The contribution of the hydrogen bond acidity on the lipophilicity of drugs estimated from chromatographic measurements

European Journal of Pharmaceutical Sciences

Volumn 48, Issue 3, 2013, Pages 484-493

  Pallicer, Juan M ^a   Pascual, Rosalia ^b   Port, Adriana ^b   Rosés, Martí ^a   Ráfols, Clara ^a   Bosch, Elisabeth ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b ESTEVE   (Spain)

Author keywords

Drugs; Hydrogen bond donor descriptors; Lipophilicity; Log Po w; Solvation parameter model; UHPLC

Indexed keywords

ACEBUTOLOL; ALPRENOLOL; ATENOLOL; BENDROFLUMETHIAZIDE; BROMAZEPAM; BROMPHENIRAMINE; BUPIVACAINE; CELECOXIB; CHRYSIN; CINCHONIDINE; CLONAZEPAM; CLOTIAZEPAM; CYPROHEPTADINE; DIAZEPAM; DICLOFENAC; DILTIAZEM; DULOXETINE; ETIRACETAM; FENBUFEN; FLUOXETINE; FLURAZEPAM; FLURBIPROFEN; FUROSEMIDE; GLIMEPIRIDE; HESPERETIN; LORMETAZEPAM; MEPIVACAINE; OCTANOL; UNINDEXED DRUG; WATER; DRUG; SOLVENT;

ACIDITY; ARTICLE; CALCULATION; CHROMATOGRAPHY; CORRELATIONAL STUDY; DATA ANALYSIS SOFTWARE; DRUG DETERMINATION; HYDROGEN BOND; LIPOPHILICITY; PARTITION COEFFICIENT; PRIORITY JOURNAL; SOLVATION; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ALGORITHM; ARTIFICIAL INTELLIGENCE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PH; REVERSED PHASE LIQUID CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY; VALIDATION STUDY;

1-OCTANOL; ALGORITHMS; ARTIFICIAL INTELLIGENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, REVERSE-PHASE; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MODELS, MOLECULAR; PHARMACEUTICAL PREPARATIONS; SOLVENTS; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 84872424550     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.12.008     Document Type: Article

References (46)

