mechanism | organic synthesis | chemical biology
Intramolecular H-Atom Transfers in Alkoxyl Radical Intermediates Underlie the
Apparent Oxidation of Lipid Hydroperoxides by Fe(II)
Dmitry D. Saraev, Zijun Wu & Derek A. Pratt*
Submitted
Leveraging the Persistent Radical Effect in the Synthesis of Trans-2,3-Diaryl-Dihydrobenzofurans
Bec J. Roldan, Travis A. Hammerstad, Matthew S. Galliher, Mitchell H. Keylor, Derek A. Pratt* & Corey R. J. Stephenson*
Submitted (click title to see chmrxiv preprint)
Development of PINO-Derived Hydrogen Atom Transfer Catalysts
Cheng Yang, Sahil Arora, Derek A. Pratt*, Stephen Maldonado* & Corey R. J. Stephenson*
Submitted
Emergence of (Hydro)persulfides as Suppressors of Lipid Peroxidation and Ferroptotic Cell Death
Zijun Wu, Uladzimir Barayeu, Danny Schilling, Tobias P. Dick* & Derek A. Pratt*
Current Opinion in Chemical Biology 2023, in press
Radical Approaches to C-S Bonds
Zijun Wu & Derek A. Pratt*
Nature Reviews Chemistry 2023, in press
vPIF-1 is an Insulin-Like Anti-Ferroptotic Viral Peptide
Alexia Belavgeni, Francesca Maremonti, Wulf Tonnus, Marlena Stadtmüller, Shubhangi Gavali, Melodie Mallais, Karolin Flade,
Anne Brucker, Jorunn Naila Becker, Kristina Beer, Mirela Tmava, Julian Stumpf, Florian Gembardt, Christian Hugo, Mauro Giacca,
Benjamin G. Hale, Nikolaos Perakakis, Wei Sha, Derek A. Pratt, Andrew V. Schally, Stefan R. Bornstein* & Andreas Linkermann*
Proceedings of the National Academy of Sciences 2023,120, e2300320120
Ferroptosis: A Flexible Constellation of Related Biochemical Mechanisms
Scott J. Dixon* & Derek A. Pratt*
Molecular Cell 2023, 83, 1030-1042
General Approach to Identify, Assess and Characterize Inhibitors of
Lipid Peroxidation and Associated Cell Death
Melodie Mallais, Carly S. Hanson, Melanie Giray & Derek A. Pratt*
ACS Chemical Biology 2023, 18, 561-571
2022
Hydropersulfides Inhibit Lipid Peroxidation and Protect Cells From Ferroptosis
Zijun Wu, Vinayak S. Khodade, Jean-Philippe R. Chauvin, Deborah Rodriguez, John P. Toscano & Derek A. Pratt*
Journal of the American Chemical Society 2022, 144, 15825-15837
(featured in Nature Chemical Biology ‘News and Views’ and a 'Spotlight' in Cell Chemical Biology)
Intrinsic & Extrinsic Limitations to the Design and Optimization of Inhibitors
of Lipid Peroxidation and Associated Cell Death
Luke A. Farmer, Zijun Wu, Jia-Fei Poon, Omkar Zilka, Svenja M. Lorenz, Stephanie Huehn,
Bettina Proneth, Marcus Conrad & Derek A. Pratt*
Journal of the American Chemical Society 2022, 144, 14706-14721
A Non-Canonical Vitamin K Cycle is a Potent Ferroptosis Suppressor
Eikan Mishima,* Junya Ito, Zijun Wu, Toshitaka Nakamura, Sebastian Doll, Wulf Tonnus, Palina Nepachalovich, Elke Eggenhofer,
Maceler Aldrovandi, Bernhard Henkelmann, Ken-ichi Yamada, Jonas Wanninger, Adam Wahida, Omkar Zilka, Emiko Sato,
Regina Feederle, Daniela Hass, Adriano Maida, André Santos Dias Mourão, Andreas Linkermann, Edward K. Geissler,
Kiyotaka Nakagawa, Takaaki Abe, Maria Fedorova, Bettina Proneth, Derek A. Pratt & Marcus Conrad*
Nature 2022, 608, 778-783
(featured in Nature ‘News and Views’ and a 'Spotlight' in Molecular Cell)
Mechanism of Visible-Light Mediated Alkene Aminoarylation with Arylsulfonylacetamides
