Carbonic anhydrase inhibitors with dual-tail moieties to match the hydrophobic and hydrophilic halves of the carbonic anhydrase active site

Journal of Medicinal Chemistry

Volumn 58, Issue 3, 2015, Pages 1494-1501

  Tanpure, Rajendra P ^a   Ren, Bin ^b   Peat, Thomas S ^b   Bornaghi, Laurent F ^a   Vullo, Daniela ^c   Supuran, Claudiu T ^c   Poulsen, Sally Ann ^a  

^a GRIFFITH UNIVERSITY   (Australia)

^b CSIRO   (Australia)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAZOLAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR;

ARTICLE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; HUMAN; HYDROPHILICITY; HYDROPHOBICITY; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CATALYTIC DOMAIN; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84922795768     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501798g     Document Type: Article

References (36)

1. Ward, C.; Langdon, S. P.; Mullen, P.; Harris, A. L.; Harrison, D. J.; Supuran, C. T.; Kunkler, I. H. New strategies for targeting the hypoxic tumour microenvironment in breast cancer Cancer Treat. Rev. 2013, 39, 171-179
2. Pastorek, J.; Pastorekova, S. Hypoxia-induced carbonic anhydrase IX as a target for cancer therapy: from biology to clinical use Semin. Cancer Biol. 2014, 10.1016/j.semcancer.2014.08.002
3. Parks, S. K.; Chiche, J.; Pouyssegur, J. pH control mechanisms of tumor survival and growth J. Cell. Physiol. 2011, 226, 299-308
4. Neri, D.; Supuran, C. T. Interfering with pH regulation in tumours as a therapeutic strategy Nat. Rev. Drug Discovery 2011, 10, 767-777
5. Supuran, C. T. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators Nat. Rev. Drug Discovery 2008, 7, 168-181
6. Alterio, V.; Di Fiore, A.; D'Ambrosio, K.; Supuran, C. T.; De Simone, G. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem. Rev. 2012, 112, 4421-4468
7. Supuran, C. T. Structure-based drug discovery of carbonic anhydrase inhibitors J. Enzyme Inhib. Med. Chem. 2012, 27, 759-772
8. Aggarwal, M.; Boone, C. D.; Kondeti, B.; McKenna, R. Structural annotation of human carbonic anhydrases J. Enzyme Inhib. Med. Chem. 2013, 28, 267-277
9. Aggarwal, M.; Kondeti, B.; McKenna, R. Insights towards sulfonamide drug specificity in alpha carbonic anhydrases Bioorg. Med. Chem. 2013, 21, 1526-1533
10. De Simone, G.; Alterio, V.; Supuran, C. T. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors Expert Opin. Drug Discovery 2013, 8, 793-810
11. Hassan, I.; Shajee, B.; Waheed, A.; Ahmad, F.; Sly, W. S. Structure, function and applications of carbonic anhydrase isozymes Bioorg. Med. Chem. 2013, 21, 1570-1582
12. Lopez, M.; Salmon, A.; Supuran, C.; Poulsen, S. Carbonic anhydrase inhibitors developed through 'click tailing' Curr. Pharm. Des. 2010, 16, 3277-3287
13. Winum, J.-Y.; Poulsen, S.-A.; Supuran, C. T. Therapeutic applications of glycosidic carbonic anhydrase inhibitors Med. Res. Rev. 2009, 29, 419-435
14. Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. 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
15. Supuran, C. T. Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnologic use for CO2 capture J. Enzyme Inhib. Med. Chem. 2013, 28, 229-230
16. 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, 6539-6548
17. Salmon, A. J.; Williams, M. L.; Hofmann, A.; Poulsen, S.-A. Protein crystal structures with ferrocene and ruthenocene-based enzyme inhibitors Chem. Commun. 2012, 48, 2328-2330
