Skip to main content
Log in

Photostability of water-soluble inclusion complexes of UV-filters and curcumin with gamma-cyclodextrin polymer

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

Abstract

The water-soluble inclusion complexes of curcumin, 2-ethylhexyl-4-methoxycinnamate (EHMC) and 4-tert-butyl-4′-methoxydibenzoylmethane (DBM) with gamma-cyclodextrin polymer (pyCD) were successfully prepared and characterized by 1H-NMR, IR and UV–Vis spectroscopies. The water-solubility of EHMC–pyCD, DBM–pyCD and curcumin–pyCD was dramatically increased because of the water-soluble pyCD. The mole ratio of gamma-CD in pyCD to EHMC, DBM and curcumin were carried out as 1:1. The photostability of all inclusion complexes was investigated in water and ethylene glycol and compared with free active ingredients. It was found that the photostability of EHMC–pyCD was greatly enhanced whereas those of DBM–pyCD and curcumin–pyCD in water were decreased due to the acceleration of the photodegradation reaction inside the gamma-CD cavity. These results were able to be used as a solubilizer for cosmetic and also pharmaceutical applications.

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

Similar content being viewed by others

References

  1. Agar, N.S., Halliday, G.M., Barnetson, R.S., Ananthaswamy, H.N., Wheeler, M., Jones, A.M.: The basal layer in human squamous tumors harbors more UVA than UVB fingerprint mutations: a role for UVA in human skin carcinogenesis. Proc. Natl Acad. Sci. U. S. A. 101, 4954–4959 (2004)

    Article  CAS  Google Scholar 

  2. Matsumura, Y., Ananthaswamy, H.N.: Toxic effects of ultraviolet radiation on the skin. Toxicol. Appl. Pharmacol. 195, 298–308 (2004)

    Article  CAS  Google Scholar 

  3. Kockler, J., Oelgemöller, M., Robertson, S., Glass, B.D.: Photostability of sunscreens.  J. Photochem. Photobiol. C Photochem. Rev. 13, 91–110 (2012)

    Article  CAS  Google Scholar 

  4. Pattanaargson, S., Munhapol, T., Hirunsuphachot, P., Limpong, P.: Photoisomerization of octyl methoxycinnamate.  J. Photochem. Photobiol. A Chem. 161, 269–274 (2004)

    Article  CAS  Google Scholar 

  5. Mturi, G.J., Martincigh, B.S.: Photostability of the sunscreening agent 4-tert-butyl-4′-methoxydibenzoylmethane (avobenzone) in solvents of different polarity and proticity. J. Photochem. Photobiol. A Chem. 200, 410–420 (2008)

    Article  CAS  Google Scholar 

  6. Kockler, J., Motti, C., Robertson, S., Oelgemöller, M., Glass, B.D.: HPLC Method for the Simultaneous Determination of the UV-Filters Butyl Methoxy Dibenzoylmethane and Octocrylene in the Presence of Their Photodegradants. Chromatographia. 76, 1721–1727 (2013)

    Article  CAS  Google Scholar 

  7. Wang, Y.J., Pan, M.H., Cheng, A.L., Lin, L.I., Ho, Y.S., Hsieh, C.Y., Lin, J.K.: Stability of curcumin in buffer solutions and characterization of its degradation products. J. Pharm. Biomed. Anal. 15, 1867-1876 (1997)

    Article  CAS  Google Scholar 

  8. Jahed, V., Zarrabi, A., Bordbar, A., Hafezi, M.S.: NMR (1H, ROESY) spectroscopic and molecular modelling investigations of supramolecular complex of β-cyclodextrin and curcumin. Food Chem. 165, 241–246 (2014)

    Article  CAS  Google Scholar 

  9. Ammala, A.: Biodegradable polymers as encapsulation materials for cosmetics and personal care markets, Int. J. Cosmet. Sci. 35, 113–124 (2013)

    Article  CAS  Google Scholar 

  10. Yallapu, M.M., Jaggi, M., Chauhan, S.C.: β-Cyclodextrin-curcumin self-assembly enhances curcumin delivery in prostate cancer cells. Colloids Surfaces B Biointerfaces. 79, 113–125 (2010)

    Article  CAS  Google Scholar 

  11. Kurkov, S. V., Loftsson, T.: Cyclodextrins. Int. J. Pharm. 453, 167–180 (2013)

    Article  CAS  Google Scholar 

  12. Anand, R., Manoli, F., Manet, I., Daoud-Mahammed, S., Agostoni, V., Gref, R., Monti, S.: β-Cyclodextrin polymer nanoparticles as carriers for doxorubicin and artemisinin: a spectroscopic and photophysical study. Photochem. Photobiol. Sci. 11, 1285-1292 (2012)

