Advanced search
Publication Cover
SAR and QSAR in Environmental Research Volume 21, 2010 - Issue 7-8: 14th International Workshop on Quantitative Structure-Activity Relationships in Environmental and Health Sciences (QSAR2010) – Part 1
Submit an article Journal homepage
728
Views
38
CrossRef citations to date
0
Altmetric
Original Articles

Examination of Michael addition reactivity towards glutathione by transition-state calculations

J.A.H. Schwöbel School of Pharmacy and Chemistry, Liverpool John Moores University, Liverpool, UK
,
J.C. Madden School of Pharmacy and Chemistry, Liverpool John Moores University, Liverpool, UK
&
M.T.D. Cronin School of Pharmacy and Chemistry, Liverpool John Moores University, Liverpool, UKCorrespondence[email protected]
Pages 693-710 | Received 25 May 2010, Accepted 01 Aug 2010, Published online: 29 Nov 2010

Citations (38)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (4)

Florian Wittlinger & Stefan A. Laufer. (2021) The pre-clinical discovery and development of osimertinib used to treat non-small cell lung cancer. Expert Opinion on Drug Discovery 16:10, pages 1091-1103.
Read now
K. Bolelli, Y. Musdal, E. Aki-Yalcin, B. Mannervik & I. Yalcin. (2017) Synthesis and activity mechanism of some novel 2-substituted benzothiazoles as hGSTP1-1 enzyme inhibitors. SAR and QSAR in Environmental Research 28:11, pages 927-940.
Read now
Amit S Kalgutkar & Deepak K Dalvie. (2012) Drug discovery for a new generation of covalent drugs. Expert Opinion on Drug Discovery 7:7, pages 561-581.
Read now
A. Furuhama, Y. Aoki & H. Shiraishi. (2012) Consideration of reactivity to acute fish toxicity of α,β-unsaturated carbonyl ketones and aldehydes. SAR and QSAR in Environmental Research 23:1-2, pages 169-184.
Read now

Articles from other publishers (34)

