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Volumn 52, Issue 19, 2009, Pages 6126-6141

Structure-affinity relationships of glutamine mimics incorporated into phosphopeptides targeted to the SH2 domain of signal transducer and activator of transcription 3

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 5 BENZYLOXYHEXANAMIDE; 4 AMINOBUTYRAMIDE; AMIDE; GLUTAMINE; PHOSPHOPEPTIDE; STAT3 PROTEIN; UNCLASSIFIED DRUG;

EID: 70349651657     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm901105k     Document Type: Article
Times cited : (35)

References (44)
  • 1
    • 0036731485 scopus 로고    scopus 로고
    • Stats: Transcriptional control and biological impact
    • Levy, D. E.; Darnell, J. E., Jr. Stats: transcriptional control and biological impact. Nat. Rev. Mol. Cell. Biol. 2002, 3, 651-662.
    • (2002) Nat. Rev. Mol. Cell. Biol. , vol.3 , pp. 651-662
    • Levy, D.E.1    Darnell Jr., J.E.2
  • 2
    • 0036782706 scopus 로고    scopus 로고
    • Transcription factors as targets for cancer therapy
    • Darnell, J. E., Jr. Transcription factors as targets for cancer therapy. Nat. Rev. Cancer 2002, 2, 740-749.
    • (2002) Nat. Rev. Cancer , vol.2 , pp. 740-749
    • Darnell Jr., J.E.1
  • 3
    • 0034657336 scopus 로고    scopus 로고
    • The role of STATs in transcriptional control and their impact on cellular function
    • Bromberg, J.; Darnell, J. E., Jr. The role of STATs in transcriptional control and their impact on cellular function. Oncogene 2000, 19, 2468-2473.
    • (2000) Oncogene , vol.19 , pp. 2468-2473
    • Bromberg, J.1    Darnell Jr., J.E.2
  • 4
    • 1042302005 scopus 로고    scopus 로고
    • The STATs of cancer;new molecular targets come of age
    • Yu, H.; Jove, R. The STATs of cancer;new molecular targets come of age. Nat. Rev. Cancer 2004, 4, 97-105.
    • (2004) Nat. Rev. Cancer , vol.4 , pp. 97-105
    • Yu, H.1    Jove, R.2
  • 8
    • 27144475507 scopus 로고    scopus 로고
    • Investigation of the binding determinants of phosphopeptides targeted to the SRC homology 2 domain of the signal transducer and activator of transcription 3. Development of a high-affinity peptide inhibitor
    • Coleman, D. R.; Ren, Z.; Mandal, P. K.; Cameron, A. G.; Dyer, G. A.; Muranjan, S.; Campbell, M.; Chen, X.; McMurray, J. S. Investigation of the binding determinants of phosphopeptides targeted to the SRC homology 2 domain of the signal transducer and activator of transcription 3. Development of a high-affinity peptide inhibitor. J. Med. Chem. 2005, 48, 6661-6670.
    • (2005) J. Med. Chem. , vol.48 , pp. 6661-6670
    • Coleman, D.R.1    Ren, Z.2    Mandal, P.K.3    Cameron, A.G.4    Dyer, G.A.5    Muranjan, S.6    Campbell, M.7    Chen, X.8    McMurray, J.S.9
  • 9
    • 40049112233 scopus 로고    scopus 로고
    • Solid phase synthesis of phosphopeptides incorporating 2,2-dimethyloxazolidine pseudoproline analogs: Evidence for trans Leu-Pro peptide bonds in Stat3 inhibitors
    • Coleman, D. R., IV; Kaluarachchi, K.; Ren, Z.; Chen, X.; McMurray, J. S. Solid phase synthesis of phosphopeptides incorporating 2,2-dimethyloxazolidine pseudoproline analogs: evidence for trans Leu-Pro peptide bonds in Stat3 inhibitors. Int. J. Pept. Res. Ther. 2008, 14, 1-9.
