Selected traditional structural descriptors and RM values for estimation and prediction of lipophilicity of homologous series of saturated fatty acids

JAOCS, Journal of the American Oil Chemists' Society

Volumn 83, Issue 9, 2006, Pages 747-752

  Pyka, Alina ^a   Bober, Katarzyna ^a  

^a MEDICAL UNIVERSITY OF SILESIA   (Poland)

Author keywords

Homologous series; Partition coefficient; Rm value; Regression analysis; RP HPTLC; Saturated fatty acids; Structural descriptors

Indexed keywords

HOMOLOGOUS SERIES; LIPOPHILICITY; PARTITION COEFFICIENT; REVERSED PHASE HIGH PERFORMANCE TLC (RP-HPTLC); SATURATED FATTY ACIDS; STRUCTURAL DESCRIPTORS;

HYDROPHOBICITY; METHANOL; MOLECULAR STRUCTURE; REGRESSION ANALYSIS; THIN LAYER CHROMATOGRAPHY; WATER;

FATTY ACIDS;

EID: 33749840766     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-006-5009-y     Document Type: Article

References (24)

1. Carballeira, N.M., A. Guzman, J.T. Nechev, K. Lahtchev, A. Ivanova, and K. Stefanov, Unusual Lipid Composition of a Bacillus sp. Isolated from Lake Pomorie in Bulgaria, Lipids 35:1371-1375 (2000).
2. Carballeira, N.M., C. Miranda, C.M. Lozano, J.T. Nechev, A. Ivanova, M. Ilieva, I. Tzvetkova, and K. Stefanov, Characterization of Novel Methyl-Branched Chain Fatty Acids from a Halophilic Bacillus Species, J. Nat. Prod. 64:256-259 (2001).
3. Murray, R.K., D.K. Granner, P.A. Mayes, and V.W. Rodwell, Harper's Biochemistry (in Polish), Wydawnictwo Lekarskie PZWL, Warsaw 1995, pp. 131-335.
4. Kubinyi, H., The Quantitative Analysis of Structure-Activity Relationships, in Burger's Medicinal Chemistry and Drug Discovery. Principles and Practice, 5th edn., edited by M.E. Wolff, John Wiley & Sons, 1995, Vol. 1, pp. 497-571.
5. Jóźwiak, K., H. Szumiło, and E. Soczewiński, Lipophilicity, Methods and Determination and Role in Biological Effect of Chemical Substances, Wiad. Chem. (in Polish) 55:1047-1074 (2001).
6. Mannhold, R., and R.F. Rekker, The Hydrophobic Fragmental Constant Approach for Calculating log P in Octanol-Water and Aliphatic Hydrocarbon/Water Systems, Perspect. Drug Discovery Des. 18:1-18 (2000).
7. Rekker, R.F., and R. Mannhold, Calculation of Drug Lipophilicity, VCH, Weinheim, 1992, pp. 2-104.
8. Kwietniewski, L., M. Janicka, and J.K. Rózyłlo, The Effect of Mobile Phase Composition on Solute Retention in Reversed-Phase Planar Chromatography, J. Planar Chromatogr. Mod. TLC 11:350-352 (1998).
9. Kastner, P., J. Klimes, P. Velenovska, and V. Klimesova, Study of Lipophilicity of Potential Antituberculotic Compounds by Reversed-Phase Thin-Layer Chromatography, J. Planar Chromatogr. Mod. TLC Ibid. 15:200-203 (2002).
10. oct Values, Quant. Struct.-Act. Relat 18:549-557 (1999).
11. Hansch, C., and A.J. Leo, Substituent Constants for Correlation Analysis in Chemistry and Biology, John Wiley, New York 1979, pp. 2-132.
12. Meylan, W.M., and P.M. Howard, Atom/Fragment Contribution Method for Estimating Octanol-Water Partition Coefficients, J. Pharm. Sci. 84:83-92 (1995).
13. Tetko, I.V., V. Yu. Tanchuk, and L. Lai, Application of Associative Neural Networks for Prediction of Lipophilicity in ALOGPS 2.1 Program, J. Chem. Inf. Comput. Sci. 42:1136-1145 (2002).
14. Wang, R., Y. Pu, and L. Lai, A New Atom-Additive Method for Calculating Partition Coefficients, J. Chem. Inf. Comput. Sci. Ibid. 37:615-621 (1997).
15. Tetko, I.V., and V.Yu. Tanchuk, Virtual Computational Chemistry Laboratory, VCC-lab 2002, http://146.107.217.178/servlets/vcclab? action=alogps (accessed September 2003)
16. Interactive Analysis log P Predictors, http://www.logp.com (accessed January 2002).
17. Pyka, A., and K. Bober, Investigation of Homologous Series of Fatty Acids by TLC. Part I. Comparison of Separations of Fatty Acids on RP-18 Plates With and Without Concentrating Zone, J. Planar Chromatogr. Mod. TLC 15:332-340 (2002).
18. M Values for Calculation and Prediction of Molar Volume of Homologous Series of Saturated Fatty Acids, Indian J. Chem. Sec. A 42A:1360-1367 (2003).
19. Pyka, A., and K. Bober, Investigation of an Homologous Series of Fatty Acids by TLC. Part II. Comparison of Separations of Fatty Acids on RP-18 Plates with Different Mobile Phases, J. Liq. Chromatogr. Rel. Technol. 26:2663-2671 (2003).
20. Pyka, A., and K. Bober, Investigation of a Homologous Series of Fatty Acids by TLC. Part III. Application of Terms Describing the Separation of Homologous Series of Saturated Fatty Acids in TLC, J. Planar Chromatogr. Mod. TLC 16:303-307 (2003).
21. Pyka, A., and K. Bober, Structural Descriptors in Evaluation of Selected Physicochemical Properties of Fatty Acids, Riv. Ital. Sostanze Grasse 87:231-238 (2004).
22. Devillers, J., and A.T. Balaban, Topological Indices and Related Descriptors in QSAR and QSPR, Gordon and Breach, Amsterdam, 1999, pp. 21-562.
23. Pyka, A., Correlation of Topological Indices with the Chromatographic Separation of Isomers, J. Planar Chromatogr. Mod. TLC 4:316-318 (1991).
24. Barysz, M., G. Jashari, R.S. Hall, V.K. Srivastava, and N. Trinajstić, On the Distance Matrix of Molecules Containing Heteroatoms. Chemical Applications of Topology and Graph Theory, Stud. Phys. Theor. Chem. 28:222-230 (1983).