Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups (655 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2012; 55(15): 6776-6783.
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Paper type: Journal Article,
Impact factor: 5.614, 5-year impact factor: 5.383
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84864917818&partnerID=40&md5=91e508eac5d24d0676acb14a19b8fd1c
Keywords: 4 (4 Acetamidophenylsulfonamido)benzoic Acid, 4 (4 Aminophenylsulfonamido)benzoic Acid, 4 [4 (sulfamoylamino)phenylsulfonamido] N (4 Sulfamoylphenethyl)benzamide, Acetazolamide, Carbonate Dehydratase Ii, Carbonate Dehydratase Inhibitor, Diclofenamide, Ethoxzolamide, N Sulfamoyl 4 Aminobenzene Sulfonamide, Sulfanilamide, Unclassified Drug, Zinc Ion, Article, Controlled Study, Drug Potency, Drug Protein Binding, Drug Structure, Enzyme Active Site, Structure Analysis, X Ray Crystallography, Carbonic Anhydrase Inhibitors, X-Ray, Enzyme Assays, Humans, Isoenzymes, Models, Molecular, Protein Conformation, Structure-Activity Relationship, 4 (4 Acetamidophenylsulfonamido) Benzoic Acid, 4 (4 Aminophenylsulfonamido) Benzoic Acid, 4 [4 (sulfamoylamino) Phenylsulfonamido] N (4 Sulfamoylphenethyl) Benzamide,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, via Mezzocannone 16, 80134 Napoli, Italy
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS-UM1-UM2, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
Universitaè Degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy
Universita Degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy
References:
Not available.
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2012; 55(15): 6776-6783.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 5.614, 5-year impact factor: 5.383
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84864917818&partnerID=40&md5=91e508eac5d24d0676acb14a19b8fd1c
Keywords: 4 (4 Acetamidophenylsulfonamido)benzoic Acid, 4 (4 Aminophenylsulfonamido)benzoic Acid, 4 [4 (sulfamoylamino)phenylsulfonamido] N (4 Sulfamoylphenethyl)benzamide, Acetazolamide, Carbonate Dehydratase Ii, Carbonate Dehydratase Inhibitor, Diclofenamide, Ethoxzolamide, N Sulfamoyl 4 Aminobenzene Sulfonamide, Sulfanilamide, Unclassified Drug, Zinc Ion, Article, Controlled Study, Drug Potency, Drug Protein Binding, Drug Structure, Enzyme Active Site, Structure Analysis, X Ray Crystallography, Carbonic Anhydrase Inhibitors, X-Ray, Enzyme Assays, Humans, Isoenzymes, Models, Molecular, Protein Conformation, Structure-Activity Relationship, 4 (4 Acetamidophenylsulfonamido) Benzoic Acid, 4 (4 Aminophenylsulfonamido) Benzoic Acid, 4 [4 (sulfamoylamino) Phenylsulfonamido] N (4 Sulfamoylphenethyl) Benzamide,
Affiliations:
*** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, via Mezzocannone 16, 80134 Napoli, Italy
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS-UM1-UM2, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France
Universitaè Degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy
Universita Degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, I-50019 Sesto Fiorentino (Firenze), Italy
References:
Not available.
Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups
A series of compounds incorporating both sulfonamide and sulfamide as zinc-binding groups (ZBGs) are reported as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Crystallographic studies on the complex of hCA II with the lead compound of this series, namely, 4-sulfamido- benzenesulfonamide, revealed the binding of two molecules in the enzyme active site cavity, the first one canonically coordinated to the zinc ion by means of the sulfonamide group and the second one located at the entrance of the cavity. This observation led to the design of elongated molecules incorporating these two ZBGs, separated by a linker of proper length, to allow the simultaneous binding to these different sites. The long inhibitors indeed showed around 10 times better enzyme inhibitory properties as compared to the shorter molecules against four physiologically relevant human (h) isoforms, hCA I, II, IX, and XII. © 2012 American Chemical Society.