    • (2008) Int. J. Pept. Res. Ther. , vol.14 , pp. 1-9
    • Coleman IV, D.R.1    Kaluarachchi, K.2    Ren, Z.3    Chen, X.4    McMurray, J.S.5
  • 10
    • 33846195506 scopus 로고    scopus 로고
    • Solid-phase synthesis of Stat3 inhibitors incorporating O-carbamoylserine and O-carbamoylthreonine as glutamine mimics
    • Mandal, P. K.; Heard, P. A.; Ren, Z.; Chen, X.; McMurray, J. S. Solid-phase synthesis of Stat3 inhibitors incorporating O-carbamoylserine and O-carbamoylthreonine as glutamine mimics. Bioorg. Med. Chem. Lett. 2007, 17, 654-656.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 654-656
    • Mandal, P.K.1    Heard, P.A.2    Ren, Z.3    Chen, X.4    McMurray, J.S.5
  • 11
    • 65249166871 scopus 로고    scopus 로고
    • Conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription 3: Evaluation and molecular modeling
    • Mandal, P. K.; Limbrick, D.; Coleman, D. R.; Dyer, G. A.; Ren, Z.; Birtwistle, J. S.; Xiong, C.; Chen, X.; Briggs, J. M.; McMurray, J. S. Conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription 3: evaluation and molecular modeling. J. Med. Chem. 2009, 52, 2429-2442.
    • (2009) J. Med. Chem. , vol.52 , pp. 2429-2442
    • Mandal, P.K.1    Limbrick, D.2    Coleman, D.R.3    Dyer, G.A.4    Ren, Z.5    Birtwistle, J.S.6    Xiong, C.7    Chen, X.8    Briggs, J.M.9    McMurray, J.S.10
  • 13
    • 3543055012 scopus 로고    scopus 로고
    • Novel peptidomimetic inhibitors of signal transducer and activator of transcription 3 dimerization and biological activity
    • Turkson, J.; Kim, J. S.; Zhang, S.; Yuan, J.; Huang, M.; Glenn, M.; Haura, E.; Sebti, S.; Hamilton, A. D.; Jove, R. Novel peptidomimetic inhibitors of signal transducer and activator of transcription 3 dimerization and biological activity. Mol. Cancer Ther. 2004, 3, 261-269.
    • (2004) Mol. Cancer Ther. , vol.3 , pp. 261-269
    • Turkson, J.1    Kim, J.S.2    Zhang, S.3    Yuan, J.4    Huang, M.5    Glenn, M.6    Haura, E.7    Sebti, S.8    Hamilton, A.D.9    Jove, R.10
  • 15
    • 33847682326 scopus 로고    scopus 로고
    • Isoform selective inhibition of STAT1 or STAT3 homo-dimerization via peptidomimetic probes: Structural recognition of STAT SH2 domains
    • Gunning, P. T.; Katt, W. P.; Glenn, M.; Siddiquee, K.; Kim, J. S.; Jove, R.; Sebti, S. M.; Turkson, J.; Hamilton, A. D. Isoform selective inhibition of STAT1 or STAT3 homo-dimerization via peptidomimetic probes: structural recognition of STAT SH2 domains. Bioorg. Med. Chem. Lett. 2007, 17, 1875-1878.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 1875-1878
    • Gunning, P.T.1    Katt, W.P.2    Glenn, M.3    Siddiquee, K.4    Kim, J.S.5    Jove, R.6    Sebti, S.M.7    Turkson, J.8    Hamilton, A.D.9
  • 16
    • 58149392583 scopus 로고    scopus 로고
    • Targeting protein-protein interactions: Suppression of Stat3 dimerization with rationally designed small-molecule, nonpeptidic SH2 domain binders
    • Gunning, P. T.; Glenn, M. P.; Siddiquee, K. A.; Katt, W. P.; Masson, E.; Sebti, S. M.; Turkson, J.; Hamilton, A. D. Targeting protein-protein interactions: suppression of Stat3 dimerization with rationally designed small-molecule, nonpeptidic SH2 domain binders. ChemBioChem 2008, 9, 2800-2803.
