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Volumn 55, Issue 7, 2012, Pages 3201-3215

Design and synthesis of active site inhibitors of the human farnesyl pyrophosphate synthase: Apoptosis and inhibition of ERK phosphorylation in multiple myeloma cells

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; GERANYLTRANSFERASE; MITOGEN ACTIVATED PROTEIN KINASE; RISEDRONIC ACID; ZOLEDRONIC ACID;

EID: 84859804837     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201657x     Document Type: Article
Times cited : (47)

References (40)
  • 1
    • 80054866000 scopus 로고    scopus 로고
    • Targeting protein prenylation for cancer theraphy
    • Berndt, N.; Hamilton, A. D.; Sebti, S. M. Targeting protein prenylation for cancer theraphy Nature Rev. 2011, 11, 775-791
    • (2011) Nature Rev. , vol.11 , pp. 775-791
    • Berndt, N.1    Hamilton, A.D.2    Sebti, S.M.3
  • 5
    • 78649813078 scopus 로고    scopus 로고
    • Molecular targets of the nitrogen containing bisphosphonates: The molecular pharmacology of prenyl synthase inhibition
    • Review: Dunford, J. E. Molecular targets of the nitrogen containing bisphosphonates: the molecular pharmacology of prenyl synthase inhibition Curr. Pharm. Des. 2010, 16, 2961-2969
    • (2010) Curr. Pharm. Des. , vol.16 , pp. 2961-2969
    • Dunford, J.E.1
  • 7
    • 33644539542 scopus 로고    scopus 로고
    • A new endogenous ATP analog (ApppI) inhibits the mitochondrial adenine nucleotide translocase (ANT) and is responsible for the apoptosis induced by nitrogen-containing bisphosphonates
    • Mönkkönen, H.; Auriola, S.; Lehenkari, P.; Kellinsalmi, M.; Hassinen, I. E.; Vepsäläinen, J.; Mönkkönen, J. A new endogenous ATP analog (ApppI) inhibits the mitochondrial adenine nucleotide translocase (ANT) and is responsible for the apoptosis induced by nitrogen-containing bisphosphonates Br. J. Pharmacol. 2006, 147, 437-445
    • (2006) Br. J. Pharmacol. , vol.147 , pp. 437-445
    • Mönkkönen, H.1    Auriola, S.2    Lehenkari, P.3    Kellinsalmi, M.4    Hassinen, I.E.5    Vepsäläinen, J.6    Mönkkönen, J.7
  • 8
    • 70350212804 scopus 로고    scopus 로고
    • The level ofATP analogs and isopentenyl pyrophosphate correlates with zoledronic acid-induced apoptosis in cancer cells in vitro
    • Mitrofan, L. M.; Pelkonen, J.; Mönkkönen, J. The level ofATP analogs and isopentenyl pyrophosphate correlates with zoledronic acid-induced apoptosis in cancer cells in vitro Bone 2009, 45, 1153-1160
    • (2009) Bone , vol.45 , pp. 1153-1160
    • Mitrofan, L.M.1    Pelkonen, J.2    Mönkkönen, J.3
  • 9
    • 33846804360 scopus 로고    scopus 로고
    • Nonpeptide antigens, presentation mechanisms, and immunological memory of human VÎ2Vδ2 T cells: Discriminating friends from foe through the recognition of prenyl pyrophosphate antigens
    • Review: Morita, C. T.; Jin, C.; Sarikonda, G.; Wang, H. Nonpeptide antigens, presentation mechanisms, and immunological memory of human VÎ2Vδ2 T cells: discriminating friends from foe through the recognition of prenyl pyrophosphate antigens Immunol. Rev. 2007, 215, 59-76
    • (2007) Immunol. Rev. , vol.215 , pp. 59-76
    • Morita, C.T.1    Jin, C.2    Sarikonda, G.3    Wang, H.4
  • 10
    • 33748861780 scopus 로고    scopus 로고
    • Activity of Nitrogen-containing and non-nitrogen-containing bisphosphonates on tumor cell lines
    • Zhang, Y.; Leon, A.; Song, Y.; Studer, D.; Haase, C.; Koscielski, L. A.; Oldfield, E. Activity of Nitrogen-containing and non-nitrogen-containing bisphosphonates on tumor cell lines J. Med. Chem. 2006, 49, 5804-5814
    • (2006) J. Med. Chem. , vol.49 , pp. 5804-5814
    • Zhang, Y.1    Leon, A.2    Song, Y.3    Studer, D.4    Haase, C.5    Koscielski, L.A.6    Oldfield, E.7
  • 12
    • 77955305765 scopus 로고    scopus 로고
    • Delivery of zoledronic acid encapsulated in folate-targeted liposome results in potent in vitro cytotoxic activity on tumor cells
    • Shmeeda, H.; Amitay, Y.; Gorin, J.; Tsemach, D.; Mak, L.; Ogorka, J.; Kumar, S.; Zhang, J. A.; Gabizon, A. Delivery of zoledronic acid encapsulated in folate-targeted liposome results in potent in vitro cytotoxic activity on tumor cells J. Controlled Release 2010, 146, 76-83
