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Volumn 153, Issue , 2015, Pages 322-333

Half-sandwich rhodium(III) transfer hydrogenation catalysts: Reduction of NAD+ and pyruvate, and antiproliferative activity

Author keywords

Anticancer; NAD+; NADH; Organo rhodium; Pyruvate; Transfer hydrogenation

Indexed keywords

1 BIPHENYL 2,3,4,5 TETRAMETHYL CYCLOPENTADIENYL; 1 PHENYL 2,3,4,5 TETRAMETHYLCYCLOPENTADIENYL; 1,10 PHENANTHROLINE; 2,2' BIPYRIDINE; BENZENESULFONAMIDE DERIVATIVE; ETHYLENEDIAMINE; FORMIC ACID; LACTATE DEHYDROGENASE; LACTIC ACID; N (2 AMINOETHYL) 4 (TRIFLUOROMETHYL)BENZENESULFONAMIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE; PENTAMETHYLCYCLOPENTADIENYL; PYRUVIC ACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; RHODIUM COMPLEX; RHODIUM III COMPLEX; UNCLASSIFIED DRUG; COORDINATION COMPOUND; FORMIC ACID DERIVATIVE; PYRUVIC ACID DERIVATIVE; RHODIUM;

EID: 84951567825     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2015.10.008     Document Type: Article
Times cited : (55)

