New ferrocene-based 2-thio-imidazol-4-ones and their copper complexes. Synthesis and cytotoxicity
Synthesis, characterization (HRMS, NMR, EPR, XANES, UV-Vis spectroscopy, and electrochemistry), DNA and BSA binding and in vitro biological screening of two new ferrocene-incorporated thiohydantoin derivatives ( 5 and 6 ) and their copper coordination compounds are reported. The ferrocene-based thio...
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Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2018-12, Vol.47 (48), p.17357-17366 |
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creator | Guk, D. A Krasnovskaya, O. O Dashkova, N. S Skvortsov, D. A Rubtsova, M. P Dyadchenko, V. P Yudina, E. S Kosarev, M. A Soldatov, A. V Shapovalov, V. V Semkina, A. S Vlasova, K. Y Pergushov, V. I Shafikov, R. R Andreeva, A. A Melnikov, M. Ya Zyk, N. V Majouga, A. G Beloglazkina, E. K |
description | Synthesis, characterization (HRMS, NMR, EPR, XANES, UV-Vis spectroscopy, and electrochemistry), DNA and BSA binding and
in vitro
biological screening of two new ferrocene-incorporated thiohydantoin derivatives (
5
and
6
) and their copper coordination compounds are reported. The ferrocene-based thiohydantoin derivatives were prepared by copper-catalyzed azide alkyne cycloaddition reactions between alkynyl ferrocenes and 5-(
Z
)-3-(2-azidoethyl)-2-(methylthio)-5-(pyridin-2-ylmethylene)-1
H
-imidazol-4
H
-one. Alkynyl ferrocenes necessary for these syntheses were prepared by new procedures. Intermolecular redox reactions between the ferrocene fragment and copper(+2) coordinated ions were studied by different methods to determine the mechanism and kinetic constants of redox processes. Ferrocene-containing imidazolones (
5
and
6
) and their copper complexes were also tested for their
in vitro
cytotoxic activity against MCF-7 and A-549 carcinoma cells, and also against the noncancerous cell line Hek-293. The results showed modest cytotoxicity against the subjected cancer cell line compared with cisplatin. The ability of the obtained compounds to cause DNA degradation and cell apoptosis was investigated, and the distribution of cytosol/pellets was studied by AAS.
Characterization and cytotoxicity of ferrocene-based imidazolones and their copper complexes. |
doi_str_mv | 10.1039/c8dt03164a |
format | Article |
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in vitro
biological screening of two new ferrocene-incorporated thiohydantoin derivatives (
5
and
6
) and their copper coordination compounds are reported. The ferrocene-based thiohydantoin derivatives were prepared by copper-catalyzed azide alkyne cycloaddition reactions between alkynyl ferrocenes and 5-(
Z
)-3-(2-azidoethyl)-2-(methylthio)-5-(pyridin-2-ylmethylene)-1
H
-imidazol-4
H
-one. Alkynyl ferrocenes necessary for these syntheses were prepared by new procedures. Intermolecular redox reactions between the ferrocene fragment and copper(+2) coordinated ions were studied by different methods to determine the mechanism and kinetic constants of redox processes. Ferrocene-containing imidazolones (
5
and
6
) and their copper complexes were also tested for their
in vitro
cytotoxic activity against MCF-7 and A-549 carcinoma cells, and also against the noncancerous cell line Hek-293. The results showed modest cytotoxicity against the subjected cancer cell line compared with cisplatin. The ability of the obtained compounds to cause DNA degradation and cell apoptosis was investigated, and the distribution of cytosol/pellets was studied by AAS.
