Evaluation of Metal-Mediated DNA Binding of Benzoxazole Ligands by Electrospray Ionization Mass Spectrometry
The binding of a series of benzoxazole analogs with different amide- and ester-linked side chains to duplex DNA in the absence and presence of divalent metal cations is examined. All ligands were found to form complexes with Ni 2+, Cu 2+, and Zn 2+, with 2:1 ligand/metal cation binding stoichiometri...
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| Veröffentlicht in: | Journal of the American Society for Mass Spectrometry 2008-02, Vol.19 (2), p.209-218 |
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| creator | Mazzitelli, Carolyn L. Rodriguez, Mireya Kerwin, Sean M. Brodbelt, Jennifer S. |
| description | The binding of a series of benzoxazole analogs with different amide- and ester-linked side chains to duplex DNA in the absence and presence of divalent metal cations is examined. All ligands were found to form complexes with Ni
2+, Cu
2+, and Zn
2+, with 2:1 ligand/metal cation binding stoichiometries dominating for ligands containing shorter side chains (
2,
6,
7, and
8), while 1:1 complexes were the most abundant for ligands with long side chains (
9,
10, and
11). Ligand binding with duplex DNA in the absence of metal cations was assessed, and the long side-chain ligands were found to form low abundance complexes with 1:1 ligand/DNA binding stoichiometries. The ligands with the shorter side chains only formed DNA complexes in the presence of metal cations, most notably for
7 and
8 binding to DNA in the presence of Cu
2+. The binding of long side-chain ligands was enhanced by Cu
2+ and to a lesser degree by Ni
2+ and Zn
2+. The cytotoxicities of all of the ligands against the A549 lung cancer and MCF7 breast cancer cell lines were also examined. The ligands exhibiting the most dramatic metal-enhanced DNA binding also demonstrated the greatest cytotoxic activity. Both
7 and
8 were found to be the most cytotoxic against the A549 lung cancer cell line and
8 demonstrated moderate cytotoxicity against MCF7 breast cancer cells. Metal ions also enhanced the DNA binding of the ligands with the long side chains, especially for
9, which also exhibited the highest level of cytotoxicity of the long side-chain compounds. |
| doi_str_mv | 10.1016/j.jasms.2007.05.009 |
| format | Article |
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2+, Cu
2+, and Zn
2+, with 2:1 ligand/metal cation binding stoichiometries dominating for ligands containing shorter side chains (
2,
6,
7, and
8), while 1:1 complexes were the most abundant for ligands with long side chains (
9,
10, and
11). Ligand binding with duplex DNA in the absence of metal cations was assessed, and the long side-chain ligands were found to form low abundance complexes with 1:1 ligand/DNA binding stoichiometries. The ligands with the shorter side chains only formed DNA complexes in the presence of metal cations, most notably for
7 and
8 binding to DNA in the presence of Cu
2+. The binding of long side-chain ligands was enhanced by Cu
2+ and to a lesser degree by Ni
2+ and Zn
2+. The cytotoxicities of all of the ligands against the A549 lung cancer and MCF7 breast cancer cell lines were also examined. The ligands exhibiting the most dramatic metal-enhanced DNA binding also demonstrated the greatest cytotoxic activity. Both
7 and
8 were found to be the most cytotoxic against the A549 lung cancer cell line and
8 demonstrated moderate cytotoxicity against MCF7 breast cancer cells. Metal ions also enhanced the DNA binding of the ligands with the long side chains, especially for
9, which also exhibited the highest level of cytotoxicity of the long side-chain compounds.</description><identifier>ISSN: 1044-0305</identifier><identifier>EISSN: 1879-1123</identifier><identifier>DOI: 10.1016/j.jasms.2007.05.009</identifier><identifier>PMID: 17583529</identifier><language>eng</language><publisher>New York: Elsevier Inc</publisher><subject>2006 Distinguished Contribution In Mass Spectrometry Awardee ; Analytical Chemistry ; Antineoplastic agents ; Awards and Prizes ; Benzoxazoles - chemistry ; Benzoxazoles - metabolism ; Benzoxazoles - toxicity ; Bioinformatics ; Biological and medical sciences ; Biotechnology ; Breast Neoplasms ; Cell Line, Tumor ; Chemistry ; Chemistry and Materials Science ; Copper - chemistry ; DNA - chemistry ; DNA - metabolism ; Focus: Cooks ; General aspects ; Humans ; Ligands ; Lung Neoplasms ; Medical sciences ; Metals - chemistry ; Nickel - chemistry ; Organic Chemistry ; Pharmacology. Drug treatments ; Proteomics ; Spectrometry, Mass, Electrospray Ionization ; Zinc - chemistry</subject><ispartof>Journal of the American Society for Mass Spectrometry, 2008-02, Vol.19 (2), p.209-218</ispartof><rights>2008 American Society for Mass Spectrometry</rights><rights>American Society for Mass Spectrometry 2008</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c539t-ae00efa7d6f8ae945b7b4ae8b51fdd27e05afdb0d6fdc1ebe7bbb9b8452d58973</citedby><cites>FETCH-LOGICAL-c539t-ae00efa7d6f8ae945b7b4ae8b51fdd27e05afdb0d6fdc1ebe7bbb9b8452d58973</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1016/j.jasms.2007.05.009$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1016/j.jasms.2007.05.009$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20147541$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17583529$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mazzitelli, Carolyn L.