Structural Basis of AZD9291 Selectivity for EGFR T790M

Yan, Xiao-E; Ayaz, Pelin; Zhu, Su-Jie; Zhao, Peng; Liang, Ling; Zhang, Casey H.; Wu, Ya-Chuang; Li, Je-Luen; Choi, Hwan Geun; Huang, Xin; Shan, Yibing; Shaw, David E.; Yun, Cai-Hong

doi:10.1021/acs.jmedchem.0c00891

Structural Basis of AZD9291 Selectivity for EGFR T790M

Journal Article · Wed Jul 01 04:00:00 EDT 2020 · J. Med. Chem.

DOI:https://doi.org/10.1021/acs.jmedchem.0c00891· OSTI ID:1834870

Yan, Xiao-E; Ayaz, Pelin; Zhu, Su-Jie; Zhao, Peng; Liang, Ling; Zhang, Casey H.; Wu, Ya-Chuang; Li, Je-Luen; Choi, Hwan Geun; Huang, Xin; Shan, Yibing; Shaw, David E.; Yun, Cai-Hong

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: DOE - Office Of Science; FOREIGN

OSTI ID:: 1834870

Journal Information:: J. Med. Chem., Journal Name: J. Med. Chem. Journal Issue: (15) Vol. 63

Country of Publication:: United States

Language:: ENGLISH

References (44)