Anthony R. Allen, Jia-Fei Poon, Rory C. McAtee, Nicholas B. Watson, Derek A. Pratt* & Corey R.J. Stephenson*
ACS Catalysis 2022,12, 8511-8526
7-Dehydrocholesterol is an Endogenous Suppressor of Ferroptosis
Florencio Porto Freitas, Palina Nepachalovich, Lohans P. Puentes, Omkar Zilka, Alex Inague, Svenja M. Lorenz, Viktoria Kunz,
Helene Nehring, Thamara N. Xavier da Silva, Zhiyi Chen, Sebastian G. Doll, Werner Schmitz, Aline Horling, Peter Imming,
Sayuri Miyamoto, Ann Wehmann, Thiago C. Genaro-Mattos, Karoly Mirnics, Lokender Kumar, Judith Klein-Seetharaman,
Svenja Meierjohann, Isabel Weigand, Matthias Kroiss, Georg W. Bornkamm, Kurt Bommert, Ralf C. Bargou, Ana Garcia-Saez,
Derek A. Pratt, Maria Fedorova, Marcus Conrad, José Pedro Friedmann Angeli*
Submitted (click title to see bioarxiv preprint)
2021
The Radical-Trapping Antioxidant Activity of Copper and Nickel bis(Thiosemicarbazone) Complexes
Underlies Their Potency as Inhibitors of Ferroptotic Cell Death
Omkar Zilka, Jia-Fei Poon & Derek A. Pratt*
Journal of the American Chemical Society 2021, 143, 19043-19057
Temperature-Dependence of Radical-Trapping Activity of Phenoxazine, Phenothiazine and their
Aza-Analogues Clarifies the Way Forward for New Antioxidant Design
Jia-Fei Poon, Luke A. Farmer, Evan A. Haidasz & Derek A. Pratt*
Chemical Science 2021, 12, 11065-11079
Dysfunction of the Key Ferroptosis-Surveilling Systems Hypersensitizes Mice to Massive
Tubular Necrosis During Acute Kidney Injury
Wulf Tonnus, Claudia Meyer, Christian Steinebach, Alexia Belavgeni, Anne von Mässenhausen, Nadia Zamora Gonzalez,
Florian Gembardt, Nina Himmerkus, Francesca Maremonti, Markus Latk, Sophie Locke, Sebastian Doll, Spencer Short, Irina Ingold, Bettina Proneth, Kerstin Amann, Christoph Daniel, Nazanin Kabgani, Rafael Kramann, Paul Hergenrother, Stefan R. Bornstein,
Christian Hugo, Jan Ulrich Becker, Michael Gütschow, Derek Pratt, Marcus Conrad & Andreas Linkermann*
Nature Communications 2021, 12, 4402
On the Mechanism of Electrochemical Generation and Decomposition of Phthalimide N-oxyl (PINO)
Cheng Yang, Luke A. Farmer, Derek A. Pratt,* Stephen Maldonado* & Corey R. J. Stephenson*
Journal of the American Chemical Society 2021, 143, 10324-10332
Autoxidation vs. Antioxidants - The Fight for Forever
Julian Helberg & Derek A. Pratt*
Chemical Society Reviews 2021, 50, 7343-7358
(invited contribution to themed collection on radical chemistry)
Zijun Wu & Derek A. Pratt*
Angewandte Chemie International Edition 2021, 60, 15598-15605
Ron Shah, Jia-Fei Poon, Evan A. Haidasz & Derek A. Pratt*
Journal of Organic Chemistry 2021, 86, 6538-6550
A Compendium of Cell Death Modulatory Profiles Identifies Ferroptosis Regulators
Megan Conlon, Carson Poltorack, Giovanni Forcina, Alex Wells, Melodie Mallais, Alexis Kahanu, Leslie Magtanong,
Derek A. Pratt & Scott J. Dixon*
Nature Chemical Biology 2021,17, 665-674
(highlighted in Nature Chemical Biology 'News and Views')
2020
Potent Ferroptosis Inhibitors Can Catalyze the Cross-Dismutation of Phospholipid-Derived
Alkylperoxyl Radicals and Hydroperoxyl Radicals
Jia-Fei Poon, Omkar Zilka & Derek A. Pratt*
