Chromatographic hydrophobicity index (CHI)

Advances in Chromatography

Volumn 50, Issue , 2015, Pages 377-414

  Rosés, Martí ^a   Bosch, Elisabeth ^a   Ràfols, Clara ^a   Fuguet, Elisabet ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL PHENOMENA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROCEDURES;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS;

EID: 84860496085     PISSN: 00652415     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (71)

1. Testa B., Crivori P., Reist M., Carrupt P. 2000. The influence of lipophilicity on the pharmacokinetic behavior of drugs: Concepts and examples. Perspectives on Drug Discovery 19:179-211.
2. Valkó K., Reynolds D. P. 2005. High-throughput physicochemical and in vitro ADMET screening: A role in pharmaceutical profiling. American Journal of Drug Delivery 3:83-100.
3. Sangster J. 1997. Octanol-water partition coefficients: Fundamentals and physical chemistry. In Wiley Series in Solution Chemistry, 2nd ed., ed. P. G. T. Fogg. John Wiley & Sons, Chichester, UK.
4. EPA product properties test guidelines, OPPTS 830.7550, partition coefficient (n-octanol/water), shake flask method. 1996. Report no.: EPA 712-C-96-038. United States Environmental Protection Agency.
5. Avdeef A. 1992. pH metric log P. Part 1. Difference plots for determining ion-pair octanol-water partition coefficients of multiprotic substances. Quantitative Structure- Activity Relationships 11:510-517.
6. Takács-Novák K., Avdeef A. 1996. Interlaboratory study of log P determination by shake-flask and potentiometric methods. Journal of Pharmaceutical and Biomedical Analysis 14:1405-1413.
7. Makovskaya V., Dean J. R., Tomlinson W. R., Hitchen S. M., Comber M. 1995. Determination of octanol-water partition coefficients using gradient liquid chromatography. Analytica Chimica Acta 315:183-192.
8. 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. Journal of Chromatography A 1209:111-119.
9. Benhaim D., Grushka E. 2010. Characterization of Ascentis RP-amide column: Lipophilicity measurement and linear solvation energy relationships. Journal of Chromatography A 1217:65-74.
10. Liu X., Tanaka H., Yamauchi A., Testa B., Chuman H. 2005. Determination of lipophilicity by reversed-phase high-performance liquid chromatography: Influence of 1-octanol in the mobile phase. Journal of Chromatography A 1091:51-59.
11. Lombardo F., Shalaeva M. Y., Tupper K. A., Gao F., Abraham M. H. 2000. ElogPoct: A tool for lipophilicity determination in drug discovery. Journal of Medicinal Chemistry 43:2922-2928.
12. Giaginis C., Theocharis 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. Journal of Chromatography A 1166:116-125.
13. Donovan S. F., Pescatore M. C. 2002. Method for measuring the logarithm of the octanol-water partition coefficient by using short octadecyl-poly(vinyl alcohol) high-performance liquid chromatography columns. Journal of Chromatography A 952:47-61.
14. Vallat P., Fan W., Tayar N. E., Carrupt P., Testa B. 1992. Solvatochromic analysis of the retention mechanism of two novel stationary phases used for measuring lipophilicity by RP-HPLC. Journal of Liquid Chromatography 15:2133.
15. Kaliszan R., Haber P., Baczek T., Siluk D., Valkó K. 2002. Lipophilicity and pKa estimates from gradient high-performance liquid chromatography. Journal of Chromatography A 965:117-127.
16. Wiczling P., Waszczuk-Jankowska M., Markuszewski M. J., Kaliszan R. 2008. The application of gradient reversed-phase high-performance liquid chromatography to the pKa and log kw determination of polyprotic analytes. Journal of Chromatography A 1214:109-114.
17. Tate P. A., Dorsey J. G. 2004. Column selection for liquid chromatographic estimation of the kw ' hydrophobicity parameter. Journal of Chromatography A 1042:37-48.