PRODRG : a tool for high-throughput crystallography of protein–ligand complexes Schüttelkopf, Alexander W.; van Aalten, Daan M. F. Acta Crystallographica Section D Biological Crystallography, Vol. 60, Issue 8 https://doi.org/10.1107/S0907444904011679	journal	July 2004
Accurate and efficient integration for molecular dynamics simulations at constant temperature and pressure Lippert, Ross A.; Predescu, Cristian; Ierardi, Douglas J. The Journal of Chemical Physics, Vol. 139, Issue 16 https://doi.org/10.1063/1.4825247	journal	October 2013
Kinetic Analysis of Epidermal Growth Factor Receptor Somatic Mutant Proteins Shows Increased Sensitivity to the Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitor, Erlotinib Carey, Kendall D.; Garton, Andrew J.; Romero, Maria S. Cancer Research, Vol. 66, Issue 16 https://doi.org/10.1158/0008-5472.CAN-06-0453	journal	August 2006
Lazertinib in patients with EGFR mutation-positive advanced non-small-cell lung cancer: results from the dose escalation and dose expansion parts of a first-in-human, open-label, multicentre, phase 1–2 study Ahn, Myung-Ju; Han, Ji-Youn; Lee, Ki Hyeong The Lancet Oncology, Vol. 20, Issue 12 https://doi.org/10.1016/S1470-2045(19)30504-2	journal	December 2019
How Does a Drug Molecule Find Its Target Binding Site? Shan, Yibing; Kim, Eric T.; Eastwood, Michael P. Journal of the American Chemical Society, Vol. 133, Issue 24 https://doi.org/10.1021/ja202726y	journal	June 2011
Binding mode of the breakthrough inhibitor AZD9291 to epidermal growth factor receptor revealed Yosaatmadja, Yuliana; Silva, Shevan; Dickson, James M. Journal of Structural Biology, Vol. 192, Issue 3 https://doi.org/10.1016/j.jsb.2015.10.018	journal	December 2015
EGFR Mutation and Resistance of Non–Small-Cell Lung Cancer to Gefitinib Kobayashi, Susumu; Boggon, Titus J.; Dayaram, Tajhal New England Journal of Medicine, Vol. 352, Issue 8 https://doi.org/10.1056/NEJMoa044238	journal	February 2005
EGFR Mutations and Resistance to Irreversible Pyrimidine-Based EGFR Inhibitors Ercan, Dalia; Choi, Hwan Geun; Yun, Cai-Hong Clinical Cancer Research, Vol. 21, Issue 17 https://doi.org/10.1158/1078-0432.CCR-14-2789	journal	May 2015
EGF receptor gene mutations are common in lung cancers from "never smokers" and are associated with sensitivity of tumors to gefitinib and erlotinib Pao, W.; Miller, V.; Zakowski, M. Proceedings of the National Academy of Sciences, Vol. 101, Issue 36 https://doi.org/10.1073/pnas.0405220101	journal	August 2004
Features and development of Coot Emsley, P.; Lohkamp, B.; Scott, W. G. Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 4 https://doi.org/10.1107/S0907444910007493	journal	March 2010
Comparison of multiple Amber force fields and development of improved protein backbone parameters Hornak, Viktor; Abel, Robert; Okur, Asim Proteins: Structure, Function, and Bioinformatics, Vol. 65, Issue 3 https://doi.org/10.1002/prot.21123	journal	November 2006
Osimertinib: First Global Approval Greig, Sarah L. Drugs, Vol. 76, Issue 2 https://doi.org/10.1007/s40265-015-0533-4	journal	January 2016
Improved side-chain torsion potentials for the Amber ff99SB protein force field Lindorff-Larsen, Kresten; Piana, Stefano; Palmo, Kim Proteins: Structure, Function, and Bioinformatics https://doi.org/10.1002/prot.22711	journal	January 2010
PHENIX: a comprehensive Python-based system for macromolecular structure solution Adams, Paul D.; Afonine, Pavel V.; Bunkóczi, Gábor Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2, p. 213-221 https://doi.org/10.1107/S0907444909052925	journal	January 2010
An Allosteric Mechanism for Activation of the Kinase Domain of Epidermal Growth Factor Receptor Zhang, Xuewu; Gureasko, Jodi; Shen, Kui Cell, Vol. 125, Issue 6 https://doi.org/10.1016/j.cell.2006.05.013	journal	June 2006
AZD9291 in EGFR Inhibitor–Resistant Non–Small-Cell Lung Cancer Jänne, Pasi A.; Yang, James Chih-Hsin; Kim, Dong-Wan New England Journal of Medicine, Vol. 372, Issue 18 https://doi.org/10.1056/NEJMoa1411817	journal	April 2015
The u -series: A separable decomposition for electrostatics computation with improved accuracy Predescu, Cristian; Lerer, Adam K.; Lippert, Ross A. The Journal of Chemical Physics, Vol. 152, Issue 8 https://doi.org/10.1063/1.5129393	journal	February 2020
Structures of Lung Cancer-Derived EGFR Mutants and Inhibitor Complexes: Mechanism of Activation and Insights into Differential Inhibitor Sensitivity Yun, Cai-Hong; Boggon, Titus J.; Li, Yiqun Cancer Cell, Vol. 11, Issue 3 https://doi.org/10.1016/j.ccr.2006.12.017	journal	March 2007
The T790M mutation in EGFR kinase causes drug resistance by increasing the affinity for ATP Yun, C. -H.; Mengwasser, K. E.; Toms, A. V. Proceedings of the National Academy of Sciences, Vol. 105, Issue 6 https://doi.org/10.1073/pnas.0709662105	journal	January 2008
HKL -3000: the integration of data reduction and structure solution – from diffraction images to an initial model in minutes Minor, Wladek; Cymborowski, Marcin; Otwinowski, Zbyszek Acta Crystallographica Section D Biological Crystallography, Vol. 62, Issue 8 https://doi.org/10.1107/S0907444906019949	journal	July 2006
Phaser crystallographic software McCoy, Airlie J.; Grosse-Kunstleve, Ralf W.; Adams, Paul D. Journal of Applied Crystallography, Vol. 40, Issue 4 https://doi.org/10.1107/S0021889807021206	journal	July 2007
Novel mutant-selective EGFR kinase inhibitors against EGFR T790M Zhou, Wenjun; Ercan, Dalia; Chen, Liang Nature, Vol. 462, Issue 7276 https://doi.org/10.1038/nature08622	journal	December 2009