    Article  CAS  Google Scholar 

  13. Scalia, S., Simeoni, S., Barbieri, A., Sostero, S.: Influence of hydroxypropyl-β-cyclodextrin on photo-induced free radical production by the sunscreen agent, butyl-methoxydibenzoylmethane. J. Pharm. Pharmacol. 54,1553–1558 (2002)

    Article  CAS  Google Scholar 

  14. Suwannateep, N., Banlunara, W., Wanichwecharungruang, S.P., Chiablaem, K., Lirdprapamongkol, K., Svasti, J.: Mucoadhesive curcumin nanospheres: Biological activity, adhesion to stomach mucosa and release of curcumin into the circulation. J. Control. Release. 151, 176–182 (2011)

    Article  CAS  Google Scholar 

  15. Scalia, S., Casolari, A., Iaconinoto, A., Simeoni, S.: Comparative studies of the influence of cyclodextrins on the stability of the sunscreen agent, 2-ethylhexyl-p-methoxycinnamate.  J. Pharm. Biomed. Anal. 30, 1181–1189 (2002)

    Article  CAS  Google Scholar 

  16. Liu, Y., Chen, G.-S., Chen, Y., Ding, F., Chen, J.: Cyclodextrins as carriers for cinchona alkaloids: a pH-responsive selective binding system. Org. Biomol. Chem. 3, 2519–23 (2005)

    Article  CAS  Google Scholar 

  17. Ciobanu, a., Mallard, I., Landy, D., Brabie, G., Nistor, D.: Fourmentin, S. Fourmentin, Inclusion interactions of cyclodextrins and crosslinked cyclodextrin polymers with linalool and camphor in Lavandula angustifolia essential oil. Carbohydr. Polym. 87, 1963–1970 (2012)

    Article  CAS  Google Scholar 

  18. Renard, E., Deratani, a., Volet, G., Sebille, B.: Preparation and characterization of water soluble high molecular weight β-cyclodextrin-epichlorohydrin polymers. Eur. Polym. J. 33, 49–57 (1997)

    Article  CAS  Google Scholar 

  19. Zhang, W., Gong, X., Cai, Y., Zhang, C., Yu, X., Fan, J., Diao, G.: Investigation of water-soluble inclusion complex of hypericin with β-cyclodextrin polymer, Carbohydr. Polym. 95, 366–370 (2013)

    Article  CAS  Google Scholar 

  20. Wintgens, V., Amiel, C.: Water-soluble γ-cyclodextrin polymers with high molecular weight and their complex forming properties. Eur. Polym. J. 46, 1915–1922 (2010)

    Article  CAS  Google Scholar 

  21. Higuchi, T., Connors, K.A.: Phase-solubility techniques. Adv. Anal. Chem. Instrum. 4, 117–212 (1965)

    CAS  Google Scholar 

  22. Patro, N.M., Sultana, A., Terao, K., Nakata, D., Jo, A., Urano, A., Ishida, Y., Gorantla, R.N., Pandit, V., Devi, K., Rohit, S., Grewal, B.K., Sophia, E.M., Suresh, A., Ekbote, V.K., Suresh, S.: Comparison and correlation of in vitro, in vivo and in silico evaluations of alpha, beta and gamma cyclodextrin complexes of curcumin. J. Incl. Phenom. Macrocycl. Chem. 78, 471–483 (2014)

    Article  CAS  Google Scholar 

  23. Fenyvesi, É., Otta, K., Kolbe, I., Novák, C., Szejtli, J.: Cyclodextrin Complexes of UV Filters.  J. Incl. Phenom. Macrocycl. Chem. 48, 117–123 (2004)

    Article  CAS  Google Scholar 

  24. Tønnesen, H.H., Másson, M., Loftsson, T.: Studies of curcumin and curcuminoids. XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability. Int. J. Pharm. 244, 127–135 (2002)

    Article  Google Scholar 

  25. Yamaji, M., Kida, M.: Photothermal tautomerization of a UV sunscreen (4-tert-butyl-4′-methoxydibenzoylmethane) in acetonitrile studied by steady-state and laser flash photolysis. J. Phys. Chem. A 117, 1946–1951 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledged the financial support from Kasetsart University Research and Development Institute (KURDI-10.57) and the Faculty of Science, Kasetsart University (URMF).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Thitinun Karpkird.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 584 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karpkird, T., Khunsakorn, R., Noptheeranuphap, C. et al. Photostability of water-soluble inclusion complexes of UV-filters and curcumin with gamma-cyclodextrin polymer. J Incl Phenom Macrocycl Chem 84, 121–128 (2016). https://doi.org/10.1007/s10847-015-0589-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-015-0589-5

Keywords

Navigation