메뉴 건너뛰기




Volumn 25, Issue 7, 2017, Pages 1120-1129.e3

Dissecting the Specificity of Adenosyl Sulfamate Inhibitors Targeting the Ubiquitin-Activating Enzyme

Author keywords

adenosyl sulfamate inhibitors; cancer; drug design; E1 enzymes; ubiquitin; ubiquitin activating enzyme; ubiquitin like protein

Indexed keywords

ABPA 3; ADENOSYL SULFAMATE INHIBITOR; LIGASE INHIBITOR; MLN 7243; PEVONEDISTAT; UBIQUITIN E1; UBIQUITIN PROTEIN LIGASE; UNCLASSIFIED DRUG; CYCLOPENTANE DERIVATIVE; ENZYME INHIBITOR; MLN7243; NUCLEOSIDE; PROTEIN BINDING; PYRIMIDINE DERIVATIVE; SACCHAROMYCES CEREVISIAE PROTEIN; SULFONAMIDE; UBE1 PROTEIN, HUMAN;

EID: 85020090314     PISSN: 09692126     EISSN: 18784186     Source Type: Journal    
DOI: 10.1016/j.str.2017.05.001     Document Type: Article
Times cited : (30)

References (56)
  • 2
    • 84887639752 scopus 로고    scopus 로고
    • Development of activity-based probes for ubiquitin and ubiquitin-like protein signaling pathways
    • An, H., Statsyuk, A.V., Development of activity-based probes for ubiquitin and ubiquitin-like protein signaling pathways. J. Am. Chem. Soc. 135 (2013), 16948–16962.
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 16948-16962
    • An, H.1    Statsyuk, A.V.2
  • 3
    • 84938912227 scopus 로고    scopus 로고
    • An inhibitor of ubiquitin conjugation and aggresome formation
    • An, H., Statsyuk, A.V., An inhibitor of ubiquitin conjugation and aggresome formation. Chem. Sci. 6 (2015), 5235–5245.
    • (2015) Chem. Sci. , vol.6 , pp. 5235-5245
    • An, H.1    Statsyuk, A.V.2
  • 4
    • 84957573418 scopus 로고    scopus 로고
    • Facile synthesis of covalent probes to capture enzymatic intermediates during E1 enzyme catalysis
    • An, H., Statsyuk, A.V., Facile synthesis of covalent probes to capture enzymatic intermediates during E1 enzyme catalysis. Chem. Commun. (Camb.) 52 (2015), 2477–2480.
    • (2015) Chem. Commun. (Camb.) , vol.52 , pp. 2477-2480
    • An, H.1    Statsyuk, A.V.2
  • 5
    • 0035665229 scopus 로고    scopus 로고
    • The linear interaction energy method for predicting ligand binding free energy
    • Åqvist, J., Marelius, J., The linear interaction energy method for predicting ligand binding free energy. Comb. Chem. High Throughput Screen. 4 (2001), 613–626.
    • (2001) Comb. Chem. High Throughput Screen. , vol.4 , pp. 613-626
    • Åqvist, J.1    Marelius, J.2
  • 6
    • 77953744624 scopus 로고    scopus 로고
    • Crystal structure of the human ubiquitin-activating enzyme 5 (UBA5) bound to ATP: mechanistic insights into a minimalistic E1 enzyme
    • Bacik, J.P., Walker, J.R., Ali, M., Schimmer, A.D., Dhe-Paganon, S., Crystal structure of the human ubiquitin-activating enzyme 5 (UBA5) bound to ATP: mechanistic insights into a minimalistic E1 enzyme. J. Biol. Chem. 285 (2010), 20273–20280.
    • (2010) J. Biol. Chem. , vol.285 , pp. 20273-20280
    • Bacik, J.P.1    Walker, J.R.2    Ali, M.3    Schimmer, A.D.4    Dhe-Paganon, S.5
  • 8
  • 9
    • 0028308828 scopus 로고
    • Site-directed mutagenesis of ubiquitin. Differential roles for arginine in the interaction with ubiquitin-activating enzyme
    • Burch, T.J., Haas, A.L., Site-directed mutagenesis of ubiquitin. Differential roles for arginine in the interaction with ubiquitin-activating enzyme. Biochemistry 33 (1994), 7300–7308.
    • (1994) Biochemistry , vol.33 , pp. 7300-7308
    • Burch, T.J.1    Haas, A.L.2
  • 10
    • 85022166405 scopus 로고    scopus 로고
    • Ubiquitin-like protein conjugation: structures, chemistry, and mechanism
    • Cappadocia, L., Lima, C.D., Ubiquitin-like protein conjugation: structures, chemistry, and mechanism. Chem. Rev., 2017, 10.1021/acs.chemrev.6b00737.
    • (2017) Chem. Rev.
