Exploring Covalent Allosteric Inhibition of Antigen 85C from Mycobacterium tuberculosis by Ebselen Derivatives

Goins, Christopher M.; Dajnowicz, Steven; Thanna, Sandeep; Sucheck, Steven J.; Parks, Jerry M.; Ronning, Donald R.

doi:10.1021/acsinfecdis.7b00003

Title: Exploring Covalent Allosteric Inhibition of Antigen 85C from Mycobacterium tuberculosis by Ebselen Derivatives

Journal Article · Tue Mar 21 00:00:00 EDT 2017 · ACS Infectious Diseases

DOI:https://doi.org/10.1021/acsinfecdis.7b00003· OSTI ID:1368347

Goins, Christopher M.; Dajnowicz, Steven; Thanna, Sandeep;

; Parks, Jerry M.;

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: National Institutes of Health (NIH)

OSTI ID:: 1368347

Journal Information:: ACS Infectious Diseases, Vol. 3, Issue 5; ISSN 2373-8227

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: ENGLISH

References (39)

India reports cases of totally drug-resistant tuberculosis Loewenberg, Samuel The Lancet, Vol. 379, Issue 9812 https://doi.org/10.1016/S0140-6736(12)60085-3	journal	January 2012
Mechanism of inhibition of Mycobacterium tuberculosis antigen 85 by ebselen Favrot, Lorenza; Grzegorzewicz, Anna E.; Lajiness, Daniel H. Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms3748	journal	November 2013
Role of the Major Antigen of Mycobacterium tuberculosis in Cell Wall Biogenesis Belisle, J. T. Science, Vol. 276, Issue 5317 https://doi.org/10.1126/science.276.5317.1420	journal	May 1997
Antigen 85C-mediated acyl-transfer between synthetic acyl donors and fragments of the arabinan Sanki, Aditya K.; Boucau, Julie; Ronning, Donald R. Glycoconjugate Journal, Vol. 26, Issue 5 https://doi.org/10.1007/s10719-008-9211-z	journal	December 2008
Disruption of the Genes Encoding Antigen 85A and Antigen 85B of Mycobacterium tuberculosis H37Rv: Effect on Growth in Culture and in Macrophages Armitige, L. Y.; Jagannath, C.; Wanger, A. R. Infection and Immunity, Vol. 68, Issue 2 https://doi.org/10.1128/IAI.68.2.767-778.2000	journal	February 2000
Study of Highly Selective and Efficient Thiol Derivatization Using Selenium Reagents by Mass Spectrometry Xu, Kehua; Zhang, Yun; Tang, Bo Analytical Chemistry, Vol. 82, Issue 16 https://doi.org/10.1021/ac1011602	journal	August 2010
Inactivation of the Mycobacterium tuberculosis Antigen 85 Complex by Covalent, Allosteric Inhibitors Favrot, Lorenza; Lajiness, Daniel H.; Ronning, Donald R. Journal of Biological Chemistry, Vol. 289, Issue 36 https://doi.org/10.1074/jbc.M114.582445	journal	July 2014
Cation-pi interactions in structural biology Gallivan, J. P.; Dougherty, D. A. Proceedings of the National Academy of Sciences, Vol. 96, Issue 17 https://doi.org/10.1073/pnas.96.17.9459	journal	August 1999
The Cation−π Interaction Ma, Jennifer C.; Dougherty, Dennis A. Chemical Reviews, Vol. 97, Issue 5 https://doi.org/10.1021/cr9603744	journal	August 1997
Thermal and Photoinduced Copper-Promoted C–Se Bond Formation: Synthesis of 2-Alkyl-1,2-benzisoselenazol-3(2 H )-ones and Evaluation against Mycobacterium tuberculosis Thanna, Sandeep; Goins, Christopher M.; Knudson, Susan E. The Journal of Organic Chemistry, Vol. 82, Issue 7 https://doi.org/10.1021/acs.joc.7b00440	journal	March 2017
Applying thermodynamic profiling in lead finding and optimization Klebe, Gerhard Nature Reviews Drug Discovery, Vol. 14, Issue 2 https://doi.org/10.1038/nrd4486	journal	January 2015
Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G. The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396 https://doi.org/10.1021/jp810292n	journal	May 2009
