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Volumn 51, Issue 22, 2008, Pages 7111-7118

Fragment-based design of small molecule X-linked inhibitor of apoptosis protein inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE 9; SECOND MITOCHONDRIAL ACTIVATOR OF CASPASE; TETRAPEPTIDE; X LINKED INHIBITOR OF APOPTOSIS;

EID: 56749182336     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8006992     Document Type: Article
Times cited : (53)

References (45)
  • 1
    • 0035900312 scopus 로고    scopus 로고
    • Structural biology. Controlling the caspases
    • Fesik, S. W.; Shi, Y. Structural biology. Controlling the caspases. Science 2001, 294, 1477-1478.
    • (2001) Science , vol.294 , pp. 1477-1478
    • Fesik, S.W.1    Shi, Y.2
  • 6
    • 2342448582 scopus 로고    scopus 로고
    • Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XLAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database
    • Nikolovska-Coleska, Z.; Xu, L.; Hu, Z. J.; Tomita, Y.; Li, P.; Roller, P. P.; Wang, R. X.; Fang, X. L.; Guo, R. B.; Zhang, M. C.; Lippman, M. E.; Yang, D. J.; Wang, S. M. Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XLAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database. J. Med. Chem. 2004, 47, 2430-2440.
    • (2004) J. Med. Chem , vol.47 , pp. 2430-2440
    • Nikolovska-Coleska, Z.1    Xu, L.2    Hu, Z.J.3    Tomita, Y.4    Li, P.5    Roller, P.P.6    Wang, R.X.7    Fang, X.L.8    Guo, R.B.9    Zhang, M.C.10    Lippman, M.E.11    Yang, D.J.12    Wang, S.M.13
  • 7
    • 0041913978 scopus 로고    scopus 로고
    • Development and characterization of nonpeptidic small molecule inhibitors of the XIAP/caspase-3 interaction
    • Wu, T. Y.; Wagner, K. W.; Bursulaya, B.; Schultz, P. G.; Deveraux, Q. L. Development and characterization of nonpeptidic small molecule inhibitors of the XIAP/caspase-3 interaction. Chem. Biol. 2003, 10, 759-767.
    • (2003) Chem. Biol , vol.10 , pp. 759-767
    • Wu, T.Y.1    Wagner, K.W.2    Bursulaya, B.3    Schultz, P.G.4    Deveraux, Q.L.5
  • 8
    • 3843086358 scopus 로고    scopus 로고
    • Structure-based design, synthesis, and evaluation of conformationally constrained mimetics of the second mitochondria-derived activator of caspase that target the X-linked inhibitor of apoptosis protein/caspase-9 interaction site
    • Sun, H. Y.; Nikolovska-Coleska, Z.; Yang, C. Y.; Xu, L.; Tomita, Y.; Krajewski, K.; Roller, P. P.; Wang, S. M. Structure-based design, synthesis, and evaluation of conformationally constrained mimetics of the second mitochondria-derived activator of caspase that target the X-linked inhibitor of apoptosis protein/caspase-9 interaction site. J. Med. Chem. 2004, 47, 4147-4150.
    • (2004) J. Med. Chem , vol.47 , pp. 4147-4150
    • Sun, H.Y.1    Nikolovska-Coleska, Z.2    Yang, C.Y.3    Xu, L.4    Tomita, Y.5    Krajewski, K.6    Roller, P.P.7    Wang, S.M.8
  • 12
    • 33749259614 scopus 로고    scopus 로고
    • Design, synthesis, and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein
    • Chen, J. Y.; Nikolovska-Coleska, Z.; Wang, G. P.; Qiu, S.; Wang, S. M. Design, synthesis, and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein. Bioorg. Med. Chem. Lett. 2006, 16, 5805-5808.
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 5805-5808
    • Chen, J.Y.1    Nikolovska-Coleska, Z.2    Wang, G.P.3    Qiu, S.4    Wang, S.M.5
  • 13
    • 37049019494 scopus 로고    scopus 로고
    • Sun, H. Y.; Nikolovska-Coleska, Z.; Lu, J. F.; Meagher, J. L.; Yang, G Y.; Qiu, S.; Tomita, Y.; Ueda, Y.; Jiang, S.; Krajewski, K.; Roller, P. P.; Stuckey, J. A.; Wang, S. M. Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. J. Am. Chem. Soc. 2007, 129, 15279-15294.
