Group 11 metal compounds with tripodal bis(imidazole) thioether ligands. applications as catalysts in the oxidation of alkenes and as antimicrobial agents

Molecules

Volumn 16, Issue 8, 2011, Pages 6701-6720

  Liu, Fangwei ^a   Anis, Reema ^a   Hwang, Eunmi ^a   Ovalle, Rafael ^b   Varela Ramírez, Armando ^c   Aguilera, Renato J ^c   Contel, María ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

^c UNIVERSITY OF TEXAS AT EL PASO   (United States)

Author keywords

Antimicrobial; Group 11 metals; Non toxic; Oxidation alkenes; Tripodal bis(imidazol) thioether pincer ligands

Indexed keywords

ALKENE; ANTIINFECTIVE AGENT; COORDINATION COMPOUND; IMIDAZOLE; IMIDAZOLE DERIVATIVE; LIGAND; SULFIDE;

ANIMAL; BACTERIUM; C57BL MOUSE; CATALYSIS; CELL DEATH; CHEMISTRY; DRUG EFFECTS; FUNGUS; HELA CELL LINE; HUMAN; IC50; MICROBIAL SENSITIVITY TEST; MOLECULAR MODEL; OXIDATION REDUCTION REACTION;

ALKENES; ANIMALS; ANTI-INFECTIVE AGENTS; BACTERIA; CATALYSIS; CELL DEATH; COORDINATION COMPLEXES; FUNGI; HELA CELLS; HUMANS; IMIDAZOLES; INHIBITORY CONCENTRATION 50; LIGANDS; MICE, INBRED C57BL; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; OXIDATION-REDUCTION; SULFIDES;

EID: 80052203436     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16086701     Document Type: Article

References (58)

