Predicting pKa values in aqueous solution for the guanidine functional group from gas phase ab initio bond lengths

Molecular Informatics

Volumn 32, Issue 4, 2013, Pages 363-376

  Griffiths, Mark Z ^a   Alkorta, Ibon ^b   Popelier, Paul L A ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Ab initio bond length; Guanidines; pKa Prediction

Indexed keywords

BOND LENGTH; MOLECULES; SET THEORY;

AB INITIO; AB INITIO BOND LENGTH; CHEMICAL SPACE; DRUG MOLECULES; GAS-PHASES; GUANIDINE; PKA PREDICTION; PREDICTION ERRORS; TAUTOMERIC FORMS; TAUTOMERIZATIONS;

FORECASTING;

GUANIDINE;

AQUEOUS SOLUTION; ARTICLE; COVALENT BOND; MOLECULAR STABILITY; PREDICTIVE VALUE; PRIORITY JOURNAL; TAUTOMERIZATION;

EID: 84876469362     PISSN: 18681743     EISSN: 18681751     Source Type: Journal    
DOI: 10.1002/minf.201300008     Document Type: Article

References (55)

1. A. P. Harding, P. L. A. Popelier, Phys. Chem. Chem. Phys. 2011, 13, 11264-11282
2. S. Trapp, M. Matthies, C. McFarlane, Environ. Toxic. Chem. 1994, 13, 413-422.
3. A. Avdeef, Absorption and Drug Development: Solubility, Permeability and Charge State, Wiley-Interscience, New Jersey, USA, 2003, p. 3.
4. S. Trapp, Environ. Sci. Poll. Res. 2004, 11, 33-39.
5. J. Comer, K. Tam, in Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical, and Computational Strategies, Wiley-VCH, Weinheim, New York, USA, 2001, pp. 275-304.
6. R. F. Cookson, Chem. Rev. 1974, 74, 5-28.
7. R. J. Prankerd, in Profiles of Drug Substances, Excipients, and Related Methodology, Vol. 33, Elsevier Academic, San Diego, CA, USA, 2007, p. 435.
8. S. Jelfs, P. Ertl, P. Selzer, J. Chem. Inf. Model. 2007, 47, 450-459.
9. M. Namazian, S. Halvani, J. Chem. Thermodynamics 2006, 12, 1495-1502.
10. H. Li, A. D. Robertson, J. H. Jensen, Protein Struct. Funct. Bioinf. 2005, 61, 704-721.
11. D. C. Bas, D. R. Rogers, J. H. Jensen, Protein Struct. Funct. Bioinf. 2008, 61, 765-783.
12. E. J. Nielson, A. McCammon, Protein Sci. 2003, 12, 313-326.
13. Y. Fu, R. Liu, L. Liu, Q.-X. Guo, J. Phys. Org. Chem. 2004, 17, 282-288.
14. K. R. Adam, J. Phys. Chem. A 2002, 106, 11963-11972.
15. A. Klamt, F. Eckert, M. Diedenhofen, J. Phys. Chem. A 2003, 107, 9380-9386.
16. Y. Zeng, X. Chen, D. Zhao, H. Li, Y. Zhang, X. Xiao, Fluid Phase Equilib. 2012, 313, 148-155.
17. M. N. Davies, C. P. Toseland, D. S. Moss, D. R. Flower, BMC Biochem. 2006, 7, 18-30.
18. C. J. Gibas, S. Subramaniam, Biophys. J. 1996, 71, 138-147.
19. A. C. Lee, G. M. Crippen, J. Chem. Inf. Model. 2009, 49, 2013-2033.
20. F. Milletti, L. Storchi, L. Goracci, S. Bendels, B. Wagner, M. Kansy, G. Cruciani, Eur. J. Med. Chem. 2010, 45, 4270-4279.
21. L. Xing, R. C. Glen, J. Chem. Inf. Comput. Sci. 2002, 42, 796-805.
22. L. Xing, R. C. Glen, R. D. Clark, J. Chem. Inf. Comput. Sci. 2003, 43, 870-879.
23. J. Zhang, T. Kleinoder, J. Gasteiger, J. Chem. Inf. Model 2006, 46, 2256-2266.
24. F. Milletti, L. Storchi, G. Sforna, G. Cruciani, J. Chem. Inf. Model 2007, 47, 2172-2181.
