(Benzyl isocyanide)gold(I) pyrimidine‐2‐thiolate complex: Synthesis and biological activity
The reaction of [(Me2S)AuCl] with an equimolar amount of benzyl isocyanide (PhCH2NC) ligand led to the formation of complex [(PhCH2NC)AuCl] (1). The solid‐state structure of 1 was determined using the X‐ray diffraction method. Through a salt metathesis reaction, the chloride ligand in 1 was replaced...
Gespeichert in:
| Veröffentlicht in: | Applied organometallic chemistry 2018-03, Vol.32 (3), p.n/a |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | n/a |
|---|---|
| container_issue | 3 |
| container_start_page | |
| container_title | Applied organometallic chemistry |
| container_volume | 32 |
| creator | Fereidoonnezhad, Masood Shahsavari, Hamid R. Lotfi, Elaheh Babaghasabha, Mojgan Fakhri, Motahareh Faghih, Zeinab Faghih, Zahra Hassan Beyzavi, M. |
| description | The reaction of [(Me2S)AuCl] with an equimolar amount of benzyl isocyanide (PhCH2NC) ligand led to the formation of complex [(PhCH2NC)AuCl] (1). The solid‐state structure of 1 was determined using the X‐ray diffraction method. Through a salt metathesis reaction, the chloride ligand in 1 was replaced by pyrimidine‐2‐thiolate (SpyN−) to afford the complex [(PhCH2NC)Au(η1‐S‐Spy)] (2), which was characterized spectroscopically. The cytotoxic activities of 1 and 2 were evaluated against three human cancer cell lines: ovarian carcinoma (SKOV3), lung carcinoma (A549) and breast carcinoma (MCF‐7). Complex 2 showed higher cytotoxicity than cisplatin against SKOV3 and MCF‐7 cancer cell lines. It showed a strong anti‐proliferative activity with IC50 of 7.80, 6.26 and 6.14 μM, compared with that measured for cisplatin which was 7.62, 12.36 and 11.47 μM, against A549, SKOV3 and MCF‐7 cell lines, respectively. The induction of cellular apoptosis by 2 was also studied on MCF‐7 cell line. Our results indicated that 2 could induce apoptosis in cancerous cells in a dose‐dependent manner.
Gold(I) complexes with isocyanide and thiolate ligands were prepared and studied for in vitro cytotoxic activity against three human cancer cell lines: ovarian carcinoma (SKOV3), lung carcinoma (A549) and breast carcinoma (MCF‐7). Complexes 1 and 2 were also investigated for their apoptosis effect. Complex 2 exhibited higher cytotoxicity than cisplatin. |
| doi_str_mv | 10.1002/aoc.4200 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2007338902</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2007338902</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3300-3088c7bda694420e939e54d4f328538dd16e3c4561215cb115fd6cd67c9222fc3</originalsourceid><addsrcrecordid>eNp1kL9OwzAQhy0EEqUg8QiRWNoh5WwnTsxWKv5UqtQBmC3XdlpXaRzitBAmHoFn5ElwKSvD6Yb7dHe_D6FLDCMMQK6lU6OEAByhHgbOY8goP0Y9ICyPCYP0FJ15vwYAznDSQ2Jwa6qProysd6qTldVmuHSlHkyHUd01dmO1rcz35xcJ1a6sK2VrIuU2dWneb6KnrmpXxlsfyUpHizB2S6tkGUnV2p1tu3N0UsjSm4u_3kcv93fPk8d4Nn-YTsazWFEKEFPIc5UttGQ8Cd8bTrlJE50UlOQpzbXGzFCVpAwTnKoFxmmhmdIsU5wQUijaR1eHvXXjXrfGt2Lttk0VToogI6M050ACNThQqnHeN6YQdYgom05gEHt9IugTe30BjQ_omy1N9y8nxvPJL_8D2J5yCw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2007338902</pqid></control><display><type>article</type><title>(Benzyl isocyanide)gold(I) pyrimidine‐2‐thiolate complex: Synthesis and biological activity</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Fereidoonnezhad, Masood ; Shahsavari, Hamid R. ; Lotfi, Elaheh ; Babaghasabha, Mojgan ; Fakhri, Motahareh ; Faghih, Zeinab ; Faghih, Zahra ; Hassan Beyzavi, M.</creator><creatorcontrib>Fereidoonnezhad, Masood ; Shahsavari, Hamid R. ; Lotfi, Elaheh ; Babaghasabha, Mojgan ; Fakhri, Motahareh ; Faghih, Zeinab ; Faghih, Zahra ; Hassan Beyzavi, M.