Electrochemical detection of the oxidative damage of a potential pyrimido[5,4-g]pteridine-derived antitumor agent toward DNA
In this work, we design and synthesize 2,2′-(7,9-dimethyl-2,4,6,8-tetraoxo-6,7,8,9-tetrahydropyrimido[5,4-g]pteridine-1,3(2H,4H)-diyl)bis( N,N -bis(2-chloroethyl)acetamide) (PT-MCA) as a novel DNA intercalator and potential antitumor agent. Electrochemical analysis reveals the redox process of PT-MC...
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| Veröffentlicht in: | Analytical and bioanalytical chemistry 2023-05, Vol.415 (12), p.2249-2260 |
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| creator | Guo, Fei-Fei Li, Tong Mu, Xi-Ping Zhang, Xue Xu, Zhi-Hao Sun, Ping Yu, Ri-Lei Xia, Ya-Mu Gao, Wei-Wei |
| description | In this work, we design and synthesize 2,2′-(7,9-dimethyl-2,4,6,8-tetraoxo-6,7,8,9-tetrahydropyrimido[5,4-g]pteridine-1,3(2H,4H)-diyl)bis(
N,N
-bis(2-chloroethyl)acetamide) (PT-MCA) as a novel DNA intercalator and potential antitumor agent. Electrochemical analysis reveals the redox process of PT-MCA on the electrode surface. The bioelectrochemical sensors are obtained by modifying the surface of GCE with calf thymus DNA (ctDNA), poly (dG), poly (dA), and G-quadruplex, respectively. The DNA oxidative damage induced by PT-MCA is investigated by comparing the peak intensity change of dGuo and dAdo and monitoring the peaks of the oxidation products of guanine and/or adenine (8-oxoGua and/or 2,8-oxoAde). UV–vis absorption and fluorescence spectra and gel electrophoresis are further employed to understand the intercalation of PT-MCA into DNA base pairs. Moreover, PT-MCA is proved to exhibit stronger anti-proliferation activity than mitoxantrone against both 4T1 and B16-F10 cancer cells. At last, the oxidative damage of PT-MCA toward ctDNA is not interfered by the coexistence of ions and also can be detected in real serums.
Graphical abstract |
| doi_str_mv | 10.1007/s00216-023-04643-5 |
| format | Article |
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N,N
-bis(2-chloroethyl)acetamide) (PT-MCA) as a novel DNA intercalator and potential antitumor agent. Electrochemical analysis reveals the redox process of PT-MCA on the electrode surface. The bioelectrochemical sensors are obtained by modifying the surface of GCE with calf thymus DNA (ctDNA), poly (dG), poly (dA), and G-quadruplex, respectively. The DNA oxidative damage induced by PT-MCA is investigated by comparing the peak intensity change of dGuo and dAdo and monitoring the peaks of the oxidation products of guanine and/or adenine (8-oxoGua and/or 2,8-oxoAde). UV–vis absorption and fluorescence spectra and gel electrophoresis are further employed to understand the intercalation of PT-MCA into DNA base pairs. Moreover, PT-MCA is proved to exhibit stronger anti-proliferation activity than mitoxantrone against both 4T1 and B16-F10 cancer cells. At last, the oxidative damage of PT-MCA toward ctDNA is not interfered by the coexistence of ions and also can be detected in real serums.
