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Research Article

A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology

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Pages 138-147 | Received 07 Sep 2009, Accepted 10 Nov 2009, Published online: 04 Aug 2011

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Kedar GhimireHelene M. AltmannAdam C. Straub & Jeffrey S. Isenberg. (2017) Nitric oxide: what’s new to NO?. American Journal of Physiology-Cell Physiology 312:3, pages C254-C262.
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Srinivas Angapelly, P.V. Sri Ramya, Andrea Angeli, Simona Maria Monti, Martina Buonanno, Mallika Alvala, Cladiu T. Supuran & Mohammed Arifuddin. (2017) Discovery of 4-sulfamoyl-phenyl-β-lactams as a new class of potent carbonic anhydrase isoforms I, II, IV and VII inhibitors: The first example of subnanomolar CA IV inhibitors. Bioorganic & Medicinal Chemistry 25:2, pages 539-544.
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Daniela Vullo, Claudiu T. Supuran, Andrea Scozzafava, Giuseppina De Simone, Simona Maria Monti, Vincenzo Alterio & Fabrizio Carta. (2016) Kinetic and X-ray crystallographic investigations of substituted 2-thio-6-oxo-1,6-dihydropyrimidine–benzenesulfonamides acting as carbonic anhydrase inhibitors. Bioorganic & Medicinal Chemistry 24:16, pages 3643-3648.
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Daniela Vullo, Mariaconcetta Durante, Francesco Saverio Di Leva, Sandro Cosconati, Emanuela Masini, Andrea Scozzafava, Ettore Novellino, Claudiu T. Supuran & Fabrizio Carta. (2016) Monothiocarbamates Strongly Inhibit Carbonic Anhydrases in Vitro and Possess Intraocular Pressure Lowering Activity in an Animal Model of Glaucoma. Journal of Medicinal Chemistry 59:12, pages 5857-5867.
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B. Richichi, V. Baldoneschi, S. Burgalassi, M. Fragai, D. Vullo, A. Akdemir, E. Dragoni, A. Louka, M. Mamusa, D. Monti, D. Berti, E. Novellino, G. De Rosa, C. T. Supuran & C. Nativi. (2016) A Divalent PAMAM-Based Matrix Metalloproteinase/Carbonic Anhydrase Inhibitor for the Treatment of Dry Eye Syndrome. Chemistry - A European Journal 22:5, pages 1714-1721.
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Sonia Del Prete, Daniela Vullo, Sameh M. Osman, Zeid AlOthman, Clemente Capasso & Claudiu T. Supuran. (2015) Anion inhibition studies of the dandruff-producing fungus Malassezia globosa β-carbonic anhydrase MgCA. Bioorganic & Medicinal Chemistry Letters 25:22, pages 5194-5198.
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Viviana De Luca, Sonia Del Prete, Vincenzo Carginale, Daniela Vullo, Claudiu T. Supuran & Clemente Capasso. (2015) Cloning, characterization and anion inhibition studies of a γ-carbonic anhydrase from the Antarctic cyanobacterium Nostoc commune. Bioorganic & Medicinal Chemistry Letters 25:21, pages 4970-4975.
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Cenzo Congiu, Valentina Onnis, Alessandro Deplano, Gianfranco Balboni, Nurcan Dedeoglu & Claudiu T. Supuran. (2015) Synthesis of sulfonamides incorporating piperazinyl-ureido moieties and their carbonic anhydrase I, II, IX and XII inhibitory activity. Bioorganic & Medicinal Chemistry Letters 25:18, pages 3850-3853.
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Marco Bragagni, Murat Bozdag, Fabrizio Carta, Andrea Scozzafava, Cecilia Lanzi, Emanuela Masini, Paola Mura & Claudiu T. Supuran. (2015) Cyclodextrin complexation highly enhances efficacy of arylsulfonylureido benzenesulfonamide carbonic anhydrase inhibitors as a topical antiglaucoma agents. Bioorganic & Medicinal Chemistry 23:18, pages 6223-6227.