1. Chomitz, W.A.; Arnold, J. Use of tetradentate monoanionic ligands for stabilizing reactive metal complexes. Chem. Eur. J. 2009, 15, 2020-2030.
2. Latest review: Liang, L.C. Metal complexes of chelating diarylamido phosphine ligands Coord. Chem. Rev. 2006, 250, 1152-1177.
3. For example: Lewis, F.A.; Tolman, W.B. Reactivity of dioxygen-copper systems. Chem. Rev. 2004, 104, 1047-1076.
4. Bai, S.-Q.; Koh, L.L.; Hor, T.S.A. Structures of copper complexes of the hybrid [SNS] ligand of bis(2-(benzylthio)ethyl)amine and facile catalytic formation of 1-benzyl-4-phenyl-1H-1,2,3-triazole through click reaction. Inorg. Chem. 2009, 48, 1207-1213 and references therein.
5. Zablotskaya, A.; Segal, I.; Lukevics, E.; Belyakov, S.; Spies, H. Tetrahydroquinoline and tetrahydroisoquinoline mixed ligand rhenium complexes with the SNS/S donor atom set. Appl. Organometal. Chem. 2007, 21, 288-293. (Pubitemid 46473418)
6. Zhang, J.-A.; Pan, M.; Zhang, J.-Y.; Zhang, H.-K.; Fan, Z.-J.; Kang, B.-S.; Su, C.-Y. Syntheses, structures and bioactivities of silver(I) complexes with a tridentate heterocyclic N- and S-ligand. Polyhedron 2009, 28, 145-149 and references therein.
7. Aragoni, M.C.; Arca, M.; Bencini, A.; Biagini, S.; Blake, A.J.; Caltagirone, C.; Demartin, F: De Filippo, G.; Devillanova. F.A.; Garau, A.; et al. Interaction of mixed-donor macrocycles containing the 1,10-phenanthroline subunit with selected transition and post-transition metal ions: metal ion recognition in competitive liquid-liquid solvent extraction of CuII, ZnII, PbII, CdII, AgI, and HgII. Inorg. Chem. 2008, 47, 8391-8404 and references therein
8. 2S thioether ligands. Inorg. Chem. 2006, 45, 10098-10107.
9. Zhou, L.; Powell, D.; Nicholas, K.M. Tripodal bis(imidazole) thioether copper(I) complexes: mimics of the Cu(B) site of hydroxylase enzymes. Inorg. Chem. 2006, 45, 3840-3842.
10. Zhou, L.; Powell, D.; Nicholas, K.M. Tripodal bis(imidazole) thioether copper(I) complexes: Mimics of the CuM site of copper hydroxylase enzymes. Inorg. Chem. 2007, 46, 7789-7799.
11. 2(thioether)CuI complexes. Inorg. Chem. 2008, 47, 4356-4367.
12. Laguna, M.; Villacampa, M.D.; Contel, M.; Garrido, J. Hexanuclear mercury-silver complexes. Novel coordination for bridging mesityl and triflate Groups. Inorg. Chem. 1998, 37, 133-135 and references therein.
13. Contel, M.; Villuendas, P.R.; Fernández-Gallardo, J.; Alonso, P.J.; Vincent, J.-M.; Fish, R.H. Fluorocarbon soluble copper(II) carboxylate complexes with nonfluoroponytailed nitrogen ligands as precatalysts for the oxidation of alkenols and alcohols under fluorous biphasic or thermomorphic modes: structural and mechanistic aspects. Inorg. Chem. 2005, 44, 9771-9778 and references therein.
14. 2] (L = 1,4,7,10,13-pentaoxacyclopentadecane). J. Chem. Soc., Dalton Trans. 1995, 3917-3924.
15. 2]. Inorg. Chem. 1990, 29, 4404-4407.
16. Bardaji, M.; Calhorda, M.J.; Costa, P.J.; Jones, P.G.; Laguna, A.; Pérez, M.R.; Villacampa, M.D. Synthesis, structural characterization and theoretical studies of gold(I) and gold(I)-gold(III) thiolate complexes: quenching of gold(I) thiolate luminescence. Inorg. Chem. 2006, 45, 1059-1068.
17. 5)( μ -dppf)] (dppf = 1,1'-bis(diphenylphosphino)ferrocene). Reactivity toward various metallic fragments. Organometallics 1999, 18, 3142-3148. (Pubitemid 129655751)
18. 2}]OTf (dppf = 1,1'- bis(diphenylphosphino)ferrocene). Organometallics 1997, 16, 3837-3844. (Pubitemid 127581734)
19. 2] (dppf = 1,1'-Bis(diphenylphosphino)ferrocene) and [S(AuPPh3)2{Au(C6F5)3}2]. Organometallics 1996, 15, 3412-3415. (Pubitemid 126562496)
20. Canales, S.; Crespo, O.; Gimeno, M.C.; Jones, P.G.; Laguna, A.; Mendizábal, F. Mixed Gold(I)-Gold(III) complexes with bridging selenido ligands. Theoretical studies of the Gold(I)-Gold(III) interactions. Organometallics 2001, 20, 4812-4818. (Pubitemid 35349221)
21. Von Petersen, A. Complexes of gold(I) with thioethers and chloride or phosphines as ligands. Archiv. Pharma. 1991, 324, 411.
22. Kostin, G.A.; Mashukov, V.I.; Torgov, V.G.; Kalchenko, V.I.; Drapaillo, A.B. Reduction kinetics of gold(III) complexes with calix[4]arenes modified by thioether groups on the upper rim. Z. Neorg. Khim. 2006, 51, 536-542.