    • Cappadocia, L.1    Lima, C.D.2
  • 13
  • 14
    • 33846823909 scopus 로고
    • Particle mesh Ewald: an N ⋅ log(N) method for Ewald sums in large systems
    • Darden, T., York, D., Pedersen, L., Particle mesh Ewald: an N ⋅ log(N) method for Ewald sums in large systems. J. Chem. Phys. 98 (1993), 10089–10092.
    • (1993) J. Chem. Phys. , vol.98 , pp. 10089-10092
    • Darden, T.1    York, D.2    Pedersen, L.3
  • 17
    • 0021102445 scopus 로고
    • Ubiquitin adenylate: structure and role in ubiquitin activation
    • Haas, A.L., Warms, J.V., Rose, I.A., Ubiquitin adenylate: structure and role in ubiquitin activation. Biochemistry 22 (1983), 4388–4394.
    • (1983) Biochemistry , vol.22 , pp. 4388-4394
    • Haas, A.L.1    Warms, J.V.2    Rose, I.A.3
  • 19
    • 33748518255 scopus 로고    scopus 로고
    • Comparison of multiple Amber force fields and development of improved protein backbone parameters
    • Hornak, V., Abel, R., Okur, A., Strockbine, B., Roitberg, A., Simmerling, C., Comparison of multiple Amber force fields and development of improved protein backbone parameters. Proteins 65 (2006), 712–725.
    • (2006) Proteins , vol.65 , pp. 712-725
    • Hornak, V.1    Abel, R.2    Okur, A.3    Strockbine, B.4    Roitberg, A.5    Simmerling, C.6
  • 20
    • 33846548206 scopus 로고    scopus 로고
    • Basis for a ubiquitin-like protein thioester switch toggling E1-E2 affinity
    • Huang, D.T., Hunt, H.W., Zhuang, M., Ohi, M.D., Holton, J.M., Schulman, B.A., Basis for a ubiquitin-like protein thioester switch toggling E1-E2 affinity. Nature 445 (2007), 394–398.
    • (2007) Nature , vol.445 , pp. 394-398
    • Huang, D.T.1    Hunt, H.W.2    Zhuang, M.3    Ohi, M.D.4    Holton, J.M.5    Schulman, B.A.6
  • 24
    • 24944497371 scopus 로고    scopus 로고
    • Features of selective kinase inhibitors
    • Knight, Z.A., Shokat, K.M., Features of selective kinase inhibitors. Chem. Biol. 12 (2005), 621–637.
    • (2005) Chem. Biol. , vol.12 , pp. 621-637
    • Knight, Z.A.1    Shokat, K.M.2
  • 25
    • 65249157397 scopus 로고    scopus 로고
    • Protonate3D: assignment of ionization states and hydrogen coordinates to macromolecular structures
    • Labute, P., Protonate3D: assignment of ionization states and hydrogen coordinates to macromolecular structures. Proteins 75 (2009), 187–205.
    • (2009) Proteins , vol.75 , pp. 187-205
    • Labute, P.1
  • 26
    • 47549111312 scopus 로고    scopus 로고
    • Structural insights into E1-catalyzed ubiquitin activation and transfer to conjugating enzymes
    • Lee, I., Schindelin, H., Structural insights into E1-catalyzed ubiquitin activation and transfer to conjugating enzymes. Cell 134 (2008), 268–278.
    • (2008) Cell , vol.134 , pp. 268-278
    • Lee, I.1    Schindelin, H.2
  • 27
    • 14844291338 scopus 로고    scopus 로고
    • Structures of the SUMO E1 provide mechanistic insights into SUMO activation and E2 recruitment to E1
    • Lois, L.M., Lima, C.D., Structures of the SUMO E1 provide mechanistic insights into SUMO activation and E2 recruitment to E1. EMBO J. 24 (2005), 439–451.
    • (2005) EMBO J. , vol.24 , pp. 439-451
    • Lois, L.M.1    Lima, C.D.2
  • 28
    • 77249098370 scopus 로고    scopus 로고
    • Designed semisynthetic protein inhibitors of Ub/Ubl E1 activating enzymes
    • Lu, X., Olsen, S.K., Capili, A.D., Cisar, J.S., Lima, C.D., Tan, D.S., Designed semisynthetic protein inhibitors of Ub/Ubl E1 activating enzymes. J. Am. Chem. Soc. 132 (2010), 1748–1749.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 1748-1749
    • Lu, X.1    Olsen, S.K.2    Capili, A.D.3    Cisar, J.S.4    Lima, C.D.5    Tan, D.S.6
  • 31
    • 37249023309 scopus 로고    scopus 로고
