Complex formation of tetrakis(4-sulfonatophenyl)porphyrin with γ-cyclodextrin, phenylalanine, and tryptophan in aqueous solution

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 67, Issue 3, 2010, Pages 471-481

  Hamai, Sanyo ^a  

^a AKITA UNIVERSITY   (Japan)

Author keywords

Cyclodextrin; Absorption spectra; Fluorescence spectra; Phenylalanine; Tetrakis(4 sulfonatophenyl)porphyrin; Tryptophan

Indexed keywords

EID: 77952879598     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-009-9730-7     Document Type: Article

References (23)

1. Tan, W. H., Ishikura, T., Maruta, A., Yamamoto, T., Matsui, Y.: Molecular recognition in ternary complexes of γ-cyclodextrin with naphthalenedicarboxylate ions and a space-regulator ion. Bull. Chem. Soc. Jpn. 71, 2323-2329 (1998).
2. Hamai, S.: Ternary inclusion complexes of γ-cyclodextrin with resorufin and organic cations in aqueous solution. Bull. Chem. Soc. Jpn. 80, 1527-1533 (2007).
3. Andrade, S. M., Costa, S. M. B.: Spectroscopic studies on the interaction of a water soluble porphyrin and two drug carrier proteins. Biophys. J. 82, 1607-1619 (2002).
4. Bonneau, S., Vever-Bizet, C., Morliere, P., Maziere, J., Brault, D.: Equilibrium and kinetic studies of the interactions of a porphyrin with low-density lipoproteins. Biophys. J. 83, 3470-3481 (2002).
5. Nitta, Y., Kuroda, R.: Quantitative analysis of DNA-porphyrin interactions. Biopolymers 81, 376-391 (2006).
6. Saenger, W.: Cyclodextrin inclusion compounds in research and industry. Angew. Chem. Int. Ed. Engl. 19, 344-362 (1980).
7. Mosseri, S., Mialocq, J. C., Perly, B., Hambright, P.: Porphyrins-cyclodextrin. 1. Photooxidation of zinc tetrakis(4-sulfonatophenyl)porphyrin in cyclodextrin cavities: the characterization of ZnTSPP dication. Photolysis, radiolysis, and NMR studies. J. Phys. Chem. 95, 2196-2203 (1991).
8. Mosseri, S., Mialocq, J. C., Perly, B., Hambright, P.: Porphyrins-cyclodextrin. 2. Dissociation, reduction, and proton relaxivity of an Iron(III) porphyrin μ-oxo dimer in cyclodextrin solutions. J. Phys. Chem. 95, 4659-4663 (1991).
9. Ribo, J. M., Farrera, J., Valero, M. L., Virgili, A.: Self-assembly of cyclodextrins with meso-tetrakis(4-sulfonatophenyl)porphyrin in aqueous solution. Tetrahedron 51, 3705-3712 (1995).
10. Kano, K., Tanaka, N., Minamizono, H., Kawakita, Y.: Tetraarylporphyrins as probes for studying mechanism of inclusion-complex formation of cyclodextrins. Effect of microscopic environment on inclusion of ionic guests. Chem. Lett. 925-926 (1996).
11. Kano, K., Nishiyabu, R., Asada, T., Kuroda, Y.: Static and dynamic behavior of 2: 1 inclusion complexes of cyclodextrins and charged porphyrins in aqueous organic media. J. Am. Chem. Soc. 124, 9937-9944 (2002).
12. Hamai, S., Koshiyama, T.: Electronic absorption, fluorescence, and circular dichroism spectroscopic studies on the inclusion complexes of tetrakis(4-sulfonatophenyl)porphyrin with cyclodextrins in basic aqueous solutions. J. Photochem. Photobiol. A 127, 135-141 (1999).
13. Mosinger, J., Kliment Jr., V., Sejbal, J., Kubat, P., Lang, K.: Host-guest complexes of anionic porphyrin sensitizers with cyclodextrins. J. Porphyr. Phthalocyanines 6, 514-526 (2002).
14. Hamai, S., Koshiyama, T.: Inclusion complexes of Fe(III) tetrakis(4-sulfonatophenyl)porphyrin with cyclodextrins in aqueous solution. Spectrochim. Acta A 57, 985-992 (2001).
15. Benesi, H. A., Hildebrand, J. H.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703-2707 (1949).
16. Hamai, S.: Association of inclusion compounds of β-cyclodextrin in aqueous solution. Bull. Chem. Soc. Jpn. 55, 2721-2729 (1982).
17. Hamai, S., Satou, H.: Effects of cyclodextrins on the complexation between Methylene Blue and tetrakis(4-sulfonatophenyl)porphyrin in aqueous solutions. Spectrochim. Acta A 57, 1745-1750 (2001).
18. Hamai, S., Sasaki, Y., Hori, T., Takahashi, A.: Interactions of tetrakis(4-sulfonatophenyl)porphyrin with γ-cyclodextrin and alkyltrimethylammonium bromides in aqueous solutions. J. Incl. Phenom. Macrocycl. Chem. 54, 67-76 (2006).
19. Hamai, S.: Interactions of tetrakis(4-N-methylpyridyl)porphyrin with cyclodextrins and disodium phthalate in aqueous solution. J. Incl. Phenom. Macrocycl. Chem. 58, 241-247 (2007).
20. Matsui, Y., Okimoto, A.: The binding and catalytic properties of a positively charged cyclodextrin. Bull. Chem. Soc. Jpn. 51, 3030-3034 (1978).
21. Kotake, Y., Janzen, E. G.: Effect of pH and salt concentration on bimodal inclusion of a nitroxide by cyclodextrins. J. Am. Chem. Soc. 111, 7319-7323 (1989).
22. Shehatta, I.: Thermodynamics of macrocyclic compounds I. Inclusion complexes of α- and β-cyclodextrins with some nonelectrolytes in water. React. Funct. Polym. 28, 183-190 (1996).
23. Tawarah, K. M., Khouri, S. J.: Determination of the stability and stoichiometry of p-methyl red inclusion complexes with γ-cyclodextrin. Dyes Pigm. 45, 229-233 (2000).