23. Zhong, C.J.; Porter, M.D. Evidence for carbon-sulfur bond cleavage in spontaneously adsorbed organosulfide-based monolayers at gold. J. Am. Chem. Soc. 1994, 116, 11616-11617 and references therein. (Pubitemid 127657992)
24. Hughes, M.D.; Xu, Y.-J.; Jenkins, P.; McMorn, P.; Landon, P.; Enache, D.I.; Carley, A.F.; Attard, G.A.; Hutchings, G.J.; King, F.; et al. Tunable gold catalysts for selective hydrocarbon oxidation under mild conditions. Nature 2005, 437, 1132-1135. (Pubitemid 41509347)
25. Guan, B.; Xing, D.; Cai, G.; Wan, X.; Yu, N.; Fang, Z.; Yang, L.; Shi, Z. Highly selective aerobic oxidation of alcohol catalyzed by a gold(I) complex with an anionic ligand. J. Am. Chem. Soc. 2005, 127, 18004-18005. (Pubitemid 43038453)
26. Xing, D.; Guan, B.; Cai, G.; Fang, Z.; Yang, L.; Shi, Z. Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water. Org. Lett. 2006, 8, 693-696. (Pubitemid 43341992)
27. Das, A.; Chaudhury, R.; Liu, R.-S. Gold-catalyzed oxidative cleavage of aryl-substituted alkynyl ethers using molecular oxygen. Simultaneous degradation of C-H and single and triple carbon-carbon bonds under ambient conditions. Chem. Commun. 2009, 4046-4048.
28. De Vos, D.E.; Sels, B.F. Gold Redox Catalysis for selective oxidation of methane to methanol. Angew. Chem. Int. Ed. 2004, 43, 2-4.
29. Jones, C.J.; Taube, D.; Ziatdinov, V.R.; Periana, R.A.; Nielsen, R.J.; Oxgaard, J.; Goddard, W.A., III. Selective oxidation of methane to methanol catalyzed, with C-H activation, by homogeneous, cationic gold. Angew. Chem. Int. Ed. 2004, 43, 4626-4629. (Pubitemid 39359127)
30. Gasparrini, F.; Giovannoli, M.; Misiti, D.; Natile, G.; Palmieri, G. Gold(III) catalyzed oxidation of sulfides to sulfoxides by nitric acid under phase-transfer conditions: A new synthesis of sulfoxides. Tetrahedron 1983, 19, 3181-3184.
31. Yuan, Y.; Bian, Y Gold(III) catalyzed oxidation of sulfides to sulfoxides with hydrogen peroxide. Tetrahedron Lett. 2007, 48, 8518-8520. (Pubitemid 350016184)
32. 2 oxidation at ambient temperature. Diversity-based discovery and mechanistic investigation of thioether oxidation by the Au(III)Cl2NO3(thioether)/O2 system. J. Am. Chem. Soc. 2001, 123, 1625-1635. (Pubitemid 32179410)
33. Boring, E.; Geletii, Y.V.; Hill, C.L. Catalytic aerobic oxidation of 2-chloroethyl ethylsulfide, a mustard stimulant, under ambient conditions. Effect of solvents, ligands, and transition metals on reactivity. J. Mol. Catal. A: Chem. 2001, 176, 49-63.
34. Shul'pin, G.B.; Shilov, A.E.; Süss-Fink, G. Alkane oxygenation catalysed by gold complexes. Tetrahedron Lett. 2001, 42, 7253-7256. (Pubitemid 32916157)
35. Li, X.-Q.; Li, C.; Song, F.-B.; Zhang, C.J. A first homogeneous gold(III)-catalysed epoxidation of aromatic alkenes. Chem. Res. 2007, 722-724.
36. Aschwanden, L.; Mallat, T.; Grunwaldt, J.-D.; Krumeich, F.; Baiker, A. Gold-catalyzed aerobic oxidation of dibenzylamine: Homogeneous or heterogeneous catalysis? J. Mol. Catal A: Chem. 2009, 300, 111-115.
37. Zhang, G.; Cui, L.; Wang, Y.; Zhang, L. Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes. J. Am. Chem. Soc. 2010, 132, 1474-1475 and references therein.
38. Liu, X.; Liu. D.; Yang, Y.; Yao, H. Complex catalyst for synthesis of carbonate ester by alcohol homogeneous phase oxidation of carbonyl. CN1792453(A), 2006.
39. Sundermeyer, J.; Jost, C. Liquid phase oxidation of organic compounds using peroxides in the presence of homogeneous sol. gold or silver complex catalysts. DE10041510(A1), 2001.
40. Elie, B.T.; Levine, C.; Ubarretxena-Belandia, I.; Varela-Ramirez, A.; Aguilera, R.J.; Ovalle, R.; Contel, M. Water-soluble (phosphane)gold(I) complexes - applications as recyclable catalysts in a three-component coupling reaction and as antimicrobial and anticancer agents. Eur. J. Inorg. Chem. 2009, 3421-3430 and references therein.
41. Novelli, F.; Recine, M.; Sparatore, F.; Juliano, C. Gold(I) complexes as antimicrobial agents. Farmaco 1999, 232-236. (Pubitemid 29259826)
