The Comparative Studies of Binding Activity of Curcumin and Didemethylated Curcumin with Selenite: Hydrogen Bonding vs Acid-Base Interactions
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 C...
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| Veröffentlicht in: | Scientific reports 2015-12, Vol.5 (1), p.17614, Article 17614 |
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| creator | Liao, Jiahn-Haur Wu, Tzu-Hua Chen, Ming-Yi Chen, Wei-Ting Lu, Shou-Yun Wang, Yi-Hsuan Wang, Shao-Pin Hsu, Yen-Min Huang, Yi-Shiang Huang, Zih-You Lin, Yu-Ching Chang, Ching-Ming Huang, Fu-Yung Wu, Shih-Hsiung |
| description | 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. |
| doi_str_mv | 10.1038/srep17614 |
| format | Article |
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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.</description><identifier>ISSN: 2045-2322</identifier><identifier>EISSN: 2045-2322</identifier><identifier>DOI: 10.1038/srep17614</identifier><identifier>PMID: 26635113</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>119/118 ; 140/131 ; 639/638/309/606 ; 639/638/563/606 ; Acids - chemistry ; Calorimetry ; Cancer ; Cataract - drug therapy ; Cataract - metabolism ; Cataracts ; Chemistry ; Comparative studies ; Crystallin ; Crystallins - chemistry ; Crystallins - metabolism ; Curcumin ; Curcumin - chemistry ; Curcumin - pharmacology ; Disease prevention ; Experiments ; Humanities and Social Sciences ; Humans ; Hydrogen bonding ; Hydrogen Bonding - drug effects ; Magnetic Resonance Spectroscopy ; multidisciplinary ; Pharmacy ; Phenolic compounds ; Phenols ; Protein Aggregates - drug effects ; Protein interaction ; Quantum physics ; Science ; Selenious Acid - chemistry ; Selenious Acid - toxicity ; Selenite ; Selenium ; Titration ; Toxicity ; Turbidity</subject><ispartof>Scientific reports, 2015-12, Vol.5 (1), p.17614, Article 17614</ispartof><rights>The Author(s) 2015</rights><rights>Copyright Nature Publishing Group Dec 2015</rights><rights>Copyright © 2015, Macmillan Publishers Limited 2015 Macmillan Publishers Limited</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-a8c299ecf9ca0b547fb26d90ff5ff7087edc759dca865636db8976fda8b324423</citedby><cites>FETCH-LOGICAL-c438t-a8c299ecf9ca0b547fb26d90ff5ff7087edc759dca865636db8976fda8b324423</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4669449/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4669449/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27903,27904,41099,42168,51554,53769,53771</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26635113$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liao, Jiahn-Haur</creatorcontrib><creatorcontrib>Wu, Tzu-Hua</creatorcontrib><creatorcontrib>Chen, Ming-Yi</creatorcontrib><creatorcontrib>Chen, Wei-Ting</creatorcontrib><creatorcontrib>Lu, Shou-Yun</creatorcontrib><creatorcontrib>Wang, Yi-Hsuan</creatorcontrib><creatorcontrib>Wang, Shao-Pin</creatorcontrib><creatorcontrib>Hsu, Yen-Min</creatorcontrib><creatorcontrib>Huang, Yi-Shiang</creatorcontrib><creatorcontrib>Huang, Zih-You</creatorcontrib><creatorcontrib>Lin, Yu-Ching</creatorcontrib><creatorcontrib>Chang, Ching-Ming</creatorcontrib><creatorcontrib>Huang, Fu-Yung</creatorcontrib><creatorcontrib>Wu, Shih-Hsiung</creatorcontrib><title>The Comparative Studies of Binding Activity of Curcumin and Didemethylated Curcumin with Selenite: Hydrogen Bonding vs Acid-Base Interactions</title><title>Scientific reports</title><addtitle>Sci Rep</addtitle><addtitle>Sci Rep</addtitle><description>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.</description><subject>119/118</subject><subject>140/131</subject><subject>639/638/309/606</subject><subject>639/638/563/606</subject><subject>Acids - chemistry</subject><subject>Calorimetry</subject><subject>Cancer</subject><subject>Cataract - drug therapy</subject><subject>Cataract - metabolism</subject><subject>Cataracts</subject><subject>Chemistry</subject><subject>Comparative studies</subject><subject>Crystallin</subject><subject>Crystallins - chemistry</subject><subject>Crystallins - metabolism</subject><subject>Curcumin</subject><subject>Curcumin - chemistry</subject><subject>Curcumin - pharmacology</subject><subject>Disease prevention</subject><subject>Experiments</subject><subject>Humanities and Social Sciences</subject><subject>Humans</subject><subject>Hydrogen bonding</subject><subject>Hydrogen Bonding - drug effects</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>multidisciplinary</subject><subject>Pharmacy</subject><subject>Phenolic compounds</subject><subject>Phenols</subject><subject>Protein Aggregates - drug effects</subject><subject>Protein interaction</subject><subject>Quantum physics</subject><subject>Science</subject><subject>Selenious Acid - chemistry</subject><subject>Selenious