Skip to main content
SpringerLink
Log in

A study on the potential interaction between cyclodextrin and lipoxygenase

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

Abstract

To get a more complete view on the lipoxygenase (LOX) catalysis in presence of cyclodextrin, the investigation into the interaction between cyclodextrins (CDs) and LOX was carried out. Effects of cyclodextrins on the activity and structure of LOX were explored in this work. It is confirmed that inhibition effect induced by complexation of CDs and LOX plays a leading role in inhibition factors of LOX catalysis in presence of CDs. Inhibition of β-cyclodextrin on LOX depended on concentration and tended to be intensified with the increase of β-CD. The enhancement of intrinsic fluorescence of LOX induced by β-CD was detected, which was probably due to the formation of complexes between aromatic amino acid residues of LOX and β-CD. The results of circular dichroism assay indicated that β-CD altered the secondary structure and microenvironment of LOX which was responsible for inhibition of enzyme catalysis.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Martin Del Valle, E.M.M.: Cyclodextrins and their uses: a review. Process. Biochem. 39, 1033–1046 (2004)

    Article  Google Scholar 

  2. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1752 (1998)

    Article  CAS  Google Scholar 

  3. Giani A. L.: The use of 2D NMR to study β-cyclodextrin complexation and debittering of amino acids and peptides. Food. Res. Int. 43(1), 187–192 (2010)

    Article  Google Scholar 

  4. J. M. López-Nicolás, Bru, R., García-Carmona, F.: Kinetic characteristics of the enzymatic conversion in presence of cyclodextrins: study of the oxidation of polyunsaturated fatty acids by lipoxygenase. Biochim. Biophys. Acta. 1347, 140–150 (1997)

    Google Scholar 

  5. K. Guzow, W. Wiczk.: Interactions of cyclodextrins with amino acids, peptides and proteins. In: Fitzpatrick, D.W., Ulrich, H.J. (eds.) Macrocyclic Chemistry: New Research Developments, pp. 233–262. Nova Science Publishers, Inc., New York (2010)

  6. Sharma, L., Sharma, A.: Influence of cyclodextrin ring substituents on folding-related aggregation of bovine carbonic anhydrase. Eur. J. Biochem. 268(8), 2456–2463 (2001)

    Article  CAS  Google Scholar 

  7. Yu, B., Tian, Y., Yang, N., Xu, X., Jin, Z.: A study on the inhibition mechanism of β-cyclodextrin on pullulanase. J. Incl. Phenom. Macrocycl. Chem. 70, 161–165 (2011)

    Article  CAS  Google Scholar 

  8. Yu, B., Wang, J., Zhang, H., Jin, Z.: Investigation of matching effect between hydrophobic cavities of cyclodextrins and pullulanase. Molecules 16(4), 3010–3017 (2011)

    Article  CAS  Google Scholar 

  9. Samra, H.S., He, F., Bhambhani, A., Pipkin, J.D., Zimmerer, R., Joshi, S.B., Middaugh, C.R.: The effects of substituted cyclodextrins on the colloidal and conformational stability of selected proteins. J. Pharm. Sci. 99(6), 2800–2818 (2010)

    CAS  Google Scholar 

  10. Serno, T., Geidobler, R., Winter, G.: Protein stabilization by cyclodextrins in the liquid and dried state. Adv. Drug. Deliv. Rev. 63(13), 1086–1106 (2011)

    Article  CAS  Google Scholar 

  11. Aachmann, F.L., Otzen, D.E., Larsen, K.L., Wimmer, R.: Structural background of cyclodextrin-protein interactions. Protein. Eng. 16(12), 905–912 (2003)

    Article  CAS  Google Scholar 

  12. Lula, I., de Sousa, F.B., Denadai, A.M.L., Ianzer, D., de Camargo, A.C.M., Santos, R.A.S., Sinisterra, R.D.: Study of the BPP7a peptide and its β-cyclodextrin complex: physicochemical characterization and complete sequence specific NMR assignments. J. Braz. Chem. Soc. 22(9), 1765–1773 (2011)

    Article  CAS  Google Scholar 

  13. Kanegae, H., Morii, H., Harata, K.: Design and synthesis of cyclodextrin-peptide conjugates and their characterization. Pept. Chem. 34, 477–480 (1996)

