메뉴 건너뛰기




Volumn 11, Issue 22, 2013, Pages 3706-3732

Structural modifications of (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene) thiazolidine-2,4-dione that improve selectivity for inhibiting the proliferation of melanoma cells containing active ERK signaling

Author keywords

[No Author keywords available]

Indexed keywords

CELL SIGNALING; DERMATOLOGY;

EID: 84877735346     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c3ob40199e     Document Type: Article
Times cited : (30)

References (48)
  • 2
    • 0031900740 scopus 로고    scopus 로고
    • Signal transduction through MAP kinase cascades
    • T. S. Lewis P. S. Shapiro N. G. Ahn Signal transduction through MAP kinase cascades Adv. Cancer Res. 1998 74 49 139
    • (1998) Adv. Cancer Res. , vol.74 , pp. 49-139
    • Lewis, T.S.1    Shapiro, P.S.2    Ahn, N.G.3
  • 4
    • 0034284027 scopus 로고    scopus 로고
    • Targeting the Ras signaling pathway: A rational, mechanism-based treatment for hematologic malignancies?
    • C. W. Reuter M. A. Morgan L. Bergmann Targeting the Ras signaling pathway: a rational, mechanism-based treatment for hematologic malignancies? Blood 2000 96 5 1655 1669
    • (2000) Blood , vol.96 , Issue.5 , pp. 1655-1669
    • Reuter, C.W.1    Morgan, M.A.2    Bergmann, L.3
  • 6
    • 0024376173 scopus 로고
    • Ras Oncogenes in human cancer: A review
    • J. L. Bos ras Oncogenes in human cancer: a review Cancer Res. 1989 49 17 4682 4689
    • (1989) Cancer Res. , vol.49 , Issue.17 , pp. 4682-4689
    • Bos, J.L.1
  • 8
    • 33746485766 scopus 로고    scopus 로고
    • Epidermal growth factor receptor targeting in cancer
    • J. Mendelsohn J. Baselga Epidermal growth factor receptor targeting in cancer Semin. Oncol. 2006 33 4 369 385
    • (2006) Semin. Oncol. , vol.33 , Issue.4 , pp. 369-385
    • Mendelsohn, J.1    Baselga, J.2
  • 10
    • 0036051342 scopus 로고    scopus 로고
    • Molecular interpretation of ERK signal duration by immediate early gene products
    • L. O. Murphy S. Smith R. H. Chen D. C. Fingar J. Blenis Molecular interpretation of ERK signal duration by immediate early gene products Nat. Cell Biol. 2002 4 8 556 564
    • (2002) Nat. Cell Biol. , vol.4 , Issue.8 , pp. 556-564
    • Murphy, L.O.1    Smith, S.2    Chen, R.H.3    Fingar, D.C.4    Blenis, J.5
  • 12
    • 0036401042 scopus 로고    scopus 로고
    • Design and discovery of small molecules targeting raf-1 kinase
    • T. B. Lowinger B. Riedl J. Dumas R. A. Smith Design and discovery of small molecules targeting raf-1 kinase Curr. Pharm. Des. 2002 8 25 2269 2278
    • (2002) Curr. Pharm. Des. , vol.8 , Issue.25 , pp. 2269-2278
    • Lowinger, T.B.1    Riedl, B.2    Dumas, J.3    Smith, R.A.4
  • 13
    • 26444574802 scopus 로고    scopus 로고
    • Development of farnesyl transferase inhibitors: A review
    • N. M. Appels J. H. Beijnen J. H. Schellens Development of farnesyl transferase inhibitors: a review Oncologist 2005 10 8 565 578
    • (2005) Oncologist , vol.10 , Issue.8 , pp. 565-578
    • Appels, N.M.1    Beijnen, J.H.2    Schellens, J.H.3
  • 15
    • 38949183695 scopus 로고    scopus 로고
