAFAVA A, SUPURAN CT: Novel carbonic anhydrase isozymes I, II and IV activators incorporating sulfonyl-histamino moieties. Bioorg. Med. Chem. Lett. (1999) 9:2043–2048.
  • SCOZZAFAVA A, SUPURAN CT: Carbonic anhydrase activators. Part 21. Novel activators of isozymes I, II and IV incorporating carboxamido- and ureido histamine moieties. Eur. J. Med. Chem. (2000) 35:31–39.
  • SUPURAN CT, SCOZZAFAVA A: Carbonic anhydrase activators. Amino acyl/dipeptidyl histamine deriva-tives bind with high affinity to isozymes 1,11 and IV and act as efficient activators. Bioorg. Med. Chem. (1999) 7:2915–2924.
  • SCOZZAFAVA A, SUPURAN CT: Carbonic anhydrase activators. Part 24. High affinity isozymes I, II and IV activators, derivatives of 4-(4-chlorophenyl-sulfonylureido-amino acyfiethy1-11-1-imidazole. Eur. J. Pharm. Sci. (2000) 10:29–41.
  • CHIRICA LC, ELLEBY B, JONSSON BH, LINDSKOG S: The complete sequence, expression in Escherichia colt, purification and some properties of carbonic anhydrase from Neisseria gonorrhoeae. Eur. J. Biochem. (1997) 244:755–760.
  • HUANG S, XUE Y, SAUER-ERIKSSON E, CHIRICA L, LINDSKOG S, JONSSON BH: Crystal structure of carbonic anhydrase from Neisseria gonorrhoeae and its, complex with the inhibitor acetazolamide. J. Mol Biol. (1998) 28:301–310.
  • EICKHOFF TC, NELSON MS: In vitro activity of carbonic anhydrase inhibitors against Neisseria meningitidis. Antimicrob. Agents Chemother. (1966) 6:389–392.
  • SANDERS E: Use of sulfonamide carbonic anhydrase inhibitors in treatment of meningococcal carriers: rationale and report of a clinical trial of ethoxzola-mide. Am. J. Med. Sci. (1967) 254:709–716.
  • VANEECHOUETTE M, VERSCHRAEGEN G, CLAEYS G, VAN DEN ABEELE AM: Selective medium for Branhamella catarrhalis with acetazolamide as a specific inhibitor of Neisseria spp. J. Clin. Microbic)]. (1988) 26:2544–2548.
  • NAFI BM, MILES RJ, BUTLER LO, CARTER ND, KELLY C, JEFFERY S: Expression of carbonic anhydrase in neisseriae and other heterotrophic bacteria. J. Med. Microbic)]. (1990) 32:1–7.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.