JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 65 No 1 (2020): Journal of the Chilean Chemical Society
Original Research Papers

THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES

Suzana Apostolov
University of Novi Sad
Published February 4, 2020
Keywords
  • N-(4-phenylmonosubstituted)-2-cyanoacetamides,
  • RP-TLC,
  • lipophilicity,
  • Lipinski’s molecular descriptors,
  • pharmacokinetic predictors
How to Cite
Apostolov, S., Vastag, G., Matijević, B., Đaković-Sekulić, T., & Marinković, A. (2020). THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES . Journal of the Chilean Chemical Society, 65(1), 4654-4660. Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/1361

Abstract

Biological activity of a molecule is closely related to its lipophilicity. This significant parameter was determinedfor a group of potentially bioactive N-(4-phenylmonosubstituted)-2-cyanoacetamides applying thin-layer chromatography on reversed phase (RP-TLC) in mixtures of water and two organic modifiers separately, i-propanol and dioxane. The effect of the chemical structure of derivatives and the influence of the applied organic modifier on their retention were studied. The determined chromatographic retention constants, RM0, and the chromatographic parameter, m, of compounds were correlated with software calculated partition coefficients, log P as the standard measure of lipophilicity and with different pharmacokinetic predictors applying classical linear and multiple regression analysis. By classical linear regression analysis in both water-modifier systems only RM0-log P and m-log P correlations were established (average r, 0.909 and 0.826).  All studied relationships were enhanced by molecular descriptors that fulfilled the modified Lipinski’s rule of five. Thereby, the performed multiple regression analysis gave better correlations (for RM0-log P and m-log Paverage r2, 0.994 and 0.993; for RM0-pharmacokinetic parameters and m-pharmacokinetic parameters average r2 0.978 and 0.980). The obtained results indicate that the chromatographic parameters, RM0 and m determined by RP-TLC at given conditions could be used successfully for the description of lipophilicity and the evaluation of pharmacokinetic properties of N-(4-phenylmonosubstituted)-2-cyanoacetamides as potential bioactive molecules.