    • (2008) ChemBioChem , vol.9 , pp. 2800-2803
    • Gunning, P.T.1    Glenn, M.P.2    Siddiquee, K.A.3    Katt, W.P.4    Masson, E.5    Sebti, S.M.6    Turkson, J.7    Hamilton, A.D.8
  • 17
    • 0043175471 scopus 로고    scopus 로고
    • Identification and characterization of signal transducer and activator of transcription 3 recruitment sites within the epidermal growth factor receptor
    • Shao, H.; Cheng, H. Y.; Cook, R. G.; Tweardy, D. J. Identification and characterization of signal transducer and activator of transcription 3 recruitment sites within the epidermal growth factor receptor. Cancer Res. 2003, 63, 3923-3930.
    • (2003) Cancer Res. , vol.63 , pp. 3923-3930
    • Shao, H.1    Cheng, H.Y.2    Cook, R.G.3    Tweardy, D.J.4
  • 18
    • 2442618276 scopus 로고    scopus 로고
    • Structural requirements for signal transducer and activator of transcription 3 binding to phosphotyrosine ligands containing the YXXQ motif
    • Shao, H.; Xu, X.; Mastrangelo, M. A.; Jing, N.; Cook, R. G.; Legge, G. B.; Tweardy, D. J. Structural requirements for signal transducer and activator of transcription 3 binding to phosphotyrosine ligands containing the YXXQ motif. J. Biol. Chem. 2004, 279, 18967-18973.
    • (2004) J. Biol. Chem. , vol.279 , pp. 18967-18973
    • Shao, H.1    Xu, X.2    Mastrangelo, M.A.3    Jing, N.4    Cook, R.G.5    Legge, G.B.6    Tweardy, D.J.7
  • 19
    • 34250367390 scopus 로고    scopus 로고
    • New syntheses of tetrazolylmethylphenylalanine and O-malonyltyrosine as pTyr mimetics for the design of STAT3 dimerization inhibitors
    • Dourlat, J.; Valentin, B.; Liu, W. Q.; Garbay, C. New syntheses of tetrazolylmethylphenylalanine and O-malonyltyrosine as pTyr mimetics for the design of STAT3 dimerization inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 3943-3946.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 3943-3946
    • Dourlat, J.1    Valentin, B.2    Liu, W.Q.3    Garbay, C.4
  • 21
    • 61349138340 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of peptidomimetics containing Freidinger lactams as STAT3 inhibitors
    • Gomez, C.; Bai, L.; Zhang, J.; Nikolovska-Coleska, Z.; Chen, J.; Yi, H.; Wang, S. Design, synthesis, and evaluation of peptidomimetics containing Freidinger lactams as STAT3 inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 1733-1736.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 1733-1736
    • Gomez, C.1    Bai, L.2    Zhang, J.3    Nikolovska-Coleska, Z.4    Chen, J.5    Yi, H.6    Wang, S.7
  • 22
    • 0028931604 scopus 로고
    • Choice of STATs and other substrates specified by modular tyrosine-based motifs in cytokine receptors
    • Stahl, N.; Farruggella, T. J.; Boulton, T. G.; Zhong, Z.; Darnell, J. E., Jr.; Yancopoulos, G. D. Choice of STATs and other substrates specified by modular tyrosine-based motifs in cytokine receptors. Science 1995, 267, 1349-1353.
    • (1995) Science , vol.267 , pp. 1349-1353
    • Stahl, N.1    Farruggella, T.J.2    Boulton, T.G.3    Zhong, Z.4    Darnell Jr., J.E.5    Yancopoulos, G.D.6
  • 23
    • 0029887373 scopus 로고    scopus 로고
    • Differential activation of acute phase response factor/STAT3 and STAT1 via the cytoplasmic domain of the interleukin 6 signal transducer gp130. I. Definition of a novel phosphotyrosine motif mediating STAT1 activation
    • Gerhartz, C.; Heesel, B.; Sasse, J.; Hemmann, U.; Landgraf, C.; Schneider-Mergener, J.; Horn, F.; Heinrich, P. C.; Graeve, L. Differential activation of acute phase response factor/STAT3 and STAT1 via the cytoplasmic domain of the interleukin 6 signal transducer gp130. I. Definition of a novel phosphotyrosine motif mediating STAT1 activation. J. Biol. Chem. 1996, 271, 12991-12998.