18. Valkó K. 2004. Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution. Journal of Chromatography A 1037:299-310.
19. 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. Journal of Chromatography A 1217:3026-3037.
20. Valkó K., Slégel P. 1993. New chromatographic hydrophobicity index (φ0) based on the slope and the intercept of the log k' versus organic phase concentration plot. Journal of Chromatography A 631:49-61.
21. Shoenmakers P. J., Billiet H. A. H., De Galan L. 1979. Influence of organic modifiers on the retention behavior in reversed-phase liquid chromatography and its consequences for gradient elution. Journal of Chromatography A 185:179-195.
22. Valkó K., Bevan C., Reynolds D. 1997. Chromatographic hydrophobicity index by fastgradient RP HPLC: A high-throughput alternative to log P/log D. Analytical Chemistry 69:2022-2029.
23. Camurri G., Zaramella A. 2001. High-throughput liquid chromatography/mass spectrometry method for the determination of the chromatographic hydrophobicity index. Analytical Chemistry 73:3716-3722.
24. Abraham M. H. 1993. Scales of solute hydrogen-bonding: Their construction and application to physicochemical and biochemical processes. Chemical Society Reviews 22:73-83.
25. 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 delta log p parameter of seiler. Journal of Pharmaceutical Sciences 83:1085-1100.
26. Abraham M. H., Chadha H. S., Dixon J. P., Leo A. J. 1994. Hydrogen bonding. 39. The partition of solutes between water and various alcohols. Journal of Physical Organic Chemistry 7:712-716.
27. Abraham M. H., Zissimos A. M., Acree W. E. 2003. Partition of solutes into wet and dry ethers; an LFER analysis. New Journal of Chemistry 27:1041-1044.
28. 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. Journal of Physical Organic Chemistry 7:672-684.
29. 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. Journal of Medicinal Chemistry 49:4861-4870.
30. Abraham M. H., Rosés M., Poole C. F., Poole S. K. 1997. Hydrogen bonding. 42. Characterization of reversed-phase high-performance liquid chromatographic C18 stationary phases. Journal of Physical Organic Chemistry 10:358-368.
31. Bolliet D. F., Poole C., Rosés M. 1998. Conjoint prediction of the retention of neutral and ionic compounds (phenols) in reversed-phase liquid chromatography using the solvation parameter model. Analytica Chimica Acta 368:129-140.
32. Lepont C., Poole C. F. 2002. Retention characteristics of an immobilized artificial membrane column in reversed-phase liquid chromatography. Journal of Chromatography A 946:107-124.
33. West C., Lesellier E. 2010. Characterization of stationary phases in supercritical fluid chromatography with the solvation parameter model. In Advances in Chromatography, 48, ed. E. Grushka and N. Grinberg, 195-253. CRC Press, Boca Raton, FL.
34. Fuguet E., Ràfols C., Bosch E., Abraham M. H., Rosés M. 2006. Selectivity of single, mixed, and modified pseudostationary phases in electrokinetic chromatography. Electrophoresis 27:1900-1914.
35. Platts J. A., Abraham M. H., Zhao Y. H., Hersey A., Ijaz L., Butina D. 2001. Correlation and prediction of a large blood-brain distribution data set-An LFER study. European Journal of Medicinal Chemistry 36:719-730.
36. Gratton J. A., Abraham M. H., Bradbury M. W., Chadha H. S. 1997. Molecular factors influencing drug transfer across the blood-brain barrier. Journal of Pharmacy and Pharmacology 49:1211-1216.
37. Abraham M. H. 2004. The factors that influence permeation across the blood-brain barrier. European Journal of Medicinal Chemistry 39:235-240.
38. Abraham M. H., Zhao Y. H., Le J., Hersey A., Luscombe C. N., Reynolds D. P., et al. 2002. On the mechanism of human intestinal absorption. European Journal of Medicinal Chemistry 37:595-605.