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References

  1. S.M. Paul, D.S. Mytelka, C.T. Dunwiddie, C.C. Persinger, B.H. Munos, S.R. Lindborg, A.L. Schacht, Nat. Rev. Drug Discovery, 9, 203, (2010)
  2. L. De Petrocellis, D. Melck, T. Bisogno, V. Di Marzo, Chem. Phys. Lipids, 108, 191, (2000)
  3. F. Soto-Morales, J.S. Gómez-Jeria, J. Chil. Chem. Soc. 52, 1214, (2007)
  4. E. Petrlíková, K. Waisser, K. Palát Jr., J. Kuneš, J. Kaustová, Chem. Pap. 65, 52, (2011)
  5. P.S. Banerjee, P.K. Sharma, Med. Chem. Res. 21, 1491, (2012)
  6. Y. Liu, G.Y. Zhang, Y. Li, Y.N. Zhang, S.Z. Zheng, Z.X. Zhou, S.J. An, Y.H. Jin, Heteroat. Chem. 24, 9, (2013)
  7. D.J. Pacheco, J. Trilleras, J. Quiroga, J. Gutiérrez, L. Prent, T. Coavas, J.C. Marín, G. Delgado, J. Braz. Chem. Soc. 24, 1685, (2013)
  8. F.F. Boyom, P.V.T. Fokou, L.R.Y Tchokouaha, T. Spangenberg, A.N. Mfopa, R.M.T. Kouipou, C.J. Mbouna, V.F.D. Donfack, P.H.A. Zollo, Antimicrob. Agents Chemother. 58, 5848, (2014)
  9. N.S. Arutyunyan, L.A. Akopyan, R.L. Nazaryan, G.A. Gevorgyan, G.M. Stepanyan, R.V. Paronikyan, G.A. Panosyan, Pharm. Chem. J. 47, 490, (2013)
  10. R. Wan, J.Q. Zhang, F. Han, P. Wang, P. Yu, Q. He, Nucleosides, Nucleotides Nucleic Acids, 30, 280, (2011)
  11. M.L. Bernards, J.T. Simmons, C.J. Guza, C.R. Schulz, D. Penner, J.J. Kells, Weed Technol. 20, 458, (2006)
  12. B. Reddy, S. Mohan, J.I. Talukdar, Int. J. ChemTech Res. 5, 2727, (2013)
  13. D.Ü. Özkay, Y. Özkay, Ö.D. Can, Med. Chem. Res. 20, 152, (2011)
  14. A.H. Tarikogullari, F.S. Kilic, K. Erol, V. Pabuccuoglu, Arzneim.-Forsch./Drug Res. 60, 593, (2010)
  15. S. Koppireddi, J.R. Komsani, S. Avula, S. Pombala, S. Vasamsetti, S. Kotamraju, R. Yadla, Eur. J. Med. Chem. 66, 305, (2013)
  16. L. Morellato, M. Lefas-Le Gall, M. Langlois, D.H. Caignard, P. Renard, P. Delagrange, M. Mathé-Allainmat, Bioorg. Med. Chem. Lett. 23, 430, (2013)
  17. H. Rajak, M.D. Kharya, P. Mishra, Arch. Pharm. 341, 247, (2008)
  18. G. Veinberg, M. Vorona, L. Zvejniece, R. Vilskersts, E. Vavers, E. Liepinsh, H. Kazoka, S. Belyakov, A. Mishnev, J. Kuznecovs, S. Vikainis, N. Orlova, A. Lebedev, Y. Ponomaryov, M. Dambrova, Bioorg. Med. Chem. 21, 2764, (2013)
  19. L. Yurttaş, Z.A. Kaplancikli, Y.J. Özkay, Enzyme Inhib. Med. Chem. 28, 1040, (2013)
  20. O. Akgül, A.H. Tarikoğullari, F.A. Köse, P.B. Kirmizibayrak, M.V. Pabuççuoğlu, Turk. J. Chem. 37, 204, (2013)
  21. M. Duran, S. Demirayak, Med. Chem. Res. 22, 4110, (2013)
  22. P. Zhan, W. Chen, Z. Li, X. Li, X. Chen, Y. Tian, C. Pannecouque, E.D. Clercq, X. Liu, Bioorg. Med. Chem. 20, 6795, (2012)
  23. J.S. Gómez-Jeria, F. Soto-Morales, J. Rivas, A.J. Sotomayor, Chil. Chem. Soc. 53, 1393, (2008)
  24. T. Baczek, R. Kaliszan, Proteomics, 9, 835, (2007)
  25. M. Karelson, V.S. Lobanov, A.R. Katritzky, Chem. Rev. 96, 1027, (1996)
  26. Z. Garkani-Nejad, F. Salehfard, J. Chil. Chem. Soc. 58, 2226, (2013)
  27. E. Rutkowska, K. Paja̧k, K. Jóźwiak, Acta Pol. Pharm. 70, 3, (2013)
  28. L. Prokai, N.M. Rivera-Portalatin, K. Prokai-Tatrai, Int. J. Mol. Sci. 14, 1443, (2013)
  29. J. Stasiak, M. Koba, T. Baczek, Lett. Drug Des. Discovery, 11, 1017, (2014)
  30. E.H. Kerns, L. Di, Drug Discov. Today, 8, 316, (2003)
  31. T. Fujita, J. Iwasa, C. Hansch, J. Am. Chem. Soc. 86, 5175, (1964)
