Lipophilicity determination using both TLC and calculations

Journal of Liquid Chromatography and Related Technologies

Volumn 32, Issue 9, 2009, Pages 1342-1358

  Kalasz H ^a   Benko, B ^b   Gulyas Zs ^c   Tekes, K ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b GEDEON RICHTER LTD   (Hungary)

^c ComGrid Ltd ^*  (Hungary)

Author keywords

Lipophilicity; Pallas program; Reversed phased chromatography; Thin layer chromatography

Indexed keywords

ALDOXIMES; CALCULATED VALUES; CYASTERONE; ECDYSTEROIDS; EXPERIMENTAL DETERMINATION; GOOD CORRELATIONS; LIPOPHILICITY; LIPOPHILICITY DETERMINATION; ORGANIC MODIFIER; PALLAS PROGRAM; PHENYL RINGS; PYRIDINIUM; REVERSED PHASE; REVERSED-PHASE THIN-LAYER CHROMATOGRAPHY; REVERSED-PHASED CHROMATOGRAPHY; STATIONARY PHASE; STRAIGHT LINES; SUBSTITUTED COMPOUNDS;

CHROMATOGRAPHY; HALOGEN COMPOUNDS; ORGANIC COMPOUNDS;

CHROMATOGRAPHIC ANALYSIS;

2 DEOXYECDYSONE; 2 DEOXYECDYSTERONE; 22 DEOXY 20 HYDROXYECDYSONE; 4 AMINODEPRENYL; AMPHETAMINE; BENZYLAMINE; CYASTERONE; ECDYSONE; ECDYSTEROID; ECDYSTERONE; ECDYSTERONE 22 ACETATE; EPHEDRINE; INTEGRISTERONE; LIQUID PARAFFIN; MAKISTERONE A; METHAMPHETAMINE; N (1 INDENYL) N METHYL N PROPARGYLAMINE; N METHYL N (2 PROPYNYL)PHENETHYLAMINE; NOREPHEDRINE; NORPSEUDOEPHEDRINE; NORSELEGILINE; PHENYLALKYLAMINE; PHOLEDRINE; POLYPODINE B; RUBROSTERONE; SELEGILINE; SILICA GEL; UNCLASSIFIED DRUG; UNINDEXED DRUG; VITOCOSTERONE E; XENOBIOTIC AGENT;

ARTICLE; CALCULATION; COMPUTER PROGRAM; CORRELATION ANALYSIS; HYDROPHILICITY; LIPOPHILICITY; PARTITION COEFFICIENT; REVERSED PHASE LIQUID CHROMATOGRAPHY; REVERSED PHASE THIN LAYER CHROMATOGRAPHY; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY;

EID: 70349972669     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826070902854466     Document Type: Article

References (28)