18. Wilkinson, B. L.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides J. Med. Chem. 2008, 51, 1945-1953
19. Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes Med. Res. Rev. 2008, 28, 278-308
20. Massarotti, A.; Aprile, S.; Mercalli, V.; Del Grosso, E.; Grosa, G.; Sorba, G.; Tron, G. C. Are 1,4- and 1,5-disubstituted 1,2,3-triazoles good pharmacophoric groups? ChemMedChem 2014, 9, 2497-2508
21. Kayser, B.; Dumont, L.; Lysakowski, C.; Combescure, C.; Haller, G.; Tramèr, M. R. Reappraisal of acetazolamide for the prevention of acute mountain sickness: a systematic review and meta-analysis High Alt. Med. Biol. 2012, 13, 82-92
22. Wu, H.; Li, H.; Kwok, R. T. K.; Zhao, E.; Sun, J. Z.; Qin, A.; Tang, B. Z. A recyclable and reusable supported Cu(I) catalyzed azide-alkyne click polymerization Sci. Rep. 2014, 4, 5107
23. The PyMOL Molecular Graphics System; Schrödinger, LLC: New York.
24. Carroux, C. J.; Moeker, J.; Motte, J.; Lopez, M.; Bornaghi, L. F.; Katneni, K.; Ryan, E.; Morizzi, J.; Shackleford, D. M.; Charman, S. A.; Poulsen, S.-A. Synthesis of acylated glycoconjugates as templates to investigate in vitro biopharmaceutical properties Bioorg. Med. Chem. Lett. 2013, 23, 455-459
25. Waghorn, P. A.; Jones, M. W.; McIntyre, A.; Innocenti, A.; Vullo, D.; Harris, A. L.; Supuran, C. T.; Dilworth, J. R. Targeting carbonic anhydrases with fluorescent BODIPY-labelled sulfonamides Eur. J. Inorg. Chem. 2012, 17, 2898-2907
26. Moeker, J.; Peat, T. S.; Bornaghi, L. F.; Vullo, D.; Supuran, C. T.; Poulsen, S.-A. Cyclic secondary sulfonamides: unusually good inhibitors of cancer-related carbonic anhydrase enzymes J. Med. Chem. 2014, 57, 3522-3531
27. Kabsch, W. XDS Acta Crystallogr., Sect. D: Biol. Crystallogr. 2010, 66, 125-132
28. Evans, P. Scaling and assessment of data quality Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 72-82
29. McCoy, A. J.; Grosse-Kunstleve, R. W.; Adams, P. D.; Winn, M. D.; Storoni, L. C.; Read, R. J. Phaser crystallographic software J. Appl. Crystallogr. 2007, 40, 658-674
30. Emsley, P.; Cowton, K. Coot: model-building tools for molecular graphics Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126-2132
31. Afonine, P. V.; Grosse-Kunstleve, R. W.; Echols, N.; Headd, J. J.; Moriarty, N. W.; Mustyakimov, M.; Terwilliger, T. C.; Urzhumtsev, A.; Zwart, P. H.; Adams, P. D. Towards automated crystallographic structure refinement with phenix.refine Acta Crystallogr., Sect. D: Biol. Crystallogr. 2012, 68, 352-367
32. Moriarty, N. W.; Grosse-Kunstleve, R. W.; Adams, P. D. Electronic ligand builder and optimization workbench (eLBOW): a tool for ligand coordinate and restraint generation Acta Crystallogr., Sect. D: Biol. Crystallogr. 2009, 65, 1074-1080
33. Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase J. Biol. Chem. 1971, 246, 2561-2573
34. Lopez, M.; Drillaud, N.; Bornaghi, L. F.; Poulsen, S.-A. Synthesis of S -glycosyl primary sulfonamides J. Org. Chem. 2009, 74, 2811-2816
35. Winum, J.-Y.; Vullo, D.; Casini, A.; Montero, J.-L.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: inhibition of cytosolic isozymes I and II and the membrane-bound, tumor associated isozyme IX with sulfamates also acting as steroid sulfatase inhibitors J. Med. Chem. 2003, 46, 2197-2204
36. Vullo, D.; Innocenti, A.; Nishimori, I.; Pastorek, J.; Scozzafava, A.; Pastoreková, S.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? Bioorg. Med. Chem. Lett. 2005, 15, 963-969