    • Sun, H. Y.; Nikolovska-Coleska, Z.; Lu, J. F.; Meagher, J. L.; Yang, G Y.; Qiu, S.; Tomita, Y.; Ueda, Y.; Jiang, S.; Krajewski, K.; Roller, P. P.; Stuckey, J. A.; Wang, S. M. Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. J. Am. Chem. Soc. 2007, 129, 15279-15294.
  • 14
    • 4444243683 scopus 로고    scopus 로고
    • A small molecule Smac mimic potentiates TRAIL- and TNFalpha-mediated cell death
    • Li, L.; Thomas, R. M.; Suzuki, H.; De Brabander, J. K.; Wang, X.; Harran, P. G. A small molecule Smac mimic potentiates TRAIL- and TNFalpha-mediated cell death. Science 2004, 305, 1471-1474.
    • (2004) Science , vol.305 , pp. 1471-1474
    • Li, L.1    Thomas, R.M.2    Suzuki, H.3    De Brabander, J.K.4    Wang, X.5    Harran, P.G.6
  • 16
    • 33845413241 scopus 로고    scopus 로고
    • Determination of the sequence specificity of XIAP BIR domains by screening a combinatorial peptide library
    • Sweeney, M. C.; Wang, X. X.; Park, J.; Liu, Y. S.; Pei, D. H. Determination of the sequence specificity of XIAP BIR domains by screening a combinatorial peptide library. Biochemistry 2006, 45, 14740-14748.
    • (2006) Biochemistry , vol.45 , pp. 14740-14748
    • Sweeney, M.C.1    Wang, X.X.2    Park, J.3    Liu, Y.S.4    Pei, D.H.5
  • 17
    • 27744526342 scopus 로고    scopus 로고
    • A small molecule Smac-mimic compound induces apoptosis and sensitizes TRAIL- and etoposide-induced apoptosis in breast cancer cells
    • Bockbrader, K. M.; Tan, M.; Sun, Y. A small molecule Smac-mimic compound induces apoptosis and sensitizes TRAIL- and etoposide-induced apoptosis in breast cancer cells. Oncogene 2005, 24, 7381-7388.
    • (2005) Oncogene , vol.24 , pp. 7381-7388
    • Bockbrader, K.M.1    Tan, M.2    Sun, Y.3
  • 19
    • 43549107334 scopus 로고    scopus 로고
    • Triptolide sensitizes AML cells to TRAIL-induced apoptosis via decrease of XIAP and p53-mediated increase of DR5
    • Carter, B. Z.; Mak, D. H.; Schober, W. D.; Dietrich, M. F.; Pinilla, C.; Vassilev, L. T.; Reed, J. C.; Andreeff, M. Triptolide sensitizes AML cells to TRAIL-induced apoptosis via decrease of XIAP and p53-mediated increase of DR5. Blood 2008, 111, 3742-3750.
    • (2008) Blood , vol.111 , pp. 3742-3750
    • Carter, B.Z.1    Mak, D.H.2    Schober, W.D.3    Dietrich, M.F.4    Pinilla, C.5    Vassilev, L.T.6    Reed, J.C.7    Andreeff, M.8
  • 20
    • 14644437742 scopus 로고    scopus 로고
    • Mechanisms of resistance to TRAIL-induced apoptosis in cancer
    • Zhang, L.; Fang, B. Mechanisms of resistance to TRAIL-induced apoptosis in cancer. Cancer Gene Ther. 2005, 12, 228-237.
    • (2005) Cancer Gene Ther , vol.12 , pp. 228-237
    • Zhang, L.1    Fang, B.2
  • 21
    • 0034989624 scopus 로고    scopus 로고
    • In vitro susceptibility to TRAIL-induced apoptosis of acute leukemia cells in the context of TRAIL receptor gene expression and constitutive NF-kappa B activity
    • Wuchter, C.; Krappmann, D.; Cai, Z.; Ruppert, V.; Scheidereit, C.; Dorken, B.; Ludwig, W. D.; Karawajew, L. In vitro susceptibility to TRAIL-induced apoptosis of acute leukemia cells in the context of TRAIL receptor gene expression and constitutive NF-kappa B activity. Leukemia 2001, 15, 921-928.
