PKa determination by 1H NMR spectroscopy - An old methodology revisited

Journal of Pharmaceutical and Biomedical Analysis

Volumn 93, Issue , 2014, Pages 147-155

  Bezençon, Jacqueline ^a   Wittwer, Matthias B ^a   Cutting, Brian ^a   Smieško, Martin ^a   Wagner, Bjoern ^b   Kansy, Manfred ^b   Ernst, Beat ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Dissociation constant; Physicochemical properties; Site of protonation

Indexed keywords

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PARAMETERS; COMPARATIVE STUDY; COMPUTER MODEL; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; ULTRAVIOLET RADIATION; VALIDATION PROCESS; CHEMISTRY; COMPUTER SIMULATION; DRUG DESIGN; DRUG DEVELOPMENT; HUMAN; PROCEDURES; REPRODUCIBILITY;

DRUG;

COMPUTER SIMULATION; DRUG DESIGN; DRUG DISCOVERY; HUMANS; HYDROGEN-ION CONCENTRATION; PHARMACEUTICAL PREPARATIONS; PROTON MAGNETIC RESONANCE SPECTROSCOPY; REPRODUCIBILITY OF RESULTS;

EID: 84900016355     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2013.12.014     Document Type: Article

References (37)

1. Horter D., Dressman J.B. Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv. Drug Deliv. Rev. 2001, 46:75-87.
2. a values in a mixed-buffer linear pH gradient system. Anal. Chem. 2003, 75:883-892.
3. Avdeef A. pH-metric logP. II: Refinement of partition coefficients and ionization constants of multiprotic substances. J. Pharm. Sci. 1993, 82:183-190.
4. a determination of drugs using pressure-assisted capillary electrophoresis with photodiode array detection in drug discovery. J. Pharm. Sci. 2002, 91:933-942.
5. a. J. Chem. Inf. Model. 2009, 49:2013-2033.
6. Farcasiu D., Ghenciu A. Determination of acidity functions and acid strengths by C-13 NMR. Prog. Nucl. Magn. Reson. Spectrosc. 1996, 29:129-168.
7. 13C-nuclear magnetic resonance spectroscopy - a case of apramycin. Org. Magn. Res. 1978, 11:632-634.
8. a, NMR shifts, and isotopic fractionations. Geochim. Cosmochim. Acta 2005, 69:5647-5658.
9. 19F NMR spectrometry evidence for bile acid conjugates of α-fluoro-β-alanine as the main biliary metabolites of antineoplastic fluoropyrimidines in humans. Drug Metab. Dispos. 1988, 16:78-84.
10. Millis K.K., Colvin M.E., Shulman-Roskes E.M., Ludeman S.M., Colvin O.M., Gamcsik M.P. Comparison of the protonation of isophosphoramide mustard and phosphoramide mustard. J. Med. Chem. 1995, 38:2166-2175.
11. Berger S., Braun S. 200 and More NMR Experiments: A Practical Course 2004, 290-292. Wiley-VCH, Weinheim.
12. 13C-NMR study. J. Lipid Res. 1982, 23:795-799.
13. Delfini M., Segre A.L., Conti F., Barbucci R., Barone V., Ferruti P. On the mechanism of protonation of triamines. J. Chem. Soc. Perkin Trans. 1980, 2:900-903.
14. a values of the lysine-residues of calmodulin. J. Biol. Chem. 1993, 268:22420-22428.
15. a values, ion pairs, hydrogen bonding, and the pH-dependence of folding the hyperthermophile proteins Sac7d and Sso7d. J. Mol. Biol. 2007, 372:992-1008.
16. Spink E., Cosgrove S., Rogers L., Hewage C., Malthouse J.P.G. C-13 and H-1 NMR studies of ionizations and hydrogen bonding in chymotrypsin-glyoxal inhibitor complexes. J. Biol. Chem. 2007, 282:7852-7861.
17. a values by use of NMR chemical shifts. J. Chem. Educ. 1973, 50:510-511.
18. a values by use of NMR chemical shifts, revisited. J. Chem. Educ. 2012, 89:1458-1460.
19. Ollig J., Hägele G. NMR-controlled titrations of phosphorus-containing acids and bases. Comp. Chem. 1995, 19:287-294.
20. Rabenstein D.L., Sayer T.L. Determination of microscopic acid dissociation-constants by nuclear magnetic resonance spectrometry. Anal. Chem. 1976, 48:1141-1145.
21. a values in the unfolded state of proteins by extrapolation to zero denaturant. Biophys. Chem. 2007, 129:242-250.
22. Avdeef A. Absorption and Drug Development: Solubility, Permeability, and Charge State 2003, Wiley-Interscience, Hoboken, NJ.
23. a modulation of new chemical series. Eur. J. Med. Chem. 2010, 45:4270-4279.
24. a prediction and protonation state generation for drug-like molecules. J. Comput. Aided Mol. Des. 2007, 21:681-691.
25. Marvin 5.6.0.2 ChemAxon 2011, http://www.chemaxon.com/marvin/help/calculations/pKa.html (23.11.13).
26. Klein T., Abgottspon D., Wittwer M., Rabbani S., Herold J., Jiang X., Kleeb S., Lüthi C., Scharenberg M., Bezençon J., Gubler E., Pang L., Smieško M., Cutting B., Schwardt O., Ernst B. FimH antagonists for the oral treatment of urinary tract infections: from design and synthesis to in vitro and in vivo evaluation. J. Med. Chem. 2010, 53:8627-8641.
27. Gottlieb H.E., Kotlyar V., Nudelman A. NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 1997, 62:7512-7515.
28. 2O. J. Inorg. Biochem. 2004, 98:161-166.
29. Sarmini K., Kenndler E. Ionization constants of weak acids and bases in organic solvents. J. Biochem. Biophys. Methods 1999, 38:123-137.
30. a determination of water-insoluble drugs in organic solvent-water mixtures. J. Pharm. Biomed. Anal. 1999, 20:631-641.
31. a and binding affinity and evidence for intermolecular CF. . .CN interactions. Org. Biomol. Chem. 2004, 2:1339-1352.
32. Ramirez-Silva T., Gomez-Hernandez M., Pacheco-Hernandez D.L., Rojas-Hernandez A., Galicia L. Spectroscopy study of 5-amino-1,10-phenanthroline. Spectrochim. Acta A 2004, 60:781-789.
33. Altun Y. Study of solvent composition effects on the protonation equilibria of various anilines by multiple linear regression and factor analysis applied to the correlation between protonation constants and solvatochromic parameters in ethanol-water mixed solvents. J. Solution Chem. 2004, 33:479-497.
34. Yasuda M., Sone K., Yamasaki K. Stability of zinc and cadmium complexes with some methyl derivatives of 1,10-phenantroline and 2,2'-bipyridine. J. Phys. Chem. 1956, 60:1667-1668.
35. Brandt W.W., Gullstrom D.K. Studies on some ferrous complexes of substituted 1,10-phenantrolines. J. Am. Chem. Soc. 1952, 74:3532-3535.
36. Bruice T.C., Schmir G.L. Imidazole catalysis. 2. The reaction of substituted imidazoles with phenyl acetates in aqueous solution. J. Am. Chem. Soc. 1958, 80:148-156.
37. Dawson R.M.C., Elliott D.C., Elliott W.H., Jones K.M. Data for Biochemical Research 1959, Clarendon Press, Oxford.