39. Abraham M. H., Martins F. 2004. Human skin permeation and partition: General linear free-energy relationship analyses. Journal of Pharmaceutical Sciences 93:1508-1523.
40. Abraham M. H., Ràfols C. 1995. Factors that influence tadpole narcosis-An LFER analysis. Journal of Chemical Society Perkin Transactions 2:1843-1851.
41. Hoover K. R., Acree W. E., Abraham M. H. 2005. Chemical toxicity correlations for several fish species based on the Abraham solvation parameter model. Chemical Research In Toxicology 18:1497-1505.
42. Hoover K. R., Flanagan K. S., Acree W. E. Jr., Abraham M. H. 2007. Chemical toxicity correlations for several protozoas, bacteria, and water fleas based on the Abraham solvation parameter model. Journal of Environmental and Engineering Science 6:165-174.
43. Poole S. K., Poole C. F. 1996. Model for the sorption of organic compounds by soil from water. Analytical Communications 33:417-419.
44. Abraham M. H., Chadha H. S., Leitao R. A. E., Mitchell R. C., Lambert W. J., Kaliszan R., et al. 1997. Determination of solute lipophilicity, as log P(octanol) and log P(alkane) using poly(styrene-divinylbenzene) and immobilized artificial membrane stationary phases in reversed-phase high-performance liquid chromatography. Journal of Chromatography A 766:35-47.
45. Krass J. D., Jastorff B., Genieser H. 1997. Determination of lipophilicity by gradient elution high-performance liquid chromatography. Analytical Chemistry 69:2575-2581.
46. Valkó K., Plass M., Bevan C., Reynolds D., Abraham M. H. 1998. Relationships between the chromatographic hydrophobicity indices and solute descriptors obtained by using several reversed-phase, diol, nitrile, cyclodextrin and immobilized artificial membranebonded high-performance liquid chromatography columns. Journal of Chromatography A 797:41-55.
47. Miyake K., Kitaura F., Mizuno N., Terada H. 1987. Phosphatidylcholine-coated silica as a useful stationary phase for high-performance liquid chromatographic determination of partition coefficients between octanol and water. Journal of Chromatography A 389:47-56.
48. Valkó K., Du C. M., Bevan C. D., Reynolds D. P., Abraham M. H. 2000. Rapid-gradient HPLC method for measuring drug interactions with immobilized artificial membrane: Comparison with other lipophilicity measures. Journal of Pharmaceutical Sciences 89:1085-1096.
49. Abraham M. H., Chadha H. S. 1996. Applications of a solvation equation to drug transport properties. In Methods and principles in medicinal chemistry. 4. Lipophilicity in drug action and toxicology, ed. B. Testa, H. V. de Waterbeemd and V. Pliska, 311-337. John Wiley & Sons, Weinheim, Germany.
50. Valkó K., Du C. M., 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 (Sigma alpha(H)(2)). Current Medicinal Chemistry 8:1137-1146.
51. Abraham M. H., Chadha H. S., Leo A. J. 1994. Hydrogen bonding: XXXV. Relationship between high-performance liquid chromatography capacity factors and water-octanol partition coefficients. Journal of Chromatography A 685:203-211.
52. Martel S., Guildume D., Henchoz Y., Galland A., Veuthey J. L., Rudoz S., Carrupt P. A. 2008. Chromatographic approaches for measuring log P. In Methods and Principles in Medicinal Chemistry. 37. Molecular Drug Properties: Measurement and Prediction, ed. R. Manhold, R. Kubinvi, and G. Folkers, 331-355. Wiley-VCH. Weinheim, Germany.
53. Shoshtari S. Z., Wen J., Alany R. G. 2008. Octanol-water partition coefficient determination for model steroids using an HPLC method. Letters in Drug Design and Discovery 5:394-400.
54. Canals I., ValkÓ K., Bosch E., Hill A. P., Rosés M. 2001. Retention of ionizable compounds on HPLC. 8. Influence of mobile-phase pH change on the chromatographic retention of acids and bases during gradient elution. Analytical Chemistry 73:4937-4945.