References (56)
  • 1
    • 80053508338 scopus 로고    scopus 로고
    • The development of aqueous transfer hydrogenation catalysts
    • S. Ogo, T. Matsumoto, and A. Robertson The development of aqueous transfer hydrogenation catalysts Dalton Trans. 40 2011 10304 10310
    • (2011) Dalton Trans. , vol.40 , pp. 10304-10310
    • Ogo, S.1    Matsumoto, T.2    Robertson, A.3
  • 2
    • 74849121420 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation in water with platinum group metal catalysts
    • X. Wu, C. Wang, and J. Xiao Asymmetric transfer hydrogenation in water with platinum group metal catalysts Platin. Met. Rev. 54 2010 3 19
    • (2010) Platin. Met. Rev. , vol.54 , pp. 3-19
    • Wu, X.1    Wang, C.2    Xiao, J.3
  • 3
    • 33644661038 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation: Chiral ligands and applications
    • S. Gladiali, and E. Alberico Asymmetric transfer hydrogenation: chiral ligands and applications Chem. Soc. Rev. 35 2006 226 236
    • (2006) Chem. Soc. Rev. , vol.35 , pp. 226-236
    • Gladiali, S.1    Alberico, E.2
  • 4
    • 33644660116 scopus 로고    scopus 로고
    • Mechanistic aspects of transition metal-catalyzed hydrogen transfer reactions
    • P. Brandt, P.G. Andersson, J. Backvall, and J.S.M. Samec Mechanistic aspects of transition metal-catalyzed hydrogen transfer reactions Chem. Soc. Rev. 35 2006 237 248
    • (2006) Chem. Soc. Rev. , vol.35 , pp. 237-248
    • Brandt, P.1    Andersson, P.G.2    Backvall, J.3    Samec, J.S.M.4
  • 5
    • 78751548138 scopus 로고    scopus 로고
    • Artificial metalloenzymes based on the biotin-avidin technology: Enantioselective catalysis and beyond
    • T.R. Ward Artificial metalloenzymes based on the biotin-avidin technology: enantioselective catalysis and beyond Acc. Chem. Res. 44 2011 47 57
    • (2011) Acc. Chem. Res. , vol.44 , pp. 47-57
    • Ward, T.R.1
  • 6
    • 33646944868 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation of imines and iminiums catalyzed by a water-soluble catalyst in water
    • J. Wu, F. Wang, Y. Ma, X. Cui, L. Cun, J. Zhu, J. Deng, and B. Yu Asymmetric transfer hydrogenation of imines and iminiums catalyzed by a water-soluble catalyst in water Chem. Commun. 1766-1768 2006
    • (2006) Chem. Commun. , vol.1766-1768
    • Wu, J.1    Wang, F.2    Ma, Y.3    Cui, X.4    Cun, L.5    Zhu, J.6    Deng, J.7    Yu, B.8
  • 7
    • 33746448277 scopus 로고    scopus 로고
    • An outstanding catalyst for asymmetric transfer hydrogenation in aqueous solution and formic acid/triethylamine
    • D.S. Matharu, D.J. Morris, G.J. Clarkson, and M. Wills An outstanding catalyst for asymmetric transfer hydrogenation in aqueous solution and formic acid/triethylamine Chem. Commun. 2006 3232 3234
    • (2006) Chem. Commun. , pp. 3232-3234
    • Matharu, D.S.1    Morris, D.J.2    Clarkson, G.J.3    Wills, M.4
  • 8
    • 84920394762 scopus 로고    scopus 로고
    • Transition-metal-mediated uncaging in living human cells - An emerging alternative to photolabile protecting groups
    • T. Völker, and E. Meggers Transition-metal-mediated uncaging in living human cells - an emerging alternative to photolabile protecting groups Curr. Opin. Chem. Biol. 25 2015 48 54
    • (2015) Curr. Opin. Chem. Biol. , vol.25 , pp. 48-54
    • Völker, T.1    Meggers, E.2
  • 10
    • 84873279753 scopus 로고    scopus 로고
    • Metal complex catalysis in living biological systems
    • P.K. Sasmal, C.N. Streu, and E. Meggers Metal complex catalysis in living biological systems Chem. Commun. 49 2013 1581 1587
    • (2013) Chem. Commun. , vol.49 , pp. 1581-1587
    • Sasmal, P.K.1    Streu, C.N.2    Meggers, E.3
  • 11
  • 12
  • 14
    • 84859768496 scopus 로고    scopus 로고
    • Organometallic ruthenium and iridium transfer-hydrogenation catalysts using coenzyme NADH as a cofactor
    • S. Betanzos-Lara, Z. Liu, A. Habtemariam, A.M. Pizarro, B. Qamar, and P.J. Sadler Organometallic ruthenium and iridium transfer-hydrogenation catalysts using coenzyme NADH as a cofactor Angew. Chem. Int. Ed. 51 2012 3897 3900
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3897-3900
    • Betanzos-Lara, S.1    Liu, Z.2    Habtemariam, A.3    Pizarro, A.M.4    Qamar, B.5    Sadler, P.J.6
  • 17
    • 84931274612 scopus 로고    scopus 로고
    • Contrasting anticancer activity of half-sandwich iridium(III) complexes bearing functionally diverse 2-phenylpyridine ligands