    Google Scholar 

  14. Gere-Paszti, E., Cserhati, T., Forgacs, E., Deyl, Z., Miksik, I., Eckhardt, A., Illes, Z.: Interaction of hydroxypropyl-β-cyclodextrin with peptides, studied by reversed-phase thin-layer chromatography. J. Liq. Chromatogr. Relat. Technol. 28(16), 2619–2632 (2005)

    Article  CAS  Google Scholar 

  15. Ignash, M., Ong, L., Freel, K., Chai, M.: (2005) NMR investigation on the interaction of cyclodextrin and amino acids. In: Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, March 13–17

  16. Ciesielski, W., Kapusniak, J.: Interactions of amino acids with β-cyclodextrin and with potato starch studied by thermogravimetric measurements. J. Incl. Phenom. Macrocycl. Chem. 64(1–2), 109–114 (2009)

    Article  CAS  Google Scholar 

  17. Shanmugam, M., Ramesh, D., Nagalakshmi, V., Kavitha, R., Rajamohan, R., Stalin, T.: Host–guest interaction of l-tyrosine with β-cyclodextrin. Mol. Biomol. Spectrosc. 71A(1), 125–132 (2008)

    Article  CAS  Google Scholar 

  18. Bikadi, Z., Ivanyi, R., Szente, L., Ilisz, I., Hazai, E.: Cyclodextrin complexes: chiral recognition and complexation behavior. Curr. Drug. Discov. Technol. 4(4), 282–294 (2007)

    Article  CAS  Google Scholar 

  19. Hashidzume, A., Harada, A.: Macromolecular recognition by cyclodextrins. Interaction of cyclodextrins with polymethacrylamides bearing hydrophobic amino acid residues. Polymer 47(10), 3448–3454 (2006)

    Article  CAS  Google Scholar 

  20. Lakowicz, J.R.: Principles of Fluorescence Spectroscopy, 3rd edn. Kluwer/Publishers, New York (2008)

    Google Scholar 

  21. Burstein, E.A., Vedenkina, N.S., Ivkova, M.N.: Fluorescence and the location of tryptophan residues in protein molecules. Photochem. Photobiol. 18, 263–279 (1973)

    Article  CAS  Google Scholar 

  22. Li, S.: Cyclodextrins and their applications in analytical chemistry. Chem. Rev. 92, 1457–1470 (1992)

    Article  CAS  Google Scholar 

  23. Ivanov, I., Heydeck, D., Hofheinz, K., Roffeis, J.: Molecular enzymology of lipoxygenases. Arch. Biochem. Biophys. 503, 161–174 (2010)

    Article  CAS  Google Scholar 

  24. Spaapen, L.J.M., Veldink, G.A., Liefkens, T.J., Vliegenthart, J.F.G., Kay, C.M.: Circular dichroism of lipoxygenase-1 from soybeans. Biochim. Biophys. Acta 574, 301–311 (1979)

    Article  CAS  Google Scholar 

  25. Ludwig, P., Tordi, M.G., Colosimo, A.: Circular dichroism observations on the lipoxygenase from reticulocytes. Biochem. Biophys. Acta 830, 136–139 (1985)

    Article  CAS  Google Scholar 

  26. Provencher, S.W., Glockner, J.: Estimation of globular protein secondary structure from circular dichroism. Biochemistry 20, 33–37 (1981)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the financial support provide by “Twelfth Five-Year” National Plan Project for Science and Technology Support (No. JUDCF10051) and the Fundamental Research Funds for the Central Universities (No. JUSRP111A30). This study was also supported by National Natural Science Foundation of China (No. 20976070 and 31071490), Nature Science Foundation of Jiangsu Province (No. BK2009069) and Scientific Research Foundation of Jiangnan University for Ph.D. Students (No. JUDCF10051).

Author information

Authors and Affiliations

  1. The State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, Wuxi, 214122, China

    Yixuan Li, Jinpeng Wang, Aiquan Jiao, Xueming Xu & Zhengyu Jin

Authors
  1. Yixuan Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jinpeng Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Aiquan Jiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xueming Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhengyu Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhengyu Jin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Li, Y., Wang, J., Jiao, A. et al. A study on the potential interaction between cyclodextrin and lipoxygenase. J Incl Phenom Macrocycl Chem 76, 107–111 (2013). https://doi.org/10.1007/s10847-012-0178-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-012-0178-9

Keywords

Search

Navigation