Development and testing of a general amber force field Wang, Junmei; Wolf, Romain M.; Caldwell, James W. Journal of Computational Chemistry, Vol. 25, Issue 9 https://doi.org/10.1002/jcc.20035	journal	January 2004
A review on progression of epidermal growth factor receptor (EGFR) inhibitors as an efficient approach in cancer targeted therapy Ayati, Adileh; Moghimi, Setareh; Salarinejad, Somayeh Bioorganic Chemistry, Vol. 99 https://doi.org/10.1016/j.bioorg.2020.103811	journal	June 2020
Discovery of a Mutant-Selective Covalent Inhibitor of EGFR that Overcomes T790M-Mediated Resistance in NSCLC Walter, A. O.; Sjin, R. T. T.; Haringsma, H. J. Cancer Discovery, Vol. 3, Issue 12 https://doi.org/10.1158/2159-8290.CD-13-0314	journal	September 2013
Activating Mutations in the Epidermal Growth Factor Receptor Underlying Responsiveness of Non–Small-Cell Lung Cancer to Gefitinib Lynch, Thomas J.; Bell, Daphne W.; Sordella, Raffaella New England Journal of Medicine, Vol. 350, Issue 21 https://doi.org/10.1056/NEJMoa040938	journal	May 2004
Novel D761Y and Common Secondary T790M Mutations in Epidermal Growth Factor Receptor-Mutant Lung Adenocarcinomas with Acquired Resistance to Kinase Inhibitors Balak, M. N.; Gong, Y.; Riely, G. J. Clinical Cancer Research, Vol. 12, Issue 21 https://doi.org/10.1158/1078-0432.CCR-06-1570	journal	November 2006
Olmutinib: First Global Approval Kim, Esther S. Drugs, Vol. 76, Issue 11 https://doi.org/10.1007/s40265-016-0606-z	journal	June 2016
Crystallography & NMR System: A New Software Suite for Macromolecular Structure Determination Brünger, A. T.; Adams, P. D.; Clore, G. M. Acta Crystallographica Section D Biological Crystallography, Vol. 54, Issue 5 https://doi.org/10.1107/S0907444998003254	journal	September 1998
Discovery of Selective and Noncovalent Diaminopyrimidine-Based Inhibitors of Epidermal Growth Factor Receptor Containing the T790M Resistance Mutation Hanan, Emily J.; Eigenbrot, Charles; Bryan, Marian C. Journal of Medicinal Chemistry, Vol. 57, Issue 23 https://doi.org/10.1021/jm501578n	journal	November 2014
Rociletinib in EGFR -Mutated Non–Small-Cell Lung Cancer Sequist, Lecia V.; Soria, Jean-Charles; Goldman, Jonathan W. New England Journal of Medicine, Vol. 372, Issue 18 https://doi.org/10.1056/NEJMoa1413654	journal	April 2015
Transitions to catalytically inactive conformations in EGFR kinase Shan, Y.; Arkhipov, A.; Kim, E. T. Proceedings of the National Academy of Sciences, Vol. 110, Issue 18 https://doi.org/10.1073/pnas.1220843110	journal	April 2013
Optimized Molecular Dynamics Force Fields Applied to the Helix−Coil Transition of Polypeptides Best, Robert B.; Hummer, Gerhard The Journal of Physical Chemistry B, Vol. 113, Issue 26 https://doi.org/10.1021/jp901540t	journal	July 2009
Acquired EGFR C797S mutation mediates resistance to AZD9291 in non–small cell lung cancer harboring EGFR T790M Thress, Kenneth S.; Paweletz, Cloud P.; Felip, Enriqueta Nature Medicine, Vol. 21, Issue 6 https://doi.org/10.1038/nm.3854	journal	May 2015
AZD9291, an Irreversible EGFR TKI, Overcomes T790M-Mediated Resistance to EGFR Inhibitors in Lung Cancer Cross, Darren A. E.; Ashton, Susan E.; Ghiorghiu, Serban Cancer Discovery, Vol. 4, Issue 9 https://doi.org/10.1158/2159-8290.CD-14-0337	journal	June 2014
Acquired Resistance of Lung Adenocarcinomas to Gefitinib or Erlotinib Is Associated with a Second Mutation in the EGFR Kinase Domain Pao, William; Miller, Vincent A.; Politi, Katerina A. PLoS Medicine, Vol. 2, Issue 3 https://doi.org/10.1371/journal.pmed.0020073	journal	February 2005
EGFR Mutations in Lung Cancer: Correlation with Clinical Response to Gefitinib Therapy Paez, J. G. Science, Vol. 304, Issue 5676 https://doi.org/10.1126/science.1099314	journal	June 2004
Constant pressure molecular dynamics algorithms Martyna, Glenn J.; Tobias, Douglas J.; Klein, Michael L. The Journal of Chemical Physics, Vol. 101, Issue 5 https://doi.org/10.1063/1.467468	journal	September 1994
Covalent EGFR inhibitor analysis reveals importance of reversible interactions to potency and mechanisms of drug resistance Schwartz, P. A.; Kuzmic, P.; Solowiej, J. Proceedings of the National Academy of Sciences, Vol. 111, Issue 1 https://doi.org/10.1073/pnas.1313733111	journal	December 2013
Comparison of simple potential functions for simulating liquid water Jorgensen, William L.; Chandrasekhar, Jayaraman; Madura, Jeffry D. The Journal of Chemical Physics, Vol. 79, Issue 2 https://doi.org/10.1063/1.445869	journal	July 1983
Canonical dynamics: Equilibrium phase-space distributions Hoover, William G. Physical Review A, Vol. 31, Issue 3 https://doi.org/10.1103/PhysRevA.31.1695	journal	March 1985
The ORCA program system: The ORCA program system Neese, Frank Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 1 https://doi.org/10.1002/wcms.81	journal	June 2011
Oncogenic Mutations Counteract Intrinsic Disorder in the EGFR Kinase and Promote Receptor Dimerization Shan, Yibing; Eastwood, Michael P.; Zhang, Xuewu Cell, Vol. 149, Issue 4 https://doi.org/10.1016/j.cell.2012.02.063	journal	May 2012
Psi4 1.1: An Open-Source Electronic Structure Program Emphasizing Automation, Advanced Libraries, and Interoperability Parrish, Robert M.; Burns, Lori A.; Smith, Daniel G. A. Journal of Chemical Theory and Computation, Vol. 13, Issue 7 https://doi.org/10.1021/acs.jctc.7b00174	journal	June 2017

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