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{{chembox |
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{{chembox |
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| verifiedrevid = 389104871 |
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| Name = Dichlorotetrakis(dimethyl sulfoxide) ruthenium (II) |
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| Name = Dichlorotetrakis(dimethyl{{SHY}}sulfoxide) ruthenium (II) |
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| ImageFileL1 = RuCl2-dmso4.PNG |
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| ImageFile1 = RuCl2-dmso4.PNG |
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| ImageSizeL1 = 150 px |
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| ImageSize1 = 150 px |
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| ImageFileR1 = Dichlorotetrakis(dimethyl-sulfoxide)-ruthenium(II)-3D-balls.png |
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| ImageFile2 = RuCl2(dmso)4 (Strem).jpg |
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| ImageSizeR1 = 170 px |
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| ImageSize2 = 300 px |
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| SystematicName = Ruthenium, dichlorotetrakis(sulfinylbis(methane))- (9CI) |
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| SystematicName = Ruthenium, dichlorotetrakis(sulfinylbis(methane))- (9CI) |
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| OtherNames = <small>Tetrakis(dimethylsulfoxide)dichlororuthenium(II), Dichlorotetrakis(methylsulfoxide)ruthenium, Dichlorotetrakis(sulfinylbis(methane))ruthenium</small> |
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| OtherNames = <small>Tetrakis(dimethylsulfoxide)dichlororuthenium(II), Dichlorotetrakis(methylsulfoxide)ruthenium, Dichlorotetrakis(sulfinylbis(methane))ruthenium</small> |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 11070-19-2 |
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| CASNo = 11070-19-2 |
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| PubChem = 150194 |
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| ChemSpiderID = 132402 |
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| StdInChI=1S/4C2H6OS.2ClH.Ru/c4*1-4(2)3;;;/h4*1-2H3;2*1H;/q;;;;;;+2/p-2 |
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| StdInChIKey = UMJDEUKQHKMAOI-UHFFFAOYSA-L |
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| SMILES = CS(=O)C.CS(=O)C.CS(=O)C.CS(=O)C.ClCl |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>24</sub>Cl<sub>2</sub>O<sub>4</sub>RuS<sub>4</sub> |
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| Formula = C<sub>8</sub>H<sub>24</sub>Cl<sub>2</sub>O<sub>4</sub>RuS<sub>4</sub> |
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| MolarMass = 484.51 g/mol |
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| MolarMass = 484.51{{nbsp}}g/mol |
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| Appearance = Various shades of yellow crystals |
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| Appearance = Various shades of yellow crystals |
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| Solubility = water miscible |
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| Solubility = Miscible in water |
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| SolubleOther = nitromethane, chloroform, dichloromethane |
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| SolubleOther = Nitromethane, chloroform, dichloromethane |
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| Section3 = {{Chembox Structure |
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| Section3 = {{Chembox Structure |
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| Coordination = octahedral coordinate |
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| Coordination = Octahedral coordinate |
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'''Dichlorotetrakis(dimethyl sulfoxide) ruthenium(II)''' describes ]s with the formula RuCl<sub>2</sub>(dmso)<sub>4</sub>, where DMSO is ]. These complexes illustrate ]ism for the ] DMSO.<ref>{{cite journal | author = Enzo Alessio | title = Synthesis and reactivity of Ru-, Os-, Rh-, and Ir-halide-sulfoxide compounds | journal = ] | year = 2004 | volume = 104 | pages = 4203–4242 | doi = 10.1021/cr0307291}}</ref> In these complexes, two chloride anions and four molecules of dmso are coordinated to a central ] (II) core. |
