Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides

Journal of Medicinal Chemistry

Volumn 51, Issue 6, 2008, Pages 1945-1953

  Wilkinson, Brendan L ^a   Innocenti, Alessio ^b   Vullo, Daniela ^b   Supuran, Claudiu T ^b   Poulsen, Sally Ann ^a  

^a GRIFFITH UNIVERSITY   (Australia)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 [4 (AMINOSULFONYL)PHENYL] 1 (2' ACETAMIDO 2' DEOXY BETA DEXTRO GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (2' DEOXY 3',4',6' TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (2',3',4' TRI O ACETYL ALPHA DEXTRO ARABINOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (2',3',4' TRI O ACETYL BETA DEXTRO GLUCURONIC ACID METHYL ESTER) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (2',3',4' TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (2',3',4',6' TETRA O ACETYL ALPHA DEXTRO MANNOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (ALPHA DEXTRO ARABINOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (ALPHA DEXTRO MANNOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (BETA DEXTRO GALACTOYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (BETA DEXTRO GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (BETA DEXTRO GLUCURONIC ACID METHYL ESTER) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (BETA DEXTRO MALTOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (BETA DEXTRO RIBOFURANOSYL) 1H 1,2,3 TRIAZOLE; 4 [4 (AMINOSULFONYL)PHENYL] 1 (HEPTA O ACETYL BETA DEXTRO MALTOPYRANOSYL) 1H 1,2,3 TRIAZOLE; 4 ETHYNYL BENZENE SULFONAMIDE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE IX; GLYCOCONJUGATE; SULFONAMIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; PHARMACOPHORE; STEREOCHEMISTRY;

ANTIGENS, NEOPLASM; BENZENE DERIVATIVES; CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; GLYCOSIDES; HUMANS; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; TRIAZOLES;

EID: 41149177054     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701426t     Document Type: Article

References (50)