    • Advances in targeting the Ras/Raf/MEK/Erk mitogen-activated protein kinase cascade with MEK inhibitors for cancer therapy
    • B. B. Friday A. A. Adjei Advances in targeting the Ras/Raf/MEK/Erk mitogen-activated protein kinase cascade with MEK inhibitors for cancer therapy Clin. Cancer Res. 2008 14 2 342 346
    • (2008) Clin. Cancer Res. , vol.14 , Issue.2 , pp. 342-346
    • Friday, B.B.1    Adjei, A.A.2
  • 16
    • 27544479318 scopus 로고    scopus 로고
    • Role of tyrosine kinase inhibitors in cancer therapy
    • A. Arora E. M. Scholar Role of tyrosine kinase inhibitors in cancer therapy J. Pharmacol. Exp. Ther. 2005 315 3 971 979
    • (2005) J. Pharmacol. Exp. Ther. , vol.315 , Issue.3 , pp. 971-979
    • Arora, A.1    Scholar, E.M.2
  • 17
    • 78650621692 scopus 로고    scopus 로고
    • Small-molecule inhibitors of the ERK signaling pathway: Towards novel anticancer therapeutics
    • J. L. Yap S. Worlikar A. D. MacKerell, Jr. P. Shapiro S. Fletcher Small-molecule inhibitors of the ERK signaling pathway: towards novel anticancer therapeutics ChemMedChem 2011 6 1 38 48
    • (2011) ChemMedChem , vol.6 , Issue.1 , pp. 38-48
    • Yap, J.L.1    Worlikar, S.2    MacKerell, Jr.A.D.3    Shapiro, P.4    Fletcher, S.5
  • 18
    • 78449275389 scopus 로고    scopus 로고
    • Basal and treatment-induced activation of AKT mediates resistance to cell death by AZD6244 (ARRY-142886) in Braf-mutant human cutaneous melanoma cells
    • Y. N. Gopal W. Deng S. E. Woodman K. Komurov P. Ram P. D. Smith M. A. Davies Basal and treatment-induced activation of AKT mediates resistance to cell death by AZD6244 (ARRY-142886) in Braf-mutant human cutaneous melanoma cells Cancer Res. 2010 70 21 8736 8747
    • (2010) Cancer Res. , vol.70 , Issue.21 , pp. 8736-8747
    • Gopal, Y.N.1    Deng, W.2    Woodman, S.E.3    Komurov, K.4    Ram, P.5    Smith, P.D.6    Davies, M.A.7
  • 19
    • 68949151964 scopus 로고    scopus 로고
    • ABA inhibits germination but not dormancy release in mature imbibed seeds of Lolium rigidum Gaud
    • D. E. Goggin K. J. Steadman R. J. Emery S. C. Farrow R. L. Benech-Arnold S. B. Powles ABA inhibits germination but not dormancy release in mature imbibed seeds of Lolium rigidum Gaud J. Exp. Bot. 2009 60 12 3387 3396
    • (2009) J. Exp. Bot. , vol.60 , Issue.12 , pp. 3387-3396
    • Goggin, D.E.1    Steadman, K.J.2    Emery, R.J.3    Farrow, S.C.4    Benech-Arnold, R.L.5    Powles, S.B.6
  • 22
    • 60749085908 scopus 로고    scopus 로고
    • Overcoming resistance to tyrosine kinase inhibitors: Lessons learned from cancer cells treated with EGFR antagonists
    • B. N. Rexer J. A. Engelman C. L. Arteaga Overcoming resistance to tyrosine kinase inhibitors: lessons learned from cancer cells treated with EGFR antagonists Cell Cycle 2009 8 1 18 22
    • (2009) Cell Cycle , vol.8 , Issue.1 , pp. 18-22
    • Rexer, B.N.1    Engelman, J.A.2    Arteaga, C.L.3
  • 24
    • 77949732073 scopus 로고    scopus 로고
    • RAF inhibitors transactivate RAF dimers and ERK signalling in cells with wild-type BRAF