Acid - toxicity</subject><subject>Selenite</subject><subject>Selenium</subject><subject>Titration</subject><subject>Toxicity</subject><subject>Turbidity</subject><issn>2045-2322</issn><issn>2045-2322</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>C6C</sourceid><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNplkc1qGzEURofS0oQ0i75AEXTVwrSjn9FIXRRiJ00CgSySrgeNdGUreCRX0rj4IfrOVXDquEQbCX2Hcy98VfUeN19wQ8XXFGGNO47Zq-qYNKytCSXk9cH7qDpN6aEppyWSYfm2OiKc0xZjelz9uV8CmodxraLKbgPoLk_GQULBopnzxvkFOtMlcXn7-Defop5G55HyBp07AyPk5XalMpjn7LfLS3QHK_Auwzd0tTUxLMCjWdgJN6k4nalnKgG69hmiKiOCT--qN1atEpw-3SfVzx8X9_Or-ub28np-dlNrRkWuldBEStBWatUMLevsQLiRjbWttV0jOjC6a6XRSvCWU24GITtujRIDJYwRelJ933nX0zAWGHyOatWvoxtV3PZBuf7_xLtlvwibnnEuGZNF8PFJEMOvCVLuH8IUfdm5x0JKwTrKcaE-7SgdQyo92f0E3PSP5fX78gr74XClPfmvqgJ83gGpRH4B8WDkC9tf2SCm0Q</recordid><startdate>20151204</startdate><enddate>20151204</enddate><creator>Liao, 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Curcumin with Selenite: Hydrogen Bonding vs Acid-Base Interactions</title><author>Liao, Jiahn-Haur ; Wu, Tzu-Hua ; Chen, Ming-Yi ; Chen, Wei-Ting ; Lu, Shou-Yun ; Wang, Yi-Hsuan ; Wang, Shao-Pin ; Hsu, Yen-Min ; Huang, Yi-Shiang ; Huang, Zih-You ; Lin, Yu-Ching ; Chang, Ching-Ming ; Huang, Fu-Yung ; Wu, Shih-Hsiung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-a8c299ecf9ca0b547fb26d90ff5ff7087edc759dca865636db8976fda8b324423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>119/118</topic><topic>140/131</topic><topic>639/638/309/606</topic><topic>639/638/563/606</topic><topic>Acids - chemistry</topic><topic>Calorimetry</topic><topic>Cancer</topic><topic>Cataract - drug therapy</topic><topic>Cataract - metabolism</topic><topic>Cataracts</topic><topic>Chemistry</topic><topic>Comparative studies</topic><topic>Crystallin</topic><topic>Crystallins - chemistry</topic><topic>Crystallins - metabolism</topic><topic>Curcumin</topic><topic>Curcumin - chemistry</topic><topic>Curcumin - pharmacology</topic><topic>Disease prevention</topic><topic>Experiments</topic><topic>Humanities and Social Sciences</topic><topic>Humans</topic><topic>Hydrogen bonding</topic><topic>Hydrogen Bonding - drug effects</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>multidisciplinary</topic><topic>Pharmacy</topic><topic>Phenolic compounds</topic><topic>Phenols</topic><topic>Protein Aggregates - drug effects</topic><topic>Protein interaction</topic><topic>Quantum physics</topic><topic>Science</topic><topic>Selenious Acid - chemistry</topic><topic>Selenious Acid - toxicity</topic><topic>Selenite</topic><topic>Selenium</topic><topic>Titration</topic><topic>Toxicity</topic><topic>Turbidity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liao, Jiahn-Haur</creatorcontrib><creatorcontrib>Wu, 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reports</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liao, Jiahn-Haur</au><au>Wu, Tzu-Hua</au><au>Chen, Ming-Yi</au><au>Chen, Wei-Ting</au><au>Lu, Shou-Yun</au><au>Wang, Yi-Hsuan</au><au>Wang, Shao-Pin</au><au>Hsu, Yen-Min</au><au>Huang, Yi-Shiang</au><au>Huang, Zih-You</au><au>Lin, Yu-Ching</au><au>Chang, Ching-Ming</au><au>Huang, Fu-Yung</au><au>Wu, Shih-Hsiung</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Comparative Studies of Binding Activity of Curcumin and Didemethylated Curcumin with Selenite: Hydrogen Bonding vs Acid-Base Interactions</atitle><jtitle>Scientific reports</jtitle><stitle>Sci Rep</stitle><addtitle>Sci Rep</addtitle><date>2015-12-04</date><risdate>2015</risdate><volume>5</volume><issue>1</issue><spage>17614</spage><pages>17614-</pages><artnum>17614</artnum><issn>2045-2322</issn><eissn>2045-2322</eissn><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.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>26635113</pmid><doi>10.1038/srep17614</doi><oa>free_for_read</oa></addata></record> |
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| subjects | 119/118 140/131 639/638/309/606 639/638/563/606 Acids - chemistry Calorimetry Cancer Cataract - drug therapy Cataract - metabolism Cataracts Chemistry Comparative studies Crystallin Crystallins - chemistry Crystallins - metabolism Curcumin Curcumin - chemistry Curcumin - pharmacology Disease prevention Experiments Humanities and Social Sciences Humans Hydrogen bonding Hydrogen Bonding - drug effects Magnetic Resonance Spectroscopy multidisciplinary Pharmacy Phenolic compounds Phenols Protein Aggregates - drug effects Protein interaction Quantum physics Science Selenious Acid - chemistry Selenious Acid - toxicity Selenite Selenium Titration Toxicity Turbidity |
| title | The Comparative Studies of Binding Activity of Curcumin and Didemethylated Curcumin with Selenite: Hydrogen Bonding vs Acid-Base Interactions |
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