</creatorcontrib><creatorcontrib>Rodriguez, Mireya</creatorcontrib><creatorcontrib>Kerwin, Sean M.</creatorcontrib><creatorcontrib>Brodbelt, Jennifer S.</creatorcontrib><title>Evaluation of Metal-Mediated DNA Binding of Benzoxazole Ligands by Electrospray Ionization Mass Spectrometry</title><title>Journal of the American Society for Mass Spectrometry</title><addtitle>J. Am. Soc. Spectrom</addtitle><addtitle>J Am Soc Mass Spectrom</addtitle><description>The binding of a series of benzoxazole analogs with different amide- and ester-linked side chains to duplex DNA in the absence and presence of divalent metal cations is examined. All ligands were found to form complexes with Ni
2+, Cu
2+, and Zn
2+, with 2:1 ligand/metal cation binding stoichiometries dominating for ligands containing shorter side chains (
2,
6,
7, and
8), while 1:1 complexes were the most abundant for ligands with long side chains (
9,
10, and
11). Ligand binding with duplex DNA in the absence of metal cations was assessed, and the long side-chain ligands were found to form low abundance complexes with 1:1 ligand/DNA binding stoichiometries. The ligands with the shorter side chains only formed DNA complexes in the presence of metal cations, most notably for
7 and
8 binding to DNA in the presence of Cu
2+. The binding of long side-chain ligands was enhanced by Cu
2+ and to a lesser degree by Ni
2+ and Zn
2+. The cytotoxicities of all of the ligands against the A549 lung cancer and MCF7 breast cancer cell lines were also examined. The ligands exhibiting the most dramatic metal-enhanced DNA binding also demonstrated the greatest cytotoxic activity. Both
7 and
8 were found to be the most cytotoxic against the A549 lung cancer cell line and
8 demonstrated moderate cytotoxicity against MCF7 breast cancer cells. Metal ions also enhanced the DNA binding of the ligands with the long side chains, especially for
9, which also exhibited the highest level of cytotoxicity of the long side-chain compounds.</description><subject>2006 Distinguished Contribution In Mass Spectrometry Awardee</subject><subject>Analytical Chemistry</subject><subject>Antineoplastic agents</subject><subject>Awards and Prizes</subject><subject>Benzoxazoles - chemistry</subject><subject>Benzoxazoles - metabolism</subject><subject>Benzoxazoles - toxicity</subject><subject>Bioinformatics</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Breast Neoplasms</subject><subject>Cell Line, Tumor</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Copper - chemistry</subject><subject>DNA - chemistry</subject><subject>DNA - metabolism</subject><subject>Focus: Cooks</subject><subject>General aspects</subject><subject>Humans</subject><subject>Ligands</subject><subject>Lung Neoplasms</subject><subject>Medical sciences</subject><subject>Metals - chemistry</subject><subject>Nickel - chemistry</subject><subject>Organic Chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Proteomics</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Zinc - chemistry</subject><issn>1044-0305</issn><issn>1879-1123</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1v1DAQhiMEoh_wC5BQLnBLGCdxnBw4tGULlXbhAJytcTypHCX2Ymcrdn893mYFN3qypXnesfw-SfKGQc6A1R-GfMAwhbwAEDnwHKB9lpyzRrQZY0X5PN6hqjIogZ8lFyEMAExAK14mZ0zwpuRFe56MqwccdzgbZ1PXpxuaccw2pA3OpNNPX6_Sa2O1sffH6TXZg_uNBzdSujb3aHVI1T5djdTN3oWtx31656w5LPs2GEL6ffs4nGj2-1fJix7HQK9P52Xy83b14-ZLtv72-e7map11vGznDAmAehS67huktuJKqAqpUZz1WheCgGOvFcS57hgpEkqpVjUVLzRvWlFeJu-XvVvvfu0ozHIyoaNxREtuF2RZFKypoX4SLKAWLWNNBMsF7OI_g6debr2Z0O8lA3m0IQf5aEMebUjgMtqIqben9Ts1kf6XOdUfgXcnAEOHY-_Rdib85QpgleAVi1y1cLHj6IK8HNzO29jhE-9_XGIUy34wMRY6Q7aLen20IrUz_83_AW3BvQo</recordid><startdate>20080201</startdate><enddate>20080201</enddate><creator>Mazzitelli, Carolyn L.</creator><creator>Rodriguez, Mireya</creator><creator>Kerwin, Sean M.</creator><creator>Brodbelt, Jennifer S.</creator><general>Elsevier Inc</general><general>Springer-Verlag</general><general>Elsevier Science</general><scope>6I.