DNA binding, cytotoxicity, apoptotic inducing activity, and molecular modeling study of quercetin zinc(II) complex
DNA cleavage activity of quercetin zinc(II) complex has been studied, but little attention has been devoted to the relationship between antitumor activity of this complex and DNA-binding properties. DNA-binding properties of quercetin zinc(II) complex were studied using UV–vis spectra, fluorescence...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2009-01, Vol.17 (2), p.614-620 |
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| creator | Tan, Jun Wang, Bochu Zhu, Liancai |
| description | DNA cleavage activity of quercetin zinc(II) complex has been studied, but little attention has been devoted to the relationship between antitumor activity of this complex and DNA-binding properties. DNA-binding properties of quercetin zinc(II) complex were studied using UV–vis spectra, fluorescence measurements, and viscosity measurements. The results obtained indicate that quercetin zinc(II) complex can intercalate into the stacked base pairs of DNA, and compete with the strong intercalator ethidium bromide for the intercalative binding sites with Stern–Volmer quenching constant,
K
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1.24. The complex was subjected to biological tests in vitro using three tumor cell lines (HepG2, SMMC7721, and A549), which showed significant cytotoxicity against three tumor cell lines. Moreover, Hoechst33258 staining showed HepG2 cells underwent the typical morphologic changes of apoptosis characterized by nuclear shrinkage, chromatin condensation, or fragmentation after exposure to the complex. In addition, Molecular modeling was performed to learn the complex could be preferentially bound to DNA in GC region. Our results suggest that antitumor activity of quercetin zinc(II) complex might be related to its intercalation into DNA. |
| doi_str_mv | 10.1016/j.bmc.2008.11.063 |
| format | Article |
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K
sq
=
1.24. The complex was subjected to biological tests in vitro using three tumor cell lines (HepG2, SMMC7721, and A549), which showed significant cytotoxicity against three tumor cell lines. Moreover, Hoechst33258 staining showed HepG2 cells underwent the typical morphologic changes of apoptosis characterized by nuclear shrinkage, chromatin condensation, or fragmentation after exposure to the complex. In addition, Molecular modeling was performed to learn the complex could be preferentially bound to DNA in GC region. Our results suggest that antitumor activity of quercetin zinc(II) complex might be related to its intercalation into DNA.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2008.11.063</identifier><identifier>PMID: 19097913</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Antineoplastic agents ; Antitumor activity ; Apoptosis ; Biological and medical sciences ; Cell Line, Tumor ; DNA - metabolism ; DNA binding ; General aspects ; Humans ; Intercalating Agents ; Intercalation ; Medical sciences ; Models, Molecular ; Pharmacology. Drug treatments ; Quercetin - chemistry ; Quercetin zinc(II) complex ; Zinc - chemistry</subject><ispartof>Bioorganic & medicinal chemistry, 2009-01, Vol.17 (2), p.614-620</ispartof><rights>2008 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c478t-e14d4f67ddcedd7856c552d2eba01bbdbf1f21a1ec426cd8146b89975945e07d3</citedby><cites>FETCH-LOGICAL-c478t-e14d4f67ddcedd7856c552d2eba01bbdbf1f21a1ec426cd8146b89975945e07d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2008.11.063$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21127098$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19097913$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tan, Jun</creatorcontrib><creatorcontrib>Wang, Bochu</creatorcontrib><creatorcontrib>Zhu, Liancai</creatorcontrib><title>DNA binding, cytotoxicity, apoptotic inducing activity, and molecular modeling study of quercetin zinc(II) complex</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>DNA cleavage activity of quercetin zinc(II) complex has been studied, but little attention has been devoted to the relationship between antitumor activity of this complex and DNA-binding properties. DNA-binding properties of quercetin zinc(II) complex were studied using UV–vis spectra, fluorescence measurements, and viscosity measurements. The results obtained indicate that quercetin zinc(II) complex can intercalate into the stacked base pairs of DNA, and compete with the strong intercalator ethidium bromide for the intercalative binding sites with Stern–Volmer quenching constant,
K
sq
=
