Accurate aqueous proton dissociation constants calculations for selected angiotensin-converting enzyme inhibitors

Journal of Biomolecular Structure and Dynamics

Volumn 25, Issue 6, 2008, Pages 599-608

  Sramko, Martin ^a   Smiesko, Martin ^b   Remko, Milan ^a  

^a Physics and Informatics   (Slovakia)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CAPTOPRIL; ENALAPRILAT; IMIDAPRILAT; PERINDOPRILAT; RAMIPRILAT; SOLVENT; SPIRAPRILAT;

ACCURACY; AQUEOUS SOLUTION; ARTICLE; CALCULATION; DENSITY FUNCTIONAL THEORY; DISSOCIATION CONSTANT; DRUG STRUCTURE; ENERGY; GAS; GEOMETRY; MATHEMATICAL COMPUTING; PKA; POLARIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; SOLVATION; THEORETICAL STUDY; THERMODYNAMICS;

EID: 44049092388     PISSN: 07391102     EISSN: 15380254     Source Type: Journal    
DOI: 10.1080/07391102.2008.10507206     Document Type: Article

References (53)

1. Natesh, R., Schwager, S. L. U., Evans, H. R., Sturrock, E. D., and Acharya, K. R., 2004. Biochemistry, 43:8718–8724.
2. Turner, A. J., and Hooper, N. M., 2002. Trends Pharmacol Sci, 23:177–183.
3. Opie, L. H., 1994. Angiotensin Converting Enzyme Inhibitors, 2nd ed. Wiley-Liss:New York
4. Natesh, R., Schwager, S. L. U., Sturrock, E. D., and Acharya, K. R., 2003. Nature, 42:551–554.
5. Corradi, H. R., Schwager, S. L. U., Nchinda, A. T., Sturrock, E. D., and Acharya, K. R., 2006. J Mol Biol, 357:964–974.
6. Corradi, H. R., Chitapi, I., Sewell, B. T., Georgiadis, D., Dive, V., Sturrock, E. D., and Acharya, K. R., 2007. Biochemistry, 46:5473–5478.
7. Wyvratt, M. J., and Patchett, A. A., 1985. Med Res Rev, 5:483–531.
8. Smiesko, M., and Remko, M., 2004. Chem Pap, 58:71–78.
9. Fernandez, M., Liu, X., Wouters, M. A., Heiberger, S., and Husain, A., 2001. J Biol Chem, 276:4998–5004.
10. Swamy, K. M. K., Lin, M.-J., and Sun, Ch.-M., 2003. Mini Rev Med Chem, 3:621–631.
11. Smiesko, M., and Remko, M., 2003. J Biomol Struct Dyn, 20:759–770.
12. Aue, D. H., Webb, H. M., and Bowers, M. T., 1976. J Am Chem Soc, 98:318–329.
13. Tunon, I., Silla, E., and Pascual-Ahuir, J. L., 1993. J Am Chem Soc, 115:2226–2230.
14. Toth, A. M., Liptak, M. D., Phillips, D. L., and Shields, G. C., 2001. J Chem Phys, 114:4595–4606.
15. Liptak, M. D., Gross, K. C., Seybold, P. G., Feldgus, S., and Shields, G. C., 2002. J Am Chem Soc, 124:6421–6427.
16. McQuarrie, D. M., 1970. Statistical Mechanics. Harper and Row:New York.
17. Tawa, G. J., Topol, I. A., Burt, S. K., Caldwell, R. A., and Rashin, A. A., 1998. J Chem Phys, 109:4852–4863.
18. Reiss, H., and Heller, A., 1985. J Phys Chem, 89:4207–4213.
19. Lim, C., Bashford, D., and Karplus, M., 1991. J Phys Chem, 95:5610–5620.
20. Gilson, M. K., and Honig, B., 1988. Proteins:Struct Funct Genet, 4:7–18.
21. Tisssiander, M. D., Cowen, K. A., Feng, W. Y., Gundlach, E., Cohen, M. H., Earhart, A. D., and Coe, J. V., 1998. J Phys Chem A, 102:7787–7794.
22. Camaioni, D. M., and Schwerdtfeger, C. A., 2005. J Phys Chem A, 109:10795–10797.