Journal of the American Chemical Society 2020, 142, 14331-14342
Metabolic Determinants of Cancer Cell Sensitivity to Distinct Modes of Ferroptosis
Mariluz Soula, Ross A. Weber, Omkar Zilka, Hanan Alwaseem, Konnor La, Henrik Molina, Javier Garcia-Bermudez,*
Derek A. Pratt* & Kıvanç Birsoy*
Nature Chemical Biology 2020, 16, 1351-1360
Radical Substitution on Tetrasulfides: A Unique Route to Disulfides
Zijun Wu & Derek A. Pratt*
Journal of the American Chemical Society 2020, 142, 10284-10290
Persistent Quinone Methide Dimers Lacking Labile H-Atoms Are Surprisingly Excellent
Radical-Trapping Antioxidants
Mark A. R. Raycroft, Jean-Philippe R. Chauvin, Matthew S. Galliher, Kevin J. Romero,
Corey R. J. Stephenson* & Derek A. Pratt*
Chemical Science 2020, 11, 5676-5689
(selected by the editors as a ‘Hot Article’ and ‘Pick of the Week’)
Reactive Sterol Electrophiles: Mechanisms of Formation and Reactions with
Proteins and Amino Acid Nucleophiles
Ned A. Porter,* Libin Xu & Derek A. Pratt
Chemistry 2020, 2, 390-417
(invited contribution to themed issue in honour of Prof. Bernd Giese’s 80th birthday)
Hydrogen Atom Abstraction from Polyolefins: Experimental and Computational Studies of Model Systems
Graham E. Garrett, Derek A. Pratt & J. Scott Parent*
Macromolecules 2020, 53, 2793-2800
Synthesis of Vitisin A & D: Thermal Isomerization Enabled by a Persistent Radical Equilibrium
Kevin J. Romero, Mitchell H. Keylor, Xu Zhu, Ethan J. Strobel,
Derek A. Pratt* & Corey R. J. Stephenson*
Journal of the American Chemical Society 2020, 142, 6499-6504
Base-Promoted C-C Bond Activation Enables Radical Allylation with Homoallylic Alcohols
Maximilian Lübbesmeyer, Emily G. Mackay, Mark A. R. Raycroft, Jonas Elfert, Derek A. Pratt* & Armido Studer*
Journal of the American Chemical Society 2020, 142, 2609-2616
On the Products of Cholesterol Autoxidation in Phospholipid Bilayers and the Formation of
Secosterols Derived Therefrom
Emily L. Schaefer, Nadia Zopyrus, Zosia A. M. Zielinski & Derek A. Pratt*
Angewandte Chemie International Edition 2020, 59, 2089-2094
(selected by the editors as a ‘Very Important Paper’)
2019
The Chemical Basis of Ferroptosis
Marcus Conrad* & Derek A. Pratt*
Nature Chemical Biology 2019, 15, 1137-1147
(commissioned ‘Perspective’; highlighted in MedicalXpress)
FSP1 is a Glutathione-Independent Ferroptosis-Suppressor
Sebastian Doll, Florencio Porto Freitas, Ron Shah, Milene Costa da Silva, Irina Ingold, Andrea Goya Grocin, Elena Panzilius, Christina Scheel, Katalin Buday, Jonas Wanninger, Thibaut Vignane, Vaishnavi Mohana, Van Lam, Aloys Schepers, Valerie O’Donnel, Maceler Aldrovandi, Michael Sattler, Edward William Tate, Bettina Proneth, Werner Schmitz, Almut Schulze, Gregorz Popowicz,
Derek A. Pratt, José Pedro Friedmann Angeli,* Marcus Conrad*
Nature 2019, 575, 693-698
(featured in Nature ‘News and Views’ and highlighted in Nature Chemical Biology)
Beyond DPPH: Use of Fluorescence-ENabled Inhibited AutoXidation (FENIX) to Predict
Oxidative Cell Death Rescue
Ron Shah, Luke Farmer, Omkar Zilka, Anthony T. M. Van Kessel & Derek A. Pratt*
Cell Chemical Biology 2019, 26, 1594-1607
(selected as a ‘Feature Article’ and highlighted in Cell Chem. Biol.)
