Reversed-phase liquid chromatography with octadecylsilyl, immobilized artificial membrane and cholesterol columns in correlation studies with in silico biological descriptors of newly synthesized antiproliferative and analgesic active compounds

Journal of Chromatography A

Volumn 1318, Issue , 2013, Pages 92-101

  Janicka, Małgorzata ^a   Sztanke, Małgorzata ^b   Sztanke, Krzysztof ^b  

^a MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

^b MEDICAL UNIVERSITY OF LUBLIN   (Poland)

Author keywords

Biological descriptors; Cholesterol column; Lipophilicity; Principal component analysis; Reversed phase liquid chromatography

Indexed keywords

DESCRIPTORS; IMMOBILIZED ARTIFICIAL MEMBRANES; LINEAR SOLVATION ENERGY RELATIONSHIPS; LIPOPHILIC PROPERTIES; LIPOPHILICITY; PREDICTIVE RELATIONSHIPS; REVERSED-PHASE LIQUID CHROMATOGRAPHY; STATISTICAL QUALITY;

LIQUID CHROMATOGRAPHY; PRINCIPAL COMPONENT ANALYSIS;

CHOLESTEROL;

2,6,7,8 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZINE 3,4 DIONE; 3 (2 FURANYL) 8 ARYL 7, 8 DIHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 4(6H) ONE; 3 (SUBSTITUTED BENZYL) 8 ARYL 7,8 DIHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 4(6H) ONE; 3 BENZYL 8 ARYL 7,8 DIHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 4(6H) ONE; 3 PHENYL 8 ARYL 7,8 DIHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 4(6H) ONE; 4 OXO 8 ARYL 4,6,7,8 TERTAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZINE 3 CARBOHYDAZIDE; 7,8 DIHYDROIMIDAZO[2,1 C][1,2,4]TRIAZIN 4(6H) ONE; 8 ARYL 2,6,7,8 TETRAHYDROIMIDAZO[2,1 C][1,2,4]TRIAZINE 3,4 DIONE; ANALGESIC AGENT; ANTINEOPLASTIC AGENT; ANTINOCICEPTIVE AGENT; BIOLOGICAL MARKER; BUFFER; CHOLESTEROL; OCTADECYLSILYL; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANALYTICAL PARAMETERS; ANTINOCICEPTION; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; ARTIFICIAL MEMBRANE; CELL STRAIN CACO 2; CHEMICAL ANALYSIS; COLUMN CHROMATOGRAPHY; COMPUTER MODEL; COMPUTER PROGRAM; CORRELATION ANALYSIS; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG DISTRIBUTION; DRUG PENETRATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; IMMOBILIZED ARTIFICIAL MEMBRANE; INTERMETHOD COMPARISON; LIPOPHILICITY; METASTASIS INHIBITION; PHARMACOLOGICAL PARAMETERS; PHASE PARTITIONING; PHYSICAL PHASE; PREDICTIVE VALUE; PREDICTOR VARIABLE; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REVERSED PHASE LIQUID CHROMATOGRAPHY; SKIN ABSORPTION; SOLVATION; STEADY STATE; TOXICITY TESTING;

BIOLOGICAL DESCRIPTORS; CHOLESTEROL COLUMN; LIPOPHILICITY; PRINCIPAL COMPONENT ANALYSIS; REVERSED-PHASE LIQUID CHROMATOGRAPHY;

ANALGESICS; CHOLESTEROL; CHROMATOGRAPHY, REVERSE-PHASE; COMPUTER SIMULATION; GROWTH INHIBITORS; MOLECULAR STRUCTURE;

EID: 84887199326     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2013.09.060     Document Type: Article

References (43)