1.24. The complex was subjected to biological tests in vitro using three tumor cell lines (HepG2, SMMC7721, and A549), which showed significant cytotoxicity against three tumor cell lines. Moreover, Hoechst33258 staining showed HepG2 cells underwent the typical morphologic changes of apoptosis characterized by nuclear shrinkage, chromatin condensation, or fragmentation after exposure to the complex. In addition, Molecular modeling was performed to learn the complex could be preferentially bound to DNA in GC region. Our results suggest that antitumor activity of quercetin zinc(II) complex might be related to its intercalation into DNA.</description><subject>Antineoplastic agents</subject><subject>Antitumor activity</subject><subject>Apoptosis</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>DNA - metabolism</subject><subject>DNA binding</subject><subject>General aspects</subject><subject>Humans</subject><subject>Intercalating Agents</subject><subject>Intercalation</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>Quercetin - chemistry</subject><subject>Quercetin zinc(II) complex</subject><subject>Zinc - chemistry</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1v1DAQQC1ERZfCD-CCfAGB1ASP4zixOFXloytV5QJnyxk7yKskDnZSdfvr8WpXcIOTx5o3o5l5hLwCVgID-WFXdiOWnLG2BCiZrJ6QDQgpiqpS8JRsmJJtwVolz8nzlHaMMS4UPCPnoJhqFFQbEj_dXdHOT9ZPPy8p7pewhAePftlfUjOHOf890pxfMRPU4OLvj8nJ0jEMDtfBxBxZNxyAtKx2T0NPf60uolv8RB_9hO-22_cUwzgP7uEFOevNkNzL03tBfnz5_P36prj99nV7fXVboGjapXAgrOhlYy06a5u2lljX3HLXGQZdZ7seeg4GHAou0bZ58a5VqqmVqB1rbHVB3h77zjHkadKiR5_QDYOZXFiTlrIVoq7Uf0HOKiEb3mQQjiDGkFJ0vZ6jH03ca2D6YETvdDaiD0Y0gM5Gcs3rU_O1G539W3FSkIE3J8AkNEMfzYQ-_eE4AG-YajP38ci5fLN776JO6N2Uj-Ojw0Xb4P8xxm-r7KpF</recordid><startdate>20090115</startdate><enddate>20090115</enddate><creator>Tan, Jun</creator><creator>Wang, Bochu</creator><creator>Zhu, Liancai</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20090115</creationdate><title>DNA binding, cytotoxicity, apoptotic inducing activity, and molecular modeling study of quercetin zinc(II) complex</title><author>Tan, Jun ; Wang, Bochu ; Zhu, Liancai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c478t-e14d4f67ddcedd7856c552d2eba01bbdbf1f21a1ec426cd8146b89975945e07d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Antineoplastic agents</topic><topic>Antitumor activity</topic><topic>Apoptosis</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>DNA - metabolism</topic><topic>DNA binding</topic><topic>General aspects</topic><topic>Humans</topic><topic>Intercalating Agents</topic><topic>Intercalation</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>Quercetin - chemistry</topic><topic>Quercetin zinc(II) complex</topic><topic>Zinc - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tan, Jun</creatorcontrib><creatorcontrib>Wang, Bochu</creatorcontrib><creatorcontrib>Zhu, Liancai</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tan, Jun</au><au>Wang, Bochu</au><au>Zhu, Liancai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>DNA binding, cytotoxicity, apoptotic inducing activity, and molecular modeling study of quercetin zinc(II) complex</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2009-01-15</date><risdate>2009</risdate><volume>17</volume><issue>2</issue><spage>614</spage><epage>620</epage><pages>614-620</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>DNA cleavage activity of quercetin zinc(II) complex has been studied, but little attention has been devoted to the relationship between antitumor activity of this complex and DNA-binding properties. DNA-binding properties of quercetin zinc(II) complex were studied using UV–vis spectra, fluorescence measurements, and viscosity measurements. The results obtained indicate that quercetin zinc(II) complex can intercalate into the stacked base pairs of DNA, and compete with the strong intercalator ethidium bromide for the intercalative binding sites with Stern–Volmer quenching constant,
K
sq
=
1.24. The complex was subjected to biological tests in vitro using three tumor cell lines (HepG2, SMMC7721, and A549), which showed significant cytotoxicity against three tumor cell lines. Moreover, Hoechst33258 staining showed HepG2 cells underwent the typical morphologic changes of apoptosis characterized by nuclear shrinkage, chromatin condensation, or fragmentation after exposure to the complex. In addition, Molecular modeling was performed to learn the complex could be preferentially bound to DNA in GC region. Our results suggest that antitumor activity of quercetin zinc(II) complex might be related to its intercalation into DNA.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19097913</pmid><doi>10.1016/j.bmc.2008.11.063</doi><tpages>7</tpages></addata></record> |
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| subjects | Antineoplastic agents Antitumor activity Apoptosis Biological and medical sciences Cell Line, Tumor DNA - metabolism DNA binding General aspects Humans Intercalating Agents Intercalation Medical sciences Models, Molecular Pharmacology. Drug treatments Quercetin - chemistry Quercetin zinc(II) complex Zinc - chemistry |
| title | DNA binding, cytotoxicity, apoptotic inducing activity, and molecular modeling study of quercetin zinc(II) complex |
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