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'''Dichlorotetrakis(dimethyl sulfoxide) ruthenium(II)''' describes ]s with the formula RuCl<sub>2</sub>(dmso)<sub>4</sub>, where DMSO is ]. Both cis and trans isomers are known, but the cis isomer is more common. The cis isomer is a yellow, air-stable solid that is soluble in some organic solvents. These ]es are used in the synthesis of various ruthenium(ii) complexes.<ref>{{Cite journal |last=Alessio |first=Enzo |date=2004-09-01 |title=Synthesis and Reactivity of Ru-, Os-, Rh-, and Ir-Halide−Sulfoxide Complexes |url=https://pubs.acs.org/doi/10.1021/cr0307291 |journal=Chemical Reviews |language=en |volume=104 |issue=9 |pages=4203–4242 |doi=10.1021/cr0307291 |issn=0009-2665}}</ref> They have also attracted attention as possible anti-cancer drugs. |
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==Structure== |
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==Structure and synthesis== |
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The ''cis'' isomer illustrates ]ism for the ] ].<ref>{{cite journal | author = Enzo Alessio | title = Synthesis and reactivity of Ru-, Os-, Rh-, and Ir-halide-sulfoxide compounds | journal = ] | year = 2004 | volume = 104 | pages = 4203–4242 | doi = 10.1021/cr0307291 | issue = 9| pmid = 15352790 }}</ref> One of the two dmso ligands that are ''cis'' to both chloride ligands is ''O''-bonded while the other three dmso ligands are ''S''-bonded. In the ''trans'' isomer, which is also yellow, all four dmso ligands are ''S''-bonded. The ''cis'' isomer is formed thermally, and the ''trans'' isomer is obtained by UV-irradiation of the ''cis'' isomer.<ref name=Bratsos2/> |
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RuCl<sub>2</sub>(dmso)<sub>4</sub> has been isolated as two isomers, but each is an octahedral ]. The ruthenium adopts a +2 ], and the compounds follows the ]. |
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{| class="wikitable" style="margin:1em auto; text-align:center;" |
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The two isomers are ''], fac''-RuCl<sub>2</sub>(dmso-S)<sub>3</sub>(dmso-O) and ''], mer''-RuCl<sub>2</sub>(dmso-S)<sub>4</sub>. The ''trans, mer'' configuration is kinetically favored, but thermodynamically unstable with respect to the cis isomer. ''Cis'' and ''trans'' refer to the relative positions of the chloride ligands. The ''fac''/''mer'' describes the binding of the dmso ligands. The notation dmso-S/O refers to the atom through which the dmso molecule is coordinated to the ruthenium center. Thus, dmso-S means that the dmso ligand coordinates through the sulfur atom, whereas dmso-O coordinates through the oxygen atom. |
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{|align="center" class="wikitable" |
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|<center>]</center>||<center>]</center> |
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|<center>''cis'',''fac'' isomer</center>||<center>''trans'',''mer'' isomer</center> |
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|''cis'' isomer||''trans'' isomer |
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</center> |
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The complexes were first prepared in 1971 by heating DMSO solutions of ] under ] atmosphere.<ref name=James>{{cite journal |author1=B. R. James |author2=E. Ochiai |author3=G.I. Rempel | journal = Inorganic and Nuclear Chemistry Letters| volume = 7 | pages = 781–784 | year = 1971 | doi = 10.1016/0020-1650(71)80091-0 | title = Ruthenium (II) halide dimethylsulphoxide complexes from hydrogenation reactions | issue = 8}}</ref> Modern procedures has been developed which avoids hydrogen gas, either using ascorbic acid or refluxing DMSO to reduce the ruthenium.