title: The Comparative Studies of Binding Activity of Curcumin and Didemethylated Curcumin with Selenite: Hydrogen Bonding vs Acid-Base Interactions.
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/SeO3(2-) and DCCM/SeO3(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.
authors.affiliation: Institute of Biological Chemistry, Academia Sinica, Taipei 11529, Taiwan.
authors.forename: Jiahn-Haur
authors.initials: JH
authors.lastname: Liao
authors.affiliation: Department of Clinical Pharmacy, School of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan.
authors.forename: Tzu-Hua
authors.initials: TH
authors.lastname: Wu
authors.affiliation: General Education Center, National Taipei University of Nursing and Health Sciences, Taipei, Taiwan.
authors.forename: Ming-Yi
authors.initials: MY
authors.lastname: Chen
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan 701 Taiwan.
authors.forename: Wei-Ting
authors.initials: WT
authors.lastname: Chen
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan 701 Taiwan.
authors.forename: Shou-Yun
authors.initials: SY
authors.lastname: Lu
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan 701 Taiwan.
authors.forename: Yi-Hsuan
authors.initials: YH
authors.lastname: Wang
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan 701 Taiwan.
authors.forename: Shao-Pin
authors.initials: SP
authors.lastname: Wang
authors.affiliation: Institute of Biochemical Sciences, National Taiwan University, Taipei 10617, Taiwan.
authors.forename: Yen-Min
authors.initials: YM
authors.lastname: Hsu
authors.affiliation: Institute of Biological Chemistry, Academia Sinica, Taipei 11529, Taiwan.|Department of Clinical Pharmacy, School of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan.
authors.forename: Yi-Shiang
authors.initials: YS
authors.lastname: Huang
authors.affiliation: Institute of Biochemical Sciences, National Taiwan University, Taipei 10617, Taiwan.
authors.forename: Zih-You
authors.initials: ZY
authors.lastname: Huang
authors.affiliation: Institute of Biological Chemistry, Academia Sinica, Taipei 11529, Taiwan.
authors.forename: Yu-Ching
authors.initials: YC
authors.lastname: Lin
authors.affiliation: Institute of Biochemical Sciences, National Taiwan University, Taipei 10617, Taiwan.
authors.forename: Ching-Ming
authors.initials: CM
authors.lastname: Chang
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan 701 Taiwan.
authors.forename: Fu-Yung
authors.initials: FY
authors.lastname: Huang
authors.affiliation: Institute of Biological Chemistry, Academia Sinica, Taipei 11529, Taiwan.|Institute of Biochemical Sciences, National Taiwan University, Taipei 10617, Taiwan.
authors.forename: Shih-Hsiung
authors.initials: SH
authors.lastname: Wu
mesh_terms: D000143:Acids / Q000737:chemistry; D002386:Cataract / Q000188:drug therapy / Q000378:metabolism; D003459:Crystallins / Q000737:chemistry* / Q000378:metabolism; D003474:Curcumin / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D006860:Hydrogen Bonding / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D066329:Protein Aggregates / Q000187:drug effects*; D020887:Selenious Acid / Q000737:chemistry / Q000633:toxicity*
chemical_list: D000143:Acids; D003459:Crystallins; D066329:Protein Aggregates; D020887:Selenious Acid; D003474:Curcumin