    • (1996) J. Biol. Chem. , vol.271 , pp. 12991-12998
    • Gerhartz, C.1    Heesel, B.2    Sasse, J.3    Hemmann, U.4    Landgraf, C.5    Schneider-Mergener, J.6    Horn, F.7    Heinrich, P.C.8    Graeve, L.9
  • 24
    • 0037507282 scopus 로고    scopus 로고
    • Characterization of phosphopeptide motifs specific for the Src homology 2 domains of signal transducer and activator of transcription 1 (STAT1) and STAT3
    • Wiederkehr-Adam, M.; Ernst, P.; Muller, K.; Bieck, E.; Gombert, F. O.; Ottl, J.; Graff, P.; Grossmuller, F.; Heim, M. H. Characterization of phosphopeptide motifs specific for the Src homology 2 domains of signal transducer and activator of transcription 1 (STAT1) and STAT3. J. Biol. Chem. 2003, 278, 16117-16128.
    • (2003) J. Biol. Chem. , vol.278 , pp. 16117-16128
    • Wiederkehr-Adam, M.1    Ernst, P.2    Muller, K.3    Bieck, E.4    Gombert, F.O.5    Ottl, J.6    Graff, P.7    Grossmuller, F.8    Heim, M.H.9
  • 25
    • 0031796005 scopus 로고    scopus 로고
    • Src homology-2 domains: Structure, mechanisms, and drug discovery
    • Sawyer, T. K. Src homology-2 domains: structure, mechanisms, and drug discovery. Biopolymers 1998, 47, 243-261. (Pubitemid 128570208)
    • (1998) Biopolymers , vol.47 , Issue.3 , pp. 243-261
    • Sawyer, T.K.1
  • 26
    • 0001558378 scopus 로고    scopus 로고
    • Peptidomimetic SH2 domain antagonists for targeting signal transduction
    • Muller, G. Peptidomimetic SH2 domain antagonists for targeting signal transduction. Top. Curr. Chem. 2001, 211, 17-59.
    • (2001) Top. Curr. Chem. , vol.211 , pp. 17-59
    • Muller, G.1
  • 27
    • 0035415663 scopus 로고    scopus 로고
    • SH2 domain inhibition: A problem solved?
    • Shakespeare, W. C. SH2 domain inhibition: a problem solved? Curr. Opin. Chem. Biol. 2001, 5, 409-415.
    • (2001) Curr. Opin. Chem. Biol. , vol.5 , pp. 409-415
    • Shakespeare, W.C.1
  • 28
    • 0035172977 scopus 로고    scopus 로고
    • Antagonists of the homology 2 (SH2) domains of Grb2, Src, Lck and ZAP-70
    • Garcia-Echeverria, C. Antagonists of the homology 2 (SH2) domains of Grb2, Src, Lck and ZAP-70. Curr. Med. Chem. 2001, 8, 1589-1604.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1589-1604
    • Garcia-Echeverria, C.1
  • 29
    • 27144446862 scopus 로고    scopus 로고
    • Src homology-2 domains and structure-based, small-molecule library approaches to drug discovery
    • Makriyannis, A., Biegel, D., Eds.; Marcel Dekker: New York
    • Metcalf, C. A., III; Sawyer, T. Src homology-2 domains and structure-based, small-molecule library approaches to drug discovery. In Drug Discovery Strategies and Methods; Makriyannis, A., Biegel, D., Eds.; Marcel Dekker: New York, 2004; pp 23-59.