Basis set consistent revision of the S22 test set of noncovalent interaction energies Takatani, Tait; Hohenstein, Edward G.; Malagoli, Massimo The Journal of Chemical Physics, Vol. 132, Issue 14 https://doi.org/10.1063/1.3378024	journal	April 2010
Erratum to “S66: A Well-balanced Database of Benchmark Interaction Energies Relevant to Biomolecular Structures” Řezáč, Jan; Riley, Kevin E.; Hobza, Pavel Journal of Chemical Theory and Computation, Vol. 10, Issue 3 https://doi.org/10.1021/ct5000692	journal	February 2014
Unexpected Substituent Effects in Face-to-Face π-Stacking Interactions Sinnokrot, Mutasem Omar; Sherrill, C. David The Journal of Physical Chemistry A, Vol. 107, Issue 41 https://doi.org/10.1021/jp030880e	journal	October 2003
Substituent Effects in π−π Interactions: Sandwich and T-Shaped Configurations Sinnokrot, Mutasem Omar; Sherrill, C. David Journal of the American Chemical Society, Vol. 126, Issue 24 https://doi.org/10.1021/ja049434a	journal	June 2004
Modeling π–π Interactions with the Effective Fragment Potential Method: The Benzene Dimer and Substituents Smith, Toni; Slipchenko, Lyudmila V.; Gordon*, Mark S. The Journal of Physical Chemistry A, Vol. 112, Issue 23 https://doi.org/10.1021/jp800107z	journal	June 2008
Cation–π interactions: computational analyses of the aromatic box motif and the fluorination strategy for experimental evaluation Davis, Matthew R.; Dougherty, Dennis A. Physical Chemistry Chemical Physics, Vol. 17, Issue 43 https://doi.org/10.1039/C5CP04668H	journal	January 2015
Improving the Force Field Description of Tyrosine–Choline Cation−π Interactions: QM Investigation of Phenol–N(Me) ₄ ⁺ Interactions Khan, Hanif M.; Grauffel, Cédric; Broer, Ria Journal of Chemical Theory and Computation, Vol. 12, Issue 11 https://doi.org/10.1021/acs.jctc.6b00654	journal	October 2016
Do denaturants interact with aromatic hydrocarbons in water? Duffy, Erin M.; Kowalczyk, Paul J.; Jorgensen, William L. Journal of the American Chemical Society, Vol. 115, Issue 20 https://doi.org/10.1021/ja00073a050	journal	October 1993
An interfacial mechanism and a class of inhibitors inferred from two crystal structures of the Mycobacterium tuberculosis 30 kda major secretory protein (antigen 85B), a mycolyl transferase11Edited by I. A. Wilson Anderson, Daniel H.; Harth, Günter; Horwitz, Marcus A. Journal of Molecular Biology, Vol. 307, Issue 2 https://doi.org/10.1006/jmbi.2001.4461	journal	March 2001
Mycobacterium tuberculosis Antigen 85A and 85C Structures Confirm Binding Orientation and Conserved Substrate Specificity Ronning, Donald R.; Vissa, Varalakshmi; Besra, Gurdyal S. Journal of Biological Chemistry, Vol. 279, Issue 35 https://doi.org/10.1074/jbc.M400811200	journal	June 2004
The Three Mycobacterium tuberculosis Antigen 85 Isoforms Have Unique Substrates and Activities Determined by Non-active Site Regions Backus, Keriann M.; Dolan, Michael A.; Barry, Conor S. Journal of Biological Chemistry, Vol. 289, Issue 36 https://doi.org/10.1074/jbc.M114.581579	journal	July 2014
High-Density Miniaturized Thermal Shift Assays as a General Strategy for Drug Discovery Pantoliano, M. W.; Petrella, E. C.; Kwasnoski, J. D. Journal of Biomolecular Screening, Vol. 6, Issue 6 https://doi.org/10.1177/108705710100600609	journal	December 2001
Biophysical characterization of recombinant proteins: A key to higher structural genomics success Vedadi, Masoud; Arrowsmith, Cheryl H.; Allali-Hassani, Abdellah Journal of Structural Biology, Vol. 172, Issue 1 https://doi.org/10.1016/j.jsb.2010.05.005	journal	October 2010