Characterization and cytotoxicity of ferrocene-based imidazolones and their copper complexes.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c8dt03164a</identifier><identifier>PMID: 30480670</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkynes ; Apoptosis ; Chemical reactions ; Coordination compounds ; Copper ; Copper compounds ; Cycloaddition ; Cytotoxicity ; Deoxyribonucleic acid ; Derivatives ; DNA ; Electrochemistry ; Ferrocenes ; NMR ; Nuclear magnetic resonance ; Redox reactions ; Synthesis ; Toxicity</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2018-12, Vol.47 (48), p.17357-17366</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-f10d9e191d2603b34d3ef33784bb6be58465ff58bb54451ac408c5dc59dc53503</citedby><cites>FETCH-LOGICAL-c337t-f10d9e191d2603b34d3ef33784bb6be58465ff58bb54451ac408c5dc59dc53503</cites><orcidid>0000-0001-8336-8596 ; 0000-0002-9349-5211 ; 0000-0001-6796-8241</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30480670$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guk, D. A</creatorcontrib><creatorcontrib>Krasnovskaya, O. O</creatorcontrib><creatorcontrib>Dashkova, N. S</creatorcontrib><creatorcontrib>Skvortsov, D. A</creatorcontrib><creatorcontrib>Rubtsova, M. P</creatorcontrib><creatorcontrib>Dyadchenko, V. P</creatorcontrib><creatorcontrib>Yudina, E. S</creatorcontrib><creatorcontrib>Kosarev, M. A</creatorcontrib><creatorcontrib>Soldatov, A. V</creatorcontrib><creatorcontrib>Shapovalov, V. V</creatorcontrib><creatorcontrib>Semkina, A. S</creatorcontrib><creatorcontrib>Vlasova, K. Y</creatorcontrib><creatorcontrib>Pergushov, V. I</creatorcontrib><creatorcontrib>Shafikov, R. R</creatorcontrib><creatorcontrib>Andreeva, A. A</creatorcontrib><creatorcontrib>Melnikov, M. Ya</creatorcontrib><creatorcontrib>Zyk, N. V</creatorcontrib><creatorcontrib>Majouga, A. G</creatorcontrib><creatorcontrib>Beloglazkina, E. K</creatorcontrib><title>New ferrocene-based 2-thio-imidazol-4-ones and their copper complexes. Synthesis and cytotoxicity</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Synthesis, characterization (HRMS, NMR, EPR, XANES, UV-Vis spectroscopy, and electrochemistry), DNA and BSA binding and
in vitro
biological screening of two new ferrocene-incorporated thiohydantoin derivatives (
5
and
6
) and their copper coordination compounds are reported. The ferrocene-based thiohydantoin derivatives were prepared by copper-catalyzed azide alkyne cycloaddition reactions between alkynyl ferrocenes and 5-(
Z
)-3-(2-azidoethyl)-2-(methylthio)-5-(pyridin-2-ylmethylene)-1
H
-imidazol-4
H
-one. Alkynyl ferrocenes necessary for these syntheses were prepared by new procedures. Intermolecular redox reactions between the ferrocene fragment and copper(+2) coordinated ions were studied by different methods to determine the mechanism and kinetic constants of redox processes. Ferrocene-containing imidazolones (
5
and
6
) and their copper complexes were also tested for their
in vitro
cytotoxic activity against MCF-7 and A-549 carcinoma cells, and also against the noncancerous cell line Hek-293. The results showed modest cytotoxicity against the subjected cancer cell line compared with cisplatin. The ability of the obtained compounds to cause DNA degradation and cell apoptosis was investigated, and the distribution of cytosol/pellets was studied by AAS.