1. (a) Maren, T. H. Carbonic Anhydrase: Chemistry, Physiology and Inhibition. Physiol. Rev. 1967, 47 (4), 595-781.
2. (b) Supuran, C. T. Carbonic anhydrases: Catalytic and inhibition mechanism, distribution and physiological roles. In Carbonic Anhydrase: Its Inhibitors and Activators; Supuran, C. T., Scozzafava, A., Conway, J., Eds., CRC Press: Boca Raton, FL, 2004; pp 1-24.
3. (a) For a series of comprehensive reviews on CA expression, distribution, and therapeutic potential of CA inhibition and activation, see: Pastorekova, S.; Parkkila, S.; Pastorek, J.; Supuran, C. T. Carbonic Anhydrases: Current State of the Art, Therapeutic Applications and Future Prospects. J. Enzyme Inhib. 2004, 19 (3), 199-229.
4. (b) Supuran, C. T.; Scozzafava, A.; Casini, A. Carbonic Anhydrase Inhibitors. Med. Res. Rev. 2003, 23 (2), 146.
5. (c) Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Carbonic Anhydrase Inhibitors and Activators and Their Use in Therapy. Expert Opin. Ther. Pat. 2006, 16 (12), 1627-1664.
6. (d) Clare, B. W.; Supuran, C. T. A Perspective on Quantitative Structure-Activity Relationships and Carbonic Anhydrase Inhibitors. Expert Opin. Drug Metab. Toxicol. 2006, 2 (1), 113-137.
7. (a) Thiry, A.; Dogne, J. -A.; Masereel, B.; Supuran, C. T. Targeting Tumour-Associated Carbonic Anhydrase IX in Cancer Therapy. Trends Pharmacol. Sci. 2006, 27 (11), 566-573.
8. (b) Parkkila, S.; Rajaniemi, H.; Parkkila, A. K.; Kivelä, J.; Waheed, A.; Pastorekova, S.; Pastorek, J.; Sly, W. S. Carbonic Anhydrase Inhibitor Suppresses Invasion of Renal Cancer Cells In Vitro. Proc. Natl. Acad. Sci. U.S.A. 2000, 97 (5), 2220.
9. (a) Scozzafava, A.; Menabuoni, L.; Mincione, F.; Supuran, C. T. Carbonic Anhydrase Inhibitors, A General Approach for the Preparation of Water-Soluble Sulfonamides Incorporating Polyamino-Polycarboxylate Tails and of Their Metal Complexes Possessing Long-Lasting, Topical Intraocular Pressure-Lowering Properties. J. Med. Chem. 2002, 45 (7), 1466-1476.
10. (b) Casini, A.; Scozzafava, A.; Mincione, F.; Menabuoni, L.; Starnotti, M.; Supuran, C. T. Carbonic Anhydrase Inhibitors: Topically Acting Antiglaucoma Sulfonamides Incorporating Esters and Amides of 3- and 4-Carboxybenzolamide. Bioorg. Med. Chem. Lett. 2003, 13 (17), 2867-2873.
11. (c) Mincione, F.; Starnotti, M.; Menabuoni, L.; Scozzafava, A.; Casini, A.; Supuran, C. T. Carbonic Anhydrase Inhibitors: 4-Sulfamoylbenzenecarboxamides and 4-Chloro-3-sulfamoyl-benzenecarboxamides with Strong Topical Antiglaucoma Properties. Bioorg. Med. Chem. Lett. 2001, 11 (13), 1787-1791.
12. Supuran, C. T. Carbonic Anhydrase Inhibitors in the Treatment and Prophylaxis of Obesity. Expert Opin. Ther. Pat. 2003, 13, 1545-1550.
13. Vullo, D.; Voipio, J.; Innocenti, A.; Rivera, C.; Ranki, H.; Scozzafava, A.; Kaila, K.; Supuran, C. T. Carbonic Anhydrase Inhibitors, Inhibition of the Human Cytosolic Isozyme VII with Aromatic and Heterocyclic Sulfonamides. Bioorg. Med. Chem. Lett. 2005, 15 (4), 971-976.
14. Maren, T. H.; Ellison, A. C. Renal Carbonic Anhydrase. Mol. Pharmacol. 1967, 3 (6), 503-8.
15. Mann, T.; Keilin, D. Sulphanilamide as a Specific Carbonic Anhydrase Inhibitor. Nature 1940, 146, 164-165.
16. Krebs, H. A. Inhibition of Carbonic Anhydrase by Sulfonamides. Biochem. J. 1948, 43, 525-528.
17. (a) Abbate, F.; Casini, A.; Scozzafava, A.; Supuran, C., T. Carbonic Anhydrase Inhibitors: X-ray Crystallographic Structure of the Adduct of Human Isozyme II with a Topically Acting Antiglaucoma Sulfonamide. Bioorg. Med. Chem. Lett. 2004, 14 (9), 2357-2361.