Use of differential scanning fluorimetry to optimize the purification and crystallization of PLP-dependent enzymes Geders, Todd W.; Gustafson, Kathryn; Finzel, Barry C. Acta Crystallographica Section F Structural Biology and Crystallization Communications, Vol. 68, Issue 5 https://doi.org/10.1107/S1744309112012912	journal	April 2012
Evaluation of fluorescence-based thermal shift assays for hit identification in drug discovery Lo, Mei-Chu; Aulabaugh, Ann; Jin, Guixian Analytical Biochemistry, Vol. 332, Issue 1 https://doi.org/10.1016/j.ab.2004.04.031	journal	September 2004
Protein thermostability in extremophiles Scandurra, Roberto; Consalvi, Valerio; Chiaraluce, Roberta Biochimie, Vol. 80, Issue 11 https://doi.org/10.1016/S0300-9084(00)88890-2	journal	November 1998
Structural differences between mesophilic, moderately thermophilic and extremely thermophilic protein subunits: results of a comprehensive survey Szilágyi, András; Závodszky, Péter Structure, Vol. 8, Issue 5 https://doi.org/10.1016/S0969-2126(00)00133-7	journal	May 2000
Effective factors in thermostability of thermophilic proteins Sadeghi, M.; Naderi-Manesh, H.; Zarrabi, M. Biophysical Chemistry, Vol. 119, Issue 3 https://doi.org/10.1016/j.bpc.2005.09.018	journal	February 2006
Mycobacterium Tuberculosis Infection and Inflammation: what is Beneficial for the Host and for the Bacterium? Sasindran, Smitha J.; Torrelles, Jordi B. Frontiers in Microbiology, Vol. 2 https://doi.org/10.3389/fmicb.2011.00002	journal	January 2011
Tuberculosis Pai, Madhukar; Behr, Marcel A.; Dowdy, David Nature Reviews Disease Primers, Vol. 2, Issue 1 https://doi.org/10.1038/nrdp.2016.76	journal	October 2016
Prolonged and tunable residence time using reversible covalent kinase inhibitors Bradshaw, J. Michael; McFarland, Jesse M.; Paavilainen, Ville O. Nature Chemical Biology, Vol. 11, Issue 7 https://doi.org/10.1038/nchembio.1817	journal	May 2015
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
Design, Synthesis, and X-ray Analysis of a Glycoconjugate Bound to Mycobacterium tuberculosis Antigen 85C Ibrahim, Diaa A.; Boucau, Julie; Lajiness, Daniel H. Bioconjugate Chemistry, Vol. 23, Issue 12 https://doi.org/10.1021/bc3004342	journal	November 2012
[20] Processing of X-ray diffraction data collected in oscillation mode Otwinowski, Zbyszek; Minor, Wladek Macromolecular Crystallography Part A, 307-326 https://doi.org/10.1016/S0076-6879(97)76066-X	book	January 1997
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
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
electronic Ligand Builder and Optimization Workbench ( eLBOW ): a tool for ligand coordinate and restraint generation Moriarty, Nigel W.; Grosse-Kunstleve, Ralf W.; Adams, Paul D. Acta Crystallographica Section D Biological Crystallography, Vol. 65, Issue 10 https://doi.org/10.1107/S0907444909029436	journal	September 2009

Cited By (3)

Mycolyltransferase from Mycobacterium tuberculosis in covalent complex with tetrahydrolipstatin provides insights into antigen 85 catalysis Goins, Christopher M.; Dajnowicz, Steven; Smith, Micholas D. Journal of Biological Chemistry, Vol. 293, Issue 10 https://doi.org/10.1074/jbc.ra117.001681	journal	January 2018
Cyclipostins and cyclophostin analogs inhibit the antigen 85C from Mycobacterium tuberculosis both in vitro and in vivo Viljoen, Albertus; Richard, Matthias; Nguyen, Phuong Chi Journal of Biological Chemistry, Vol. 293, Issue 8 https://doi.org/10.1074/jbc.ra117.000760	journal	January 2018
Trehalose Conjugation Enhances Toxicity of Photosensitizers against Mycobacteria Dutta, Amit K.; Choudhary, Eira; Wang, Xuan ACS Central Science, Vol. 5, Issue 4 https://doi.org/10.1021/acscentsci.8b00962	journal	March 2019

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