    • P. I. Poulikakos C. Zhang G. Bollag K. M. Shokat N. Rosen RAF inhibitors transactivate RAF dimers and ERK signalling in cells with wild-type BRAF Nature 2010 464 7287 427 430
    • (2010) Nature , vol.464 , Issue.7287 , pp. 427-430
    • Poulikakos, P.I.1    Zhang, C.2    Bollag, G.3    Shokat, K.M.4    Rosen, N.5
  • 28
    • 22244490088 scopus 로고    scopus 로고
    • Identification of novel extracellular signal-regulated kinase docking domain inhibitors
    • C. N. Hancock A. Macias E. K. Lee S. Y. Yu A. D. Mackerell, Jr. P. Shapiro Identification of novel extracellular signal-regulated kinase docking domain inhibitors J. Med. Chem. 2005 48 14 4586 4595
    • (2005) J. Med. Chem. , vol.48 , Issue.14 , pp. 4586-4595
    • Hancock, C.N.1    MacIas, A.2    Lee, E.K.3    Yu, S.Y.4    MacKerell, Jr.A.D.5    Shapiro, P.6
  • 29
    • 0034284131 scopus 로고    scopus 로고
    • Docking domains and substrate-specificity determination for MAP kinases
    • A. D. Sharrocks S. H. Yang A. Galanis Docking domains and substrate-specificity determination for MAP kinases Trends Biochem. Sci. 2000 25 9 448 453
    • (2000) Trends Biochem. Sci. , vol.25 , Issue.9 , pp. 448-453
    • Sharrocks, A.D.1    Yang, S.H.2    Galanis, A.3
  • 30
    • 0033788484 scopus 로고    scopus 로고
    • A conserved docking motif in MAP kinases common to substrates, activators and regulators
    • T. Tanoue M. Adachi T. Moriguchi E. Nishida A conserved docking motif in MAP kinases common to substrates, activators and regulators Nat. Cell Biol. 2000 2 2 110 116
    • (2000) Nat. Cell Biol. , vol.2 , Issue.2 , pp. 110-116
    • Tanoue, T.1    Adachi, M.2    Moriguchi, T.3    Nishida, E.4
  • 31
    • 0035254671 scopus 로고    scopus 로고
    • Identification of a docking groove on ERK and p38 MAP kinases that regulates the specificity of docking interactions
    • T. Tanoue R. Maeda M. Adachi E. Nishida Identification of a docking groove on ERK and p38 MAP kinases that regulates the specificity of docking interactions EMBO J. 2001 20 3 466 479
    • (2001) EMBO J. , vol.20 , Issue.3 , pp. 466-479
    • Tanoue, T.1    Maeda, R.2    Adachi, M.3    Nishida, E.4
  • 32
    • 28944440837 scopus 로고    scopus 로고
    • Lead validation and SAR development via chemical similarity searching, application to compounds targeting the pY+3 site of the SH2 domain of p56lck
    • A. T. Macias M. Y. Mia G. Xia J. Hayashi A. D. MacKerell, Jr. Lead validation and SAR development via chemical similarity searching, application to compounds targeting the pY+3 site of the SH2 domain of p56lck J. Chem. Inf. Model. 2005 45 6 1759 1766
    • (2005) J. Chem. Inf. Model. , vol.45 , Issue.6 , pp. 1759-1766
    • MacIas, A.T.1    Mia, M.Y.2    Xia, G.3    Hayashi, J.4    MacKerell, Jr.A.D.5
  • 33
    • 71749119790 scopus 로고    scopus 로고
    • Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4- ethoxy-benzylidene)-thiazolidine-2,4-dione: Development of potential substrate-specific ERK1/2 inhibitors
    • Q. Li A. Al-Ayoubi T. Guo H. Zheng A. Sarkar T. Nguyen S. T. Eblen S. Grant G. E. Kellogg S. Zhang Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors Bioorg. Med. Chem. Lett. 2009 19 21 6042 6046