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Diaa A. Ibrahim, Deena S. Lasheen, Maysoun Y. Zaky, Amany W. Ibrahim, Daniela Vullo, Mariangela Ceruso, Claudiu T. Supuran & Dalal A. Abou El Ella. (2015) Design and synthesis of benzothiazole-6-sulfonamides acting as highly potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII. Bioorganic & Medicinal Chemistry 23:15, pages 4989-4999.
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Nadia Touisni, Nasreddine Kanfar, Sébastien Ulrich, Pascal Dumy, Claudiu T. Supuran, Ahmad Mehdi & Jean‐Yves Winum. (2015) Fluorescent Silica Nanoparticles with Multivalent Inhibitory Effects towards Carbonic Anhydrases. Chemistry – A European Journal 21:29, pages 10306-10309.
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Nurcan Dedeoglu, Viviana De Luca, Semra Isik, Hatice Yildirim, Feray Kockar, Clemente Capasso & Claudiu T. Supuran. (2015) Cloning, characterization and anion inhibition study of a β-class carbonic anhydrase from the caries producing pathogen Streptococcus mutans. Bioorganic & Medicinal Chemistry 23:13, pages 2995-3001.
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Nurcan Dedeoglu, Viviana DeLuca, Semra Isik, Hatice Yildirim, Feray Kockar, Clemente Capasso & Claudiu T. Supuran. (2015) Sulfonamide inhibition study of the β-class carbonic anhydrase from the caries producing pathogen Streptococcus mutans. Bioorganic & Medicinal Chemistry Letters 25:11, pages 2291-2297.
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Mustafa Durgun, Hasan Turkmen, Mariangela Ceruso & Claudiu T. Supuran. (2015) Synthesis of Schiff base derivatives of 4-(2-aminoethyl)-benzenesulfonamide with inhibitory activity against carbonic anhydrase isoforms I, II, IX and XII. Bioorganic & Medicinal Chemistry Letters 25:11, pages 2377-2381.
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Fabrizio Carta, Sameh M. Osman, Daniela Vullo, Antonella Gullotto, Jean-Yves Winum, Zeid AlOthman, Emanuela Masini & Claudiu T. Supuran. (2015) Poly(amidoamine) Dendrimers with Carbonic Anhydrase Inhibitory Activity and Antiglaucoma Action. Journal of Medicinal Chemistry 58:9, pages 4039-4045.
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Leo Syrjänen, Marianne Kuuslahti, Martti Tolvanen, Daniela Vullo, Seppo Parkkila & Claudiu T. Supuran. (2015) The β-carbonic anhydrase from the malaria mosquito Anopheles gambiae is highly inhibited by sulfonamides. Bioorganic & Medicinal Chemistry 23:10, pages 2303-2309.
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Daniela Vullo, Viviana De Luca, Sonia Del Prete, Vincenzo Carginale, Andrea Scozzafava, Clemente Capasso & Claudiu T. Supuran. (2015) Sulfonamide inhibition studies of the γ-carbonic anhydrase from the Antarctic cyanobacterium Nostoc commune. Bioorganic & Medicinal Chemistry 23:8, pages 1728-1734.
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Fabrizio Carta, Lorenzo Di Cesare Mannelli, Melissa Pinard, Carla Ghelardini, Andrea Scozzafava, Robert McKenna & Claudiu T. Supuran. (2015) A class of sulfonamide carbonic anhydrase inhibitors with neuropathic pain modulating effects. Bioorganic & Medicinal Chemistry 23:8, pages 1828-1840.
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Aiga Grandane, Muhammet Tanc, Raivis Žalubovskis & Claudiu T. Supuran. (2015) Synthesis of 6-aryl-substituted sulfocoumarins and investigation of their carbonic anhydrase inhibitory action. Bioorganic & Medicinal Chemistry 23:7, pages 1430-1436.
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Simone Carradori, Adriano Mollica, Celeste De Monte, Arianna Granese & Claudiu Supuran. (2015) Nitric Oxide Donors and Selective Carbonic Anhydrase Inhibitors: A Dual Pharmacological Approach for the Treatment of Glaucoma, Cancer and Osteoporosis. Molecules 20:4, pages 5667-5679.
