Effect of donor atom identity on metal-binding pharmacophore coordination

Journal of Biological Inorganic Chemistry

Volumn 22, Issue 4, 2017, Pages 605-613

  Dick, Benjamin L ^a   Patel, Ashay ^a   McCammon, J Andrew ^a   Cohen, Seth M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Computational chemistry; Density functional theory; Ligand binding; Metalloenzyme; X ray crystallography

Indexed keywords

1,2 HOPTO; CARBONATE DEHYDRATASE II; METAL; ORGANIC COMPOUND; THIOTROPOLONE; TROPOLONE; UNCLASSIFIED DRUG; CARBONATE DEHYDRATASE INHIBITOR; ORGANOMETALLIC COMPOUND; PYRIDINE DERIVATIVE; PYRITHIONE; THIOKETONE; ZINC;

ARTICLE; ATOM; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DONOR ATOM IDENTITY; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; PHARMACOPHORE; PRIORITY JOURNAL; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; HUMAN; METABOLISM; MOLECULAR MODEL; QUANTUM THEORY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CRYSTALLOGRAPHY, X-RAY; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PYRIDINES; QUANTUM THEORY; THIONES; TROPOLONE; ZINC;

EID: 85017097386     PISSN: 09498257     EISSN: 14321327     Source Type: Journal    
DOI: 10.1007/s00775-017-1454-3     Document Type: Article

References (39)

1. Andreini C, Bertini I, Cavallaro G, Holliday GL, Thornton JM (2008) J Biol Inorg Chem 13:1205–1218
2. Rouffet M, Cohen SM (2011) Dalton Trans 40:3445–3454
3. Supuran CT, Scozzafava A, Casini A (2003) Med Res Rev 23:146–189
4. Paris M, Porcelloni M, Binaschi M, Fattori D (2008) J Med Chem 51:1505–1529
5. Fernández-Montero JV, Vispo E, Soriano V (2014) Expert Opin Pharmacother 15:211–219
6. Jacobsen FE, Lewis JA, Cohen SM (2007) ChemMedChem 2:152–171
7. Mutule I, Borovika D, Rozenberga E, Romanchikova N, Zalubovskis R, Shestakova I, Trapencieris P (2015) J Enzyme Inhib Med Chem 30:216–223
8. Puerta DT, Lewis JA, Cohen SM (2004) J Am Chem Soc 126:8388–8389
9. Göçer H, Akincioğlu A, Göksu S, Gülçin İ, Supuran CT (2015) J Enzyme Inhib Med Chem 30:316–320
10. Moradei O, Vaisburg A, Martell RE (2008) Curr Top Med Chem 8:841–858
11. Martin DP, Hann ZS, Cohen SM (2013) Inorg Chem 52:12207–12215
12. Martin DP, Blachly PG, Marts AR, Woodruff TM, de Oliveira CAF, McCammon JA, Tierney DL, Cohen SM (2014) J Am Chem Soc 136:5400–5406
13. Puerta DT, Cohen SM (2003) Inorg Chem 42:3423–3430
14. Puerta DT, Schames JR, Henchman RH, McCammon JA, Cohen SM (2003) Angew Chem Int Ed Engl 42:3772–3774
15. Cook SA, Hill EA, Borovik AS (2015) Biochemistry 54:4167–4180
16. Jacobsen FE, Lewis JA, Heroux KJ, Cohen SM (2007) Inorg Chim Acta 360:264–272
17. Nair SK, Krebs JF, Christianson DW, Fierke CA (1995) Biochemistry 34:3981–3989
18. Machiguchi T, Hasegawa T, Kano Y (1993) Bull Chem Soc Jpn 66:3699–3706
19. Monnard FW, Heinisch T, Nogueira ES, Schirmer T, Ward TR (2011) Chem Commun (Camb) 47:8238–8240
20. Yung-Chi C, Prusoff WH (1973) Biochem Pharmacol 22:3099–3108
21. Avvaru BS, Kim CU, Sippel KH, Gruner SM, Agbandje-McKenna M, Silverman DN, McKenna R (2010) Biochemistry 49:249–251
22. Murshudov GN, Vagin AA, Dodson EJ (1997) Acta Crystallogr Sect D: Biol Crystallogr 53:240–255
23. Emsley P, Cowtan K (2004) Acta Crystallogr Sect D: Biol Crystallogr 60:2126–2132
24. Schüttelkopf AW, van Aalten DMF (2004) Acta Crystallogr Sect D: Biol Crystallogr 60:1355–1363
25. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd J, Brothers EN, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09. Gaussian Inc., Wallingford
26. Becke AD (1993) J Chem Phys 98:5648
27. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789
28. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) J Phys Chem 98:11623–11627
29. Vosko SH, Wilk L, Nusair M (1980) Can J Phys 58:1200–1211
30. Barone V, Cossi M (1998) J Phys Chem A 102:1995–2001
31. Cossi M, Rega N, Scalmani G, Barone V (2003) J Comput Chem 24:669–681
32. Klamt A, Schüürmann G (1993) J. Chem. Soc. Perkin Trans. 2:799–805
33. Ryde U (1999) Biophys J 77:2777–2787
34. Dudev T, Lim C (2000) J Am Chem Soc 122:11146–11153
35. Jacobsen JA, Fullagar JL, Miller MT, Cohen SM (2011) J Med Chem 54:591–602
36. Costa G, Gidaro MC, Vullo D, Supuran CT, Alcaro S (2016) J Agric Food Chem 64:5295–5300
37. Schulze Wischeler J, Innocenti A, Vullo D, Agrawal A, Cohen SM, Heine A, Supuran CT, Klebe G (2010) ChemMedChem 5:1609–1615
38. Martin DP, Blachly PG, McCammon JA, Cohen SM (2014) J Med Chem 57:7126–7135
39. Sigel H, McCormick DB (1970) Acc Chem Res 3:201–208