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , Issue.21 , pp. 6042-6046
    • Li, Q.1    Al-Ayoubi, A.2    Guo, T.3    Zheng, H.4    Sarkar, A.5    Nguyen, T.6    Eblen, S.T.7    Grant, S.8    Kellogg, G.E.9    Zhang, S.10
  • 34
    • 77955413802 scopus 로고    scopus 로고
    • Discovery of 3-(2-aminoethyl)-5-(3-phenyl-propylidene)-thiazolidine-2,4- dione as a dual inhibitor of the Raf/MEK/ERK and the PI3K/Akt signaling pathways
    • Q. Li J. Wu H. Zheng K. Liu T. L. Guo Y. Liu S. T. Eblen S. Grant S. Zhang Discovery of 3-(2-aminoethyl)-5-(3-phenyl-propylidene)-thiazolidine-2,4- dione as a dual inhibitor of the Raf/MEK/ERK and the PI3K/Akt signaling pathways Bioorg. Med. Chem. Lett. 2010 20 15 4526 4530
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , Issue.15 , pp. 4526-4530
    • Li, Q.1    Wu, J.2    Zheng, H.3    Liu, K.4    Guo, T.L.5    Liu, Y.6    Eblen, S.T.7    Grant, S.8    Zhang, S.9
  • 35
    • 78449275389 scopus 로고    scopus 로고
    • Basal and treatment-induced activation of AKT mediates resistance to cell death by AZD6244 (ARRY-142886) in Braf-mutant human cutaneous melanoma cells
    • Y. N. Gopal W. Deng S. E. Woodman K. Komurov P. Ram P. D. Smith M. A. Davies Basal and treatment-induced activation of AKT mediates resistance to cell death by AZD6244 (ARRY-142886) in Braf-mutant human cutaneous melanoma cells Cancer Res. 2010 70 21 8736 8747
    • (2010) Cancer Res. , vol.70 , Issue.21 , pp. 8736-8747
    • Gopal, Y.N.1    Deng, W.2    Woodman, S.E.3    Komurov, K.4    Ram, P.5    Smith, P.D.6    Davies, M.A.7
  • 36
    • 78651418282 scopus 로고    scopus 로고
    • Mutant BRAF melanomas-dependence and resistance
    • P. I. Poulikakos N. Rosen Mutant BRAF melanomas-dependence and resistance Cancer Cell 2011 19 1 11 15
    • (2011) Cancer Cell , vol.19 , Issue.1 , pp. 11-15
    • Poulikakos, P.I.1    Rosen, N.2
  • 37
    • 41749096110 scopus 로고    scopus 로고
    • Signaling of DNA damage is not sufficient to induce p53 response: (Re)activation of wt p53 protein strongly depends on cellular context
    • J. Wesierska-Gadek M. Gueorguieva O. Komina G. Schmid M. P. Kramer Signaling of DNA damage is not sufficient to induce p53 response: (re)activation of wt p53 protein strongly depends on cellular context J. Cell. Biochem. 2008 103 5 1607 1620
    • (2008) J. Cell. Biochem. , vol.103 , Issue.5 , pp. 1607-1620
    • Wesierska-Gadek, J.1    Gueorguieva, M.2    Komina, O.3    Schmid, G.4    Kramer, M.P.5
  • 38
    • 0029837307 scopus 로고    scopus 로고
    • Gain-of-function p53 mutations enhance alteration of the T-cell receptor following X-irradiation, independently of the cell cycle and cell survival
    • K. S. Iwamoto T. Mizuno T. Ito N. Tsuyama S. Kyoizumi T. Seyama Gain-of-function p53 mutations enhance alteration of the T-cell receptor following X-irradiation, independently of the cell cycle and cell survival Cancer Res. 1996 56 17 3862 3865
    • (1996) Cancer Res. , vol.56 , Issue.17 , pp. 3862-3865
    • Iwamoto, K.S.1    Mizuno, T.2    Ito, T.3    Tsuyama, N.4    Kyoizumi, S.5    Seyama, T.6