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Fabrizio Carta, Sameh M. Osman, Daniela Vullo, Zeid AlOthman & Claudiu T. Supuran. (2015) Dendrimers incorporating benzenesulfonamide moieties strongly inhibit carbonic anhydrase isoforms I–XIV. Organic & Biomolecular Chemistry 13:23, pages 6453-6457.
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Claudiu T. Supuran, Clemente Capasso & Giuseppina De Simone. 2015. Carbonic Anhydrases as Biocatalysts. Carbonic Anhydrases as Biocatalysts 51 90 .
Murat Bozdag, Melissa Pinard, Fabrizio Carta, Emanuela Masini, Andrea Scozzafava, Robert McKenna & Claudiu T. Supuran. (2014) A Class of 4-Sulfamoylphenyl-ω-aminoalkyl Ethers with Effective Carbonic Anhydrase Inhibitory Action and Antiglaucoma Effects. Journal of Medicinal Chemistry 57:22, pages 9673-9686.
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Murat Bozdag, Marta Ferraroni, Fabrizio Carta, Daniela Vullo, Laura Lucarini, Elisabetta Orlandini, Armando Rossello, Elisa Nuti, Andrea Scozzafava, Emanuela Masini & Claudiu T. Supuran. (2014) Structural Insights on Carbonic Anhydrase Inhibitory Action, Isoform Selectivity, and Potency of Sulfonamides and Coumarins Incorporating Arylsulfonylureido Groups. Journal of Medicinal Chemistry 57:21, pages 9152-9167.
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Alaa A.-M. Abdel-Aziz, Adel S. El-Azab, Mariangela Ceruso & Claudiu T. Supuran. (2014) Carbonic anhydrase inhibitory activity of sulfonamides and carboxylic acids incorporating cyclic imide scaffolds. Bioorganic & Medicinal Chemistry Letters 24:22, pages 5185-5189.
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Busra Sarikaya, Mariangela Ceruso, Fabrizio Carta & Claudiu T. Supuran. (2014) Inhibition of carbonic anhydrase isoforms I, II, IX and XII with novel Schiff bases: Identification of selective inhibitors for the tumor-associated isoforms over the cytosolic ones. Bioorganic & Medicinal Chemistry 22:21, pages 5883-5890.
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Ahmed M. Alafeefy, Mariangela Ceruso, Abdul-Malek S. Al-Tamimi, Sonia Del Prete, Clemente Capasso & Claudiu T. Supuran. (2014) Quinazoline–sulfonamides with potent inhibitory activity against the α-carbonic anhydrase from Vibrio cholerae. Bioorganic & Medicinal Chemistry 22:19, pages 5133-5140.
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Sonia Del Prete, Daniela Vullo, Gillian M. Fisher, Katherine T. Andrews, Sally-Ann Poulsen, Clemente Capasso & Claudiu T. Supuran. (2014) Discovery of a new family of carbonic anhydrases in the malaria pathogen Plasmodium falciparum —The η-carbonic anhydrases. Bioorganic & Medicinal Chemistry Letters 24:18, pages 4389-4396.
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Anthony P. Khawaja, Michelle P.Y. Chan, David C. Broadway, David F. Garway-Heath, Robert Luben, Jennifer L.Y. Yip, Shabina Hayat, Nicholas J. Wareham, Kay-Tee Khaw & Paul J. Foster. (2014) Systemic Medication and Intraocular Pressure in a British Population. Ophthalmology 121:8, pages 1501-1507.
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Mostafa M. Ghorab, Mansour S. Alsaid, Mariangela Ceruso, Yassin M. Nissan & Claudiu T. Supuran. (2014) Carbonic anhydrase inhibitors: Synthesis, molecular docking, cytotoxic and inhibition of the human carbonic anhydrase isoforms I, II, IX, XII with novel benzenesulfonamides incorporating pyrrole, pyrrolopyrimidine and fused pyrrolopyrimidine moieties. Bioorganic & Medicinal Chemistry 22:14, pages 3684-3695.