18. (b) Supuran, C. T. Clinical Applications of Carbonic Anhydrase Inhibitors in Opthamology. Carbonic Anhydrase: Its Inhibitors and Activators; Supuran, C. T., Scozzafava, A., Conway, J., Eds.;CRC Press: Boca Raton, FL, 2004; pp 243-253.
19. (a) Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Modulation of Carbonic Anhydrase Activity and its Applications in Therapy. Expert Opin. Ther. Pat. 2004, 14 (5), 667-702.
20. (b) Vullo, D.; Voipio, J.; Innocenti, A.; Rivera, C.; Ranki, H.; Scozzafava, A.; Kaila, K.; Supuran, C. T. Carbonic Anhydrase Inhibitors. Inhibition of the Human Cytosolic Isozyme VII with Aromatic and Heterocyclic Sulfonamides. Bioorg. Med. Chem. Lett. 2005, 15 (4), 971-976.
21. Svastova, E.; Hulikova, A.; Rafajova, M.; Zatovicova, M.; Gibadulinova, A.; Casini, A.; Cecchi, A.; Scozzafava, A.; Supuran, C. T.; Pastorek, J.; Pastorekova, S. Hypoxia Activates the Capacity of Tumour-Associated Carbonic Anhydrase IX to Acidify Extracellular pH. FEBS Lett. 2004, 577, 439-445.
22. Haapasalo, J. A.; Nordfors, K. M.; Hilvo, M.; Rantala, I. J.; Soini, Y.; Parkkila, A.-S.; Pastorekova, S.; Pastorek, J.; Parkkila, S. M.; Haapasalo, H. K. Expression of Carbonic Anhydrase IX in Astrocytic Tumours Predicts Poor Prognosis. Clin. Cancer Res. 2006, 12 (2), 473-477.
23. 14C] Indisulam following i.v. Infusion in Cancer Patients. Invest. New Drugs 2005, 23 (4), 317-330.
24. Scozzafava, A.; Briganti, F.; Ilies, M. A.; Supuran, C. T. Carbonic Anhydrase Inhibitors: Synthesis of Membrane-Impermeant, Low Molecular Weight Sulfonamides Possessing In Vivo Selectivity for the Membrane-Bound versus Cytosolic Isozymes. J. Med. Chem. 2000, 43 (2), 292-300.
25. Menehise, V.; De Simone, G.; Alterio, V.; Di Fiore, A.; Pedone, C.; Scozzafava, A.; Supuran, C. T. 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 Antitumour Sulfonamide Complexed with Isozyme II. J. Med. Chem. 2005, 48 (18), 5721-5727.
26. (a) Macmillan, D.; Daines, A. M. Recent Developments in the Synthesis and Discovery of Oligosaccharides and Glycoconjugates for the Treatment of Disease. Curr. Med. Chem. 2003, 10 (24), 2733-2773.
27. (b) Davis, B. J. Synthesis of Glycoproteins. Chem. Rev. 2002, 102 (2), 579-601.
28. (a) Thorson, J. S.; Vogt, T. Glycosylated Natural Products. In Carbohydrate-Based Drug Discovery; Wong, C. -H., Ed.; Wiley VCH: Germany, 2003; pp 803-829.
29. (b) Wessjohann, L. A.; Ruijter, E.; Garcia-Rivera, D.; Brandt, W. What can a Chemist Learn from nature's Macrocycles? A Brief, Conceptual View. Mol. Div. 2005, 9 (1-3), 171-186.
30. (a) Tietze, L. F.; Lieb, M.; Herzig, T.; Haunert, F.; Schubert, I. A Strategy for Tumor-Selective Chemotherapy by Enzymatic Liberation of seco-Duocarmycin SA-Derivatives from Nontoxic Prodrugs. Bioorg. Med. Chem. 2001, 9 (7), 1929-1939.
31. (c) Robinson, M. A.; Charlton, S. T.; Garnier, P.; Wang, X. -T.; Davis, S. S.; Perkins, A. C.; Frier, M.; Duncan, R.; Savage, T. J.; Wyatt, D. A.; Watson, S.; Davis, B. G. LEAPT: Lectin-Directed Enzyme-Activated Prodrug Therapy. Proc. Nat. Acad. Sci. U.S.A. 2004, 101 (40), 14527-14532.
32. (a) For reviews on click chemistry in drug discovery and biotechnology, see: Kolb, H. C.; Sharpless, K. B. The Growing Impact of Click Chemistry on Drug Discovery. Drug Discovery Today 2003, 8 (24), 1128-1136.
33. (b) Röper, S.; Kolb, H. C. Click Chemistry for Drug Discovery. In Fragment-Based Approaches in Drug Discovery; Jahnke, W., Erlanson, D. A., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2006 andreferences therein,
34. (c) Sharpless, K. B.; Manetsch, R. In Situ Click Chemistry: A Powerful Means for Lead Discovery. Expert Opin. Drug Discovery 2006, 1, 525-538.
