'Unconventional' coordination chemistry by metal chelating fragments in a metalloprotein active site

Journal of the American Chemical Society

Volumn 136, Issue 14, 2014, Pages 5400-5406

  Martin, David P ^a   Blachly, Patrick G ^a   Marts, Amy R ^b   Woodruff, Tessa M ^b   De Oliveira, César A F ^a   McCammon, J Andrew ^a   Tierney, David L ^a   Cohen, Seth M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b MIAMI UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; METALS; PROTEINS; X RAY CRYSTALLOGRAPHY; X RAY SPECTROSCOPY;

CO-ORDINATION CHEMISTRIES; COORDINATION COMPOUNDS; DENSITY FUNCTIONAL COMPUTATIONS; ENZYME ACTIVE SITES; HUMAN CARBONIC ANHYDRASE II; METAL COORDINATION; METAL-LIGAND BONDS; METALLO-PROTEINS;

LIGANDS;

CARBONATE DEHYDRATASE II; COORDINATION COMPOUND; ZINC; CARBONATE DEHYDRATASE INHIBITOR; CHELATING AGENT;

ARTICLE; BINDING AFFINITY; CHEMICAL BOND; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; GEOMETRY; LIGAND BINDING; METAL BINDING; PROTEIN STRUCTURE; ROENTGEN SPECTROSCOPY; X RAY CRYSTALLOGRAPHY; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION;

CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CATALYTIC DOMAIN; CHELATING AGENTS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84897998448     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja500616m     Document Type: Article

References (43)