1. Abraham, M.H., 1993. Scales of solute hydrogen-bonding: Their construction and application to physicochemical and biochemical processes. Chem. Soc. Rev. 22, 73-83.
2. Abraham, M.H., Rosés, M., 1994. Hydrogen bonding. 38. Effect of solute structure and mobile phase composition on reversed-phase high-performance liquid chromatographic capacity factors. J. Phys. Org. Chem. 7, 672-684.
3. Abraham, M.H., Chadha, H.S., Whiting, G.S., Mitchell, R.C., 1994. Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the D log P parameter of seiler. J. Pharm. Sci. 83, 1085-1100.
4. Avdeef, A., 1992. PH-metric log P. Part 1. Difference plots for determining ion-pair octanol-water partition coefficients of multiprotic substances. Quant. Struct. Act. Rel. 11, 510-517.
5. Avdeef, A., 1993. PH-Metric log P. II. Refinement of partition coefficients and ionization constants of multiprotic substances. J. Pharm. Sci. 82, 183-190.
6. Avdeef, A., 2003. Partitioning into Octanol. In: Absorption and Drug Development. John Wiley & Sons, Inc., Hoboken, NJ, USA, pp. 42-66.
7. Benhaim, D., Grushka, E., 2008. Effect of n-octanol in the mobile phase on lipophilicity determination by reversed-phase high-performance liquid chromatography on a modified silica column. J. Chromatogr. A 1209, 111-119.
8. Bosch, E., Bou, P., Rosés, M., 1994. Linear description of solute retention in reversedphase liquid chromatography by a new mobile phase polarity parameter. Anal. Chim. Acta 299, 219-229.
9. Bosque, R., Sales, J., Bosch, E., Rosés, M., García- Álvarez-Coque, M.C., Torres-Lapasió, J.R., 2003. A QSPR study of the p solute polarity parameter to estimate retention in HPLC. J. Chem. Inf. Comput. Sci. 43, 1240-1247.
10. Cruciani, G., Crivori, P., Carrupt, P.-A., Testa, B., 2000. Molecular fields in quantitative structure-permeation relationships: The VolSurf approach. J. Mol. Struc.-THEOCHEM 503, 17-30.
11. Du, C.M., Valkó, K., Bevan, C., Reynolds, D., Abraham, M.H., 2001. Rapid method for estimating octanol-water partition coefficient (log Poct) from isocratic RP-HPLC and a hydrogen bond acidity term (A). J. Liq. Chromatogr. R.T. 24, 635-649.
12. EPA, 1996. Product Properties Test Guidelines OPPTS 830.7550 Partition Coefficient (n-Octanol/Water), Shake Flask Method. .
13. Fikri, K., Debord, J., Bollinger, J., Cledat, D., Penicaut, B., Robert, J.H., 2011. RP-HPLC Lipophilicity Studies for some (hetero)arylamides Derived From 2-Amino-4,6-Dimethypyridine. Introduction of an Hydrogen Bond Descriptor. J. Liq. Chromatogr. R. T. 34, 1356-1366.
14. Giaginis, C., Teocharis, S., Tsantili-Kakoulidou, A., 2007. Octanol/water partitioning simulation by reversed-phase high performance liquid chromatography for structurally diverse acidic drugs: Effect of n-octanol as mobile phase additive. J. Chromatogr. A 1166, 116-127.
15. Henchoz, Y., Guillarme, D., Martel, S., Rudaz, S., Veuthey, J.-L., Carrupt, P.-A., 2009. Fast log P determination by ultra-high-pressure liquid chromatography coupled with UV and mass spectrometry detections. Anal. Bioanal. Chem. 394, 1919-1930.
16. Henchoz, Y., Romand, S., Schappler, J., Rudaz, S., Veuthey, J., Carrupt, P.-A., 2010. High-throughput log P determination by MEEKC coupled with UV and MS detections. Electrophoresis 31, 952-964.
17. Hidalgo-Rodríguez, M., Fuguet, E., Ràfols, C., Rosés, M., 2010. Estimation of biological properties by means of chromatographic systems: Evaluation of the factors that contribute to the variance of biological-chromatographic correlations. Anal. Chem. 82, 10236-10245.
18. Izquierdo, P., Rosés, M., Bosch, E., 2006. Polarity parameters of the symmetry C18 and Chromolith Performance RP-18 monolithic chromatographic columns. J. Chromatogr. A 1107, 96-103.
19. Jover, J., Bosque, R., Sales, J., 2004. Determination of Abraham solute parameters from molecular structure. J. Chem. Inf. Comput. Sci. 44, 1098-1106.
20. Kaliszan, R., 2007. QSRR: Quantitative structure-(chromatographic) retention relationships. Chem. Rev. 107, 3212-3246.
21. Kaliszan, R., Haber, P., Baczek, T., Siluk, D., Valkó, K., 2002. Lipophilicity and pKa estimates from gradient high-performance liquid chromatography. J. Chromatogr. A 965, 117-127.
22. Lázaro, E., Ràfols, C., Rosés, M., 2005. Characterization of immobilized artificial membrane (IAM) and XTerra columns by means of chromatographic models. J. Chromatogr. A 1081, 163-173.
23. Lázaro, E., Ràfols, C., Abraham, M.H., Rosés, M., 2006. Chromatographic estimation of drug disposition properties by means of immobilized artificial membranes (IAM) and C18 columns. J. Med. Chem. 49, 4861-4870.