35. Wilkinson, B. L.; Bornaghi, L. F.; Poulsen, S.-A.; Houston, T. A. Synthetic Utility of Glycosyl Triazoles in Carbohydrate Chemistry. Tetrahedron 2006, 62, 8115-8125.
36. (a) Mocharla, V. P.; Colasson, B.; Lee, L. V.; Roeper, S.; Sharpless, K. B.; Wong, C.-H.; Kolb, H. C. In Situ Click Chemistry: Enzyme-Generated Inhibitors of Carbonic Anhydrase II. Angew. Chem., Int. Ed. 2005, 44, 116-120.
37. (b) Wang, J.; Sui, G.; Mocharla, V. P.; Lin, R. J.; Phelps, M. E.; Kolb, H. C.; Tseng, H.-R. Integrated Microfluidics for Parallel Screening of an In Situ Click Chemistry Library. Angew. Chem., Int. Ed. 2006, 45, 5276-5281.
38. Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Supuran, C. T.; Poulsen, S.-A. A Novel Class of Carbonic Anhydrase Inhibitors: Glycoconjugate Benzene Sulfonamides Prepared by "Click-Tailing". J. Med. Chem. 2006, 49 (22), 6539-6548.
39. Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Carbonic Anhydrase Inhibitors: Inhibition of Isozymes I, II and IX with Triazole-linked O-Glycosides of Benzene Sulfonamides. J. Med. Chem. 2007, 50, 1651-1657.
40. Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Inhibition of Membrane-Associated Carbonic Anhydrase Isozymes IX, XII and XIV with a Library of Glycoconjugate Benzene Sulfonamides. Bioorg. Med. Chem. Lett. 2007, 17 (4), 987-992.
41. Rossi, L. L.; Basu, A. Glycosidase Inhibition by 1-Glycosyl-4-phenyl Triazoles. Bioorg. Med. Chem. Lett. 2005, 15 (15), 3596-3599.
42. Chang, K. -H.; Huang, C. -C.; Liu, Y.-H.; Hu, Y.-H.; Chou, P. -T.; Lin, Y. -C. Synthesis of Photo-Luminescent Zn(II) Schiff Base Complexes and its Derivative Containing Pd(II) Moiety. Dalton Trans. 2004, 11, 1731-1738.
43. Kunz, H.; Waldmann, H. Construction of N-Glycopeptide Disaccharides. Synthesis of the Linkage Region of the Transmembrane Neuraminidase of an Influenza Virus. Construction of Disaccharide N-Glycopeptides - Synthesis of the Linkage Region of the Transmembrance-Neuraminidase of an Influenza Virus. Angew. Chem., Int. Ed. Engl. 1985, 24, 883-885.
44. Stimac, A.; Kobe, J. An Improved Preparation of 2,3,5-Tri-O-acyl- â-D-ribofuranosyl Azides by the Lewis Acid-Catalyzed Reaction of â-D-Ribofuranosyl Acetates and Trimethylsilyl Azide: An Example of Concomitant Formation of the ́-Anomer by Trimethylsilyl Triflate Catalysis. Carbohydr. Res. 1992, 232 (2), 359-365.
45. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes. Angew. Chem., Int. Ed. 2002, 41 (14), 2596-2599.
46. Khalifah, R. G. T. The Carbon Dioxide Hydration Activity of Carbonic Anhydrase. J. Biol. Chem. 1971, 246 (8), 2561-2573.
47. Salmon, A. S.; Williams, M. L.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Inhibition of Carbonic Anhydrase Isozymes I, II and IX with Benzenesulfonamides Containing an Organometallic Moiety. Bioorg. Med. Chem. Lett. 2007, 17, 532-535.
48. Winum, J.-Y.; Vullo, D.; Casini, A.; Montera, J.-L.; Scozzafava, A.; Supuran, C. T. Carbonic Anhydrase Inhibitors: Inhibition of Transmembrane, Tumor-Associated Isozyme IX, and Cytosolic Isozymes I and II with Aliphatic Sulfamates. J. Med. Chem. 2003, 46, 5471-5477.
49. Winum, J.-Y.; Vullo, D.; Casini, A.; Montera, J.-L.; Scozzafava, A.; Supuran, C. T. Carbonic Anhydrase Inhibitors. Inhibition of Cytosolic Isozymes I and II and Transmembrane, Tumor-Associated Isozyme IX with Sulfamates Including EMATE also Acting as Steroid Sulfatase Inhibitors. J. Med. Chem. 2003, 46, 2197-2204.
50. Casey, J. R.; Morgan, P. E.; Vullo, D.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Carbonic Anhydrase Inhibitors. Design of Selective, Membrane-Impermeant Inhibitors Targeting the Human Tumor-Associated Isozyme IX. J. Med. Chem. 2004, 47, 2337-2347.