Phosphonium‐Ring‐Fused Bicyclic Metallafuran Complexes of Ruthenium and Osmium
Metallafuran complexes with a fused five‐membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis‐[Ru/Os(dppm)2Cl2] (dppm=1,1‐bis(diphenylphosphino)methane). A metal–vinylidene‐involving pathway was found to be an energetically feasible formation mechanism...
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| Published in | Chemistry : a European journal Vol. 25; no. 39; pp. 9159 - 9163 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Germany
Wiley Subscription Services, Inc
11.07.2019
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| Abstract | Metallafuran complexes with a fused five‐membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis‐[Ru/Os(dppm)2Cl2] (dppm=1,1‐bis(diphenylphosphino)methane). A metal–vinylidene‐involving pathway was found to be an energetically feasible formation mechanism for these complexes. These phosphonium‐containing metallafurans, like many phosphonium‐functionalized drugs, have the ability to induce mitochondrial dysfunction. They also exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. Overall, this work provides structural and mechanistic insights for the rational design of functional metallacycles via activation of alkynes by RuII and OsII centers.
Ruthenafuran and osmafuran with a fused five‐membered phosphonium ring can be synthesized from reactions between terminal ynones HC≡C(C=O)R and cis‐[Ru/Os(dppm)2Cl2] (dppm=1,1‐bis(diphenylphosphino)methane, see scheme). The metallafurans are able to induce mitochondrial dysfunction, and exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. |
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| AbstractList | Metallafuran complexes with a fused five‐membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis‐[Ru/Os(dppm)2Cl2] (dppm=1,1‐bis(diphenylphosphino)methane). A metal–vinylidene‐involving pathway was found to be an energetically feasible formation mechanism for these complexes. These phosphonium‐containing metallafurans, like many phosphonium‐functionalized drugs, have the ability to induce mitochondrial dysfunction. They also exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. Overall, this work provides structural and mechanistic insights for the rational design of functional metallacycles via activation of alkynes by RuII and OsII centers.
Ruthenafuran and osmafuran with a fused five‐membered phosphonium ring can be synthesized from reactions between terminal ynones HC≡C(C=O)R and cis‐[Ru/Os(dppm)2Cl2] (dppm=1,1‐bis(diphenylphosphino)methane, see scheme). The metallafurans are able to induce mitochondrial dysfunction, and exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. Metallafuran complexes with a fused five‐membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis ‐[Ru/Os(dppm) 2 Cl 2 ] (dppm=1,1‐bis(diphenylphosphino)methane). A metal–vinylidene‐involving pathway was found to be an energetically feasible formation mechanism for these complexes. These phosphonium‐containing metallafurans, like many phosphonium‐functionalized drugs, have the ability to induce mitochondrial dysfunction. They also exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. Overall, this work provides structural and mechanistic insights for the rational design of functional metallacycles via activation of alkynes by Ru II and Os II centers. Metallafuran complexes with a fused five-membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis-[Ru/Os(dppm) Cl ] (dppm=1,1-bis(diphenylphosphino)methane). A metal-vinylidene-involving pathway was found to be an energetically feasible formation mechanism for these complexes. These phosphonium-containing metallafurans, like many phosphonium-functionalized drugs, have the ability to induce mitochondrial dysfunction. They also exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. Overall, this work provides structural and mechanistic insights for the rational design of functional metallacycles via activation of alkynes by Ru and Os centers. Metallafuran complexes with a fused five‐membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis‐[Ru/Os(dppm)2Cl2] (dppm=1,1‐bis(diphenylphosphino)methane). A metal–vinylidene‐involving pathway was found to be an energetically feasible formation mechanism for these complexes. These phosphonium‐containing metallafurans, like many phosphonium‐functionalized drugs, have the ability to induce mitochondrial dysfunction. They also exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. Overall, this work provides structural and mechanistic insights for the rational design of functional metallacycles via activation of alkynes by RuII and OsII centers. Metallafuran complexes with a fused five-membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis-[Ru/Os(dppm)2 Cl2 ] (dppm=1,1-bis(diphenylphosphino)methane). A metal-vinylidene-involving pathway was found to be an energetically feasible formation mechanism for these complexes. These phosphonium-containing metallafurans, like many phosphonium-functionalized drugs, have the ability to induce mitochondrial dysfunction. They also exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. Overall, this work provides structural and mechanistic insights for the rational design of functional metallacycles via activation of alkynes by RuII and OsII centers.Metallafuran complexes with a fused five-membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis-[Ru/Os(dppm)2 Cl2 ] (dppm=1,1-bis(diphenylphosphino)methane). A metal-vinylidene-involving pathway was found to be an energetically feasible formation mechanism for these complexes. These phosphonium-containing metallafurans, like many phosphonium-functionalized drugs, have the ability to induce mitochondrial dysfunction. They also exhibit stronger cytotoxicity against several human cancer cell lines in comparison with their metal precursors and the classic anticancer drug cisplatin. Overall, this work provides structural and mechanistic insights for the rational design of functional metallacycles via activation of alkynes by RuII and OsII centers. |
| Author | Chung, Lai‐Hon Shek, Hau‐Lam Ng, Sze‐Wing Yiu, Shek‐Man Chan, Siu‐Chung Tse, Man‐Kit Tse, Sheung‐Ying Wong, Chun‐Yuen Yeung, Chi‐Fung |
| Author_xml | – sequence: 1 givenname: Chi‐Fung orcidid: 0000-0003-1444-6989 surname: Yeung fullname: Yeung, Chi‐Fung organization: City University of Hong Kong – sequence: 2 givenname: Lai‐Hon orcidid: 0000-0002-0482-1362 surname: Chung fullname: Chung, Lai‐Hon organization: City University of Hong Kong – sequence: 3 givenname: Sze‐Wing orcidid: 0000-0003-4449-341X surname: Ng fullname: Ng, Sze‐Wing organization: City University of Hong Kong – sequence: 4 givenname: Hau‐Lam orcidid: 0000-0003-0907-5634 surname: Shek fullname: Shek, Hau‐Lam organization: City University of Hong Kong – sequence: 5 givenname: Sheung‐Ying orcidid: 0000-0002-6536-2489 surname: Tse fullname: Tse, Sheung‐Ying organization: City University of Hong Kong – sequence: 6 givenname: Siu‐Chung orcidid: 0000-0001-5728-9624 surname: Chan fullname: Chan, Siu‐Chung organization: City University of Hong Kong – sequence: 7 givenname: Man‐Kit orcidid: 0000-0002-7882-0848 surname: Tse fullname: Tse, Man‐Kit organization: City University of Hong Kong – sequence: 8 givenname: Shek‐Man orcidid: 0000-0002-2011-7391 surname: Yiu fullname: Yiu, Shek‐Man organization: City University of Hong Kong – sequence: 9 givenname: Chun‐Yuen orcidid: 0000-0003-4780-480X surname: Wong fullname: Wong, Chun‐Yuen email: acywong@cityu.edu.hk organization: City University of Hong Kong |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31037776$$D View this record in MEDLINE/PubMed |
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| Copyright | 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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| Keywords | ruthenium osmium alkyne activation metallacycles |
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| Snippet | Metallafuran complexes with a fused five‐membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis‐[Ru/Os(dppm)2Cl2]... Metallafuran complexes with a fused five‐membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis ‐[Ru/Os(dppm) 2... Metallafuran complexes with a fused five-membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis-[Ru/Os(dppm) Cl ]... Metallafuran complexes with a fused five-membered phosphonium ring were synthesized from reactions between terminal ynones HC≡C(C=O)R and cis-[Ru/Os(dppm)2 Cl2... |
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| SubjectTerms | alkyne activation Alkynes Chemical synthesis Chemistry Cisplatin Cytotoxicity metallacycles Mitochondria Organometallic compounds Osmium Ruthenium Toxicity Tumor cell lines Vinylidene |
| Title | Phosphonium‐Ring‐Fused Bicyclic Metallafuran Complexes of Ruthenium and Osmium |
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