Characterization and cytotoxicity of ferrocene-based imidazolones and their copper complexes.</description><subject>Alkynes</subject><subject>Apoptosis</subject><subject>Chemical reactions</subject><subject>Coordination compounds</subject><subject>Copper</subject><subject>Copper compounds</subject><subject>Cycloaddition</subject><subject>Cytotoxicity</subject><subject>Deoxyribonucleic acid</subject><subject>Derivatives</subject><subject>DNA</subject><subject>Electrochemistry</subject><subject>Ferrocenes</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Redox reactions</subject><subject>Synthesis</subject><subject>Toxicity</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpd0UtLxDAUBeAgiu-Ne6XgRoRonp10OYxPEF04rkua3DKRtqlJB2f89UZHR3ARbuB8XMIJQkeUXFDCi0uj7EA4zYXeQLtUjEa4YFxsru8s30F7Mb4SwhiRbBvtcCIUyUdkF-lHeM9qCMEb6ABXOoLNGB5mzmPXOqs_fIMF9h3ETHc2G2bgQmZ838PXaPsGFhAvsudll6LoVsosBz_4hTNuWB6grVo3EQ5_5j56ubmeTu7ww9Pt_WT8gA3nowHXlNgCaEEtywmvuLAc6pQoUVV5BVKJXNa1VFUlhZBUG0GUkdbIIh0uCd9HZ6u9ffBvc4hD2bpooGl0B34eS0a5ynlRsCLR03_01c9Dl16XlBRMKCpEUucrZYKPMUBd9sG1OixLSsqv4suJupp-Fz9O-ORn5bxqwa7pb9MJHK9AiGad_v0c_wRnAIcM</recordid><startdate>20181211</startdate><enddate>20181211</enddate><creator>Guk, D. A</creator><creator>Krasnovskaya, O. O</creator><creator>Dashkova, N. S</creator><creator>Skvortsov, D. A</creator><creator>Rubtsova, M. P</creator><creator>Dyadchenko, V. P</creator><creator>Yudina, E. S</creator><creator>Kosarev, M. A</creator><creator>Soldatov, A. V</creator><creator>Shapovalov, V. V</creator><creator>Semkina, A. S</creator><creator>Vlasova, K. Y</creator><creator>Pergushov, V. I</creator><creator>Shafikov, R. R</creator><creator>Andreeva, A. A</creator><creator>Melnikov, M. Ya</creator><creator>Zyk, N. V</creator><creator>Majouga, A. G</creator><creator>Beloglazkina, E. K</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8336-8596</orcidid><orcidid>https://orcid.org/0000-0002-9349-5211</orcidid><orcidid>https://orcid.org/0000-0001-6796-8241</orcidid></search><sort><creationdate>20181211</creationdate><title>New ferrocene-based 2-thio-imidazol-4-ones and their copper complexes. Synthesis and cytotoxicity</title><author>Guk, D. A ; Krasnovskaya, O. O ; Dashkova, N. S ; Skvortsov, D. A ; Rubtsova, M. P ; Dyadchenko, V. P ; Yudina, E. S ; Kosarev, M. A ; Soldatov, A. V ; Shapovalov, V. V ; Semkina, A. S ; Vlasova, K. Y ; Pergushov, V. I ; Shafikov, R. R ; Andreeva, A. A ; Melnikov, M. Ya ; Zyk, N. V ; Majouga, A. G ; Beloglazkina, E. K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-f10d9e191d2603b34d3ef33784bb6be58465ff58bb54451ac408c5dc59dc53503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkynes</topic><topic>Apoptosis</topic><topic>Chemical reactions</topic><topic>Coordination compounds</topic><topic>Copper</topic><topic>Copper compounds</topic><topic>Cycloaddition</topic><topic>Cytotoxicity</topic><topic>Deoxyribonucleic acid</topic><topic>Derivatives</topic><topic>DNA</topic><topic>Electrochemistry</topic><topic>Ferrocenes</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Redox reactions</topic><topic>Synthesis</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guk, D. A</creatorcontrib><creatorcontrib>Krasnovskaya, O. O</creatorcontrib><creatorcontrib>Dashkova, N. S</creatorcontrib><creatorcontrib>Skvortsov, D. A</creatorcontrib><creatorcontrib>Rubtsova, M. P</creatorcontrib><creatorcontrib>Dyadchenko, V. P</creatorcontrib><creatorcontrib>Yudina, E. S</creatorcontrib><creatorcontrib>Kosarev, M. A</creatorcontrib><creatorcontrib>Soldatov, A. V</creatorcontrib><creatorcontrib>Shapovalov, V. V</creatorcontrib><