The Comparative Studies of Binding Activity of Curcumin and Didemethylated Curcumin with Selenite: Hydrogen Bonding vs Acid-Base Interactions

Jiahn Haur Liao, Tzu Hua Wu, Ming Yi Chen, Wei Ting Chen, Shou Yun Lu, Yi Hsuan Wang, Shao Pin Wang, Yen Min Hsu, Yi Shiang Huang, Zih You Huang, Yu Ching Lin, Ching Ming Chang, Fu Yung Huang, Shih Hsiung Wu

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Abstract

In this report, the in vitro relative capabilities of curcumin (CCM) and didemethylated curcumin (DCCM) in preventing the selenite-induced crystallin aggregation were investigated by turbidity tests and isothermal titration calorimetry (ITC). DCCM showed better activity than CCM. The conformers of CCM/SeO 3 2- and DCCM/SeO 3 2- complexes were optimized by molecular orbital calculations. Results reveal that the selenite anion surrounded by CCM through the H-bonding between CCM and selenite, which is also observed via IR and NMR studied. For DCCM, the primary driving force is the formation of an acid-base adduct with selenite showing that the phenolic OH group of DCCM was responsible for forming major conformer of DCCM. The formation mechanisms of selenite complexes with CCM or DCCM explain why DCCM has greater activity than CCM in extenuating the toxicity of selenite as to prevent selenite-induced lens protein aggregation.

Original languageEnglish
Article number17614
JournalScientific Reports
Volume5
DOIs
Publication statusPublished - Dec 4 2015

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Liao, J. H., Wu, T. H., Chen, M. Y., Chen, W. T., Lu, S. Y., Wang, Y. H., Wang, S. P., Hsu, Y. M., Huang, Y. S., Huang, Z. Y., Lin, Y. C., Chang, C. M., Huang, F. Y., & Wu, S. H. (2015). The Comparative Studies of Binding Activity of Curcumin and Didemethylated Curcumin with Selenite: Hydrogen Bonding vs Acid-Base Interactions. Scientific Reports, 5, [17614]. https://doi.org/10.1038/srep17614