</creatorcontrib><description>The reaction of [(Me2S)AuCl] with an equimolar amount of benzyl isocyanide (PhCH2NC) ligand led to the formation of complex [(PhCH2NC)AuCl] (1). The solid‐state structure of 1 was determined using the X‐ray diffraction method. Through a salt metathesis reaction, the chloride ligand in 1 was replaced by pyrimidine‐2‐thiolate (SpyN−) to afford the complex [(PhCH2NC)Au(η1‐S‐Spy)] (2), which was characterized spectroscopically. The cytotoxic activities of 1 and 2 were evaluated against three human cancer cell lines: ovarian carcinoma (SKOV3), lung carcinoma (A549) and breast carcinoma (MCF‐7). Complex 2 showed higher cytotoxicity than cisplatin against SKOV3 and MCF‐7 cancer cell lines. It showed a strong anti‐proliferative activity with IC50 of 7.80, 6.26 and 6.14 μM, compared with that measured for cisplatin which was 7.62, 12.36 and 11.47 μM, against A549, SKOV3 and MCF‐7 cell lines, respectively. The induction of cellular apoptosis by 2 was also studied on MCF‐7 cell line. Our results indicated that 2 could induce apoptosis in cancerous cells in a dose‐dependent manner.
Gold(I) complexes with isocyanide and thiolate ligands were prepared and studied for in vitro cytotoxic activity against three human cancer cell lines: ovarian carcinoma (SKOV3), lung carcinoma (A549) and breast carcinoma (MCF‐7). Complexes 1 and 2 were also investigated for their apoptosis effect. Complex 2 exhibited higher cytotoxicity than cisplatin.</description><identifier>ISSN: 0268-2605</identifier><identifier>EISSN: 1099-0739</identifier><identifier>DOI: 10.1002/aoc.4200</identifier><language>eng</language><publisher>Chichester: Wiley Subscription Services, Inc</publisher><subject>Apoptosis ; apoptosis study ; Biological activity ; Biotechnology ; Cancer ; Chemical synthesis ; Chemistry ; Gold ; gold complexes ; isocyanide ligand ; Ligands ; Metathesis ; thiolate ligand ; Toxicity</subject><ispartof>Applied organometallic chemistry, 2018-03, Vol.32 (3), p.n/a</ispartof><rights>Copyright © 2018 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3300-3088c7bda694420e939e54d4f328538dd16e3c4561215cb115fd6cd67c9222fc3</citedby><cites>FETCH-LOGICAL-c3300-3088c7bda694420e939e54d4f328538dd16e3c4561215cb115fd6cd67c9222fc3</cites><orcidid>0000-0003-3405-0228 ; 0000-0002-2579-2185 ; 0000-0002-6415-8996</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Faoc.4200$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Faoc.4200$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Fereidoonnezhad, Masood</creatorcontrib><creatorcontrib>Shahsavari, Hamid R.</creatorcontrib><creatorcontrib>Lotfi, Elaheh</creatorcontrib><creatorcontrib>Babaghasabha, Mojgan</creatorcontrib><creatorcontrib>Fakhri, Motahareh</creatorcontrib><creatorcontrib>Faghih, Zeinab</creatorcontrib><creatorcontrib>Faghih, Zahra</creatorcontrib><creatorcontrib>Hassan Beyzavi, M.</creatorcontrib><title>(Benzyl isocyanide)gold(I) pyrimidine‐2‐thiolate complex: Synthesis and biological activity</title><title>Applied organometallic chemistry</title><description>The reaction of [(Me2S)AuCl] with an equimolar amount of benzyl isocyanide (PhCH2NC) ligand led to the formation of complex [(PhCH2NC)AuCl] (1). The solid‐state structure of 1 was determined using the X‐ray diffraction method. Through a salt metathesis reaction, the chloride ligand in 1 was replaced by pyrimidine‐2‐thiolate (SpyN−) to afford the complex [(PhCH2NC)Au(η1‐S‐Spy)] (2), which was characterized spectroscopically. The cytotoxic activities of 1 and 2 were evaluated against three human cancer cell lines: ovarian carcinoma (SKOV3), lung carcinoma (A549) and breast carcinoma (MCF‐7). Complex 2 showed higher cytotoxicity than cisplatin against SKOV3 and MCF‐7 cancer cell lines. It showed a strong anti‐proliferative activity with IC50 of 7.80, 6.26 and 6.14 μM, compared with that measured for cisplatin which was 7.62, 12.36 and 11.47 μM, against A549, SKOV3 and MCF‐7 cell lines, respectively. The induction of cellular apoptosis by 2 was also studied on MCF‐7 cell line. Our results indicated that 2 could induce apoptosis in cancerous cells in a dose‐dependent manner.