    • (2001) Leukemia , vol.15 , pp. 921-928
    • Wuchter, C.1    Krappmann, D.2    Cai, Z.3    Ruppert, V.4    Scheidereit, C.5    Dorken, B.6    Ludwig, W.D.7    Karawajew, L.8
  • 23
    • 34548662911 scopus 로고    scopus 로고
    • Effect of the XIAP inhibitor embelin on TRAIL-induced apoptosis of pancreatic cancer cells
    • Mori, T.; Doi, R.; Kida, A.; Nagai, K.; Kami, K.; Ito, D.; Toyoda, E.; Kawaguchi, Y.; Uemoto, S. Effect of the XIAP inhibitor embelin on TRAIL-induced apoptosis of pancreatic cancer cells. J. Surg. Res. 2007, 142, 281-286.
    • (2007) J. Surg. Res , vol.142 , pp. 281-286
    • Mori, T.1    Doi, R.2    Kida, A.3    Nagai, K.4    Kami, K.5    Ito, D.6    Toyoda, E.7    Kawaguchi, Y.8    Uemoto, S.9
  • 24
    • 8844228917 scopus 로고    scopus 로고
    • Potent antileukemic interactions between flavopiridol and TRAIL/Apo2L involve flavopiridol-mediated XIAP downregulation
    • Rosato, R. R.; Dai, Y.; Almenara, J. A.; Maggio, S. C.; Grant, S. Potent antileukemic interactions between flavopiridol and TRAIL/Apo2L involve flavopiridol-mediated XIAP downregulation. Leukemia 2004, 18, 1780-1788.
    • (2004) Leukemia , vol.18 , pp. 1780-1788
    • Rosato, R.R.1    Dai, Y.2    Almenara, J.A.3    Maggio, S.C.4    Grant, S.5
  • 25
    • 2342615480 scopus 로고    scopus 로고
    • X-linked inhibitor of apoptosis protein (XIAP) is a nonredundant modulator of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-mediated apoptosis in human cancer cells
    • Cummins, J. M.; Kohli, M.; Rago, C.; Kinzler, K. W.; Vogelstein, B.; Bunz, F. X-linked inhibitor of apoptosis protein (XIAP) is a nonredundant modulator of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-mediated apoptosis in human cancer cells. Cancer Res. 2004, 64, 3006-3008.
    • (2004) Cancer Res , vol.64 , pp. 3006-3008
    • Cummins, J.M.1    Kohli, M.2    Rago, C.3    Kinzler, K.W.4    Vogelstein, B.5    Bunz, F.6
  • 27
    • 13444278636 scopus 로고    scopus 로고
    • Rottlerin sensitizes glioma cells to TRAIL-induced apoptosis by inhibition of Cdc2 and the subsequent downregulation of survivin and XIAP
    • Kim, E. H.; Kim, S. U.; Choi, K. S. Rottlerin sensitizes glioma cells to TRAIL-induced apoptosis by inhibition of Cdc2 and the subsequent downregulation of survivin and XIAP. Oncogene 2005, 24, 838-849.
    • (2005) Oncogene , vol.24 , pp. 838-849
    • Kim, E.H.1    Kim, S.U.2    Choi, K.S.3
  • 29
    • 0029836953 scopus 로고    scopus 로고
    • Discovering high-affinity ligands for proteins: SAR by NMR
    • Shuker, S. B.; Hajduk, P. J.; Meadows, R. P.; Fesik, S. W. Discovering high-affinity ligands for proteins: SAR by NMR. Science 1996, 274, 1531-1534.
    • (1996) Science , vol.274 , pp. 1531-1534
    • Shuker, S.B.1    Hajduk, P.J.2    Meadows, R.P.3    Fesik, S.W.4
  • 30
    • 56749127363 scopus 로고    scopus 로고
    • Goddard, T. D, Kneller, D. G. SPARKY, version 3; University of California: San Francisco, CA
    • Goddard, T. D.; Kneller, D. G. SPARKY, version 3; University of California: San Francisco, CA.
  • 31
    • 13844312649 scopus 로고    scopus 로고
    • ZINC: A free database of commercially available compounds for virtual screening
    • Irwin, J. J.; Shoichet, B. K. ZINC: a free database of commercially available compounds for virtual screening. J. Chem. Inf. Model. 2005, 45, 177-182. (http://zinc.docking.org).