1. Sangster J. Octanol-Water Partition Coefficients: Fundamentals and Physical Chemistry 1997, John Wiley & Sons.
2. Testa B., Crivori P., Reist M., Carrupt P.A. Persp. Drug Discov. Des. 2000, 19:179.
3. Kaliszan R. Quantitative Structure-Chromatographic Retention Relationships 1987, John Wiley & Sons.
4. Kaliszan R. Chem. Rev. 2007, 107:3212.
5. Valkó K. J. Chromatogr. A 2004, 1037:299.
6. Barbato F., di Martino G., Grumetto L., La Rotonda M.I. Eur. J. Pharm. Sci. 2004, 22:261.
7. Vrakas D., Giaginis G., Tsantili-Kakaulidou A. J. Chromatogr. A 2006, 1116:58.
8. Li J., Sun J., Cui Sh., He Zh. J. Chromatogr. A 2006, 1132:174.
9. Li J., Sun J., He Zh J. Chromatogr. A 2007, 1140:174.
10. Sprunger L., Blake-Taylor B.H., Wairegi A., Acree W.E., Abraham M.H. J. Chromatogr. A 2007, 1160:235.
11. Liu X.Y., Nakamura Ch., Yang Q., Kamo N., Miyake J. J. Chromatogr. A 2002, 961:113.
12. Escuder-Gilabert L., Molero-Monfort M., Villanueva-Camañas R.M. J. Chromatogr. B 2004, 807:193.
13. Kawczak P., Heyden Y.V., Nasal A., Baczek T., Drabczyńska A., Kieć-Kononowicz K., Kaliszan R. J. Sep. Sci. 2010, 33:1546.
14. Kawczak P., Baczek T. Cent. Eur. J. Chem. 2012, 10:570.
15. Escuder-Gilabert L., Martínez-Pla J.J., Sagrado S. J. Chromatogr. B 2003, 797:21.
16. Sztanke K., Pasternak K., Sztanke M., Kandefer-Szerszeń M., Kozioł A.E., Dybała I. Bioorg. Med. Chem. Lett. 2009, 19:5095.
17. K. Sztanke, Polish Patent, PL 199750, 2008.
18. Tuzimski T., Sztanke K. J. Planar Chromatogr. 2005, 18:274.
19. Sztanke K. Acta Pol. Pharm. Drug-Res. 2004, 64:373.
20. K. Sztanke, T. Tkaczyński, in: Proceedings of the 1st World Meeting APGI/APV on Pharmaceutics, Biopharmaceutics and Pharmaceutical Technology, Budapest, 9-11 May1995, p. 107.
21. Sztanke K., Tuzimski T., Sztanke M., Rzymowska J., Pasternak K. Bioorg. Med. Chem. 2011, 19:5103.
22. A. Hordyjewska, K. Sztanke, S. Radej, J. Rzymowska, K. Pasternak, J. Roliński, in: Pierwiastki, środowisko i życie człowieka, Kazimierz Pasternak (Eds.), Pol. Tow. Magnezol., Lublin, 2009, p. 75.
23. Sztanke K., Tkaczyński T. Acta Pol. Pharm. Drug.-Res. 1997, 54:71.
24. K. Sztanke, M. Sztanke, K. Pasternak, Polish Patent, PL 212442, 2012.
25. K. Sztanke, M. Sztanke, K. Pasternak, Polish Patent, PL 212447, 2012.
26. Sztanke K., Pasternak K., Rzymowska J., Sztanke M., Kandefer-Szerszeń M. Eur. J. Med. Chem. 2008, 43:1085.
27. K. Sztanke, Polish Patent, PL 201092, 2009.
28. M. Kandefer-Szerszeń, A. Szuster-Ciesielska, K. Sztanke, K. Pasternak, PL Patent Appl. No. 388162, 2009.
29. Szuster-Ciesielska A., Sztanke K., Kandefer-Szerszeń M. Chem. Biol. Interact. 2012, 195:18.
30. Sztanke K., Fidecka S., Kedzierska E., Karczmarzyk Z., Pihlaja K., Matosiuk D. Eur. J. Med. Chem. 2005, 40:127.
31. Sztanke K., Pasternak K., Rzymowska J., Sztanke M., Kandefer-Szerszeń M., Dybała I., Kozioł A.E. Bioorg. Med. Chem. 2007, 15:2837.
32. K. Sztanke, D. Matosiuk, S. Fidecka, Polish Patent, PL 196752, 2008.
33. Sztanke K., Markowski W., Świeboda R., Polak B. Eur. J. Med. Chem. 2010, 45:2644.
34. Buszewski B., Jezierska M., Wełniak M., Kaliszan R. J. Chromatogr. A 1999, 845:433.
35. Pesek J.J., Matyska M., Dawson G.B., Wilsdorf A., Marc P., Padki M. J. Chromatogr. A 2003, 986:253.
36. Courtois C., Allais Ch., Constantieus Th., Rodriques J., Caldarelli S., Delaurent C. Anal. Bioanal. Chem. 2008, 392:1345.
37. Bocian Sz., Matyska M., Pesek J., Buszewski B. J. Chromatogr. A 2010, 1217:6891.
38. K. Sztanke, Polish Patent, PL 211550, 2012.
39. Vitha M., Carr P.W. J. Chromatogr. A 2006, 1126:143.
40. Soczewiński E., Wachtmeister C.A. J. Chromatogr. 1962, 7:311.
41. Van de Waterbeemd H., Kansy M., Wagner B., Fischer H. Lipophilicity in Drug Action and Toxicology 1996, 73. VCH Publishers. V. Pliska, B. Testa, H. Van de Waterbeemd (Eds.).
42. Carrupt P.A., Testa B., Gaillard P. Reviews in Computational Chemistry 1997, vol. 11. Wiley-VCH, John Wiley & Sons, Inc., New York, (Chapter 5).
43. Yamashita S., Furubayashi T., Kataoka M., Sakane T., Sezaki H., Tokuda H. Eur. J. Pharm. 2000, 10:195.