Skip to main content
Log in

Host–guest complexation between 5-aminoisoquinoline and β-cyclodextrin and its effect on spectral and prototropic characteristics

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

The effects of the addition of β-cyclodextrin (β-CDx) on the absorption and emission properties of the 5-aminoisoquinoline (5AIQ) have been investigated in aqueous media. The formation of host–guest inclusion complex with 1:1 stoichiometry was revealed by absorption, steady state and time-resolved emission spectroscopy. The complex formation has also been confirmed by FT-IR spectra and SEM image analysis of the solid inclusion complex between 5AIQ and β-CDx. No significant change was observed in the ground and excited state pKa values in β-CDx medium. Based on photophysical and prototropic characteristics of 5AIQ in β-CDx, the structure of the 1:1 inclusion complex is proposed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Saenger, W.: Angew. Chem. Int. Ed. Engl. 19, 344 (1980)

    Article  Google Scholar 

  2. Bender, M.L., Komiyama, M.: Cyclodextrin Chemistry. New York, Springer (1978)

    Book  Google Scholar 

  3. Uekama, K., Hirayama, F.: In: Wermuth, C.G. (ed.) The Practice of Medicinal Chemistry, p. 793. Academic Press, London (1996)

    Google Scholar 

  4. Tabushi, I.: Cyclodextrin catalysis as a model for enzyme action. Acc. Chem. Res. 15, 66–72 (1982)

    Article  CAS  Google Scholar 

  5. Tabushi, I., Kuroda, Y.: Cyclodextrins and cyclophanes as enzyme models. Adv. Catal. 32, 417–466 (1983)

    Article  CAS  Google Scholar 

  6. Szejtli, J.: Cyclodextrin and Their Inclusion Complexes. Academic Kiado, Budapest (1982)

    Google Scholar 

  7. Szejtli, J.: Cyclodextrin Technology. Kluwer, Dordrecht (1988)

    Google Scholar 

  8. Ramamurthy, V., Weiss, R.G., Hammond, G.: Adv. Photochem. 18, 67 (1993)

    Article  CAS  Google Scholar 

  9. Kalyanasundaram, K.: Photochemistry in Microheterogeneous Systems. Academic Press, New York (1987)

    Google Scholar 

  10. Bortolus, P., Monti, S.: Adv. Photochem. 21, 1 (1996)

    Article  CAS  Google Scholar 

  11. Kleinman, M.H., Bohne, C.: Organic Photochemistry: Molecular and Supramolecular Photochemistry, p. 838. Marcel Dekker Inc, New York (1997)

    Google Scholar 

  12. Santra, S., Dogra, S.K.: Spectral characteristics of 2-(2′-aminoophenyl) benzimidazole in b-cyclodextrin. J. Photochem. Photobiol. A: Chem. 101, 221–227 (1996)

    Article  CAS  Google Scholar 

  13. Burai, T.N., Panda, D., Datta, A.: Fluorescence enhancement of epicocconone in its complexes with cyclodextrins. Chem. Phys. Lett. 455, 42–46 (2008)

    Article  CAS  Google Scholar 

  14. Sainz-Rozas, P.R., Isai, J.R., Sanchez, M., Tardajos, G., Gonzelez-Gaitano, G.: Effects of natural cyclodextrins on the photophysical properties of dibenzofuron-2-carboxylic acid. J. Phys. Chem. A 108, 392–402 (2004)

    Article  CAS  Google Scholar 

  15. Armarego, W.L.F.: Fused Pyrimidines: Part I-Quinazolines. Interscience, New York (1967)

    Google Scholar 

  16. Kametani, T., Fukumoto, K.: Isoquinolines Part 1, vol. 38. John Wiley, New York (1981)

    Google Scholar 

  17. Fry, D.W., Kraker, A.J., McMichael, A., Ambroso, L.A., Nelson, J.M., Leopold, W.R., Connors, R.W., Bridges, A.J.: A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 265, 1093–1095 (1994)

    Article  CAS  Google Scholar 

  18. Traxler, T.M., Furet, P., Melt, H., Buchdunger, E., Meyer, T., Lydon, N.: 4-(Phenylamino)pyrrolopyrimidines: # potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase. J. Med. Chem. 39, 2285–2292 (1996)

    Article  CAS  Google Scholar 

  19. Hynes, J.B., Tomazić, A., Kumar, A., Kumar, V., Freisheim, J.H.: Inhibition of human dihydrofolate reductase by 2,4-diaminoquinazolines bearing simple substituents on the aromatic ring. J. Heterocycl. Chem. 28, 1981–1986 (1991)

    Article  CAS  Google Scholar 

  20. Harris, N.V., Smith, C., Bowden, K.: Antifolate and antibacterial activities of 5-substituted 2, 4-diaminoquinazolines. J. Med. Chem. 33, 433–444 (1990)

    Article  Google Scholar 

  21. Dempcy, R.O., Skibo, E.B.: Rational design of quinazoline-based irreversible inhibitors of human erythrocyte purine nucleoside phosphorylase. Biochemistry 30, 8480–8487 (1991)