    • A.J. Millett, A. Habtemariam, I. Romero-Canelón, G.J. Clarkson, and P.J. Sadler Contrasting anticancer activity of half-sandwich iridium(III) complexes bearing functionally diverse 2-phenylpyridine ligands Organometallics 34 2015 2683 2694
    • (2015) Organometallics , vol.34 , pp. 2683-2694
    • Millett, A.J.1    Habtemariam, A.2    Romero-Canelón, I.3    Clarkson, G.J.4    Sadler, P.J.5
  • 22
    • 84896556750 scopus 로고    scopus 로고
    • Recent trends in biomimetic NADH regeneration
    • T. Quinto, V. Köhler, and T.R. Ward Recent trends in biomimetic NADH regeneration Top. Catal. 57 2014 321 331
    • (2014) Top. Catal. , vol.57 , pp. 321-331
    • Quinto, T.1    Köhler, V.2    Ward, T.R.3
  • 23
  • 24
    • 84898004861 scopus 로고    scopus 로고
    • Cofactor regeneration - An important aspect of biocatalysis
    • V. Uppada, S. Bhaduri, and S.B. Noronha Cofactor regeneration - an important aspect of biocatalysis Curr. Sci. 106 2014 946 957
    • (2014) Curr. Sci. , vol.106 , pp. 946-957
    • Uppada, V.1    Bhaduri, S.2    Noronha, S.B.3
  • 25
    • 79960999137 scopus 로고    scopus 로고
    • Chemically engineered papain as artificial formate dehydrogenase for NAD(P)H regeneration
    • P. Haquette, B. Talbi, L. Barilleau, N. Madern, C. Fosse, and M. Salmain Chemically engineered papain as artificial formate dehydrogenase for NAD(P)H regeneration Org. Biomol. Chem. 9 2011 5720 5727
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 5720-5727
    • Haquette, P.1    Talbi, B.2    Barilleau, L.3    Madern, N.4    Fosse, C.5    Salmain, M.6
  • 26
    • 35848962068 scopus 로고    scopus 로고
    • Water-soluble phenanthroline complexes of rhodium, iridium and ruthenium for the regeneration of NADH in the enzymatic reduction of ketones
    • J. Canivet, G. Süss-Fink, and P. Štěpnička Water-soluble phenanthroline complexes of rhodium, iridium and ruthenium for the regeneration of NADH in the enzymatic reduction of ketones Eur. J. Inorg. Chem. 2007 4736 4742
    • (2007) Eur. J. Inorg. Chem. , pp. 4736-4742
    • Canivet, J.1    Süss-Fink, G.2    Štěpnička, P.3
  • 28
    • 11844296083 scopus 로고    scopus 로고
    • Bioorganometallic chemistry: Biocatalytic oxidation reactions with biomimetic NAD +/NADH co-factors and [Cp∗Rh(bpy)H] + for selective organic synthesis
    • J. Lutz, F. Hollmann, T.V. Ho, A. Schnyder, R.H. Fish, and A. Schmid Bioorganometallic chemistry: biocatalytic oxidation reactions with biomimetic NAD +/NADH co-factors and [Cp∗Rh(bpy)H] + for selective organic synthesis J. Organomet. Chem. 689 2004 4783 4790
    • (2004) J. Organomet. Chem. , vol.689 , pp. 4783-4790
    • Lutz, J.1    Hollmann, F.2    Ho, T.V.3    Schnyder, A.4    Fish, R.H.5    Schmid, A.6
  • 31
    • 33750193289 scopus 로고    scopus 로고
    • On water and in air: Fast and highly chemoselective transfer hydrogenation of aldehydes with iridium catalysts
    • X. Wu, J. Liu, X. Li, A. Zanotti-Gerosa, F. Hancock, D. Vinci, J. Ruan, and J. Xiao On water and in air: fast and highly chemoselective transfer hydrogenation of aldehydes with iridium catalysts Angew. Chem. Int. Ed. 45 2006 6718 6722
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 6718-6722
    • Wu, X.1    Liu, J.2    Li, X.3    Zanotti-Gerosa, A.4    Hancock, F.5    Vinci, D.6    Ruan, J.7    Xiao, J.8
  • 33
    • 79956196513 scopus 로고    scopus 로고
    • Metal complexes as DNA intercalators
    • H.K. Liu, and P.J. Sadler Metal complexes as DNA intercalators Acc. Chem. Res. 44 2011 349 359
    • (2011) Acc. Chem. Res. , vol.44 , pp. 349-359
    • Liu, H.K.1    Sadler, P.J.2
  • 34
    • 79960748491 scopus 로고    scopus 로고
    • II catalysts in the asymmetric transfer hydrogenation of ketones and imines
    • II catalysts in the asymmetric transfer hydrogenation of ketones and imines Molecules 16 2011 5460 5495
    • (2011) Molecules , vol.16 , pp. 5460-5495
    • Václavík, J.1    Kačer, P.2    Kuzma, M.3    Červený, L.4
  • 35
    • 80053508338 scopus 로고    scopus 로고
    • The development of aqueous transfer hydrogenation catalysts
    • A. Robertson, T. Matsumoto, and S. Ogo The development of aqueous transfer hydrogenation catalysts Dalton Trans. 40 2011 10304 10310
    • (2011) Dalton Trans. , vol.40 , pp. 10304-10310
    • Robertson, A.1    Matsumoto, T.2    Ogo, S.3
  • 39
    • 64349112979 scopus 로고    scopus 로고
    • Organometallic osmium(II) arene anticancer complexes containing picolinate derivatives