<ref name=Bratsos2>{{cite book |author1=I. Bratsos |author2=E. Alessio | series = ] | volume = 35 | pages = 148–152 | year = 2010 | title = Ruthenium(II) Chloro Complexes of dimethylsulfoxide | doi = 10.1002/9780470651568.ch8 }}</ref><ref>{{cite journal |author1=Nagy, E. M. |author2=Pettenuzzo, A. | journal = ] | volume = 18 | pages = 14464–14472 | year = 2012 | title = Ruthenium(II/III)-Based Compounds with Encouraging Antiproliferative Activity against Non-small-Cell Lung Cancer |issue=45 | doi=10.1002/chem.201202171|pmid=23012112 }}</ref><ref>{{Citation |last=Abdou |first=Hanan E. |title=SYNTHESIS OF SELECTED TRANSITION METAL AND MAIN GROUP COMPOUNDS WITH SYNTHETIC APPLICATIONS |date=2018-07-27 |work=Inorganic Syntheses |volume=37 |pages=155–204 |editor-last=Power |editor-first=Philip P. |url=https://onlinelibrary.wiley.com/doi/10.1002/9781119477822.ch8 |access-date=2024-01-30 |edition=1 |publisher=Wiley |language=en |doi=10.1002/9781119477822.ch8 |isbn=978-1-119-47782-2 |last2=Mohamed |first2=Ahmed A. |last3=Fackler |first3=John P. |author3-link=John P. Fackler Jr. |last4=Ghimire |first4=Mukunda M. |last5=Omary |first5=Mohammad A. |last6=Schilter |first6=David |last7=Rauchfuss |first7=Thomas B. |last8=Denny |first8=Jason A. |last9=Darensbourg |first9=Marcetta Y.}}</ref> |
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==Synthesis== |
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The complexes were first prepared by heating DMSO solutions of ].<ref name=James>{{cite journal | author = B. R. James, E. Ochiai, and G.I. Rempel | journal = ] | volume = 7 | pages = 781 | year = 1971 | doi = 10.1016/0020-1650(71)80091-0 | title = Ruthenium (II) halide dimethylsulphoxide complexes from hydrogenation reactions}}</ref> Ruthenium-dmso complexes inhibit or kill tumors. ''Trans''-RuCl<sub>4</sub>(dmso-S)L are being tested for their <ref name=Bratsos/> |
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==Potential applications== |
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==Applications== |
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RuCl<sub>2</sub>(dmso)<sub>4</sub> was identified as a potential anticancer agent in the early 1980s.<ref>{{cite journal|last1=Sava|first1=Gianni|last2=Giraldi|first2=Tullio|last3=Mestroni|first3=Giovanni|last4=Zassinovich|first4=Grazia|title=Antitumor effects of rhodium(I), iridium(I) and ruthenium(II) complexes in comparison with cis-dichlorodiammino platinum(II) in mice bearing Lewis lung carcinoma|journal=Chemico-Biological Interactions|date=July 1983|volume=45|issue=1|pages=1–6|doi=10.1016/0009-2797(83)90037-6|pmid=6683595 }}</ref> Continued research<ref>{{cite journal|last1=Coluccia|first1=Mauro|last2=Sava|first2=Gianni|last3=Loseto|first3=Francesco|last4=Nassi|first4=Anna|last5=Boccarelli|first5=Angela|last6=Giordano|first6=Domenico|last7=Alessio|first7=Enzo|last8=Mestroni|first8=Giovanni|title=Anti-leukaemic action of RuCl2(DMSO)4 isomers and prevention of brain involvement on P388 leukaemia and on subline|journal=European Journal of Cancer|date=January 1993|volume=29|issue=13|pages=1873–1879|doi=10.1016/0959-8049(93)90541-M|pmid=8260245 }}</ref><ref name=Bratsos>{{cite journal |author1=Bratsos, I |author2=Serli, B |author3=Zangranko, E |author4=Katsaros, N |author5=Alessio, E. | title = Replacement of chlorides with dicarboxylate ligands in anticancer active Ru(II)-DMSO compounds: A new strategy that might lead to improved activity | journal = ] | volume = 46 | pages = 975–992 | doi = 10.1021/ic0613964 | year = 2007 | pmid=17257042 | issue = 3}}</ref> has led to the development of several related dmso-containing ruthenium compounds, some of which have undergone early-stage clinical trials.<ref>{{cite journal|last1=Enzo Alessio|first1=Bentham Science Publisher|last2=Giovanni Mestroni|first2=Bentham Science Publisher|last3=Alberta Bergamo|first3=Bentham Science Publisher|last4=Gianni Sava|first4=Bentham Science Publisher|title=Ruthenium Antimetastatic Agents|journal=Current Topics in Medicinal Chemistry|date=1 November 2004|volume=4|issue=15|pages=1525–1535|doi=10.2174/1568026043387421|pmid=15579094 }}</ref> |
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These and related dmso-containing ruthenium compounds have attracted attention due to their cancer therapeutic properties.<ref name=Bratsos>{{cite journal | author = Bratsos, I; Serli, B; Zangranko, E; Katsaros, N; Alessio, E. | title = Replacement of chlorides with dicarboxylate ligands in anticancer active Ru(II)-DMSO compounds: A new strategy that might lead to improved activity | journal = ] | volume = 46 | pages = 975–992 | doi = 10.1021/ic0613964 | year = 2007}}</ref> |
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==References== |
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==References== |
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{{Reflist}} |
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{{Ruthenium compounds}} |
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