Ras Baizureen Roseli, Angus B. Keto & Elizabeth H. Krenske. (2022) Mechanistic aspects of thiol additions to Michael acceptors: Insights from computations. WIREs Computational Molecular Science 13:2.
Crossref
Piers A. Townsend, Elliot H. E. Farrar & Matthew N. Grayson. (2022) Eliminating Transition State Calculations for Faster and More Accurate Reactivity Prediction in Sulfa-Michael Additions Relevant to Human Health and the Environment. ACS Omega 7:30, pages 26945-26951.
Crossref
Elliot H. E. Farrar & Matthew N. Grayson. (2022) Machine learning and semi-empirical calculations: a synergistic approach to rapid, accurate, and mechanism-based reaction barrier prediction. Chemical Science 13:25, pages 7594-7603.
Crossref
Levente M. Mihalovits, György G. Ferenczy & György M. Keserű. (2021) The role of quantum chemistry in covalent inhibitor design. International Journal of Quantum Chemistry 122:8.
Crossref
Markus R. Hermann, Alexander Pautsch, Marc A. Grundl, Alexander Weber & Christofer S. Tautermann. (2020) Covalent inhibitor reactivity prediction by the electrophilicity index—in and out of scope. Journal of Computer-Aided Molecular Design 35:4, pages 531-539.
Crossref
Mark Tristan Quimque, Kin Israel Notarte, Arianne Letada, Rey Arturo Fernandez, Delfin Yñigo PilapilIVIV, Kirstin Rhys Pueblos, Jay Carl Agbay, Hans-Martin Dahse, Arlette Wenzel-Storjohann, Deniz Tasdemir, Abbas Khan, Dong-Qing Wei & Allan Patrick Gose Macabeo. (2021) Potential Cancer- and Alzheimer’s Disease-Targeting Phosphodiesterase Inhibitors from Uvaria alba : Insights from In Vitro and Consensus Virtual Screening . ACS Omega 6:12, pages 8403-8417.
Crossref
Piers A. Townsend & Matthew N. Grayson. (2020) Density Functional Theory in the Prediction of Mutagenicity: A Perspective. Chemical Research in Toxicology 34:2, pages 179-188.
Crossref
Jonathan C. Bristow, Isaac Naftalin, Stacey V. A. Cliff, Songjie Yang, Marina Carravetta, Ivo Heinmaa, Raivo Stern & John D. Wallis. (2020) Modelling of an aza-Michael reaction from crystalline naphthalene derivatives containing peri – peri interactions: very long N–C bonds? . CrystEngComm 22:41, pages 6783-6795.
Crossref
Ferruccio Palazzesi, Markus R. Hermann, Marc A. Grundl, Alexander Pautsch, Daniel Seeliger, Christofer S. Tautermann & Alexander Weber. (2020) BIreactive: A Machine-Learning Model to Estimate Covalent Warhead Reactivity. Journal of Chemical Information and Modeling 60:6, pages 2915-2923.
Crossref
. (2020) Development of a fragment-based in silico profiler for SN2 thiol reactivity and its application in predicting toxicity of chemicals towards Tetrahymena pyriformis. Computational Toxicology 13, pages 100117.
Crossref
Ferruccio Palazzesi, Marc A. Grundl, Alexander Pautsch, Alexander Weber & Christofer S. Tautermann. (2019) A Fast Ab Initio Predictor Tool for Covalent Reactivity Estimation of Acrylamides. Journal of Chemical Information and Modeling 59:8, pages 3565-3571.
Crossref
Fjodor Melnikov, Dianne Botta, Collin C. White, Stefanie C. Schmuck, Matthew Winfough, Christopher M. Schaupp, Evan P. Gallagher, Bryan W. Brooks, Edward Spencer Williams, Philip Coish, Paul T. Anastas, Adelina Voutchkova-Kostal, Jakub Kostal & Terrance J. Kavanagh. (2018) Kinetics of Glutathione Depletion and Antioxidant Gene Expression as Indicators of Chemical Modes of Action Assessed in Vitro in Mouse Hepatocytes with Enhanced Glutathione Synthesis . Chemical Research in Toxicology 32:3, pages 421-436.
Crossref
Timothy E. H. Allen, Matthew N. Grayson, Jonathan M. Goodman, Steve Gutsell & Paul J. Russell. (2018) Using Transition State Modeling To Predict Mutagenicity for Michael Acceptors. Journal of Chemical Information and Modeling 58:6, pages 1266-1271.
Crossref
Mark T.D. CroninAndrea-Nicole Richarz. (2017) Relationship Between Adverse Outcome Pathways and Chemistry-Based In Silico Models to Predict Toxicity . Applied In Vitro Toxicology 3:4, pages 286-297.
Crossref
Zheng Zhao, Qingsong Liu, Spencer Bliven, Lei Xie & Philip E. Bourne. (2017) Determining Cysteines Available for Covalent Inhibition Across the Human Kinome. Journal of Medicinal Chemistry 60:7, pages 2879-2889.
Crossref
Larissa Geiger, Martin Nieger & Stefan Bräse. (2017) Scope and Limitations of the Domino Vinylogous Aldol/ oxa -Michael Reaction . ChemistrySelect 2:11, pages 3268-3275.
Crossref
R.A. Ward & M.R.V Finlay. 2017. Comprehensive Medicinal Chemistry III. Comprehensive Medicinal Chemistry III 1 32 .
David J. Ebbrell, Judith C. Madden, Mark T. D. Cronin, Terry W. Schultz & Steven J. Enoch. (2016) Development of a Fragment-Based in Silico Profiler for Michael Addition Thiol Reactivity . Chemical Research in Toxicology 29:6, pages 1073-1081.
Crossref