24. Lázaro, E., Izquierdo, P., Ràfols, C., Rosés, M., Bosch, E., 2009. Prediction of retention in reversed-phase liquid chromatography by means of the polarity parameter model. J. Chromatogr. A 1216, 5214-5227.
25. Lipinski, C.A., Lombardo, F., Dominy, B.W., Feeney, P.J., 1997. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 23, 3-25.
26. Liu, X., Hefesha, H., Tanaka, H., Scriba, G., Fahr, A., 2008. Lipophilicity measurement of drugs by reversed phase HPLC over wide pH range using an alkaline-resistant silica-based stationary phase, XBridge shield RP18. Chem. Pharm. Bull. 56, 1417-1422.
27. Lombardo, F., Shalaeva, M.Y., Tupper, K.Y., Gao, F., Abraham, M.H., 2000. E log Poct: A tool for lipophilicity determination in drug discovery. J. Med. Chem. 43, 2922-2928.
28. Lombardo, F., Shalaeva, M.Y., Tupper, K.Y., Gao, F., 2001. E log Poct: A tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds. J. Med. Chem. 44, 2490-2497.
29. Pallicer, J.M., Pous-Torres, S., Sales, J., Rosés, M., Ràfols, C., Bosch, E., 2010. Determination of the hydrophobicity of organic compounds measured as log Po/w through a new chromatographic method. J. Chromatogr. A 1217, 3026-3037.
30. Pallicer, J.M., Sales, J., Rosés, M., Ràfols, C., Bosch, E., 2011. Lipophilicity assessment of basic drugs (log Po/w determination) by a chromatographic method. J. Chromatogr. A 1218, 6356-6368.
31. Pallicer, J.M., Calvet, C., Port, A., Rosés, M., Ràfols, C., Bosch, E., 2012. Critical evaluation of a new chromatographic method to assess the lipophilicity of acidic, basic and amphoteric drugs. J. Chromatogr. A 1240, 113-122.
32. Platts, J.A., Butina, D., Abraham, M.H., Hersey, A., 1999. Estimation of molecular linear free energy relation descriptors using a group contribution approach. J. Chem. Inf. Comput. Sci. 39, 835-845.
33. Platts, J.A., Abraham, M.H., Butina, D., Hersey, A., 2000. Estimation of molecular linear free energy relationship descriptors by a group contribution approach. 2. Prediction of partition coefficients. J. Chem. Inf. Comput. Sci. 40, 71-80.
34. Ràfols, C., Bosch, E., Ruiz, R., Box, K.J., Reis, M., Ventura, C., Santos, S., Araújo, M.E., Martins, F., 2012. Acidity and hydrophobicity of several new potential antitubercular drugs: Isoniazid and benzimidazole derivatives. J. Chem. Eng. Data 57, 330-338.
35. Rosés, M., Bosch, E., 1993. Linear solvation energy relationships in reversed-phase liquid chromatography. Prediction of retention from a single solvent and a single solute parameter. Anal. Chim. Acta 274, 147-162.
36. Rosés, M., Bosch, E., Ràfols, C., Fuguet, E., 2012. Chromatographic hydrophobicity index (CHI). Avd. Chromatogr. 50, 377-414.
37. Schwöbel, J.A.H., Ebert, R.U., Kühne, R., Schüürmann, G., 2011. Prediction models for the Abraham hydrogen bond donor strength: Comparison of semi-empirical, ab initio and DFT methods. J. Phys. Org. Chem. 24, 1072-1080.
38. Sheldon, T.J., Adjiman, C.S., Cordiner, J.L., 2005. Pure component properties from group contribution: Hydrogen-bond basicity, hydrogen-bond acidity, hildebrand solubility parameter, macroscopic surface tension, dipole moment, refractive index and dielectric constant. Fluid Phase Equilibr. 231, 27-57.
39. Testa, B., Krämer, S.D., Wunderli-Allenspach, H., Folkers, G., 2006. Pharmacokinetic Profiling in Drug Research: Biological, Physicochemical, and Computational Strategies. Wiley-VCH, Weinheim (Germany) and Zurich (Switzerland).
40. Torres-Lapasió, J.R., Garcia-Alvarez-Coque, M.C., Rosés, M., Bosch, E., Zissimos, A.M., Abraham, M.H., 2004. Analysis of a solute polarity parameter in reversed-phase liquid chromatography on a linear solvation relationship basis. Anal. Chim. Acta 515, 209-227.
41. Tropsha, A., Gramatica, P., Gombar, V.K., 2003. The importance of being earnest: Validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb. Sci. 22, 69-77.
42. Valkó, K., 2004. Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution. J. Chromatogr. A 1037, 299-310.
43. Valkó, K., Bevan, C., Reynolds, D., 1997. Chromatographic hydrophobicity index by fast-gradient RP-HPLC: A high-throughput alternative to log P/log D. Anal. Chem. 69, 2022-2029.
44. Valkó, K., My Du, C., Bevan, C., Reynolds, D.P., Abraham, M.H., 2001. Rapid method for the estimation of octanol/water partition coefficient (log P(oct)) from gradient RP-HPLC retention and a hydrogen bond acidity term (zetaalpha(2)(H)). Curr. Med. Chem. 8, 1137-1146.
45. Van de Waterbeemd, H., 2003. Drug Bioavailability: Estimation of solubility, permeability, absorption and bioavailability. [In: Methods Princ. Med. Chem., 2003 18].
46. Ventura, C., Martins, F., 2008. Application of quantitative structure-activity relationships to the modeling of antitubercular compounds. 1. The Hydrazide Family. J. Med. Chem. 51, 612-624.