Graphical abstract</description><identifier>ISSN: 1618-2642</identifier><identifier>EISSN: 1618-2650</identifier><identifier>DOI: 10.1007/s00216-023-04643-5</identifier><identifier>PMID: 36920495</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Adenine ; Analysis ; Analytical Chemistry ; Anticancer properties ; Antimitotic agents ; Antineoplastic agents ; Antineoplastic Agents - pharmacology ; Biochemistry ; Calf thymus ; calves ; Cell proliferation ; Characterization and Evaluation of Materials ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Damage ; Deoxyribonucleic acid ; DNA ; DNA - genetics ; DNA Damage ; Electrochemical analysis ; Electrochemistry ; electrodes ; Electrophoresis ; fluorescence ; Food Science ; Gel electrophoresis ; guanine ; Laboratory Medicine ; Mitoxantrone ; Monitoring/Environmental Analysis ; Oxidation ; Oxidative Stress ; Properties ; Pteridine ; Pteridines ; Research Paper ; ultraviolet-visible spectroscopy</subject><ispartof>Analytical and bioanalytical chemistry, 2023-05, Vol.415 (12), p.2249-2260</ispartof><rights>Springer-Verlag GmbH Germany, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><rights>2023. Springer-Verlag GmbH Germany, part of Springer Nature.</rights><rights>COPYRIGHT 2023 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c475t-eaacc94efc168534ee3e4b4f4b4372f35b2214c035d853b8fba6962337da15ee3</citedby><cites>FETCH-LOGICAL-c475t-eaacc94efc168534ee3e4b4f4b4372f35b2214c035d853b8fba6962337da15ee3</cites><orcidid>0000-0003-0676-790X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00216-023-04643-5$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00216-023-04643-5$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36920495$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guo, Fei-Fei</creatorcontrib><creatorcontrib>Li, Tong</creatorcontrib><creatorcontrib>Mu, Xi-Ping</creatorcontrib><creatorcontrib>Zhang, Xue</creatorcontrib><creatorcontrib>Xu, Zhi-Hao</creatorcontrib><creatorcontrib>Sun, Ping</creatorcontrib><creatorcontrib>Yu, Ri-Lei</creatorcontrib><creatorcontrib>Xia, Ya-Mu</creatorcontrib><creatorcontrib>Gao, Wei-Wei</creatorcontrib><title>Electrochemical detection of the oxidative damage of a potential pyrimido[5,4-g]pteridine-derived antitumor agent toward DNA</title><title>Analytical and bioanalytical chemistry</title><addtitle>Anal Bioanal Chem</addtitle><addtitle>Anal Bioanal Chem</addtitle><description>In this work, we design and synthesize 2,2′-(7,9-dimethyl-2,4,6,8-tetraoxo-6,7,8,9-tetrahydropyrimido[5,4-g]pteridine-1,3(2H,4H)-diyl)bis(
N,N
-bis(2-chloroethyl)acetamide) (PT-MCA) as a novel DNA intercalator and potential antitumor agent. Electrochemical analysis reveals the redox process of PT-MCA on the electrode surface. The bioelectrochemical sensors are obtained by modifying the surface of GCE with calf thymus DNA (ctDNA), poly (dG), poly (dA), and G-quadruplex, respectively. The DNA oxidative damage induced by PT-MCA is investigated by comparing the peak intensity change of dGuo and dAdo and monitoring the peaks of the oxidation products of guanine and/or adenine (8-oxoGua and/or 2,8-oxoAde). UV–vis absorption and fluorescence spectra and gel electrophoresis are further employed to understand the intercalation of PT-MCA into DNA base pairs. Moreover, PT-MCA is proved to exhibit stronger anti-proliferation activity than mitoxantrone against both 4T1 and B16-F10 cancer cells. At last, the oxidative damage of PT-MCA toward ctDNA is not interfered by the coexistence of ions and also can be detected in real serums.