    • (2004) Drug Discovery Strategies and Methods , pp. 23-59
    • Metcalf III, C.A.1    Sawyer, T.2
  • 30
    • 63749111953 scopus 로고    scopus 로고
    • Inhibitors of signaling interfaces: Targeting Src homology 2 domains in drug discovery
    • Garcia-Echeverria, C. Inhibitors of signaling interfaces: targeting Src homology 2 domains in drug discovery. Protein Tyrosine Kinases 2006, 31-52.
    • (2006) Protein Tyrosine Kinases , pp. 31-52
    • Garcia-Echeverria, C.1
  • 31
    • 39149090322 scopus 로고    scopus 로고
    • Structural basis for the binding of high affinity phosphopeptides to Stat3
    • McMurray, J. S. Structural basis for the binding of high affinity phosphopeptides to Stat3. Biopolymers 2008, 90, 69-79.
    • (2008) Biopolymers , vol.90 , pp. 69-79
    • McMurray, J.S.1
  • 32
    • 66349129641 scopus 로고    scopus 로고
    • Application of triethylsilane and palladium-charcoal-induced reductions in the synthesis of Fmoc-glutamic acid analogues
    • A preliminary account of the syntheses of 63c-h and 64c-h was presented at the 20th American Peptide Symposium, June 2007.
    • A preliminary account of the syntheses of 63c-h and 64c-h was presented at the 20th American Peptide Symposium, June 2007. Mandal, P. K.; McMurray, J. S. Application of triethylsilane and palladium-charcoal-induced reductions in the synthesis of Fmoc-glutamic acid analogues. Adv. Exp. Med. Biol. 2009, 611, 181-182.
    • (2009) Adv. Exp. Med. Biol. , vol.611 , pp. 181-182
    • Mandal, P.K.1    McMurray, J.S.2
  • 33
    • 45249127652 scopus 로고
    • Trialkylsilanes as scavengers for the trifluoroacetic acid deblocking of protecting groups in peptide synthesis
    • Pearson, D. A.; Blanchette, M.; Baker, M. L.; Guindon, C. A. Trialkylsilanes as scavengers for the trifluoroacetic acid deblocking of protecting groups in peptide synthesis. Tetrahedron Lett. 1989, 30, 2739-2742.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2739-2742
    • Pearson, D.A.1    Blanchette, M.2    Baker, M.L.3    Guindon, C.A.4
  • 34
    • 0033992005 scopus 로고    scopus 로고
    • Solid phase synthesis of 5,6,7,8-tetrahydro - 1H-imidazo[4,5-g] quinoxalin-6-ones
    • Mazurov, A. Solid phase synthesis of 5,6,7,8-tetrahydro - 1H-imidazo[4,5-g]quinoxalin-6-ones. Tetrahedron Lett. 2000, 41, 7-10.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7-10
    • Mazurov, A.1
  • 35
    • 0032486152 scopus 로고    scopus 로고
    • Synthesis of 9-fluorenylmethoxycarbonylprotected amino aldehydes
    • Wen, J. J.; Crews, C. M. Synthesis of 9-fluorenylmethoxycarbonylprotected amino aldehydes. Tetrahedron: Asymmetry 1998, 9, 1855-1858.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1855-1858
    • Wen, J.J.1    Crews, C.M.2
  • 36
    • 0036189198 scopus 로고    scopus 로고
    • Animproved synthesis of 4-aminotetrolic acid
    • Ahern, D. G.; Lassiter, A. G.; Filer, C. N. Animproved synthesis of 4-aminotetrolic acid. Synth. Commun. 2002, 32, 665-667.
    • (2002) Synth. Commun. , vol.32 , pp. 665-667
    • Ahern, D.G.1    Lassiter, A.G.2    Filer, C.N.3
  • 37
    • 18944362270 scopus 로고    scopus 로고
    • Synthesis of N-phthalimido [beta]-aminoethanesulfonyl chlorides: The use of thionyl chloride for a simple and efficient synthesis of new peptidosulfonamide building blocks
    • Humljan, J.; Gobec, S. Synthesis of N-phthalimido [beta]- aminoethanesulfonyl chlorides: the use of thionyl chloride for a simple and efficient synthesis of new peptidosulfonamide building blocks. Tetrahedron Lett. 2005, 46, 4069-4072.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 4069-4072
    • Humljan, J.1    Gobec, S.2
  • 38
    • 34547936934 scopus 로고    scopus 로고
    • Pd-C-induced catalytic transfer hydrogenation with triethylsilane
    • Mandal, P. K.; McMurray, J. S. Pd-C-induced catalytic transfer hydrogenation with triethylsilane. J. Org. Chem. 2007, 72, 6599-6601.
