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Volumn 3, Issue 1, 2012, Pages 15-19

S-farnesyl-thiopropionic acid triazoles as potent inhibitors of isoprenylcysteine carboxyl methyltransferase

Author keywords

dipolar cycloaddition; Isoprenylcysteine carboxyl methyltransferase (Icmt); prenylcysteine; Ras; S farnesyl thiopropionic acid (FTPA); triazole

Indexed keywords

FARNESYL THIOPROPIONIC ACID TRIAZOLE; METHYLTRANSFERASE INHIBITOR; PROTEIN S ISOPRENYLCYSTEINE O METHYLTRANSFERASE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84855907701     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200106d     Document Type: Article
Times cited : (35)

References (32)
  • 1
    • 0024376173 scopus 로고
    • Ras Oncogenes in human cancer: A review
    • Bos, J. L. ras oncogenes in human cancer: A review Cancer Res. 1989, 49 (17) 4682-4689 (Pubitemid 19213607)
    • (1989) Cancer Research , vol.49 , Issue.17 , pp. 4682-4689
    • Bos, J.L.1
  • 4
    • 0034625181 scopus 로고    scopus 로고
    • Targeted inactivation of the isoprenyleysteine carboxyl methyltransferase gene causes mislocalization of K-Ras in mammalian cells
    • DOI 10.1074/jbc.C000079200
    • Bergo, M. O.; Leung, G. K.; Ambroziak, P.; Otto, J. C.; Casey, P. J.; Young, S. G. Targeted Inactivation of the Isoprenylcysteine Carboxyl Methyltransferase Gene Causes Mislocalization of K-Ras in Mammalian Cells J. Biol. Chem. 2000, 275, 17605-17610 (Pubitemid 30430806)
    • (2000) Journal of Biological Chemistry , vol.275 , Issue.23 , pp. 17605-17610
    • Bergo, M.O.1    Leung, G.K.2    Ambroziak, P.3    Otto, J.C.4    Casey, P.J.5    Young, S.G.6
  • 7
    • 25844452832 scopus 로고    scopus 로고
    • Synthesis of desthio prenylcysteine analogs: Sulfur is important for biological activity
    • DOI 10.1016/j.bmcl.2005.07.075, PII S0960894X05009893
    • Henriksen, B. S.; Anderson, J. L.; Hrycyna, C. A.; Gibbs, R. A. Synthesis of desthio prenylcysteine analogs: Sulfur is important for biological activity Bioorg. Med. Chem. Lett. 2005, 15, 5080-5083 (Pubitemid 41400188)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.22 , pp. 5080-5083
    • Henriksen, B.S.1    Anderson, J.L.2    Hrycyna, C.A.3    Gibbs, R.A.4
  • 8
    • 0029000603 scopus 로고
    • Farnesylcysteine Analogs to Probe Role of Prenylated Protein Methyltransferase
    • Ma, Y. T.; Gilbert, B. A.; Rando, R. R. Farnesylcysteine Analogs to Probe Role of Prenylated Protein Methyltransferase Methods Enzymol. 1995, 250, 226-234
    • (1995) Methods Enzymol. , vol.250 , pp. 226-234
    • Ma, Y.T.1    Gilbert, B.A.2    Rando, R.R.3
  • 9
    • 0028959539 scopus 로고
    • Farnesyl Derivatives of Rigid Carboxylic Acids-Inhibitors of ras-Dependent Cell Growth
    • Marciano, D.; Ben-Baruch, G.; Marom, M.; Egozi, Y.; Haklai, R.; Kloog, Y. Farnesyl Derivatives of Rigid Carboxylic Acids-Inhibitors of ras-Dependent Cell Growth J. Med. Chem. 1995, 38, 1267-1272
    • (1995) J. Med. Chem. , vol.38 , pp. 1267-1272
    • Marciano, D.1    Ben-Baruch, G.2    Marom, M.3    Egozi, Y.4    Haklai, R.5    Kloog, Y.6
  • 11
    • 0028234889 scopus 로고
    • Mechanistic studies on human platelet isoprenylated protein methyltransferase: Farnesylcysteine analogs block platelet aggregation without inhibiting the methyltransferase
    • DOI 10.1021/bi00184a009
    • Ma, Y. T.; Shi, Y. Q.; Lim, Y. H.; McGrail, S. H.; Ware, J. A.; Rando, R. R. Mechanistic Studies on Human Platelet Isoprenylated Protein Methyltransferase: Farnesylcysteine Analogs Block Platelet Aggregation without Inhibiting the Methyltransferase Biochemistry 1994, 33, 5414-5420 (Pubitemid 24162975)