  • 39
    • 0001606206 scopus 로고
    • Major deletions in the gene encoding the p53 tumor antigen cause lack of p53 expression in HL-60 cells
    • D. Wolf V. Rotter Major deletions in the gene encoding the p53 tumor antigen cause lack of p53 expression in HL-60 cells Proc. Natl. Acad. Sci. U. S. A. 1985 82 3 790 794
    • (1985) Proc. Natl. Acad. Sci. U. S. A. , vol.82 , Issue.3 , pp. 790-794
    • Wolf, D.1    Rotter, V.2
  • 42
    • 33947706654 scopus 로고    scopus 로고
    • Flipped out: Structure-guided of selective pyrazolylpyrrole ERK inhibitors
    • A. M. Aronov C. Baker G. W. Bemis et al., Flipped out: structure-guided of selective pyrazolylpyrrole ERK inhibitors J. Med. Chem. 2007 50 1280 1287
    • (2007) J. Med. Chem. , vol.50 , pp. 1280-1287
    • Aronov, A.M.1    Baker, C.2    Bemis, G.W.3
  • 43
    • 0027965563 scopus 로고
    • Ras/MAP kinase-dependent and -independent signaling pathways target distinct ternary complex factors
    • R. A. Hipskind D. Buscher A. Nordheim M. Baccarini Ras/MAP kinase-dependent and -independent signaling pathways target distinct ternary complex factors Genes Dev. 1994 8 15 1803 1816
    • (1994) Genes Dev. , vol.8 , Issue.15 , pp. 1803-1816
    • Hipskind, R.A.1    Buscher, D.2    Nordheim, A.3    Baccarini, M.4
  • 44
    • 0029937701 scopus 로고    scopus 로고
    • Phosphorylation of c-Fos at the C-terminus enhances its transforming activity
    • R. H. Chen P. C. Juo T. Curran J. Blenis Phosphorylation of c-Fos at the C-terminus enhances its transforming activity Oncogene 1996 12 7 1493 1502
    • (1996) Oncogene , vol.12 , Issue.7 , pp. 1493-1502
    • Chen, R.H.1    Juo, P.C.2    Curran, T.3    Blenis, J.4
  • 45
    • 0030830220 scopus 로고    scopus 로고
    • Cross-cascade activation of ERKs and ternary complex factors by Rho family proteins
    • J. A. Frost H. Steen P. Shapiro T. Lewis N. Ahn P. E. Shaw M. H. Cobb Cross-cascade activation of ERKs and ternary complex factors by Rho family proteins EMBO J. 1997 16 21 6426 6438
    • (1997) EMBO J. , vol.16 , Issue.21 , pp. 6426-6438
    • Frost, J.A.1    Steen, H.2    Shapiro, P.3    Lewis, T.4    Ahn, N.5    Shaw, P.E.6    Cobb, M.H.7
  • 46
    • 65249099572 scopus 로고    scopus 로고
    • Peroxisome proliferator-activating receptors: A new way to treat melanoma?
    • D. Schadendorf Peroxisome proliferator-activating receptors: a new way to treat melanoma? J. Invest. Dermatol. 2009 129 5 1061 1063
    • (2009) J. Invest. Dermatol. , vol.129 , Issue.5 , pp. 1061-1063
    • Schadendorf, D.1
  • 48
    • 78650995733 scopus 로고    scopus 로고
    • Characterization of ERK docking domain inhibitors that induce apoptosis by targeting Rsk-1 and caspase-9
    • S. R. Boston R. Deshmukh S. Strome U. D. Priyakumar A. D. MacKerell, Jr. P. Shapiro Characterization of ERK docking domain inhibitors that induce apoptosis by targeting Rsk-1 and caspase-9 BMC Cancer 2011 11 7
    • (2011) BMC Cancer , vol.11 , pp. 7
    • Boston, S.R.1    Deshmukh, R.2    Strome, S.3    Priyakumar, U.D.4    MacKerell, Jr.A.D.5    Shapiro, P.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.