</scope><scope>AAFTH</scope><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>7TM</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20080201</creationdate><title>Evaluation of Metal-Mediated DNA Binding of Benzoxazole Ligands by Electrospray Ionization Mass Spectrometry</title><author>Mazzitelli, Carolyn L. ; Rodriguez, Mireya ; Kerwin, Sean M. ; Brodbelt, Jennifer S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c539t-ae00efa7d6f8ae945b7b4ae8b51fdd27e05afdb0d6fdc1ebe7bbb9b8452d58973</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>2006 Distinguished Contribution In Mass Spectrometry Awardee</topic><topic>Analytical Chemistry</topic><topic>Antineoplastic agents</topic><topic>Awards and Prizes</topic><topic>Benzoxazoles - chemistry</topic><topic>Benzoxazoles - metabolism</topic><topic>Benzoxazoles - toxicity</topic><topic>Bioinformatics</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Breast Neoplasms</topic><topic>Cell Line, Tumor</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Copper - chemistry</topic><topic>DNA - chemistry</topic><topic>DNA - metabolism</topic><topic>Focus: Cooks</topic><topic>General aspects</topic><topic>Humans</topic><topic>Ligands</topic><topic>Lung Neoplasms</topic><topic>Medical sciences</topic><topic>Metals - chemistry</topic><topic>Nickel - chemistry</topic><topic>Organic Chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Proteomics</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Zinc - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mazzitelli, Carolyn L.</creatorcontrib><creatorcontrib>Rodriguez, Mireya</creatorcontrib><creatorcontrib>Kerwin, Sean M.</creatorcontrib><creatorcontrib>Brodbelt, Jennifer S.</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><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>Nucleic Acids Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of the American Society for Mass Spectrometry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mazzitelli, Carolyn L.</au><au>Rodriguez, Mireya</au><au>Kerwin, Sean M.</au><au>Brodbelt, Jennifer S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Evaluation of Metal-Mediated DNA Binding of Benzoxazole Ligands by Electrospray Ionization Mass Spectrometry</atitle><jtitle>Journal of the American Society for Mass Spectrometry</jtitle><stitle>J. Am. Soc. Spectrom</stitle><addtitle>J Am Soc Mass Spectrom</addtitle><date>2008-02-01</date><risdate>2008</risdate><volume>19</volume><issue>2</issue><spage>209</spage><epage>218</epage><pages>209-218</pages><issn>1044-0305</issn><eissn>1879-1123</eissn><abstract>The binding of a series of benzoxazole analogs with different amide- and ester-linked side chains to duplex DNA in the absence and presence of divalent metal cations is examined. All ligands were found to form complexes with Ni
2+, Cu
2+, and Zn
2+, with 2:1 ligand/metal cation binding stoichiometries dominating for ligands containing shorter side chains (
2,
6,
7, and
8), while 1:1 complexes were the most abundant for ligands with long side chains (
9,
10, and
11). Ligand binding with duplex DNA in the absence of metal cations was assessed, and the long side-chain ligands were found to form low abundance complexes with 1:1 ligand/DNA binding stoichiometries. The ligands with the shorter side chains only formed DNA complexes in the presence of metal cations, most notably for
7 and
8 binding to DNA in the presence of Cu
2+. The binding of long side-chain ligands was enhanced by Cu
2+ and to a lesser degree by Ni
2+ and Zn
2+. The cytotoxicities of all of the ligands against the A549 lung cancer and MCF7 breast cancer cell lines were also examined. The ligands exhibiting the most dramatic metal-enhanced DNA binding also demonstrated the greatest cytotoxic activity. Both
7 and
8 were found to be the most cytotoxic against the A549 lung cancer cell line and
8 demonstrated moderate cytotoxicity against MCF7 breast cancer cells. Metal ions also enhanced the DNA binding of the ligands with the long side chains, especially for
9, which also exhibited the highest level of cytotoxicity of the long side-chain compounds.</abstract><cop>New York</cop><pub>Elsevier Inc</pub><pmid>17583529</pmid><doi>10.1016/j.jasms.2007.05.009</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| issn | 1044-0305 1879-1123 |
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| source | MEDLINE; SpringerNature Journals; EZB-FREE-00999 freely available EZB journals; Alma/SFX Local Collection; Free Full-Text Journals in Chemistry |
| subjects | 2006 Distinguished Contribution In Mass Spectrometry Awardee Analytical Chemistry Antineoplastic agents Awards and Prizes Benzoxazoles - chemistry Benzoxazoles - metabolism Benzoxazoles - toxicity Bioinformatics Biological and medical sciences Biotechnology Breast Neoplasms Cell Line, Tumor Chemistry Chemistry and Materials Science Copper - chemistry DNA - chemistry DNA - metabolism Focus: Cooks General aspects Humans Ligands Lung Neoplasms Medical sciences Metals - chemistry Nickel - chemistry Organic Chemistry Pharmacology. Drug treatments Proteomics Spectrometry, Mass, Electrospray Ionization Zinc - chemistry |
| title | Evaluation of Metal-Mediated DNA Binding of Benzoxazole Ligands by Electrospray Ionization Mass Spectrometry |
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