1. Andreini, C.; Bertini, I.; Cavallaro, G.; Holliday, G. L.; Thornton, J. M. J. Biol. Inorg. Chem. 2008, 13, 1205-1218
2. Supuran, C. T.; Winum, J.-Y. Drug Design of Zinc-Enzyme Inhibitors; John Wiley & Sons, Inc.: Hoboken, NJ, 2009.
3. Martin, D. P.; Hann, Z. S.; Cohen, S. M. Inorg. Chem. 2012, 52, 12207-12215
4. Jacobsen, F. E.; Lewis, J. A.; Cohen, S. M. ChemMedChem 2007, 2, 152-171
5. Kawai, K.; Nagata, N. Eur. J. Med. Chem. 2012, 51, 271-276
6. Jacobsen, J. A.; Fullagar, J. L.; Miller, M. T.; Cohen, S. M. J. Med. Chem. 2011, 54, 591-602
7. Serrao, E.; Odde, S.; Ramkumar, K.; Neamati, N. Retrovirology 2009, 6, 25
8. Saito, A.; Yamashita, T.; Mariko, Y.; Nosaka, Y.; Tsuchiya, K.; Ando, T.; Suzuki, T.; Tsuruo, T.; Nakanishi, O. Proc. Nat. Acad. Sci. U.S.A. 1999, 96, 4592-4597
9. Johns, B. A.; Kawasuji, T.; Weatherhead, J. G.; Taishi, T.; Temelkoff, D. P.; Yoshida, H.; Akiyama, T.; Taoda, Y.; Murai, H.; Kiyama, R.; Fuji, M.; Tanimoto, N.; Jeffrey, J.; Foster, S. A.; Yoshinaga, T.; Seki, T.; Kobayashi, M.; Sato, A.; Johnson, M. N.; Garvey, E. P.; Fujiwara, T. J. Med. Chem. 2013, 56, 5901-5916
10. Looney, A.; Parkin, G.; Alsfasser, R.; Ruf, M.; Vahrenkamp, H. Angew. Chem., Int. Ed. 1992, 31, 92-93
11. Looney, A.; Han, R.; McNeill, K.; Parkin, G. J. Am. Chem. Soc. 1993, 115, 4690-4697
12. Parkin, G. Chem. Rev. 2004, 104, 699-767
13. Puerta, D. T.; Cohen, S. M. Inorg. Chem. 2002, 41, 5075-5082
14. Puerta, D. T.; Schames, J. R.; Henchman, R. H.; McCammon, J. A.; Cohen, S. M. Angew. Chem., Int. Ed. 2003, 42, 3772-3774
15. Puerta, D. T.; Lewis, J. A.; Cohen, S. M. J. Am. Chem. Soc. 2004, 126, 8388-8389
16. Jacobsen, F. E.; Breece, R. M.; Myers, W. K.; Tierney, D. L.; Cohen, S. M. Inorg. Chem. 2006, 45, 7306-7315
17. Cho, J. H.; Kim, D. H.; Chung, S. J.; Ha, N.-C.; Oh, B.-H.; Choi, K. Y. Bioorg. Med. Chem. 2002, 10, 2015-2022
18. Gaucher, J. F.; Selkti, M.; Tiraboschi, G.; Prangé, T.; Roques, B. P.; Tomas, A.; Fournié-Zaluski, M. C. Biochemistry 1999, 38, 12569-12576
19. Supuran, C. T.; Scozzafava, A.; Casini, A. Med. Res. Rev. 2003, 23, 146-189
20. Krishnamurthy, V. M.; Kaufman, G. K.; Urbach, A. R.; Gitlin, I.; Gudiksen, K. L.; Weibel, D. B.; Whitesides, G. M. Chem. Rev. 2008, 108, 946-1051
21. Breiten, B.; Lockett, M. R.; Sherman, W.; Fujita, S.; Al-Sayah, M.; Lange, H.; Bowers, C. M.; Heroux, A.; Krilov, G.; Whitesides, G. M. J. Am. Chem. Soc. 2013, 135, 15579-15584
22. Agrawal, A.; Johnson, S. L.; Jacobsen, J. A.; Miller, M. T.; Chen, L.-H.; Pellecchia, M.; Cohen, S. M. ChemMedChem 2010, 5, 195-199
23. Martin, D. P.; Cohen, S. M. Chem. Commun. 2012, 48, 5259-5261
24. Avvaru, B. S.; Kim, C. U.; Sippel, K. H.; Gruner, S. M.; Agbandje-McKenna, M.; Silverman, D. N.; McKenna, R. Biochemistry 2010, 49, 249-251
25. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr. 1997, D53, 240-255
26. Emsley, P.; Cowtan, K. Acta Crystallogr. 2004, D60, 2126-2132
27. Schüttelkopf, A. W.; Aalten, D. M. F. v. Acta Crystallogr. 2004, D60, 1355-1363
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyenga r, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
29. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
30. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
31. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
32. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
33. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001
34. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681
35. Klamt, A.; Schuurmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799-805
36. Ryde, U. Biophys. J. 1999, 77, 2777-2787
37. Dudev, T.; Lim, C. J. Am. Chem. Soc. 2000, 122, 11146-11153
38. Rao, C. P.; Dorfman, J. R.; Holm, R. H. Inorg. Chem. 1986, 25, 428-439
39. Wischeler, J. S.; Innocenti, A.; Vullo, D.; Agrawal, A.; Cohen, S. M.; Heine, A.; Supuran, C. T.; Klebe, G. ChemMedChem 2010, 5, 1609-1615
40. Barrese, A. A.; Genis, C.; Fisher, S. Z.; Orwenyo, J. N.; Kumara, M. T.; Dutta, S. K.; Phillips, E.; Kiddle, J. J.; Tu, C.; Silverman, D. N.; Govindasamy, L.; Agbandje-McKenna, M.; McKenna, R.; Tripp, B. C. Biochemistry 2008, 47, 3174-3184
41. Tekeste, T.; Vahrenkamp, H. Inorg. Chem. 2006, 45, 10799-10806
42. Mongan, J.; Case, D. A.; McCammon, J. A. J. Comput. Chem. 2004, 25, 2038-2048
43. Enyedy, é. A.; Dömötör, O.; Varga, E.; Kiss, T.; Trondl, R.; Hartinger, C. G.; Keppler, B. B. J. Inorg. Biochem. 2012, 117, 189-197