1. Kalant, H.; Woodland, C.; Seeman, P. Drug solubility, absorption, and movement across body membranes, in Principles of Medical Pharmacology, 7th Ed.; Kalant, H., Grant, D.M., Mitchell, J., Eds.; Elsevier: Canada, Toronto, 2007, 11-26.
2. Overton, E. Über die osmotische Eigenschaften der Zelle in ihrer Bedeutung für die Toxicologie und Pharmacologie. Z. Physical. Chem. 1897, 22, 189.
3. Overton, E. Studien über die Narkose; G. Fischer Verlag: Jena, 1901.
4. Meyer, H. Zur Theorie der Alkoholnarkose. Erste Mitteilung. Welche Eigenschaft der Anasthetica bedingt ihre narkotische Wirkung? Arch. Exptl. Pathol. Pharmakol. 1899, 42, 109.
5. Meyer, H., Zur Theorie der Alkoholnarkose. Dritte Mitteilung. Der Einfluss wechselnder Temperatur auf Wirkungstarke und Teilungscoefficient der Narkotica. Arch. Exptl. Pathol. Pharmakol. 1901, 46, 338.
6. Baum, F. Zur Theorie der Alkoholnarkose, Zweite Mitteilung. Ein physikalisch-chemisher Beitrag zur Theorie der Narkotica. Arch. Exptl. Pathol. Pharmakol. 1899, 42, 119.
7. Ferguson, J. The use of chemical potentials as indices of toxicity. Proc. Royal Soc., Ser. B. 1939, 127, 787.
8. Collander, R. The partition of organic compounds between higher alcohols and water. Acta Chem. Scand. 1951, 5, 774.
9. Collander, R. The permeability of Nitella cells to non-electrolites. Physiol. Plant. 1954, 7, 420.
10. Zahradnik, R. Influence of the structure of aliphatic substituents of the magnitude of the biological effect of substances. Arch. Int. Pharmacodyn. Ther. 1962, 135, 311.
11. Hemker, H.C. Lipid solubility as a factor influencing the activity of uncoupling phenols. Biochim. Biophys. Acta. 1962, 63, 46.
12. Leo, A.J.; Hansch, C.; Elkins, D. Partition coefficients and their uses. Chem. Rev. 1971, 71, 525.
13. Hansch, C.; Leo, A.J. Substituent Constants for Correlation Analysis in Chemistry and Biology; Wiley: New York, 1979.
14. Biagi, G.L.; Barbaro, A.M.; Guerra, M.C.; Cantelli Forte, G.; Borea, P.A.; Pietrogrande, M.C.; Salvadori, S.; Tomatis, R. In Chromatography, the State of the Art; Kalász, H.; Ettre, L.S., Eds.; Akadémiai Kiadó: Budapest, 1985; 719-730.
15. Nahum, A.; Horváth, Cs. Evaluation of octanol-water partition coefficient by using high-performance liquid chromatography. J. Chromatogr. 1980, 192, 315-322. (Pubitemid 10054189)
16. Valkó, K.; Plass, M.; Bevan, C.; Reynolds, D.; Abraham, M.H. Relationships between the chromatographic hydrophobicilty indices and solute descriptors obtained by using several reversed-phase, diol, nitrile, cyclodextrin and immobilized artificial membrane bonded high-performance liquid chromatography columns. J. Chromatogr. A. 1988, 797, 41-55.
17. Boyce, C.B.C.; Milborrow, B.V. A simple assesement of partition data for correlating structure and biological activity using thin-layer chromatography. Nature. 1965, 208, 537.
18. Biagi, G.L.; Barbaro, A.M.; Gamba, M.F.; Guerra, M.C. Partition data of penicillins determined by means of reversed-phase thin-layer chromatography. J. Chromatogr. 1983, 259, 329.
19. Biagi, G.L.; Guerra, M.C.; Barbaro, A.M.; Sapone, A.; Recanatini, M. Lipophilic character of cardiac glycosides: correlation between RM values and acute toxicity data in different animal species. J. Chromatogr. 1991, 547, 523-530.
20. Kalász, H.; Báthori, M.; Csermely, T. Planar versus microcolumn chromatography. Am. Lab. 2000, 32 (9), 28-32.
21. Csermely, T.; Kalász, H.; Rischák, K.; Báthori, M.; Tarjányi, Zs.; Fürst, S. Planar chromatography of (-)-deprenyl and some structurally related compounds. JPC-J. Planar Chromatogr. 1998, 11, 247-253.
22. Laufer, R.; Báthori, M.; Csermely, T.; Petroianu, G.; Kuca, K.; Tóth, N.; Kalász, H. TLC determination of hydrophilicity parameter of some pyridinium aldoximes. J. Liq. Chromatogr. & Rel. Technol. 2004, 30, 2337-2344.
23. Báthori, M. Purification and characterization of plant ecdysteroids of Silene otites. Trends Anal. Chem. 1998, 17, 372-383.
24. Báthori, M. Phytoecdysteroids effects on mammalian, isolation and analysis. Mini Rev. Med. Chem. 2002, 2, 285-293.
25. Báthori, M.; Hunyadi, J.; Janicsák, G.; Máthé, I. TLC of ecdysteroids with four-mobile phases and three-stationary phases. J. Planar Chromatogr. 2004, 17, 23-25.
26. The Pallas and the PrologP are softwares of CompuDrug International, Inc. (115 Morgan Drive, Sedona, AZ 86351, USA).
27. Molnár, L.; Keserü, Gy.; Papp, Á.; Gulyás, Zs.; Darvas, F. A neural network based prediction of octanol-water partition coefficients using atomic 5 fragmental descriptors. Bioorg. Med. Chem. Lett. 2004, 14, 851-853.
28. Ertl, P.; Rohde, B.; Selzer, P. Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties. J. Med. Chem. 2000, 43, 3714-3717.