Inclusion complex formation of α- And β-cyclodextrins with aminobenzoic acids in aqueous solution studied by 1H NMR

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 59, Issue 3-4, 2007, Pages 301-306

  Terekhova, Irina V ^a   Kumeev, Roman S ^a   Alper, Gennadiy A ^a  

^a INSTITUTE OF SOLUTION CHEMISTRY   (Russian Federation)

Author keywords

Aminobenzoic acid; Binding mode; Cyclodextrin; Inclusion complexes; NMR; Stability constant

Indexed keywords

EID: 36048987334     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-007-9327-y     Document Type: Article

References (24)

1. Szejtli, J.: Cyclodextrin Technology, Kluwer Academic Publishers, Netherlands (1988).
2. Szejtli, J.: Industrial applications of cyclodextrins. In: Atwood, J.L., Davies, J.E.D., MacNicol, D.D. (eds.) Inclusion Compounds, vol. 3. Academic Press, London (1984).
3. Hedges A.R.: Industrial applications of cyclodextrins. Chem. Rev. 98, 2035-2044 (1998).
4. Uekama, K., Hirayama, F., Irie, T.: Cyclodextrin drug carrier systems. Chem. Rev. 98, 2045-2076 (1998).
5. Terekhova, I.V., Kulikov, O.V.: Cyclodextrins. Physical-chemical aspects of formation of complexes "host-guest" and molecular selectivity in relation to biologically active molecules.In: Zaikov, G.E. (ed.) Chemistry of Polysaccharides. Brill Academic Publishers, Netherlands (2005).
6. Terekhova, I.V., Scriba, G.K.E.: Study on complex formation of biologically active pyridine derivatives with cyclodextrins by capillary electrophoresis. J. Pharm. Biomed. Anal. (2007) doi: 10.1016/j.jpba.2007.02.003.
7. Vasilieva, S.: Para-aminobenzoic acid inhibits a set of SOS functions in Escherichia coliK12. Mutat. Res. 496, 89-95 (2001).
8. Hirt, R., Hurni, H.: Helv. Chim. Acta 32, 378 (1949).
9. Bruze, M., Gruvberger, B., Thulin I.: PABA, benzocaine, and other PABA esters in sunscreens and after-sun products. Photodermatol. Photoimmunol. Photomed. 7, 106-108 (1990).
10. Mackie, B.S., Mackie, L.E.: The PABA story. Aust. J. Dermatol. 40, 51-53 (1999).
11. Salvador, A., Chisvert, A., Rodríguez, A., March, J.G.: Indirect spectrophotometric determination of p-aminobenzoic acid in sunscreen formulations by sequential injection analysis. Anal. Chem. Acta 493, 233-239 (2003).
12. Dromgoole, S.H., Mailbach, H.I.: Sunscreening agent intolerance: contact and photocontact sensitization and contact urticaria. J. Am. Acad. Dermatol. 22, 1068-1078 (1990).
13. Shaw, A.A., Wainschel, L.A., Shetlar, M.D.: Photoaddition of p-aminobenzoic acid to thymine and thymidine. Photochem. Photobiol. 55, 657-663 (1992).
14. Setnička, V., Urbanová, M., Král, V., Volka, K.: Interactions of cyclodextrins with aromatic compounds studied by vibrational circular dichroism spectroscopy. Spectrochim. Acta A 58, 2983-2989 (2002).
15. Harata, K.: Induced circular dichroism of cycloamylose complexes with meta-and para-disubstituted benzenes. Bioorg. Chem. 10, 255-265 (1981).
16. Lewis, E.A., Hansen, L.D.: Thermodynamics of binding of guest molecules to α- and β-cyclodextrins. J. Chem. Soc. Perkin Trans. 2, 2081-2085 (1973).
17. Shaomin, S., Yu, Y., Jinghao, P.: Study on molecular recognition of para-aminobenzoic acid species by α-, β- and hydroxypropyl-β- cyclodextrin. Anal. Chim. Acta 458, 305-310 (2002).
18. Stalin, T., Rajendiran, N.: Intramolecular charge transfer effects on 3-aminobenzoic acid. Chem. Phys. 322, 311-322 (2006).
19. Stalin, T., Shanthi, B., Vasantha Rani, P., Rajendiran, N.: Solvatochroism, prototropism and complexation of p-aminobenzoic acid. J. Inclus. Phenom. Macrocycl. Chem. 55, 21-29 (2006).
20. Stalin, T., Rajendiran, N.: Intramolecular charge transfer associated with hydrogen bonding effects on 2-aminobenzoic acid. J. Photochem. Photobiol. A 182, 137-150 (2006).
21. Job, P.: Ann. Chim. 9, 113-203 (1928).
22. Schneider, H.-J., Hacket, F., Rudiger, V.: NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98, 1755-1785 (1998).
23. Simova, S., Schneider, H.-J.: NMR analyses of cyclodextrin complexes with substituted benzoic acids and benzoate anions. J. Chem. Soc. Perkin Trans. 2, 1717-1722 (2000).
24. Rudiger, V., Eliseev, A., Simova, S., Schneider, H.-J., Blandamer, M.J., Cullis, P.M., Meyer, A.J.: Conformational, calorimetric and NMR spectroscopic studies on inclusion complexes of cyclodextrins with substituted phenyl and adamantine derivatives. J. Chem. Soc. Perkin Trans. 2, 2119- 2123 (1996).