Influence of Polyvinylpyrrolidone K30 on The Complexation of Tetrahydrocurcumin with Hydroxypropyl β-Cyclodextrin

Srikanya Thongyai; Nattha Kaewnopparat; Sarunyoo Songkro

Authors

Srikanya Thongyai Student in Master degree, Cosmetic Sciences, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla, Thailand, 90112.
Nattha Kaewnopparat Associate Professor, Drug Delivery System Excellence Center, Faculty of Pharmaceutical Sciences, Prince of Songkla University. Hat-Yai, Songkhla, Thailand, 90112.
Sarunyoo Songkro Assistant Professor, Drug Delivery System Excellence Center, Faculty of Pharmaceutical Sciences, Prince of Songkla University. Hat-Yai, Songkhla, Thailand, 90112.

Keywords:

Tetrahydrocurcumin, Hydroxypropyl β-cyclodextrin, polyvinylpyrrolidone K30,, Complexation, Solubility

Abstract

Tetrahydrocurcumin (THC) is a polyphenolic compound which exhibits strong antioxidant and tyrosinase inhibition activities. The use of THC in cosmetic or pharmaceutical formulations is limited because THC is slightly soluble in water. Ternary complexes consist of drug-cyclodextrin and polymer as ternary component can enhance drug solubility. The objective of this present study was to evaluate the potential synergistic effect of a ternary component, polyvinylpyrrolidone K30 (PVP K30), on the solubility and physicochemical properties of THC-hydroxypropyl β-cyclodextrin (HPβCD) inclusion complex. Phase solubility analysis was used to investigate the interaction of THC in both binary (THC-HPβCD) and ternary systems (THC-HPβCD-PVP K30). The phase solubility curves were classified as A_L-type with indicated a stoichiometry of 1:1 molar ratio between THC and HPβCD. By adding the PVP K30 (ternary system), the stability constant was enhanced. The binary and ternary inclusion complexes in 1:1 molar ratio were prepared by kneading and coevaporation methods. The solubility of THC from both systems was determined and the physicochemical properties were characterized by Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC) and powder X-ray diffractometry (PXRD) compared with pure THC and their corresponding physical mixtures. The results revealed that the solubility of THC in ternary systems was significantly greater than binary complexes, physical mixtures and pure THC. Ternary inclusion complex prepared by coevaporation method was found to be most effective in increasing the THC solubility. From FTIR, DSC and PXRD studies, the binary and ternary coevaporated samples gave THC in amorphous state and stronger complex formation than that of kneaded samples and physical mixtures.

References

Chowdary, K. P. R., & Srinivas, S. V. (2006). Influence of hydrophilic polymers on celecoxib complexation with hydroxypropyl beta-cyclodextrin. AAPS PharmSciTech, 7, 79.

Dos Santos, C., Buera, M. del P., & Mazzobre, M. F. (2011). Phase solubility studies of terpineol with β-cyclodextrins and stability of the freeze-dried inclusion complex. Procedia Food Science, 1, 355–362.

Higuchi, T., & Connors, K.A. (1965). Phase Solubility Techniques. Advances in Analytical Chemistry and Instrumentation, 4, 117-212.

Hirlekar, R. S., Sonawane, S. N., & Kadam, V. J. (2009). Studies on the Effect of Water-Soluble Polymers on Drug–Cyclodextrin Complex Solubility. AAPS PharmSciTech, 10, 858–863.

Jullian, C., Morales-Montecinos, J., Zapata-Torres, G., Aguilera, B., Rodriguez, J., Arán, V., & Olea-Azar, C. (2008). Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins. Bioorganic & Medicinal Chemistry, 16, 5078–5084.

Khopde, S. M., Priyadarsini, K. I., Guha, S. N., Satav, J. G., Venkatesan, P., & Rao, M. N. (2000). Inhibition of radiation-induced lipid peroxidation by tetrahydrocurcumin: possible mechanisms by pulse radiolysis. Bioscience, Biotechnology, and Biochemistry, 64, 503–509.

Lavecchia, R., & Zuorro, A. (2009). Experimental study of the inclusion of triclosan in hydroxypropyl-β-cyclodextrins. Chemical Engineering Transactions, 17, 1083–1087.

Nakamura, Y., Ohto, Y., Murakami, A., Osawa, T., & Ohigashi, H. (1998). Inhibitory effects of curcumin and tetrahydrocurcuminoids on the tumor promoter-induced reactive oxygen species generation in leukocytes in vitro and in vivo. Japanese Journal of Cancer Research, 89, 361–370.

Okada, K., Wangpoengtrakul, C., Tanaka, T., Toyokuni, S., Uchida, K., & Osawa, T. (2001). Curcumin and especially tetrahydrocurcumin ameliorate oxidative stress-induced renal injury in mice. The Journal of Nutrition, 131, 2090–2095.

Pan, M. H., Huang, T. M., & Lin, J. K. (1998). Biotransformation of curcumin through reduction and glucuronidation in mice. The American Society for Pharmacology and Experimental Therapeutics, 27, 486-494.

Patel, A. R., & Vavia, P. R. (2006). Effect of hydrophilic polymer on solubilization of fenofibrate by cyclodextrin complexation. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 56, 247–251.

Sammour, O. A., Hammad, M. A., Megrab, N. A., & Zidan, A. S. (2006). Formulation and optimization of mouth dissolve tablets containing rofecoxib solid dispersion. AAPS PharmSciTech, 7, E1-E9.

Sapkal, N. P., Kilor, V. A., Shewale, B. D., Bhusari, K. P., & Daud, A. S. (2010). Study of the Complexation Behaviour of Fexofenadine with β-Cyclodextrin. Indian J Pharm Sci, 72, 318–323.

Savolainen, J., Järvinen, K., Taipale, H., Jarho, P., Loftsson, T., & Järvinen, T. (1998). Co-administration of a water-soluble polymer increases the usefulness of cyclodextrins in solid oral dosage forms. Pharmaceutical Research, 15, 1696–1701.