    • New and original pKa prediction method using grid molecular interaction fields
    • Milletti, F., Storchi, L., Sforna, G., Cruciani, G., New and original pKa prediction method using grid molecular interaction fields. J. Chem. Inf. Model. 47 (2007), 2172–2181.
    • (2007) J. Chem. Inf. Model. , vol.47 , pp. 2172-2181
    • Milletti, F.1    Storchi, L.2    Sforna, G.3    Cruciani, G.4
  • 34
    • 84866532722 scopus 로고    scopus 로고
    • MLN4924: a novel first-in-class inhibitor of NEDD8-activating enzyme for cancer therapy
    • Nawrocki, S.T., Griffin, P., Kelly, K.R., Carew, J.S., MLN4924: a novel first-in-class inhibitor of NEDD8-activating enzyme for cancer therapy. Expert Opin. Investig. Drugs 21 (2012), 1563–1573.
    • (2012) Expert Opin. Investig. Drugs , vol.21 , pp. 1563-1573
    • Nawrocki, S.T.1    Griffin, P.2    Kelly, K.R.3    Carew, J.S.4
  • 36
    • 77249138804 scopus 로고    scopus 로고
    • Active site remodelling accompanies thioester bond formation in the SUMO E1
    • Olsen, S.K., Capili, A.D., Lu, X., Tan, D.S., Lima, C.D., Active site remodelling accompanies thioester bond formation in the SUMO E1. Nature 463 (2010), 906–912.
    • (2010) Nature , vol.463 , pp. 906-912
    • Olsen, S.K.1    Capili, A.D.2    Lu, X.3    Tan, D.S.4    Lima, C.D.5
  • 39
    • 84904790793 scopus 로고    scopus 로고
    • Deciphering key features in protein structures with the new ENDscript server
    • Robert, X., Gouet, P., Deciphering key features in protein structures with the new ENDscript server. Nucleic Acids Res. 42 (2014), W320–W324.
    • (2014) Nucleic Acids Res. , vol.42 , pp. W320-W324
    • Robert, X.1    Gouet, P.2
  • 40
    • 84880022273 scopus 로고    scopus 로고
    • PTRAJ and cpptraj: software for processing and analysis of molecular dynamics trajectory data
    • Roe, D.R., Cheatham, T.E. III, PTRAJ and cpptraj: software for processing and analysis of molecular dynamics trajectory data. J. Chem. Theor. Comput 9 (2013), 3084–3095.
    • (2013) J. Chem. Theor. Comput , vol.9 , pp. 3084-3095
    • Roe, D.R.1    Cheatham, T.E.2
  • 42
    • 84900439199 scopus 로고    scopus 로고
    • Structure of the ubiquitin-activating enzyme loaded with two ubiquitin molecules
    • Schäfer, A., Kuhn, M., Schindelin, H., Structure of the ubiquitin-activating enzyme loaded with two ubiquitin molecules. Acta Crystallogr. D Biol. Crystallogr. 70 (2014), 1311–1320.
    • (2014) Acta Crystallogr. D Biol. Crystallogr. , vol.70 , pp. 1311-1320
    • Schäfer, A.1    Kuhn, M.2    Schindelin, H.3
  • 43
    • 67349256160 scopus 로고    scopus 로고
    • Ubiquitin-like protein activation by E1 enzymes: the apex for downstream signalling pathways
    • Schulman, B.A., Harper, J.W., Ubiquitin-like protein activation by E1 enzymes: the apex for downstream signalling pathways. Nat. Rev. Mol. Cell Biol. 10 (2009), 319–331.
    • (2009) Nat. Rev. Mol. Cell Biol. , vol.10 , pp. 319-331
    • Schulman, B.A.1    Harper, J.W.2
  • 44
    • 84954478601 scopus 로고    scopus 로고
    • Phase I study of the novel investigational NEDD8-activating enzyme inhibitor Pevonedistat (MLN4924) in patients with relapsed/refractory multiple myeloma or lymphoma
    • Shah, J.J., Jakubowiak, A.J., O'Connor, O.A., Orlowski, R.Z., Harvey, R.D., Smith, M.R., Lebovic, D., Diefenbach, C., Kelly, K., Hua, Z., et al. Phase I study of the novel investigational NEDD8-activating enzyme inhibitor Pevonedistat (MLN4924) in patients with relapsed/refractory multiple myeloma or lymphoma. Clin. Cancer Res. 22 (2016), 34–43.
    • (2016) Clin. Cancer Res. , vol.22 , pp. 34-43
    • Shah, J.J.1    Jakubowiak, A.J.2    O'Connor, O.A.3    Orlowski, R.Z.4    Harvey, R.D.5    Smith, M.R.6    Lebovic, D.7    Diefenbach, C.8    Kelly, K.9    Hua, Z.10