23. Kelly, C. P., Cramer, C. J., and Truhlar, D. G., 2006. J Phys Chem A, 110:2493–2499.
24. Pliego, J. R., and Riveros, J. M., 2002. Phys Chem Chem Phys, 4:1622–1627.
25. Saracino, G. A. A., Improta, R., and Barone, V., 2003. Chem Phys Lett, 373:411–415.
26. Chipman, D. M., 2002. J Phys Chem, 106:7413–7422.
27. Liptak, M. D., and Shields, G. C., 2001. Int J Quant Chem, 85:727–741.
28. Liptak, M. D., and Shields, G. C., 2001. J Am Chem Soc, 123:7314–7319.
29. Liptak, M. D., and Shields, G. C., 2005. Int J Quant Chem, 105:580–587.
30. Pokon, E. K., Liptak, M. D., Feldgus, S., and Shields, G. C., 2001. Dat J Phys Chem, 105:10483–10487.
31. Klicic, J. J., Friesner, R. A., Liu, S. Y., and Guida, W. C., 2002. J Phys Chem, 106:1327–1335.
32. Ulander, J., and Broo, A., 2005. Int J Quantum Chem, 105:866–874.
33. Busch, M. S., and Knapp, E. W., 2004. Chem Phys Chem, 5:1513–1522.
34. Adam, K. R., 2002. J Phys Chem, 106:11963–11972.
35. Pliego, J. R., and Riveros, J. M., 2002. J Phys Chem, 106:7434–7439.
36. Smiesko, M., and Remko, M., 2002. Chem Pap, 56:138–143.
37. Sramko, M., Remko, M., and Garaj, V., 2005. Struct Chem, 16:391–399.
38. Barone, V., and Cossi, M., 1998. J Phys Chem, 102:1995–2001.
39. Barone, V., Cossi, M., and Tomasi, J., 1997. J Chem Phys, 107:3210–3221.
40. Hawkins, G. D., Giesen, D. J., Lynch, G. C., Chambers, C. C., Rossi, I., Storer, J. W., Li, J., Zhu, T., Thompson, J. D., Winget, P., Lynch, B. J., Rinaldi, D., Liotard, D. A., Cramer, C. J., and Truhlar, D. G., 2003. (AMSOL-version 7.0, distributed at comp. chem.)
41. Jakt, M., Johannissen, L., Rzepa, H. S., Widdowson, D. A., and Wilhelm, R., 2002. J Chem Soc, Perkin Trans, 2:576–581.
42. De Angelis, P., Fantacci, S., and Selloni, A., 2004. Chem Phys Lett, 389:204–208.
43. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, T. K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Adamo, C., Jaramillo, C., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Gaussian, J. A., 2003. Gaussian 2003. Inc 44Pittsburgh, PA
44. http://ibmlc2.chem.uga.edu/sparc/
45. Hilal, S., Karickhoff, S. W., and Carreira, L. A., 1995. Quant Struct Act Rel, 14:348–355.
46. Carreira, L. A., Hilal, S., and Karickhoff, S. W., 1994. Theoretical and Computational Chemistry, Quantitative Treatment of Solute/Solvent Interactions. Edited by:Politzer, P., Murray, J. S., and Elsevier. Amsterdam:Publishers. In
47. Hilal, S., Karickhoff, S. W., and Carreira, L. A., 2003. QSAR Comb Sci, 22:917–925.
48. Remko, M., 2007. Chem Pap, 61:133–141.
49. Cossi, M., Barone, V., and Mennucci, B., 1998. Tomasi. J Chem Phys Lett, 286:253–260.
50. Pratuangdejkul, J., Nosoongnoen, W., Guerin, G.-A., Loric, S., Conti, M., Launay, J.-M., and Manivet, P., 2006. Chem Phys Lett, 420:538–544.
51. Hillaert, S., and Van den Bossche, W. J., 2000. Chromatogr, 895:33–42.
52. Andujar-Sanches, M., Camara-Artigas, A., and Jara-Perez, V., 2004. Biophys Chem, 111:183–189.
53. Ozoemena, K. I., Raluca-Ioana, S., van Staden, J. F., and Aboul-Enein, Y. A., 2005. Sens Actuators B, 105:425–429.