A series of compounds incorporating both sulfonamide and sulfamide as zinc-binding groups (ZBGs) are reported as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Crystallographic studies on the complex of hCA II with the lead compound of this series, namely, 4-sulfamido- benzenesulfonamide, revealed the binding of two molecules in the enzyme active site cavity, the first one canonically coordinated to the zinc ion by means of the sulfonamide group and the second one located at the entrance of the cavity. This observation led to the design of elongated molecules incorporating these two ZBGs, separated by a linker of proper length, to allow the simultaneous binding to these different sites. The long inhibitors indeed showed around 10 times better enzyme inhibitory properties as compared to the shorter molecules against four physiologically relevant human (h) isoforms, hCA I, II, IX, and XII. © 2012 American Chemical Society.
Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups
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Development of potent carbonic anhydrase inhibitors incorporating both sulfonamide and sulfamide groups
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View Export to BibTeX Export to EndNote
Di Fiore A, Monti SM, Hilvo M, Parkkila S, Romano V, Scaloni A, Pedone C, Scozzafava A, Supuran CT, De Simone G
* Crystal structure of human carbonic anhydrase XIII and its complex with the inhibitor acetazolamide (1325 views)
Proteins (ISSN: 1097-0134, 0887-3585, 1097-0134electronic), 2009 Jan; 74(1): 164-175.
Impact Factor: 3.085
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Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A, Scozzafava A, Monti SM, Di Fiore A, De Simone G, Lindfors M, Janis J, Valjakka J, Pastorekova S, Pastorek J, Kulomaa MS, Nordlund HR, Supuran CT, Parkkila S
* Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes (1107 views)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 2008 Oct 10; 283(41): 27799-27809.
Impact Factor: 5.52
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Supuran CT, Di Fiore A, De Simone G
* Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity (856 views)
Expert Opin Emerg Drugsexpert Opinion On Emerging Drugs (ISSN: 1472-8214), 2008 Jun; 13(2): 383-392.
Impact Factor: 3.08
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Innocenti A, Scozzafava A, Parkkila S, Puccetti L, De Simone G, Supuran CT
* Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates (679 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2008 Apr 1; 18(7): 2267-2271.
Impact Factor: 2.531
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Leese MP, Jourdan FL, Gaukroger K, Mahon MF, Newman SP, Foster PA, Stengel C, Regis-Lydi S, Ferrandis E, Di Fiore A, De Simone G, Supuran CT, Purohit A, Reed MJ, Potter BVL
* Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents (748 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2008 Mar 13; 51(5): 1295-1308.
Impact Factor: 4.898
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De Simone G, Di Fiore A, Supuran CT
* Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? (717 views)
Curr Pharm Des Current Pharmaceutical Design (ISSN: 1381-6128, 1873-4286), 2008 Mar; 14(7): 655-660.
Impact Factor: 4.399
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D'Ambrosio K, Masereel B, Thiry A, Scozzafava A, Supuran CT, De Simone G
* Carbonic anhydrase inhibitors: Binding of indanesulfonamides to the human isoform II (762 views)
Chemmedchem (ISSN: 1860-7179, 1860-7187, 1860-7187electronic), 2008 Mar; 3(3): 473-477.
Impact Factor: 3.15
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Hilvo M, Innocenti A, Monti SM, De Simone G, Supuran CT, Parkkila S
* Recent advances in research on the most novel carbonic anhydrases, CA XIII and XV (1084 views)
Curr Pharm Des Current Pharmaceutical Design (ISSN: 1381-6128, 1873-4286), 2008; 14(7): 672-678.
Impact Factor: 4.399
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Calabrese V, Mancuso C, Calvani M, Rizzarelli E, Butterfield DA, Stella AM
* Nitric oxide in the central nervous system: neuroprotection versus neurotoxicity (1504 views)
Nature Reviews Neuroscience (ISSN: 1471-0048), 2007 Oct; 8(10): 766-775.