  32. A. Leo, C. Hansch, D. Elkins, Chem. Rev. 71, 525, (1971)
  33. S. Gocan, S. Cobzac, N. Grinberg, J. Liq. Chromatogr. Relat. Technol. 30, 1669, (2007)
  34. D. Łazewska, P. Maludziński, E. Szymańska, K. Kieć-Kononiwicz, Biomed. Chromatogr. 21, 291, (2007)
  35. A. Hawrył, E. Kumierz, P. Pisarczyk, M. Wujec, M. Waksmundzka-Hajnos, Acta Chromatogr. 24, 271, (2012)
  36. G. Vastag, S. Apostolov, N. Perišić-Janjić, B. Matijević, Anal. Chim. Acta 767, 44, (2013)
  37. G.Gy. Vastag, S.Lj. Apostolov, B.M. Matijević, A.D. Marinković, J. Braz. Chem. Soc. 25, 1948, (2014)
  38. N. Perisic-Janjic, R. Kaliszan, N. Milosevic, G. Uscumlic, N. Banjac, J. Pharm. Biomed. Anal. 72, 65, (2013)
  39. C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug Delivery Rev. 23, 3, (1997)
  40. T. Hetal, P. Bindesh, T. Sneha, Int. J. Pharm. Sci. Rev. Res. 4, 203, (2010)
  41. W.K. Sietsema, Int. J. Clin. Pharmacol., Ther. Toxicol. 27, 179, (1989)
  42. Y.H. Zhao, J. Le, M.H. Abraham, A. Hersey, P.J. Eddershaw, C.N. Luscombe, D. Boutina, G. Beck, B. Sherborne, I. Cooper, J.A. Platts, J. Pharm. Sci. 90, 749, (2001)
  43. H.J. Lennernäs, Pharm. Sci. 87, 403, (1998)
  44. T.J. Hou, W. Zhang, K. Xia, X.B. Qiao, X.J. Xu, J. Chem. Inf. Model. 44, 1585, (2004)
  45. P. Paixão, L.F. Gouveia, J.A.G. Morais, Eur. J. Pharm. Sci. 36, 544, (2009)
  46. R.T. Scheife, Ann. Pharmacother. 23, 27, (1989)
  47. L.Z. Benet, D.L. Kroetz, L.B. Sheiner in The pharmacological basis of therapeutics Pharmacokinetics. The dynamics of drug absorption distribution and elimination Goodman G.A., Gilman eds. McGraw-Hill, New York, 1996; pp. 3-27.
  48. M. Hacker, K. Bachmann, W. Messer Pharmacology: Principles and Practice. Academic Press, Burlington, 2009
  49. P.L. Toutain, A. Bousquet-Mélou, J. Vet. Pharmacol. Ther. 27, 441, (2004)
  50. M. Iyer, R. Mishra, Y. Han, A.J. Hopfinger, Pharm. Res. 19, 1611, (2002)
  51. A.D. Marinković, D. Brkić, J.S. Martinović, D.Ž. Mijin, M. Milčić, S.D. Petrović, Chem. Ind. Chem. Eng. Q. 19, 67, (2013)
  52. http://www.vcclab.org Accessed May 2011.
  53. http://www.molinspiration.com Accessed June 2014.
  54. http://www.simulations-plus.com September 2013.
  55. G. Vastag, S. Apostolov, J. Nakomčić, B. Matijević, J. Liq. Chromatogr. Relat. Technol. 37, 2529, (2014)
  56. T.Lj. Djaković-Sekulić, N.U. Perišić-Janjić, S.D. Petrović, J. Planar Chromatogr.--Mod. TLC, 15, 274, (2002)
  57. S.M. Petrović, E. Lončar, N.U. Perišić-Janjić, M.J. Lazarević, Planar Chromatogr.--Mod. TLC, 10, 26, (1997)
  58. C. Sârbu, C. Onişor, M. Posa, S. Kevresan, K. Kuhajda, Talanta, 75, 651, (2008)
  59. Gy. Vastag, S. Apostolov, B. Matijević, S. Petrović, J. Chromatogr. Sci. 53, 312, (2014)
  60. G.L. Biagi, A.M. Barbaro, A. Sapone, M. Recanatini, J. Chromatogr. A, 662, 341, (1994)
  61. A. Kowalska, K. Pluta, J. Liq. Chromatogr. Relat. Technol. 35, 1686, (2012)
  62. N.P. Milošević, S.Z. Stojanović, K. Penov-Gaši, N. Perišić-Janjić, R. Kaliszan, J. Pharm. Biomed. Anal. 88, 636, (2014)
  63. S.S. Singh, Curr. Drug Metab. 7, 165, (2006)
  64. S. Apostolov, G. Vastag, B. Matijevic, S. Petrovic, J. Liq. Chromatogr. Relat. Technol. 38, 1691, (2015)
  65. N.P. Milošević, V.B. Dimova, N.U. Perišić-Janjić, Eur. J. Pharm. Sci. 49, 10, (2013)

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