Recognition and Binding of Aliphatic Dicarboxylic Acids C4 – C10 by Diiminocalix[4]arene

Olga Kalchenko, Andrew Solovyov, Vitaly Kalchenko

Abstract

Host-Guest complexation of 5,17-bis-(N-tolyliminomethyl)-25,27-dipropoxycalix[4]arenewithaliphatic dicarboxylicacidsC4 – C10 hasbeenstudiedin water-organic solution by the RP HPLC and molecular modeling methods. The stability constants (log KA =2.56– 3.05) of the supramolecular complexes are depended on structure, pKa and log Pvalues of the acids. The complexation is determined by the hydrogen bonds of the COOH group of the dicarboxylic acids with nitrogen atoms at the upper rim or oxygen atoms at the lower rim of the calixarene.

Keywords

calix[4]arenes; reversible-phase high performance liquid chromatography; aliphatic dicarboxylic acids; Host-Guest inclusion complexes; supramolecular interactions; binding constants

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References

Persch E, Dumele O, Diederich F. Molecular Recognition in Chemical and Biological Systems. Angewandte Chemie International Edition 2015;54(11):3290-3327. https://doi.org/10.1002/anie.201408487

Gutsche CD: Calixarenes revisited. Cambridge: RSC.; 1998 https://doi.org/10.1039/9781847550293

Sansone F, Segura M, Ungaro R. Calixarenes in Bioogranic and Biomimetic Chemistry. Calixarenes 2001 ;:496-512. https://doi.org/10.1007/0-306-47522-7_27

Casnati A, Sansone F, Ungaro R. Peptido- and Glycocalixarenes: Playing with Hydrogen Bonds around Hydrophobic Cavities. Accounts of Chemical Research 2003;36(4):246-254. https://doi.org/10.1021/ar0200798

Diamond D, Nolan K. Peer Reviewed: Calixarenes: Designer Ligands for Chemical Sensors. Analytical Chemistry 2001;73(1):22 A-29 A. https://doi.org/10.1021/ac012376g

Coleman A, Perret F, Moussa A, Dupin M, Guo Y, Perron H. Calix[n]arenes as Protein Sensors. Creative Chemical Sensor Systems ;:31-88. https://doi.org/10.1007/128_2007_115

Kalchenko O, Lipkowski J, Kalchenko V. Chromatography in Supramolecular and Analytical Chemistry of Calixarenes. Comprehensive Supramolecular Chemistry II 2017;:239-261. https://doi.org/10.1016/b978-0-12-409547-2.13799-0

Rodik R, Boyko V, Kalchenko V. Calixarenes in Bio-Medical Researches. Current Medicinal Chemistry 2009;16(13):1630-1655. https://doi.org/10.2174/092986709788186219

de Fatima A, Fernandes S, Sabino A. Calixarenes as New Platforms for Drug Design. Current Drug Discovery Technologies 2009;6(2):151-170. https://doi.org/10.2174/157016309788488302

Kalchenko O, Solovyov A, Kalchenko V. The reserved-phase HPLC study of the complexation of 5,17-bis-(N-tolylimino-methyl)-25,27-dipropoxycalix[4]arene with aromatic carboxylic acids. Žurnal organìčnoï ta farmacevtičnoï hìmìï 2015;13(3(51)):3-8. https://doi.org/10.24959/ophcj.15.856

Solovyov A, Cherenok S, Tsymbal I, Failla S, Consiglio G, Finocchiaro P, Kalchenko V. Calix[4]arenes bearing?-amino- or?-hydroxyphosphonic acid fragments at the upper rim. Heteroatom Chemistry 2001;12(2):58-67. https://doi.org/10.1002/hc.2

http://www.hyper.com/Download/All Downloads/tabid/470/Default.aspx

Lipkowski J, Kalchenko O, Slowikowska J, Kalchenko V, Lukin O, Markovsky L, Nowakowski R. Host-guest interactions of calix[4]resorcinarenes with benzene derivatives in conditions of reversed-phase high-performance liquid chromatography. Determination of stability constants. Journal of Physical Organic Chemistry 1998;11(6):426-437. https://doi.org/10.1002/(sici)1099-1395(199806)11:6<426::aid-poc963>3.0.co;2-r

Kalchenko O, Lipkowsk J, Kalchenko V, Vysotsky M, Markovsky L. Effect of Octakis(diethoxyphosphoryloxy)-tert-butyl-calix[8]arene in Mobile Phase on the Reversed-Phase Retention Behavior of Aromatic Compounds: Host-Guest Complex Formation and Stability Constants Determination. Journal of Chromatographic Science 1998;36(5):269-273. https://doi.org/10.1093/chromsci/36.5.269

Hansch C., Leo A., Hoekman D.H. Exploring QSAR: hydrophobic, electronic, and steric constants (ACS Professional Reference Book). American Chemical Society, Medical.; 1995.

www.chemspider.com/Chemical-Structure.191.html

www.drugbank.ca/drugs/db07645

www.chemspider.com/Chemical-Structure.844.html

Serjeant E.P., Dempsey B., Ionization constants of organic acids in aqueous solution. Oxford: Pergamon.; 1979.

Sober H.A., Ed., pKa Prediction for organic acids and bases, Handbook of biochemistry. Boca Raton: FL CRC Press.; 1968.