creatorcontrib>Semkina, A. S</creatorcontrib><creatorcontrib>Vlasova, K. Y</creatorcontrib><creatorcontrib>Pergushov, V. I</creatorcontrib><creatorcontrib>Shafikov, R. R</creatorcontrib><creatorcontrib>Andreeva, A. A</creatorcontrib><creatorcontrib>Melnikov, M. Ya</creatorcontrib><creatorcontrib>Zyk, N. V</creatorcontrib><creatorcontrib>Majouga, A. G</creatorcontrib><creatorcontrib>Beloglazkina, E. K</creatorcontrib><collection>PubMed</collection><collection>CrossRef</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><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guk, D. A</au><au>Krasnovskaya, O. O</au><au>Dashkova, N. S</au><au>Skvortsov, D. A</au><au>Rubtsova, M. P</au><au>Dyadchenko, V. P</au><au>Yudina, E. S</au><au>Kosarev, M. A</au><au>Soldatov, A. V</au><au>Shapovalov, V. V</au><au>Semkina, A. S</au><au>Vlasova, K. Y</au><au>Pergushov, V. I</au><au>Shafikov, R. R</au><au>Andreeva, A. A</au><au>Melnikov, M. Ya</au><au>Zyk, N. V</au><au>Majouga, A. G</au><au>Beloglazkina, E. K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New ferrocene-based 2-thio-imidazol-4-ones and their copper complexes. Synthesis and cytotoxicity</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2018-12-11</date><risdate>2018</risdate><volume>47</volume><issue>48</issue><spage>17357</spage><epage>17366</epage><pages>17357-17366</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Synthesis, characterization (HRMS, NMR, EPR, XANES, UV-Vis spectroscopy, and electrochemistry), DNA and BSA binding and
in vitro
biological screening of two new ferrocene-incorporated thiohydantoin derivatives (
5
and
6
) and their copper coordination compounds are reported. The ferrocene-based thiohydantoin derivatives were prepared by copper-catalyzed azide alkyne cycloaddition reactions between alkynyl ferrocenes and 5-(
Z
)-3-(2-azidoethyl)-2-(methylthio)-5-(pyridin-2-ylmethylene)-1
H
-imidazol-4
H
-one. Alkynyl ferrocenes necessary for these syntheses were prepared by new procedures. Intermolecular redox reactions between the ferrocene fragment and copper(+2) coordinated ions were studied by different methods to determine the mechanism and kinetic constants of redox processes. Ferrocene-containing imidazolones (
5
and
6
) and their copper complexes were also tested for their
in vitro
cytotoxic activity against MCF-7 and A-549 carcinoma cells, and also against the noncancerous cell line Hek-293. The results showed modest cytotoxicity against the subjected cancer cell line compared with cisplatin. The ability of the obtained compounds to cause DNA degradation and cell apoptosis was investigated, and the distribution of cytosol/pellets was studied by AAS.
Characterization and cytotoxicity of ferrocene-based imidazolones and their copper complexes.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30480670</pmid><doi>10.1039/c8dt03164a</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0001-8336-8596</orcidid><orcidid>https://orcid.org/0000-0002-9349-5211</orcidid><orcidid>https://orcid.org/0000-0001-6796-8241</orcidid></addata></record> |
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language | eng |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Alkynes Apoptosis Chemical reactions Coordination compounds Copper Copper compounds Cycloaddition Cytotoxicity Deoxyribonucleic acid Derivatives DNA Electrochemistry Ferrocenes NMR Nuclear magnetic resonance Redox reactions Synthesis Toxicity |
title | New ferrocene-based 2-thio-imidazol-4-ones and their copper complexes. Synthesis and cytotoxicity |
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