25. C. O. da Silva, E. C. da Silva, M. A. C. Nascimento, J. Phys. Chem. A 2000, 104, 2402-2409.
26. F. Eckert, M. Diedenhofen, A. Klamt, Mol. Phys. 2010, 108, 229-241.
27. M. D. Liptak, G. C. Shields, J. Am. Chem. Soc. 2001, 123, 7314-7319.
28. M. D. Liptak, G. C. Shields, Int. J. Quant. Chem. 2001, 85, 727-741.
29. H. Lu, X. Chen, C. G. Zhan, J. Phys. Chem. B. 2007, 111, 10599-10605.
30. M. Namazian, M. Zakery, M. R. Noorbala, M. L. Coote, Chem. Phys. Lett. 2008, 451, 163-168.
31. I. Tetko, V. Tanchuk, A. Makarenko, IEEE Int. Workshop on Intelligent Data Acquisition and Adv. Comput. Sys.: Technology and Applications 2003, 378-381; http://www.vcclab.org.
32. ADMET Predictor, Lancaster, California, USA; http://www.simulations-plus. com/.
33. PIPELINE PILOT, http://accelrys.com/.
34. J. C. Shelley, A. Cholleti, L. L. Frye, G. R. Greenwood, M. R. Timlin, M. Uchimaya, J. Comput. Aided Mol. Des. 2007, 21, 681-691, Epik; http://www.schrodinger.com/.
35. SPARC, http://sparc.chem.uga.edu/sparc/.
36. J. Szegezdi, F. Csizmadia, 233rd ACS National Meeting, Chicago, USA, 2007; http://www.chemaxon.com.
37. a, Advanced Chemistry Development, Inc., ACD Labs, Toronto, ON, Canada, http://www.acdlabs.com/products.
38. F. Csizmadia, J. Szegezdi, F. Darvas, PALLAS, in QSAR and Modeling (Ed. C. G. Wermuth), ESCOM, Leiden, The Netherlands, 1993, p. 507-510; http://www.compudrug.com/.
39. P. L. A. Popelier, P. J. Smith, Eur. J. Med. Chem. 2006, 41, 862-873.
40. P. L. A. Popelier, in Quantum Biochemistry: Electronic Structure and Biological Activity, Vol. Part IV, (Ed:, C. F. Matta,), Wiley-VCH, Weinheim, Germany, 2010, p. 669-692.
41. P. L. A. Popelier, J. Phys. Chem. A 1999, 103, 2883-2890.
42. P. Popelier, U. Chaudry, P. Smith, J. Chem. Soc. Perkin Trans. 2 2002, 1231-1237.
43. R. J. Loader, N. K. Singh, P. J. O'Malley, P. L. A. Popelier, Bioorg. Med. Chem. Lett. 2006, 16, 1249-1254.
44. S. E. O'Brien, P. L. A. Popelier, J. Chem. Soc. Perkin Trans. 2 2002, 478-483.
45. U. A. Chaudry, P. L. A. Popelier, J. Phys. Chem. A 2003, 107, 4578-4582.
46. U. A. Chaudry, P. L. A. Popelier, J. Org. Chem. 2004, 69, 233-241.
47. S. E. O'Brien, P. L. A. Popelier, Can. J. Chem. 1999, 77, 28-36.
48. A. P. Harding, P. L. A. Popelier, Phys. Chem. Chem. Phys. 2011, 13, 11283-11293.
49. A. P. Harding, D. C. Wedge, P. L. A. Popelier, J. Chem. Inf. Model. 2009, 49, 1914-1924.
50. S. Kar, A. P. Harding, K. Roy, P. L. A. Popelier, SAR QSAR Environ. Res. 2010, 21, 149-168.
51. G. T. Balogh, B. Gyarmati, B. Nagy, L. Molnar, G. M. Keseru, QSAR Comb. Sci. 2009, 28, 1148-1155.
52. A. Albert, R. Goldacre, J. Phillips, J. Chem. Soc. 1948, 2240-2249.
53. J. Bjerrum, G. Schwarzenbach, L. G. Sillen, Stability Constants, The Chemical Society, London, 1958, p. 8.
54. D. A. Williams, T. L. Lemke, Foye's Principles of Medicinal Chemistry, Williams and Wilkins, Philadelphia, PA, 2002, p. 30.
55. R. L. Smith, W. D. Cochran, P. Gund, E. J. Cragoe, J. Am. Chem. Soc. 1978, 101, 1501.