Impact Factor: 24.52
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Vitale RM, Pedone C, Amodeo P, Antel J, Wurl M, Scozzafava A, Supuran CT, De Simone G
* Molecular modeling study for the binding of zonisamide and topiramate to the human mitochondrial carbonic anhydrase isoform VA (525 views)
Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 1464-3391electronic), 2007 Jun 15; 15(12): 4152-4158.
Impact Factor: 2.662
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De Simone G, Supuran CT
* Antiobesity carbonic anhydrase inhibitors (839 views)
Curr Top Med Chem (ISSN: 1568-0266, 1568-0266linking, 1873-4294electronic), 2007; 7(9): 879-884.
Impact Factor: 4.325
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Leese MP, Leblond B, Smith A, Newman SP, Di Fiore A, De Simone G, Supuran CT, Purohit A, Reed MJ, Potter BVL
* 2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity (1345 views)
J Med Chem (ISSN: 0022-2623print, 0022-2623linking, 1520-4804), 2006 Dec 28; 49(26): 7683-7696.
Impact Factor: 5.115
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De Simone G, Vitale RM, Di Fiore A, Pedone C, Scozzafava A, Montero JL, Winum JY, Supuran CT
* Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX (852 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2006 Sep 7; 49(18): 5544-5551.
Impact Factor: 5.115
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Di Fiore A, Pedone C, D'Ambrosio K, Scozzafava A, De Simone G, Supuran CT
* Carbonic anhydrase inhibitors: Valdecoxib binds to a different active site region of the human isoform II as compared to the structurally related cyclooxygenase II 'selective' inhibitor celecoxib (532 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2006 Jan 15; 16(2): 437-442.
Impact Factor: 2.538
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Menchise V, De Simone G, Alterio V, Di Fiore A, Pedone C, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: Stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II (721 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2005 Sep 8; 48(18): 5721-5727.
Impact Factor: 4.926
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De Simone G, Di Fiore A, Menchise V, Pedone C, Antel J, Casini A, Scozzafava A, Wurl M, Supuran CT
* Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies (1213 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2005 May 2; 15(9): 2315-2320.
Impact Factor: 2.478
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Di Fiore A, De Simone G, Menchise V, Pedone C, Casini A, Scozzafava A, Supuran CT
* Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II (685 views)
Bioorg Med Chem Lett Bioorganic And Medicinal Chemistry Letters (ISSN: 0960-894x), 2005 Apr 1; 15(7): 1937-1942.
Impact Factor: 2.478
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Soricelli A, Postiglione A, Cuocolo A, De Chiara S, Ruocco A, Brunetti A, Salvatore M, Ell PJ
EFFECT OF ADENOSINE ON CEREBRAL BLOOD-FLOW AS EVALUATED BY SINGLE-PHOTON EMISSION COMPUTED-TOMOGRAPHY IN NORMAL SUBJECTS AND IN PATIENTS WITH OCCLUSIVE CAROTID DISEASE - A COMPARISON WITH ACETAZOLAMIDE (476 views)
Stroke (ISSN: 0039-2499), 1995 Sep; 26(9): 1572-1576.
Impact Factor: 4.323
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Mancini M, De Chiara S, Ferrara LA, Gallotta G, Postiglione A
TRANSCRANIAL DOPPLER EVALUATION OF CEREBROVASCULAR REACTIVITY TO ACETAZOLAMIDE IN NORMAL SUBJECTS (832 views)
15th World Congress Angiology Rome, 1989; 20(4): 284-284.
Impact Factor: 0
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35 Records (33 excluding Abstracts).
Total impact factor: 156.554 (151.439 excluding Abstracts).
Total 5 year impact factor: 152.426 (146.922 excluding Abstracts).
Total impact factor: 156.554 (151.439 excluding Abstracts).
Total 5 year impact factor: 152.426 (146.922 excluding Abstracts).
655 views. Last view on Saturday 22 March 2025, 17:06:04
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