55. Canals I., Portal J. A., Bosch E., Rosés M. 2000. Retention of ionizable compounds on HPLC. 4. Mobile-phase pH measurement in methanol/water. Analytical Chemistry 72:1802-1809.
56. Canals I., Oumada F. Z., Rosés M., Bosch E. 2001. Retention of ionizable compounds on HPLC. 6. pH Measurements with the glass electrode in methanol-water mixtures. Journal of Chromatography A 911:191-202.
57. Rived F., Canals I., Bosch E., Rosés M. 2001. Acidity in methanol-water. Analytica Chimica Acta 439:315-333.
58. Espinosa S., Bosch E., Rosés M. 2000. Retention of ionizable compounds on HPLC. 5. pH scales and the retention of acids and bases with acetonitrile-water mobile phases. Analytical Chemistry 72:5193-5200.
59. Bosch E., Espinosa S., Rosés M. 1998. Retention of ionizable compounds on highperformance liquid chromatography. III. Variation of pK values of acids and pH values of buffers in acetonitrile-water mobile phases. Journal of Chromatography A 824:137-146.
60. Espinosa S., Bosch E., Rosés M. 2002. Retention of ionizable compounds in high-performance liquid chromatography IX. Modeling retention in reversed-phase liquid chromatography as a function of pH and solvent composition with acetonitrile-water mobile phases. Journal of Chromatography A 947:47-58.
61. Fuguet E., Ràfols C., Bosch E., Rosés M. 2007. Determination of the chromatographic hydrophobicity index for ionisable solutes. Journal of Chromatography A 1173:110-119.
62. Fuguet E., Ràfols C., Bosch E., Rosés M. 2009. Chromatographic hydrophobicity index: PH profile for polyprotic compounds. Journal of Chromatography A 1216:7798-7805.
63. Espinosa S., Bosch E., Rosés M., Valkó K. 2002. Change of mobile phase pH during gradient reversed-phase chromatography with 2, 2, 2-trifluoroethanol-water as mobile phase and its effect on the chromatographic hydrophobicity index determination. Journal of Chromatography A 954:77-87.
64. Chitra R., Smith P. E. 2001. Properties of 2, 2, 2-trifluoroethanol and water mixtures. Journal of Chemical Physics 114:426-435.
65. Espinosa S., Bosch E., Rosés M. 2002. Acid-base constants of neutral bases in acetonitrile- water mixtures. Analytica Chimica Acta 454:157-166.
66. Rosés M., Bosch E. 2002. Influence of mobile phase acid-base equilibria on the chromatographic behavior of protolytic compounds. Journal of Chromatography A 982:1-30.
67. Bosch E., Bou P., Allemann H., Rosés M. 1996. Retention of ionizable compounds on HPLC. pH scale in methanol-water and the pK and pH values of buffers. Analytical Chemistry 68:3651-3657.
68. Pagliara A., Carrupt P., Caron G., Gaillard P., Testa B. 1997. Lipophilicity profiles of ampholytes. Chemical Reviews 97:3385-3400.
69. Karcher S. C., Laufer S. A. 2009. Aza-analogue dibenzepinone scaffolds as p38 mitogen-activated protein kinase inhibitors: Design, synthesis, and biological data of inhibitors with improved physicochemical properties. Journal of Medicinal Chemistry 52:1778-1782.
70. Bartalis J., Halaweish F. T. 2005. Relationship between cucurbitacins reversed-phase high-performance liquid chromatography hydrophobicity index and basal cytotoxicity on HepG2 cells. Journal of Chromatography B 818:159-166.
71. Casartelli A., Bonato M., Cristofori P., Crivellente F., Dal Negro G., Masotto I., et al. 2003. A cell-based approach for the early assessment of the phospholipidogenic potential in pharmaceutical research and drug development. Cell Biology and Toxicology 19:161.