    • (2010) J. Controlled Release , vol.146 , pp. 76-83
    • Shmeeda, H.1    Amitay, Y.2    Gorin, J.3    Tsemach, D.4    Mak, L.5    Ogorka, J.6    Kumar, S.7    Zhang, J.A.8    Gabizon, A.9
  • 13
    • 0035146537 scopus 로고    scopus 로고
    • Structure-activity relationship for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates
    • Dunford, J. E.; Thompson, K.; Coxon, F. P.; Luckma, S. P.; Hahn, F. M.; Poulter, C. D.; Ebetino, F. H.; Rogers, M. J. Structure-activity relationship for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates J. Pharmacol. Exp. Ther. 2001, 296, 235-242
    • (2001) J. Pharmacol. Exp. Ther. , vol.296 , pp. 235-242
    • Dunford, J.E.1    Thompson, K.2    Coxon, F.P.3    Luckma, S.P.4    Hahn, F.M.5    Poulter, C.D.6    Ebetino, F.H.7    Rogers, M.J.8
  • 15
    • 41849123834 scopus 로고    scopus 로고
    • Structure-activity relationship among the nitrogen containing bisphosphonates in clinical use and other analogues: Time-dependent inhibition of human farnesyl pyrophosphate synthase
    • Dunford, J. E.; Kwaasi, A. A.; Rogers, M. J.; Barnett, B. L.; Ebetino, F. H.; Russell, R. G. G.; Oppermann, U.; Kavanagh, K. L. Structure-activity relationship among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase J. Med. Chem. 2008, 51, 2187-2195
    • (2008) J. Med. Chem. , vol.51 , pp. 2187-2195
    • Dunford, J.E.1    Kwaasi, A.A.2    Rogers, M.J.3    Barnett, B.L.4    Ebetino, F.H.5    Russell, R.G.G.6    Oppermann, U.7    Kavanagh, K.L.8
  • 17
  • 21
    • 80054095438 scopus 로고    scopus 로고
    • A novel bisphosphonate inhibitor of squalene synthase combined with a statin or a nitrogenous bisphosphonate in vitro
    • Wasko, B. M.; Smits, J. P.; Shull, L. W.; Wiemer, D. F.; Hohl, R. J. A novel bisphosphonate inhibitor of squalene synthase combined with a statin or a nitrogenous bisphosphonate in vitro J. Lipid. Res. 2011, 52, 1957-1964
    • (2011) J. Lipid. Res. , vol.52 , pp. 1957-1964
    • Wasko, B.M.1    Smits, J.P.2    Shull, L.W.3    Wiemer, D.F.4    Hohl, R.J.5
  • 24
    • 34447307124 scopus 로고    scopus 로고
    • New catalysts for Suzuki-Miyaura coupling reactions of heteroatom-substituted heteroaryl chlorides
    • Guram, A. S.; Wang, X.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J. New catalysts for Suzuki-Miyaura coupling reactions of heteroatom-substituted heteroaryl chlorides J. Org. Chem. 2007, 72, 5104-5112
    • (2007) J. Org. Chem. , vol.72 , pp. 5104-5112
    • Guram, A.S.1    Wang, X.2    Bunel, E.E.3    Faul, M.M.4    Larsen, R.D.5    Martinelli, M.J.6
  • 25
    • 50549091784 scopus 로고    scopus 로고
    • Highly efficient Suzuki-Miyaura coupling of heterocyclic substrates through rational reaction design
    • Fleckenstein, C. A.; Plenio, H. Highly efficient Suzuki-Miyaura coupling of heterocyclic substrates through rational reaction design Chem.-Eur. J. 2008, 14, 4267-4279
    • (2008) Chem.-Eur. J. , vol.14 , pp. 4267-4279
    • Fleckenstein, C.A.1    Plenio, H.2
  • 26
    • 31144463668 scopus 로고    scopus 로고
    • Solid state and solution behaviour of N -(2-pyridyl)- and N -(4-methyl-2-pyridyl)aminomethane-1,1-diphosphonic acids
    • Matczak-Jon, E.; Ślepokura, K.; Kafarski, P. Solid state and solution behaviour of N -(2-pyridyl)- and N -(4-methyl-2-pyridyl)aminomethane-1, 1-diphosphonic acids J. Mol. Struct. 2006, 782, 81-93
    • (2006) J. Mol. Struct. , vol.782 , pp. 81-93
    • Matczak-Jon, E.1    Ślepokura, K.2    Kafarski, P.3
  • 28
    • 0033527417 scopus 로고    scopus 로고
    • Nitrogen-containing bisphosphonates as carbocation transition state analogs for isoprenoid biosynthesis
    • Martin, M. B.; Arnold, W.; Heath, H. T., III; Urbina, J. A.; Oldfield, E. Nitrogen-containing bisphosphonates as carbocation transition state analogs for isoprenoid biosynthesis Biochem. Biophys. Res. Commun. 1999, 263, 754-758
    • (1999) Biochem. Biophys. Res. Commun. , vol.263 , pp. 754-758