Graphical abstract</description><subject>Adenine</subject><subject>Analysis</subject><subject>Analytical Chemistry</subject><subject>Anticancer properties</subject><subject>Antimitotic agents</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biochemistry</subject><subject>Calf thymus</subject><subject>calves</subject><subject>Cell proliferation</subject><subject>Characterization and Evaluation of Materials</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Damage</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>DNA - genetics</subject><subject>DNA Damage</subject><subject>Electrochemical analysis</subject><subject>Electrochemistry</subject><subject>electrodes</subject><subject>Electrophoresis</subject><subject>fluorescence</subject><subject>Food Science</subject><subject>Gel electrophoresis</subject><subject>guanine</subject><subject>Laboratory Medicine</subject><subject>Mitoxantrone</subject><subject>Monitoring/Environmental Analysis</subject><subject>Oxidation</subject><subject>Oxidative Stress</subject><subject>Properties</subject><subject>Pteridine</subject><subject>Pteridines</subject><subject>Research Paper</subject><subject>ultraviolet-visible 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detection of the oxidative damage of a potential pyrimido[5,4-g]pteridine-derived antitumor agent toward DNA</title><author>Guo, Fei-Fei ; Li, Tong ; Mu, Xi-Ping ; Zhang, Xue ; Xu, Zhi-Hao ; Sun, Ping ; Yu, Ri-Lei ; Xia, Ya-Mu ; Gao, Wei-Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c475t-eaacc94efc168534ee3e4b4f4b4372f35b2214c035d853b8fba6962337da15ee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Adenine</topic><topic>Analysis</topic><topic>Analytical Chemistry</topic><topic>Anticancer properties</topic><topic>Antimitotic agents</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biochemistry</topic><topic>Calf thymus</topic><topic>calves</topic><topic>Cell proliferation</topic><topic>Characterization and Evaluation of Materials</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Damage</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>DNA - genetics</topic><topic>DNA Damage</topic><topic>Electrochemical analysis</topic><topic>Electrochemistry</topic><topic>electrodes</topic><topic>Electrophoresis</topic><topic>fluorescence</topic><topic>Food Science</topic><topic>Gel electrophoresis</topic><topic>guanine</topic><topic>Laboratory Medicine</topic><topic>Mitoxantrone</topic><topic>Monitoring/Environmental Analysis</topic><topic>Oxidation</topic><topic>Oxidative Stress</topic><topic>Properties</topic><topic>Pteridine</topic><topic>Pteridines</topic><topic>Research Paper</topic><topic>ultraviolet-visible spectroscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guo, Fei-Fei</creatorcontrib><creatorcontrib>Li, Tong</creatorcontrib><creatorcontrib>Mu, Xi-Ping</creatorcontrib><creatorcontrib>Zhang, Xue</creatorcontrib><creatorcontrib>Xu, 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Chem</addtitle><date>2023-05-01</date><risdate>2023</risdate><volume>415</volume><issue>12</issue><spage>2249</spage><epage>2260</epage><pages>2249-2260</pages><issn>1618-2642</issn><eissn>1618-2650</eissn><abstract>In this work, we design and synthesize 2,2′-(7,9-dimethyl-2,4,6,8-tetraoxo-6,7,8,9-tetrahydropyrimido[5,4-g]pteridine-1,3(2H,4H)-diyl)bis(
N,N
-bis(2-chloroethyl)acetamide) (PT-MCA) as a novel DNA intercalator and potential antitumor agent. Electrochemical analysis reveals the redox process of PT-MCA on the electrode surface. The bioelectrochemical sensors are obtained by modifying the surface of GCE with calf thymus DNA (ctDNA), poly (dG), poly (dA), and G-quadruplex, respectively. The DNA oxidative damage induced by PT-MCA is investigated by comparing the peak intensity change of dGuo and dAdo and monitoring the peaks of the oxidation products of guanine and/or adenine (8-oxoGua and/or 2,8-oxoAde). UV–vis absorption and fluorescence spectra and gel electrophoresis are further employed to understand the intercalation of PT-MCA into DNA base pairs. Moreover, PT-MCA is proved to exhibit stronger anti-proliferation activity than mitoxantrone against both 4T1 and B16-F10 cancer cells. At last, the oxidative damage of PT-MCA toward ctDNA is not interfered by the coexistence of ions and also can be detected in real serums.
Graphical abstract</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>36920495</pmid><doi>10.1007/s00216-023-04643-5</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0003-0676-790X</orcidid></addata></record> |
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| ispartof | Analytical and bioanalytical chemistry, 2023-05, Vol.415 (12), p.2249-2260 |
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| subjects | Adenine Analysis Analytical Chemistry Anticancer properties Antimitotic agents Antineoplastic agents Antineoplastic Agents - pharmacology Biochemistry Calf thymus calves Cell proliferation Characterization and Evaluation of Materials Chemical synthesis Chemistry Chemistry and Materials Science Damage Deoxyribonucleic acid DNA DNA - genetics DNA Damage Electrochemical analysis Electrochemistry electrodes Electrophoresis fluorescence Food Science Gel electrophoresis guanine Laboratory Medicine Mitoxantrone Monitoring/Environmental Analysis Oxidation Oxidative Stress Properties Pteridine Pteridines Research Paper ultraviolet-visible spectroscopy |
| title | Electrochemical detection of the oxidative damage of a potential pyrimido[5,4-g]pteridine-derived antitumor agent toward DNA |
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