Investigation of sorption of calix[4]arene and calix[4]resorcinarene tetraalkyl derivatives with the LiChrosorb RP 18 surface by RP HPLC and molecular modelling methods

O. I. Kalchenko, S. O. Cherenok, L. I. Savonik, A. V. Solovyov, V. V. Gorbachuk, V. I. Kalchenko

Abstract


Tetrahydroxycalix[4]arene, tetraalkoxycalix[4]arenes and tetraalkylcalix[4]resorcinarenes are capable to reversible adsorption on the surface of the hydrophobic support LiChrosorb RP 18 under conditions of the reversed-phase high performance liquid chromatography. The main chromatographic characteristics of tetrahydroxycalix[4]arene, a series of tetraalkoxycalix[4]arenes and tetraalkylcalix[4]resorcinarenes have been determined. It has been found that in the conditions selected (the mobile phase is acetonitrile/water, 86/14, v/v) the retention times of the compounds studied are in the wide range from 4.67 min to 88.0 min depending on the nature of the substituents in the macrocyclic skeleton of the molecule. Thus, the retention times increase with increase of the length of the alkyl substituents at the lower rim of the calixarene macrocycle. According to the molecular modelling data the most effective sorption is explained by the inclusion of LiChrosorb RP 18 octadecyl groups into the lipophilic cavity formed by the alkyl substituents at the lower rim of the macrocycle of calixarene/calixresorcinarene. Thus, the molecular cavity formed by the benzene rings remains opened for the Host-Guest complexation with the analyte molecules. This sorption of tetraalkoxycalix[4]arenes and tetraalkylcalix[4]arenes on the LiChrosorb RP 18 surface can significantly improve its resolution ability in RP HPLC analysis. The influence of replacement of tetrahydroxycalix[4]arene hydroxyl protons with the alkyl groups on the conformation of the macrocycle has been studied.


Keywords


tetraalkoxycalix[4]arenes; tetraalkylcalix[4]resorcinarenes; reversed-phase high performance liquid chromatography; molecular modelling; complexation

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References


Ludwig R. Microchimica Acta. 2005, Vol. 152, pp.1-19.

Menon K., Sewani M. Reviews in Analytical Chemistry, 2006, Vol. 25, pp.49-82.

Mutihac L., Buschmann H.J. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2005, Vol. 51, pp.53-57.

De Fátima A., Fernandes S.A., Sabino A.A. Current Drug Discovery Technologies, 2009, Vol. 6, pp.151-170.

Rodik R.V., Boyko V.I., Kalchenko V.I. Current Medicinal Chemistry, 2009, Vol. 16, pp.1630-1655.

Cherenok S., Kalchenko V. Topics in Heterocyclic Chemistry, 2009, Vol. 20, pp.229-273.

Sansone F., Baldini L., Casnati A., Ungaro R. New Journal of Chemistry, 2010, Vol. 34, pp.2715-2728.

Boyko V.I., Yakovenko A.V., Matvieiev Yu.I., Kalchenko O.I., Shishkin O.V., Shishkina S.V., Kalchenko V.I. Tetrahedron, 2008, Vol. 64, pp.7567-7573.

Kalchenko O., Cherenok S., Yushchenko O., Kalchenko V. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2013, Vol. 76, pp.29-36.

Xiao X.Z., Feng Y.Q., Da S.L., Zhang Y. Chromatographia, 1999, Vol. 49, pp.643-648.

Li L.S., Da S.L., Feng Y.-Q., Liu M. Journal of Liquid Chromatography & Related Technologies, 2004, Vol. 27, pp.2167-2188.

Lee Y.K., Ryu Y.K., Ryu J.W., Kim B.E., Park J.H. Chromatographia, 1997, Vol. 46, pp.507-510.

Sokolieβ T., Schonherr J., Menyes U., Roth U., Jira T. Journal of Chromatography A, 2003, Vol. 1021, pp.71-82.

Sokolieβ T., Menyes U., Roth U., Jira T. Journal of Chromatography A, 2002, Vol. 948, pp.309-319.

Hashem H., Jira T. Die Pharmazie, 2005, Vol. 60, pp.186-192.

Hashem H., Trundelberg C., Jira T. Chromatographia, 2010, Vol. 71, pp.91-94.

Hashem H. Chromatographia, 2010, Vol. 71, pp.31-35.

Arduini A., Casnati A. In Macrocycle Synthesis. A Practical Approach, Parker D. (ed.) Oxford, Oxford University Press, 1996, pp.159.

Hansch C., Leo A., Hoekman D.H. Exploring QSAR: Hydrophobic, Electronic, and Steric Constants (ACS Professional Reference Book) American Chemical Society, Medical, 1995, 580 p.

Kalchenko O.I., Lipkowski J., Nowakowski R., Kalchenko V.I., Visotsky M.A., Markovsky L.N. Journal of Chromatographic Science, 1997, Vol. 35, pp.49-52.


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DOI: https://doi.org/10.24959/ophcj.14.799

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Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)