Gold(I) complexes with isocyanide and thiolate ligands were prepared and studied for in vitro cytotoxic activity against three human cancer cell lines: ovarian carcinoma (SKOV3), lung carcinoma (A549) and breast carcinoma (MCF‐7). Complexes 1 and 2 were also investigated for their apoptosis effect. Complex 2 exhibited higher cytotoxicity than cisplatin.</description><subject>Apoptosis</subject><subject>apoptosis study</subject><subject>Biological activity</subject><subject>Biotechnology</subject><subject>Cancer</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Gold</subject><subject>gold complexes</subject><subject>isocyanide ligand</subject><subject>Ligands</subject><subject>Metathesis</subject><subject>thiolate ligand</subject><subject>Toxicity</subject><issn>0268-2605</issn><issn>1099-0739</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kL9OwzAQhy0EEqUg8QiRWNoh5WwnTsxWKv5UqtQBmC3XdlpXaRzitBAmHoFn5ElwKSvD6Yb7dHe_D6FLDCMMQK6lU6OEAByhHgbOY8goP0Y9ICyPCYP0FJ15vwYAznDSQ2Jwa6qProysd6qTldVmuHSlHkyHUd01dmO1rcz35xcJ1a6sK2VrIuU2dWneb6KnrmpXxlsfyUpHizB2S6tkGUnV2p1tu3N0UsjSm4u_3kcv93fPk8d4Nn-YTsazWFEKEFPIc5UttGQ8Cd8bTrlJE50UlOQpzbXGzFCVpAwTnKoFxmmhmdIsU5wQUijaR1eHvXXjXrfGt2Lttk0VToogI6M050ACNThQqnHeN6YQdYgom05gEHt9IugTe30BjQ_omy1N9y8nxvPJL_8D2J5yCw</recordid><startdate>201803</startdate><enddate>201803</enddate><creator>Fereidoonnezhad, Masood</creator><creator>Shahsavari, Hamid R.</creator><creator>Lotfi, Elaheh</creator><creator>Babaghasabha, Mojgan</creator><creator>Fakhri, Motahareh</creator><creator>Faghih, Zeinab</creator><creator>Faghih, Zahra</creator><creator>Hassan Beyzavi, M.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-3405-0228</orcidid><orcidid>https://orcid.org/0000-0002-2579-2185</orcidid><orcidid>https://orcid.org/0000-0002-6415-8996</orcidid></search><sort><creationdate>201803</creationdate><title>(Benzyl isocyanide)gold(I) pyrimidine‐2‐thiolate complex: Synthesis and biological activity</title><author>Fereidoonnezhad, Masood ; Shahsavari, Hamid R. ; Lotfi, Elaheh ; Babaghasabha, Mojgan ; Fakhri, Motahareh ; Faghih, Zeinab ; Faghih, Zahra ; Hassan Beyzavi, M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3300-3088c7bda694420e939e54d4f328538dd16e3c4561215cb115fd6cd67c9222fc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Apoptosis</topic><topic>apoptosis study</topic><topic>Biological activity</topic><topic>Biotechnology</topic><topic>Cancer</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Gold</topic><topic>gold complexes</topic><topic>isocyanide ligand</topic><topic>Ligands</topic><topic>Metathesis</topic><topic>thiolate ligand</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fereidoonnezhad, Masood</creatorcontrib><creatorcontrib>Shahsavari, Hamid R.</creatorcontrib><creatorcontrib>Lotfi, Elaheh</creatorcontrib><creatorcontrib>Babaghasabha, Mojgan</creatorcontrib><creatorcontrib>Fakhri, Motahareh</creatorcontrib><creatorcontrib>Faghih, Zeinab</creatorcontrib><creatorcontrib>Faghih, Zahra</creatorcontrib><creatorcontrib>Hassan Beyzavi, M.</creatorcontrib><collection>CrossRef</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>Applied organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fereidoonnezhad, Masood</au><au>Shahsavari, Hamid R.