Iain D.G. Campuzano, Tisha San Miguel, Todd Rowe, Daniel Onea, Victor J. Cee, Tara Arvedson & John D. McCarter. (2016) High-Throughput Mass Spectrometric Analysis of Covalent Protein-Inhibitor Adducts for the Discovery of Irreversible Inhibitors: A Complete Workflow. SLAS Discovery 21:2, pages 136-144.
Crossref
M. Raymond V. FinlayMark AndertonSusan AshtonPeter BallardPaul A. BethelMatthew R. BoxRobert H. BradburySimon J. BrownSam ButterworthAndrew CampbellChristopher ChorleyNicola ColcloughDarren A. E. CrossGordon S. CurrieMatthew GristLorraine HassallGeorge B. HillDaniel JamesMichael JamesPaul KemmittTeresa KlinowskaGillian LamontScott G. LamontNathaniel MartinHeather L. McFarlandMartine J. MellorJonathon P. OrmeDavid PerkinsPaula PerkinsGraham RichmondPeter SmithRichard A. WardMichael J. WaringDavid WhittakerStuart WellsGail L. Wrigley. (2014) Discovery of a Potent and Selective EGFR Inhibitor (AZD9291) of Both Sensitizing and T790M Resistance Mutations That Spares the Wild Type Form of the Receptor. Journal of Medicinal Chemistry 57:20, pages 8249-8267.
Crossref
Shan Feng, Xiaoyan Zheng, Dong Wang, Yiyi Gong, Qingtao Wang & Haiteng Deng. (2014) Systematic Analysis of Reactivities and Fragmentation of Glutathione and Its Isomer GluCysGly. The Journal of Physical Chemistry A 118:37, pages 8222-8228.
Crossref
P. Kočovský. 2014. Organic Reaction Mechanisms 2011. Organic Reaction Mechanisms 2011 371 447 .
Margarita E. Aliaga, William Tiznado, Bruce K. Cassels, Marco T. Nuñez, Daniela Millán, Edwin G. Pérez, Olimpo García-Beltrán & Paulina Pavez. (2014) Substituent effects on reactivity of 3-cinnamoylcoumarins with thiols of biological interest. RSC Adv. 4:2, pages 697-704.
Crossref
Richard A. Ward, Mark J. Anderton, Susan Ashton, Paul A. Bethel, Matthew Box, Sam Butterworth, Nicola Colclough, Christopher G. Chorley, Claudio Chuaqui, Darren A. E. Cross, Les A. Dakin, Judit É. Debreczeni, Cath Eberlein, M. Raymond V. Finlay, George B. Hill, Matthew Grist, Teresa C. M. Klinowska, Clare Lane, Scott Martin, Jonathon P. Orme, Peter Smith, Fengjiang Wang & Michael J. Waring. (2013) Structure- and Reactivity-Based Development of Covalent Inhibitors of the Activating and Gatekeeper Mutant Forms of the Epidermal Growth Factor Receptor (EGFR). Journal of Medicinal Chemistry 56:17, pages 7025-7048.
Crossref
Bernhard Kluger, Christoph Bueschl, Marc Lemmens, Franz Berthiller, Georg Häubl, Günther Jaunecker, Gerhard Adam, Rudolf Krska & Rainer Schuhmacher. (2012) Stable isotopic labelling-assisted untargeted metabolic profiling reveals novel conjugates of the mycotoxin deoxynivalenol in wheat. Analytical and Bioanalytical Chemistry 405:15, pages 5031-5036.
Crossref
S. J. Enoch & D. W. Roberts. (2013) Predicting Skin Sensitization Potency for Michael Acceptors in the LLNA Using Quantum Mechanics Calculations. Chemical Research in Toxicology 26:5, pages 767-774.
Crossref
Denis Mulliner & Gerrit Schüürmann. (2013) Model Suite for Predicting the Aquatic Toxicity of α,β-Unsaturated Esters Triggered by Their Chemoavailability. Molecular Informatics 32:1, pages 98-107.
Crossref
Jakub Kostal, Adelina Voutchkova-Kostal, Brian Weeks, Julie B. Zimmerman & Paul T. Anastas. (2012) A Free Energy Approach to the Prediction of Olefin and Epoxide Mutagenicity and Carcinogenicity. Chemical Research in Toxicology 25:12, pages 2780-2787.
Crossref
Amit S. Kalgutkar, Deepak Dalvie, R. Scott Obach & Dennis A. Smith. 2012. Reactive Drug Metabolites. Reactive Drug Metabolites 313 334 .
Diana Thaens, Daniel Heinzelmann, Alexander Böhme, Albrecht Paschke & Gerrit Schüürmann. (2012) Chemoassay Screening of DNA-Reactive Mutagenicity with 4-(4-Nitrobenzyl)pyridine – Application to Epoxides, Oxetanes, and Sulfur Heterocycles. Chemical Research in Toxicology 25:10, pages 2092-2102.
Crossref
Peter Nagy, Thomas P. Lechte, Andrew B. Das & Christine C. Winterbourn. (2012) Conjugation of Glutathione to Oxidized Tyrosine Residues in Peptides and Proteins. Journal of Biological Chemistry 287:31, pages 26068-26076.
Crossref
Taku Kitanosono, Masaru Sakai, Masaharu Ueno & Shū Kobayashi. (2012) Chiral-Sc catalyzed asymmetric Michael addition/protonation of thiols with enones in water. Organic & Biomolecular Chemistry 10:35, pages 7134.
Crossref
Elizabeth H. Krenske, Russell C. Petter, Zhendong Zhu & K. N. Houk. (2011) Transition States and Energetics of Nucleophilic Additions of Thiols to Substituted α,β-Unsaturated Ketones: Substituent Effects Involve Enone Stabilization, Product Branching, and Solvation. The Journal of Organic Chemistry 76:12, pages 5074-5081.
Crossref
Denis Mulliner, Dominik Wondrousch & Gerrit Schüürmann. (2011) Predicting Michael-acceptor reactivity and toxicity through quantum chemical transition-state calculations. Organic & Biomolecular Chemistry 9:24, pages 8400.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.