    • (2007) J. Org. Chem. , vol.72 , pp. 6599-6601
    • Mandal, P.K.1    McMurray, J.S.2
  • 39
    • 0037603385 scopus 로고    scopus 로고
    • Efficient protocols for the synthesis of enantiopure gamma-amino acids with proteinogenic side chains
    • Loukas, V.; Noula, C.; Kokotos, G. Efficient protocols for the synthesis of enantiopure gamma-amino acids with proteinogenic side chains. J. Pept. Sci. 2003, 9, 312-319.
    • (2003) J. Pept. Sci. , vol.9 , pp. 312-319
    • Loukas, V.1    Noula, C.2    Kokotos, G.3
  • 40
    • 32344450611 scopus 로고    scopus 로고
    • Mild and efficient synthesis of Fmoc-protected amino azides from Fmoc-protected amino alcohols
    • DOI 10.1055/s-2005-923589
    • Mondal, S.; Fan, E. Mild and efficient synthesis of Fmoc-protected amino azides from Fmoc-protected amino alcohols. Synlett 2006, 306-308. (Pubitemid 43221322)
    • (2006) Synlett , Issue.2 , pp. 306-308
    • Mondal, S.1    Fan, E.2
  • 41
    • 0028266884 scopus 로고
    • Solid-phase N-glycopeptide synthesis using allyl side-chain protected Fmoc-amino acids
    • DOI 10.1016/S0040-4039(00)79958-8
    • Kates, S. A.; De La Torre, B. G.; Eritja, R.; Albericio, F. Solid-phase N-glycopeptide synthesis using allyl side-chain protected Fmoc-amino acids. Tetrahedron Lett. 1994, 35, 1033-1034. (Pubitemid 24084855)
    • (1994) Tetrahedron Letters , vol.35 , Issue.7 , pp. 1033-1034
    • Kates, S.A.1    De La Torre, B.G.2    Eritja, R.3    Albericio, F.4
  • 42
    • 0035861714 scopus 로고    scopus 로고
    • Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy
    • Boeijen, A.; van Ameijde, J.; Liskamp, R. M. Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy. J. Org. Chem. 2001, 66, 8454-8462.
    • (2001) J. Org. Chem. , vol.66 , pp. 8454-8462
    • Boeijen, A.1    Van Ameijde, J.2    Liskamp, R.M.3
  • 43
    • 34249296349 scopus 로고    scopus 로고
    • Expanding the scope of PNA-encoded libraries: Divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases
    • DOI 10.1016/j.tet.2007.03.033, PII S004040200700395X, Tetrahedron 50th Anniversary Symposium-in-Print (Part 3)
    • Debaene, F.; Da Silva, J. A.; Pianowski, Z.; Duran, F. J.; Winssinger, N. Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases. Tetrahedron 2007, 63, 6577-6586. (Pubitemid 46817614)
    • (2007) Tetrahedron , vol.63 , Issue.28 , pp. 6577-6586
    • Debaene, F.1    Da Silva, J.A.2    Pianowski, Z.3    Duran, F.J.4    Winssinger, N.5
  • 44
    • 0034720932 scopus 로고    scopus 로고
    • Solid-phase synthesis of new S-glycoamino acid building blocks
    • Jobron, L.; Hummel, G. Solid-phase synthesis of new S-glycoamino acid building blocks. Org. Lett. 2000, 2, 2265-2267.
    • (2000) Org. Lett. , vol.2 , pp. 2265-2267
    • Jobron, L.1    Hummel, G.2


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