    • S.H. van Rijt, A.F.A. Peacock, R.D.L. Johnstone, S. Parsons, and P.J. Sadler Organometallic osmium(II) arene anticancer complexes containing picolinate derivatives Inorg. Chem. 48 2009 1753 1762
    • (2009) Inorg. Chem. , vol.48 , pp. 1753-1762
    • Van Rijt, S.H.1    Peacock, A.F.A.2    Johnstone, R.D.L.3    Parsons, S.4    Sadler, P.J.5
  • 41
    • 84867877340 scopus 로고    scopus 로고
    • The NAD metabolome - A key determinant of cancer cell biology
    • A. Chiarugi, C. Dölle, R. Felici, and M. Ziegler The NAD metabolome - a key determinant of cancer cell biology Nat. Rev. 12 2012 741 752
    • (2012) Nat. Rev. , vol.12 , pp. 741-752
    • Chiarugi, A.1    Dölle, C.2    Felici, R.3    Ziegler, M.4
  • 43
    • 37549068090 scopus 로고    scopus 로고
    • +/NADPH in cellular functions and cell death: Regulation and biological consequences
    • +/NADPH in cellular functions and cell death: regulation and biological consequences Antioxid. Redox Signal. 10 2008 179 206
    • (2008) Antioxid. Redox Signal. , vol.10 , pp. 179-206
    • Ying, W.1
  • 45
    • 33744480316 scopus 로고    scopus 로고
    • NAD + and NADH in cellular functions and cell death
    • W. Ying NAD + and NADH in cellular functions and cell death Front. Biosci. 1 2006 3129 3148
    • (2006) Front. Biosci. , vol.1 , pp. 3129-3148
    • Ying, W.1
  • 46
    • 84922244573 scopus 로고    scopus 로고
    • Deactivation in homogeneous transition metal catalysis: Causes, avoidance, and cure
    • R.H. Crabtree Deactivation in homogeneous transition metal catalysis: causes, avoidance, and cure Chem. Rev. 115 2015 127 150
    • (2015) Chem. Rev. , vol.115 , pp. 127-150
    • Crabtree, R.H.1
  • 47
    • 84903281049 scopus 로고    scopus 로고
    • Neutralizing the detrimental effect of glutathione on precious metal catalysts
    • Y.M. Wilson, M. Dürrenberger, E.S. Nogueira, and T.R. Ward Neutralizing the detrimental effect of glutathione on precious metal catalysts J. Am. Chem. Soc. 136 2014 8928 8932
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 8928-8932
    • Wilson, Y.M.1    Dürrenberger, M.2    Nogueira, E.S.3    Ward, T.R.4
  • 48
    • 66249108601 scopus 로고    scopus 로고
    • Understanding the Warburg effect: The metabolic requirements of cell proliferation
    • M.G. Vander Heiden, L.C. Cantley, and C.B. Thompson Understanding the Warburg effect: the metabolic requirements of cell proliferation Science 324 2009 1029 1033
    • (2009) Science , vol.324 , pp. 1029-1033
    • Vander Heiden, M.G.1    Cantley, L.C.2    Thompson, C.B.3
  • 51
    • 84908552170 scopus 로고    scopus 로고
    • Progress towards ioorthogonal catalysis with organometallic compounds
    • T. Völker, F. Dempwolff, P.L. Graumann, and E. Meggers Progress towards ioorthogonal catalysis with organometallic compounds Angew. Chem. Int. Ed. 53 2014 10536 10540
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 10536-10540
    • Völker, T.1    Dempwolff, F.2    Graumann, P.L.3    Meggers, E.4
  • 52
    • 84901487587 scopus 로고    scopus 로고
    • Insight into the recognition, binding, and reactivity of catalytic metallodrugs targeting stem loop IIb of hepatitis C IRES RNA
    • S.S. Bradford, M.J. Ross, I. Fidai, and J.A. Cowan Insight into the recognition, binding, and reactivity of catalytic metallodrugs targeting stem loop IIb of hepatitis C IRES RNA Chem. Med. Chem. 9 2014 1275 1285
    • (2014) Chem. Med. Chem. , vol.9 , pp. 1275-1285
    • Bradford, S.S.1    Ross, M.J.2    Fidai, I.3    Cowan, J.A.4
  • 53
    • 84874640680 scopus 로고    scopus 로고
    • Kinetics and mechanisms of oxidative cleavage of HIV RRE RNA by rev-coupled transition metal chelates
    • J.C. Joyner, K.D. Keuper, and J.A. Cowan Kinetics and mechanisms of oxidative cleavage of HIV RRE RNA by rev-coupled transition metal chelates Chem. Sci. 4 2013 1707 1718
    • (2013) Chem. Sci. , vol.4 , pp. 1707-1718
    • Joyner, J.C.1    Keuper, K.D.2    Cowan, J.A.3
  • 55
    • 29344458540 scopus 로고    scopus 로고
    • Competition between glutathione and guanine for a ruthenium(II) arene anticancer complex: Detection of a sulfenato intermediate
    • F. Wang, J. Xu, A. Habtemariam, and P.J. Sadler Competition between glutathione and guanine for a ruthenium(II) arene anticancer complex: detection of a sulfenato intermediate J. Am. Chem. Soc. 127 2005 17734 17743
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 17734-17743
    • Wang, F.1    Xu, J.2    Habtemariam, A.3    Sadler, P.J.4


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