42. Fillat, M.F.; Gimeno, M.C.; Laguna, A.; Latorre, E.; Ortego, L.; Villacampa, M.D. Synthesis, structure and bactericide activity of (aminophosphane)gold(I) thiolate complexes. Eur. J. Inorg. Chem. 2011, 1487-1495 and references therein.
43. Sreekanth, A.; Fun, H.-K.; Kurup, M.R.P. Formation of first gold(III) complex of an N(4)-disubstituted thiosemicarbazone derived from 2-benzoylpyridine: structural and spectral studies. Inorg. Chem. Commun. 2004, 7, 1250 and references therein.
44. Ray, S.; Mohan, R.; Singh, J.K.; Samantaray, M.K.; Shaikh, M.M.; Panda, D.; Ghosh, P. Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes. J. Am. Chem. Soc. 2007, 129, 15042-15043.
45. Kasuga, N.C.; Sugie, A.; Nomiya, K. Syntheses, structures and antimicrobial activities of water-soluble silver(I)-oxygen bonding complexes with chiral and racemic camphanic acid (Hca) ligands. Dalton Trans. 2004, 3732-3740.
46. Melaiye, A.; Simons, R.S.; Milsted, A.; Pingitore, F.; Wesdemiotis, C.; Tessier, C.A.; Youngs, W.J. Formation of water-soluble pincer silver(I)-carbene complexes: A novel antimicrobial agent. J. Med. Chem. 2004, 47, 973-977. (Pubitemid 38176799)
47. Melaiye, A.; Sun, Z.H.; Hindi, K.; Milsted, A.; Ely, D.; Reneker, D.H.; Tessier, C.A.; Youngs, W.J. Silver(I)-imidazole cyclophane gem-diol complexes encapsulated by electrospun tecophilic nanofibers: Formation of nanosilver particles and antimicrobial activity. J. Am. Chem. Soc. 2005, 127, 2285-2291. (Pubitemid 40270533)
48. Roland, S.; Jolivat, C.; Cresteil, T.; Eloy, L.; Bouhours, P.; Hequet, A.; Mansuy, V.; Vanucci, C.; Paris, J.-M. Investigation of a series of silver-N-Heterocyclic carbenes as antibacterial agents: Activity, synergistic effects, and cytotoxicity. Chem. Eur. J. 2011, 17, 1442-1446.
49. Kascatan-Nebioglu, A.; Melaiye, A.; Hindi, K.; Durmus, S.; Panzner, M.J.; Hogue, L.A.; Mallett, R.J.; Hovis, CE.; Coughenour, M.; Crosby, S.D.; et al. Synthesis from caffeine of a mixed N-heterocyclic carbene-silver acetate complex active against resistant respiratory pathogens. J. Med. Chem. 2006, 49, 6811-6818. (Pubitemid 44749748)
50. Hindi, K.M.; Siciliano, T.J.; Durmus, S.; Panzner, M.J.; Medvetz, D.A.; Reddy, D.V.; Hogue, LA.; Hovis, CE.; Hilliard, J.K.; Mallet, R.J.; et al. Synthesis, stability, and antimicrobial studies of electronically tuned silver acetate N-heterocyclic carbenes. J. Med. Chem. 2008, 51, 1577-1583. (Pubitemid 351438841)
51. Panzner, M.J.; Deeraksa, A.; Smith, A.; Wright, B.D.; Hindi, K.M.; Kascatan-Nebioglu, A.; Torres, A.G.; Judy, B.M.; Hovis, C.E.; Hilliard, J.K.; et al. Synthesis and in vitro efficacy studies of silver carbene complexes on biosafety level 3 bacteria. Eur. J. Inorg. Chem. 2009, 1739-1745.
52. Zhang, J.-A.; Pan, M.; Zhang, J.-Y.; Zhagn, H.-K.; Fan, Z.-J.; Kang, B.-S. Syntheses, structures and bioactivities of silver(I) complexes with a tridentate heterocyclic N- and S-ligand. Polyhedron 2009, 28, 145-149.
53. van Waasbergen, L.G.; Fajdetic, I.; Fianchini, M.; Dias, H.V.R. Antimicrobial properties of highly fluorinated tris(pyrazolyl)borates. J. Inorg. Biochem. 2007, 101, 1180-1183 and references therein.
54. Montoya, J.; Varela-Ramirez, A.; Estrada, A.; Martinez, L.E.; Garza, K.; Aguilera, R.J. A fluorescence-based rapid screening assay for cytotoxic compounds. Biochem. Biophys. Res. Commun. 2004, 325, 1517-1523. (Pubitemid 39535934)
55. Shaik, N.; Martinez, A.; Augustin, I.; Giovinazzo, H.; Varela, A.; Aguilera, R.; Sanaú, M.; Contel, M. Synthesis of apoptosis-inducing iminophosphorane organogold(III) complexes and study of their interactions with biomolecular targets. Inorg. Chem. 2009, 48, 1577-1587.
56. Kanda, T.; Sullivan, K.F.; Wahl, G.M. Histone-GFP fusion protein enables sensitive analysis of chromosome dynamics in living mammalian cells. Curr. Biol. 1998, 8, 377-385. (Pubitemid 28173996)
57. Askanas, V.; Engel, W.K. A new program for investigating adult human skeletal muscle grown aneurally in tissue culture. Neurology 1975, 25, 58.
58. Lema, C.; Varela-Ramirez, A.; Aguilera, R.J. Differential nuclear staining assay for high-throughput screening to identify cytotoxic compounds. 2011, Curr. Cell. Biochem., Submitted.