    • (1994) Biochemistry , vol.33 , Issue.18 , pp. 5414-5420
    • Ma, Y.-T.1    Shi, Y.-Q.2    Young Hee Lim3    McGrail, S.H.4    Ware, J.A.5    Rando, R.R.6
  • 13
    • 23844534430 scopus 로고    scopus 로고
    • The isoprenoid substrate specificity of isoprenylcysteine carboxylmethyltransferase: Development of novel inhibitors
    • DOI 10.1074/jbc.M504982200
    • Anderson, J. L.; Henriksen, B. S.; Gibbs, R. A.; Hrycyna, C. A. The Isoprenoid Substrate Specificity of Isoprenylcysteine Carboxylmethyltransferase: Development of Novel Inhibitors J. Biol. Chem. 2005, 280, 29454-29461 (Pubitemid 41177018)
    • (2005) Journal of Biological Chemistry , vol.280 , Issue.33 , pp. 29454-29461
    • Anderson, J.L.1    Henriksen, B.S.2    Gibbs, R.A.3    Hrycyna, C.A.4
  • 14
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41 (14) 2596-2599 (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 15
    • 4344561878 scopus 로고    scopus 로고
    • Enantioselective synthesis of (-)-terpestacin and structural revision of siccanol using catalytic stereoselective fragment couplings and macrocyclizations
    • Chan, J.; Jamison, T. F. Enantioselective synthesis of (-)-terpestacin and structural revision of siccanol using catalytic stereoselective fragment couplings and macrocyclizations J. Am. Chem. Soc. 2004, 126, 91-92
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 91-92
    • Chan, J.1    Jamison, T.F.2
  • 17
    • 0029022640 scopus 로고
    • Yeast STE14 methyltransferase, expressed as TrpE-STE14 fusion protein in Escherichia coli, for in vitro carboxylmethylation of prenylated polypeptides
    • Hrycyna, C. A.; Wait, S. J.; Backlund, P. S.; Michaelis, S. Yeast STE14 methyltransferase, expressed as TrpE-STE14 fusion protein in Escherichia coli, for in vitro carboxylmethylation of prenylated polypeptides Methods Enzymol. 1995, 250, 251-266
    • (1995) Methods Enzymol. , vol.250 , pp. 251-266
    • Hrycyna, C.A.1    Wait, S.J.2    Backlund, P.S.3    Michaelis, S.4
  • 19
    • 0037140840 scopus 로고    scopus 로고
    • Aromatic farnesyl diphosphate analogues: Vinyl triflate-mediated synthesis and preliminary enzymatic evaluation
    • DOI 10.1016/S0960-894X(02)00187-7, PII S0960894X02001877
    • Zhou, C.; Shao, Y.; Gibbs, R. A. Aromatic Farnesyl Diphosphate Analogues: Vinyl Triflate-Mediated Synthesis and Preliminary Evaluation Bioorg. Med. Chem. Lett. 2002, 12, 1417-1420 (Pubitemid 34454825)
    • (2002) Bioorganic and Medicinal Chemistry Letters , vol.12 , Issue.10 , pp. 1417-1420
    • Zhou, C.1    Shao, Y.2    Gibbs, R.A.3
  • 20
    • 0345269998 scopus 로고    scopus 로고
    • Biochemical and structural studies with prenyl diphosphate analogues provide insights into isoprenoid recognition by protein farnesyl transferase
    • DOI 10.1021/bi0266838
    • Turek-Etienne, T. C.; Strickland, C. L.; Distefano, M. D. Biochemical and Structural Studies with Prenyl Diphosphate Analogues Provide Insights into Isoprenoid Recognition by Protein Farnesyl Transferase Biochemistry 2003, 42, 3716-3724 (Pubitemid 36402664)
    • (2003) Biochemistry , vol.42 , Issue.13 , pp. 3716-3724
    • Turek-Etienne, T.C.1    Strickland, C.L.2    Distefano, M.D.3
  • 22
    • 33845377563 scopus 로고
    • Controlled carbometalation. 20. Carbometalation reaction of alkynes with organoalene-zirconocene derivatives as a route to stereo-and regiodefined trisubstituted alkenes
