Carbonic anhydrase inhibitors. Inhibition of isoforms I, II, IV, VA, VII, IX, and XIV with sulfonamides incorporating fructopyranose-thioureido tails

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 10, 2007, Pages 2685-2691

  Winum, Jean Yves ^a   Thiry, Anne ^b   Cheikh, Khaled El ^a   Dogné, Jean Michel ^b   Montero, Jean Louis ^a   Vullo, Daniela ^c   Scozzafava, Andrea ^c   Masereel, Bernard ^b   Supuran, Claudiu T ^c  

^a INSTITUT CHARLES GERHARDT   (France)

^b UNIVERSITY OF NAMUR   (Belgium)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Anticonvulsant; Carbonic anhydrase; MES test; Sulfamate; Sulfonamide; Topiramate

Indexed keywords

ACETAZOLAMIDE; CARBAMAZEPINE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; CARBONIC ANHYDRASE VA; CARBONIC ANHYDRASE VII; CARBONIC ANHYDRASE XIV; ISOENZYME; PHENYTOIN; SULFANILAMIDE DERIVATIVE; TOPIRAMATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG EFFICACY; DRUG SYNTHESIS; ELECTRIC SHOCK; ENZYME INHIBITION; INHIBITION KINETICS; MALE; MOUSE; NONHUMAN; SEIZURE;

ACETAZOLAMIDE; CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; HUMANS; ISOENZYMES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

MUS;

EID: 34247485893     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.03.008     Document Type: Article

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49. The compounds were tested for their anticonvulsant activity by the maximal electroshock seizure (MES) test. The experiments were carried out on male OF1 mice (weighing 28-40 g, from Charles River Laboratories, Belgium) after at least one-week acclimatization. All experimental procedures applied in this study were conducted at the University of Liège (Belgium) and were approved by the Ethics Committee of the University of Liège. The animals were housed under standard laboratory conditions (ambient temperature of 20 °C, natural light-dark cycle). Tap water and pellets were freely available before the experiment. Each experimental group consisted of eight animals. The synthesized compounds and the reference antiepileptic drugs (carbamazepine, phenytoine, and topiramate) were suspended in an aqueous solution of 1% Tween 80 (Acros Organics) administered intraperitoneally (ip) 2 h before the stimulation in a standard volume of 3mL/kg at 30 mg/kg body weight dose for phenytoine and carbamazepine and at 50 mg/kg body weight dose for the other compounds. Control animals received appropriated volumes of the solvent. Carbamazepine and phenytoine were purchased from Acros Organics. Topiramate was purchased from Sigma. The electroconvulsions were produced by a Hugo Sachs generator (15 mA, 50 Hz, 500 V, 200 ms, Rodent Shocker Type-221, Feiburg, Germany) and delivered via saline moistened eye electrodes. A drop of Unicaine (oxybuprocaine HCl 4 mg/mL, Théa Pharma, Belgium) is instilled in the eye prior to application of the electrodes in order to induce local anesthesia and ensure a good conductivity of the electroshock current. Abolition of the hind-leg tonic extension component of the seizure is defined as protection.