</au><au>Lotfi, Elaheh</au><au>Babaghasabha, Mojgan</au><au>Fakhri, Motahareh</au><au>Faghih, Zeinab</au><au>Faghih, Zahra</au><au>Hassan Beyzavi, M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(Benzyl isocyanide)gold(I) pyrimidine‐2‐thiolate complex: Synthesis and biological activity</atitle><jtitle>Applied organometallic chemistry</jtitle><date>2018-03</date><risdate>2018</risdate><volume>32</volume><issue>3</issue><epage>n/a</epage><issn>0268-2605</issn><eissn>1099-0739</eissn><abstract>The reaction of [(Me2S)AuCl] with an equimolar amount of benzyl isocyanide (PhCH2NC) ligand led to the formation of complex [(PhCH2NC)AuCl] (1). The solid‐state structure of 1 was determined using the X‐ray diffraction method. Through a salt metathesis reaction, the chloride ligand in 1 was replaced by pyrimidine‐2‐thiolate (SpyN−) to afford the complex [(PhCH2NC)Au(η1‐S‐Spy)] (2), which was characterized spectroscopically. The cytotoxic activities of 1 and 2 were evaluated against three human cancer cell lines: ovarian carcinoma (SKOV3), lung carcinoma (A549) and breast carcinoma (MCF‐7). Complex 2 showed higher cytotoxicity than cisplatin against SKOV3 and MCF‐7 cancer cell lines. It showed a strong anti‐proliferative activity with IC50 of 7.80, 6.26 and 6.14 μM, compared with that measured for cisplatin which was 7.62, 12.36 and 11.47 μM, against A549, SKOV3 and MCF‐7 cell lines, respectively. The induction of cellular apoptosis by 2 was also studied on MCF‐7 cell line. Our results indicated that 2 could induce apoptosis in cancerous cells in a dose‐dependent manner.
Gold(I) complexes with isocyanide and thiolate ligands were prepared and studied for in vitro cytotoxic activity against three human cancer cell lines: ovarian carcinoma (SKOV3), lung carcinoma (A549) and breast carcinoma (MCF‐7). Complexes 1 and 2 were also investigated for their apoptosis effect. Complex 2 exhibited higher cytotoxicity than cisplatin.</abstract><cop>Chichester</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/aoc.4200</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-3405-0228</orcidid><orcidid>https://orcid.org/0000-0002-2579-2185</orcidid><orcidid>https://orcid.org/0000-0002-6415-8996</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0268-2605 |
| ispartof | Applied organometallic chemistry, 2018-03, Vol.32 (3), p.n/a |
| issn | 0268-2605 1099-0739 |
| language | eng |
| recordid | cdi_proquest_journals_2007338902 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Apoptosis apoptosis study Biological activity Biotechnology Cancer Chemical synthesis Chemistry Gold gold complexes isocyanide ligand Ligands Metathesis thiolate ligand Toxicity |
| title | (Benzyl isocyanide)gold(I) pyrimidine‐2‐thiolate complex: Synthesis and biological activity |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-31T07%3A47%3A45IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=(Benzyl%20isocyanide)gold(I)%20pyrimidine%E2%80%902%E2%80%90thiolate%20complex:%20Synthesis%20and%20biological%20activity&rft.jtitle=Applied%20organometallic%20chemistry&rft.au=Fereidoonnezhad,%20Masood&rft.date=2018-03&rft.volume=32&rft.issue=3&rft.epage=n/a&rft.issn=0268-2605&rft.eissn=1099-0739&rft_id=info:doi/10.1002/aoc.4200&rft_dat=%3Cproquest_cross%3E2007338902%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2007338902&rft_id=info:pmid/&rfr_iscdi=true |