    • Negishi, E.; Horn, D. E. V.; Yoshida, T. Controlled carbometalation. 20. Carbometalation reaction of alkynes with organoalene-zirconocene derivatives as a route to stereo-and regiodefined trisubstituted alkenes J. Am. Chem. Soc. 1985, 107, 6639-6647
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 6639-6647
    • Negishi, E.1    Horn, D.E.V.2    Yoshida, T.3
  • 23
    • 0001136978 scopus 로고
    • A Method for Selective Conversion of Allylic and Benzylic Alcohols to Halides under Neutral Conditions
    • Corey, E. J.; Kim, C. U.; Takeda, M. A Method for Selective Conversion of Allylic and Benzylic Alcohols to Halides Under Neutral Conditions Tetrahedron Lett. 1972, 4339-4342
    • (1972) Tetrahedron Lett. , pp. 4339-4342
    • Corey, E.J.1    Kim, C.U.2    Takeda, M.3
  • 25
    • 0001512821 scopus 로고
    • Structure activity studies on the retinal rod outer segment isoprenylated protein methyltransferase
    • Gilbert, B. A.; Tan, E. W.; Perezsala, D.; Rando, R. R. Structure activity studies on the retinal rod outer segment isoprenylated protein methyltransferase J. Am. Chem. Soc. 1992, 114 (10) 3966-3973
    • (1992) J. Am. Chem. Soc. , vol.114 , Issue.10 , pp. 3966-3973
    • Gilbert, B.A.1    Tan, E.W.2    Perezsala, D.3    Rando, R.R.4
  • 27
    • 0035829731 scopus 로고    scopus 로고
    • Galectin-1 binds oncogenic H-Ras to mediate Ras membrane anchorage and cell transformation
    • DOI 10.1038/sj.onc.1204950
    • Paz, A.; Haklai, R.; Elad-Sfadia, G.; Ballan, E.; Kloog, Y. Galectin-1 binds oncogenic H-Ras to mediate Ras membrane anchorage and cell transformation Oncogene 2001, 20, 7486-7493 (Pubitemid 33086908)
    • (2001) Oncogene , vol.20 , Issue.51 , pp. 7486-7493
    • Paz, A.1    Haklai, R.2    Elad-Sfadia, G.3    Ballan, E.4    Kloog, Y.5
  • 28
    • 71349085359 scopus 로고    scopus 로고
    • Phase 1 First-in-human clinical study of S-trans, trans- farnesylthiosalicylic acid (salirasib) in patients with solid tumors
    • Tsimberidou, A. M.; Rudek, M. A.; Hong, D.; Ng, N. S.; Blair, J.; Goldsweig, H.; Kurzrock, R. Phase 1 First-in-human clinical study of S-trans, trans-farnesylthiosalicylic acid (salirasib) in patients with solid tumors Cancer Chemother. Pharmacol. 2010, 65, 235-241
    • (2010) Cancer Chemother. Pharmacol. , vol.65 , pp. 235-241
    • Tsimberidou, A.M.1    Rudek, M.A.2    Hong, D.3    Ng, N.S.4    Blair, J.5    Goldsweig, H.6    Kurzrock, R.7
  • 29
    • 0037264633 scopus 로고    scopus 로고
    • Targeting RAS signalling pathways in cancer therapy
    • DOI 10.1038/nrc969
    • Downward, J. Targeting ras signalling pathways in cancer therapy Nature Rev. Cancer 2003, 3 (1) 11-22 (Pubitemid 37328883)
    • (2003) Nature Reviews Cancer , vol.3 , Issue.1 , pp. 11-22
    • Downward, J.1
  • 30
    • 65649108558 scopus 로고    scopus 로고
    • A Gene Expression Signature Associated with "k-Ras Addiction" Reveals Regulators of EMT and Tumor Cell Survival
    • Singh, A.; Greninger, P.; Rhodes, D.; Koopman, L.; Violette, S.; Bardeesy, N.; Settleman, J. A Gene Expression Signature Associated with "K-Ras Addiction" Reveals Regulators of EMT and Tumor Cell Survival Cancer Cell 2009, 15 (6) 489-500
    • (2009) Cancer Cell , vol.15 , Issue.6 , pp. 489-500
    • Singh, A.1    Greninger, P.2    Rhodes, D.3    Koopman, L.4    Violette, S.5    Bardeesy, N.6    Settleman, J.7


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