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Gihane Nasr, Alina Cristian, Mihail Barboiu, Daniella Vullo, Jean-Yves Winum & Claudiu T. Supuran. (2014) Carbonic anhydrase inhibitors. Inhibition of human cytosolic isoforms I and II with (reduced) Schiff’s bases incorporating sulfonamide, carboxylate and carboxymethyl moieties. Bioorganic & Medicinal Chemistry 22:10, pages 2867-2874.
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Aiga Grandane, Muhammet Tanc, Raivis Zalubovskis & Claudiu T. Supuran. (2014) Synthesis of 6-tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor-associated carbonic anhydrase isoforms IX and XII. Bioorganic & Medicinal Chemistry 22:5, pages 1522-1528.
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Murat Bozdag, Marta Ferraroni, Elisa Nuti, Daniela Vullo, Armando Rossello, Fabrizio Carta, Andrea Scozzafava & Claudiu T. Supuran. (2014) Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: Solution and X-ray crystallographic studies. Bioorganic & Medicinal Chemistry 22:1, pages 334-340.
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Andrea Scozzafava & Claudiu T. Supuran. 2014. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications 349 359 .
Robert McKenna & Claudiu T. Supuran. 2014. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications 291 323 .
Mariangela Ceruso, Daniela Vullo, Andrea Scozzafava & Claudiu T. Supuran. (2013) Inhibition of human carbonic anhydrase isoforms I–XIV with sulfonamides incorporating fluorine and 1,3,5-triazine moieties. Bioorganic & Medicinal Chemistry 21:22, pages 6929-6936.
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Özlen Güzel-Akdemir, Atilla Akdemir, Peiwen Pan, Alane B. Vermelho, Seppo Parkkila, Andrea Scozzafava, Clemente Capasso & Claudiu T. Supuran. (2013) A Class of Sulfonamides with Strong Inhibitory Action against the α-Carbonic Anhydrase from Trypanosoma cruzi . Journal of Medicinal Chemistry 56:14, pages 5773-5781.
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Fabrizio Carta, Atilla Akdemir, Andrea Scozzafava, Emanuela Masini & Claudiu T. Supuran. (2013) Xanthates and Trithiocarbonates Strongly Inhibit Carbonic Anhydrases and Show Antiglaucoma Effects in Vivo. Journal of Medicinal Chemistry 56:11, pages 4691-4700.
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Shyamasri Biswas, Fabrizio Carta, Andrea Scozzafava, Robert McKenna & Claudiu T. Supuran. (2013) Structural effect of phenyl ring compared to thiadiazole based adamantyl-sulfonamides on carbonic anhydrase inhibition. Bioorganic & Medicinal Chemistry 21:8, pages 2314-2318.
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Daniela Vullo, Semra Isik, Sonia Del Prete, Viviana De Luca, Vincenzo Carginale, Andrea Scozzafava, Claudiu T. Supuran & Clemente Capasso. (2013) Anion inhibition studies of the α-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae. Bioorganic & Medicinal Chemistry Letters 23:6, pages 1636-1638.
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Claudiu T. Supuran. (2013) Carbonic anhydrases. Bioorganic & Medicinal Chemistry 21:6, pages 1377-1378.
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Laszlo Tarko & Claudiu T. Supuran. (2013) QSAR studies of sulfamate and sulfamide inhibitors targeting human carbonic anhydrase isozymes I, II, IX and XII. Bioorganic & Medicinal Chemistry 21:6, pages 1404-1409.
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Gianfranco Balboni, Cenzo Congiu, Valentina Onnis, Alfonso Maresca, Andrea Scozzafava, Jean-Yves Winum, Annalisa Maietti & Claudiu T. Supuran. (2012) Flavones and structurally related 4-chromenones inhibit carbonic anhydrases by a different mechanism of action compared to coumarins. Bioorganic & Medicinal Chemistry Letters 22:9, pages 3063-3066.
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Fabrizio Carta, Mayank Aggarwal, Alfonso Maresca, Andrea Scozzafava, Robert McKenna, Emanuela Masini & Claudiu T. Supuran. (2012) Dithiocarbamates Strongly Inhibit Carbonic Anhydrases and Show Antiglaucoma Action in Vivo. Journal of Medicinal Chemistry 55:4, pages 1721-1730.
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