    Article  CAS  Google Scholar 

  22. Neumeyer, J.L., Weinhardt, K.K., Carrano, R.A., McCurdy, D.H.: Isoquinolines. 3. 3-Aminoisoquinoline derivatives with central nervous system depessant activity. J. Med. Chem. 16, 808–813 (1973)

    Article  CAS  Google Scholar 

  23. Shun-li, W., Tze-wei, Y., Tong-Ing, H.: Photophysics and excited-state proton transfer of 2′-hydroxy-2-trans-styrylquinoline. Chem. Phys. Lett. 418, 397–401 (2006)

    Article  Google Scholar 

  24. Dey, J.K., Dogra, S.K.: Dual fluorescence of 2-[4-(Dimethylamino)phenyl]benzothiazole and its benzimidazole analog: effect of solvent and pH on electronic spectra. J. Phys. Chem. 98, 3638–3644 (1994)

    Article  CAS  Google Scholar 

  25. Kothai Nayaki, S., Swaminathan, M.: A study of solvatochromism and proton transfer kinetics of 2, 2′-dihydroxybiphenyl. J. Photochem. Photobiol. A.: Chem. 102, 217–221 (1997)

    Article  CAS  Google Scholar 

  26. Kothai Nayaki, S., Swaminathan, M.: Unusual luminescence characteristics of aminobiphenyls. Spectrochim. Acta A 58, 2931–2940 (2002)

    Article  CAS  Google Scholar 

  27. Sivakumar, P., Kothai Nayaki, S., Swaminathan, M.: Photophysical behaviour of 2, 6-diaminoanthraquinone in different solvents and at various pH. Spectrochim Acta 68, 651–655 (2007)

    Article  CAS  Google Scholar 

  28. Enoch, I.M.V., Swaminathan, M.: Fluorimetric and prototropic studies on the inclusion complexation of 2-amino and 4-aminodiphenyl ethers with β-cyclodextrin: Unusual behavior of 4-aminodiphenyl ether. J. Lumin. 127, 713–720 (2007)

    Article  CAS  Google Scholar 

  29. Rajamohan, R., Kothai Nayaki, S., Swaminathan, M.: Inclusion complexation and photoprototropic behaviour of 3-amino-5-nitrobenzisothiazole with β-cyclodextrin. Spectrochim. Acta A 69, 371–377 (2008)

    Article  CAS  Google Scholar 

  30. Rajamohan, R., Kothai Nayaki, S., Swaminathan, M.: Spectrofluorimetric study on inclusion complexation of 2-amino-6-fluorobenzothiazole with β-cyclodextrin. Collect. Czech. Chem. Commun. 73, 147–160 (2008)

    Article  CAS  Google Scholar 

  31. Jorgenson, M.J., Hartter, D.A.: A critical re-evaluation of the hammett acidity function at moderate and high acid concentrations of sulfuric acid. New H 0 values based solely on a set of primary aniline indicators. J. Am. Chem. Soc. 85, 878–883 (1963)

    Article  CAS  Google Scholar 

  32. 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)

    Article  CAS  Google Scholar 

  33. Cho, D.W., Kim, Y.H., Yoon, M., Kang, S.G., Kim, D.: Cyclodextrin effects on intramolecular charge transfer of 2-biphenylcarboxylic acid: a pre-twisted molecule. J. Chem. Soc. Faraday Trans. 92, 29–33 (1996)

    Article  CAS  Google Scholar 

  34. Lasser, N., Feitelson, J.: Excited state pK values from fluorescence measurements. J. Phys. Chem. 70, 1011–1016 (1973)

    Article  Google Scholar 

  35. Hoshino, M., Imamura, M., Ikehara, K., Hamai, Y.: Fluorescence enhancement of benzene derivatives by forming inclusion complexes with beta.-cyclodextrin in aqueous solutions. J. Phys. Chem. 85, 1820–1823 (1981)

    Article  CAS  Google Scholar 

  36. Al-Hassan, K.A., Klein, V.K.A., Sawaiyan, A.: Normal and twisted intramolecular charge-transfer fluorescence of 4-dimethylaminobenzonitrile in α-cyclodextrine cavities. Chem. Phys. Lett. 212, 581–587 (1993)

    Article  CAS  Google Scholar 

  37. Monti, S., Kohler, G., Grabner, G.: Photophysics and photochemistry of methylated phenols in beta.-cyclodextrin inclusion complexes. J. Phys. Chem. 97, 13011–13016 (1993)

    Article  CAS  Google Scholar 

  38. Nayak, M.K., Dogra, S.K.: Photophysics of 1-hydroxy-9-fluorenone: absence of excited state intramolecular proton transfer reaction. J. Photochem. Photobiol. A 169, 79–88 (2005)

    Article  CAS  Google Scholar 

Download references

Acknowledgement

We are grateful to the National Centre for Ultrafast Processes, University of Madras, Chennai, for the assistance in the measurements of the fluorescence lifetimes.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Meenakshisundaram Swaminathan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rajamohan, R., Kothai Nayaki, S. & Swaminathan, M. Host–guest complexation between 5-aminoisoquinoline and β-cyclodextrin and its effect on spectral and prototropic characteristics. J Incl Phenom Macrocycl Chem 73, 99–108 (2012). https://doi.org/10.1007/s10847-011-0025-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-011-0025-4

Keywords

Navigation