    • Martin, M.B.1    Arnold, W.2    Heath III, H.T.3    Urbina, J.A.4    Oldfield, E.5
  • 29
    • 79954989286 scopus 로고    scopus 로고
    • Correlation between time-dependent inhibition of human farnesyl pyrophosphate synthase and blockade of mevalonate pathway by nitrogen-containing bisphosphonate in cultured cells
    • Räikkönen, J.; Taskinen, M.; Dunford, J. E.; Mönkkönen, H.; Auriola, S.; Mönkkönen, J. Correlation between time-dependent inhibition of human farnesyl pyrophosphate synthase and blockade of mevalonate pathway by nitrogen-containing bisphosphonate in cultured cells Biochem. Biophys. Res. Commun. 2011, 407, 663-667
    • (2011) Biochem. Biophys. Res. Commun. , vol.407 , pp. 663-667
    • Räikkönen, J.1    Taskinen, M.2    Dunford, J.E.3    Mönkkönen, H.4    Auriola, S.5    Mönkkönen, J.6
  • 30
    • 0028288134 scopus 로고
    • Yeast farnesyl-diphosphate synthase: Site-directed mutagenesis of residues in highly conserved prenyltransferase domains i and II
    • Song, L.; Poulter, C. D. Yeast farnesyl-diphosphate synthase: site-directed mutagenesis of residues in highly conserved prenyltransferase domains I and II Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3044-3048
    • (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.91 , pp. 3044-3048
    • Song, L.1    Poulter, C.D.2
  • 31
    • 33746836518 scopus 로고    scopus 로고
    • The Crystal structure of human geranylgeranyl pyrophosphate synthase reveals a novel hexameric arrangement and inhibitory product binding
    • Kavanagh, K. L.; Dunford, J. E.; Bunkoczi, G.; Russell, R. G. G.; Oppermann, U. The Crystal structure of human geranylgeranyl pyrophosphate synthase reveals a novel hexameric arrangement and inhibitory product binding J. Biol. Chem. 2006, 281, 22004-22012
    • (2006) J. Biol. Chem. , vol.281 , pp. 22004-22012
    • Kavanagh, K.L.1    Dunford, J.E.2    Bunkoczi, G.3    Russell, R.G.G.4    Oppermann, U.5
  • 32
    • 1642310340 scopus 로고    scopus 로고
    • Glide : €‰ a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening
    • Halgren, T. A.; Murphy, R. B.; Friesner, R. A.; Beard, H. S.; Frye, L. L.; Pollard, W. T.; Banks, J. L. Glide: €‰ a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening J. Med. Chem. 2004, 47, 1750-1759
    • (2004) J. Med. Chem. , vol.47 , pp. 1750-1759
    • Halgren, T.A.1    Murphy, R.B.2    Friesner, R.A.3    Beard, H.S.4    Frye, L.L.5    Pollard, W.T.6    Banks, J.L.7
  • 35
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray Diffraction Data Collected in Oscillation mode
    • Carter, C. W. Jr. Sweet, R. M. Elsevier: New York, Vol. Macromolecular Crystallography, Part A
    • Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation mode. In Methods in Enzymology; Carter, C. W., Jr.; Sweet, R. M., Eds.; Elsevier: New York, 1997; Vol. 276, Macromolecular Crystallography, Part A, pp 307-326.
    • (1997) Methods in Enzymology , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2
  • 37
    • 13244281317 scopus 로고    scopus 로고
    • Coot: Model-building tools for molecular graphics
    • Emsley, P.; Cowtan, K. Coot: model-building tools for molecular graphics Acta Crystallogr., Sect. D 2004, 60, 2126-2132
    • (2004) Acta Crystallogr., Sect. D , vol.60 , pp. 2126-2132
    • Emsley, P.1    Cowtan, K.2
  • 40
    • 50249187635 scopus 로고    scopus 로고
    • Overcoming undesirable CYP1A2 inhibition of pyridylnaphthalene-type aldosterone synthase inhibitors: Influence of heteroaryl derivatization on potency and selectivity
    • Heim, R.; Lucas, S.; Grombein, C. M.; Ries, C.; Schewe, K. E.; Negri, M.; Müller-Vieira, U.; Birk, B.; Hartmann, R. W. Overcoming undesirable CYP1A2 inhibition of pyridylnaphthalene-type aldosterone synthase inhibitors: influence of heteroaryl derivatization on potency and selectivity J. Med. Chem. 2008, 51, 5064-5074
    • (2008) J. Med. Chem. , vol.51 , pp. 5064-5074
    • Heim, R.1    Lucas, S.2    Grombein, C.M.3    Ries, C.4    Schewe, K.E.5    Negri, M.6    Müller-Vieira, U.7    Birk, B.8    Hartmann, R.W.9


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