    • (2005) J. Chem. Inf. Model , vol.45 , pp. 177-182
    • Irwin, J.J.1    Shoichet, B.K.2
  • 32
    • 0005757079 scopus 로고    scopus 로고
    • Combinatorial chemistry library design using pharmacophore diversity
    • Davies, K.; Briant, C. Combinatorial chemistry library design using pharmacophore diversity Network Sci. 1996, 1 (http://www.netsci.org/Science/combichem/feature05.html).
    • (1996) Network Sci , vol.1
    • Davies, K.1    Briant, C.2
  • 33
    • 56749108994 scopus 로고    scopus 로고
    • ChemBridgeSoft Cambridgsoft Corporation, Cambridge, MA
    • ChemBridgeSoft (Cambridgsoft Corporation, Cambridge, MA). http://www.cambridgesoft.com/webinars/info/default.aspx?webinarid=236.
  • 35
    • 0004062041 scopus 로고    scopus 로고
    • Tripos: St. Louis, MO
    • Pearlman, R. S. CONCORD; Tripos: St. Louis, MO, 1998.
    • (1998) CONCORD
    • Pearlman, R.S.1
  • 36
    • 56749090144 scopus 로고    scopus 로고
    • SYBYL, version 7.0; Tripos Inc, 1699 South Hanley Road, St. Louis, MO, 63144
    • SYBYL, version 7.0; Tripos Inc. (1699 South Hanley Road, St. Louis, MO, 63144).
  • 37
    • 0034700491 scopus 로고    scopus 로고
    • Structural basis of IAP recognition by Smac/DIABLO
    • Wu, G.; Chai, J.; Suber, T. L.; Wu, J. W.; Du, C.; Wang, X.; Shi, Y. Structural basis of IAP recognition by Smac/DIABLO. Nature 2000, 408, 1008-1012.
    • (2000) Nature , vol.408 , pp. 1008-1012
    • Wu, G.1    Chai, J.2    Suber, T.L.3    Wu, J.W.4    Du, C.5    Wang, X.6    Shi, Y.7
  • 38
    • 0028854034 scopus 로고
    • Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation
    • Jones, G.; Willett, P.; Glen, R. C. Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation. J. Mol. Biol. 1995, 245, 43-53.
    • (1995) J. Mol. Biol , vol.245 , pp. 43-53
    • Jones, G.1    Willett, P.2    Glen, R.C.3
  • 39
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
    • (1997) J. Mol. Biol , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 43
    • 0021698630 scopus 로고
    • Bioluminescence of cellular ATP: A new method for evaluating cytotoxic agents in vitro
    • Kangas, L.; Gronroos, M.; Nieminen, A. L. Bioluminescence of cellular ATP: a new method for evaluating cytotoxic agents in vitro. Med. Biol. 1984, 62, 338-343.
    • (1984) Med. Biol , vol.62 , pp. 338-343
    • Kangas, L.1    Gronroos, M.2    Nieminen, A.L.3
  • 44
    • 0032054804 scopus 로고    scopus 로고
    • The correlation of the weakening effect on gastric mucosal integrity by 5-HT with neutrophil activation
    • Ko, J. K.; Ma, J. J.; Chow, J. Y.; Ma, L.; Cho, C. H. The correlation of the weakening effect on gastric mucosal integrity by 5-HT with neutrophil activation. Free Radical Biol. Med. 1998, 24, 1007-1014.
    • (1998) Free Radical Biol. Med , vol.24 , pp. 1007-1014
    • Ko, J.K.1    Ma, J.J.2    Chow, J.Y.3    Ma, L.4    Cho, C.H.5
  • 45
    • 0034321407 scopus 로고    scopus 로고
    • A norbornenyl derivative with through-space ketone pi-interaction
    • Lloyd, B. A.; Arif, A. M.; Allred, E. L. A norbornenyl derivative with through-space ketone pi-interaction. Acta Crystallogr. C 2000, 56 (Part 11), 1377-1379.
    • (2000) Acta Crystallogr. C , vol.56 , Issue.PART 11 , pp. 1377-1379
    • Lloyd, B.A.1    Arif, A.M.2    Allred, E.L.3


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