  • 45
    • 84875735840 scopus 로고    scopus 로고
    • Exploring a new frontier in cancer treatment: targeting the ubiquitin and ubiquitin-like activating enzymes
    • da Silva, S.R., Paiva, S.L., Lukkarila, J.L., Gunning, P.T., Exploring a new frontier in cancer treatment: targeting the ubiquitin and ubiquitin-like activating enzymes. J. Med. Chem. 56 (2013), 2165–2177.
    • (2013) J. Med. Chem. , vol.56 , pp. 2165-2177
    • da Silva, S.R.1    Paiva, S.L.2    Lukkarila, J.L.3    Gunning, P.T.4
  • 47
    • 84863856481 scopus 로고    scopus 로고
    • Mitigating heterocycle metabolism in drug discovery
    • St Jean, D.J. Jr., Fotsch, C., Mitigating heterocycle metabolism in drug discovery. J. Med. Chem. 55 (2012), 6002–6020.
    • (2012) J. Med. Chem. , vol.55 , pp. 6002-6020
    • St Jean, D.J.1    Fotsch, C.2
  • 48
    • 84934876880 scopus 로고    scopus 로고
    • Activation of ubiquitin and ubiquitin-like proteins
    • Streich, F.C. Jr., Haas, A.L., Activation of ubiquitin and ubiquitin-like proteins. Subcell Biochem. 54 (2010), 1–16.
    • (2010) Subcell Biochem. , vol.54 , pp. 1-16
    • Streich, F.C.1    Haas, A.L.2
  • 49
    • 84861167946 scopus 로고    scopus 로고
    • A gatekeeper residue for NEDD8-activating enzyme inhibition by MLN4924
    • Toth, J.I., Yang, L., Dahl, R., Petroski, M.D., A gatekeeper residue for NEDD8-activating enzyme inhibition by MLN4924. Cell Rep. 1 (2012), 309–316.
    • (2012) Cell Rep. , vol.1 , pp. 309-316
    • Toth, J.I.1    Yang, L.2    Dahl, R.3    Petroski, M.D.4
  • 51
    • 14244273182 scopus 로고    scopus 로고
    • Theory and applications of the generalized Born solvation model in macromolecular simulations
    • Tsui, V., Case, D.A., Theory and applications of the generalized Born solvation model in macromolecular simulations. Biopolymers 56 (2001), 275–291.
    • (2001) Biopolymers , vol.56 , pp. 275-291
    • Tsui, V.1    Case, D.A.2
  • 53
    • 33748538349 scopus 로고    scopus 로고
    • Automatic atom type and bond type perception in molecular mechanical calculations
    • Wang, J., Wang, W., Kollman, P.A., Case, D.A., Automatic atom type and bond type perception in molecular mechanical calculations. J. Mol. Graph. Model. 25 (2006), 247–260.
    • (2006) J. Mol. Graph. Model. , vol.25 , pp. 247-260
    • Wang, J.1    Wang, W.2    Kollman, P.A.3    Case, D.A.4
  • 54
    • 0025050664 scopus 로고
    • A specific inhibitor of the ubiquitin activating enzyme: synthesis and characterization of adenosyl-phospho-ubiquitinol, a nonhydrolyzable ubiquitin adenylate analogue
    • Wilkinson, K.D., Smith, S.E., O'Connor, L., Sternberg, E., Taggart, J.J., Berges, D.A., Butt, T., A specific inhibitor of the ubiquitin activating enzyme: synthesis and characterization of adenosyl-phospho-ubiquitinol, a nonhydrolyzable ubiquitin adenylate analogue. Biochemistry 29 (1990), 7373–7380.
    • (1990) Biochemistry , vol.29 , pp. 7373-7380
    • Wilkinson, K.D.1    Smith, S.E.2    O'Connor, L.3    Sternberg, E.4    Taggart, J.J.5    Berges, D.A.6    Butt, T.7
  • 56
    • 77950421253 scopus 로고    scopus 로고
    • The ubiquitin-activating enzyme E1 as a therapeutic target for the treatment of leukemia and multiple myeloma
    • Xu, G.W., Ali, M., Wood, T.E., Wong, D., Maclean, N., Wang, X., Gronda, M., Skrtic, M., Li, X., Hurren, R., et al. The ubiquitin-activating enzyme E1 as a therapeutic target for the treatment of leukemia and multiple myeloma. Blood 115 (2010), 2251–2259.
    • (2010) Blood , vol.115 , pp. 2251-2259
    • Xu, G.W.1    Ali, M.2    Wood, T.E.3    Wong, D.4    Maclean, N.5    Wang, X.6    Gronda, M.7    Skrtic, M.8    Li, X.9    Hurren, R.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.