Threshold Protective Effect of Deuterated Polyunsaturated Fatty Acids on the Peroxidation of Lipid Bilayers
Alexander M. Firsov, Maksim A. Fomich, Andrei V. Bekish, Olga L. Sharko, Elena A. Kotova, Harry J. Saal, Dragoslav Vidovic,
Vadim V. Shmanai, Derek A. Pratt, Yuri N. Antonenko* & Mikhail S. Shchepinov*
FEBS J. 2019, 286, 2099-2017
The Antioxidant Activity of Polysulfides: It’s Radical!
Jean-Philippe R. Chauvin, Markus Griesser & Derek A. Pratt*
Chemical Science 2019, 10, 4999-5010
(selected as a ‘Hot Article’ and highlighted in the Royal Society of Chemistry’s Chemistry World)
H-Atom Abstraction vs. Addition: Accounting for the Diverse Product Distribution in the
Autoxidation of Cholesterol & its Esters
Zosia A. M. Zielinski & Derek A. Pratt*
Journal of the American Chemical Society 2019, 141, 3037-3051
2018
Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the
Resultant Quinone Methide Dimers
Kevin J. Romero, Matthew S. Galliher, Irene Bosque, Mark A. R. Raycroft, Jean-Philippe R. Chauvin,
Derek A. Pratt* & Corey R. J. Stephenson*
Angewandte Chemie International Edition 2018, 57, 17125-17129
Radicals in Natural Product Synthesis
Kevin J. Romero, Matthew S. Galliher, Derek A. Pratt* & Corey R. J. Stephenson*
Chemical Society Reviews 2018, 47, 7851-7866
(invited tutorial review)
Recent Insights on Hydrogen Atom Transfer in the Inhibition of Hydrocarbon Autoxidation
Jia-Fei Poon & Derek A. Pratt*
Accounts of Chemical Research 2018, 51, 1996-2005
(invited for special issue on H-atom transfer)
The Hydrogen Atom Transfer Reactivity of Sulfinic Acids
Markus Griesser, Jean-Philippe R. Chauvin & Derek A. Pratt*
Chemical Science 2018, 9, 7218-7229
Inhibition of Hydrocarbon Autoxidation by Nitroxide-Catalyzed Cross-Dismutation of Hydroperoxyl and Alkylperoxyl Radicals
Kareem A. Harrison, Evan A. Haidasz, Markus Griesser & Derek A. Pratt*
Chemical Science 2018, 9, 6068-6079
The Catalytic Reaction of Nitroxides with Peroxyl Radicals its Relevance to their Cytoprotective Properties
Markus Griesser, Ron Shah, Antonius T. M. Van Kessel, Omkar Zilka, Evan A. Haidasz & Derek A. Pratt*
Journal of the American Chemical Society 2018, 140, 3798-3808
Resolving the Role of Lipoxygenases in the Initiation and Execution of Ferroptosis
Ron Shah, Mikhail S. Shchepinov & Derek A. Pratt*
ACS Central Science 2018, 4, 387-396
(selected for an ACS Central Science ‘First Reaction’)
2017
Phenoxazine: A Privileged Scaffold for Radical-Trapping Antioxidants
Luke Farmer, Evan A. Haidasz, Markus Griesser & Derek A. Pratt*
Journal of Organic Chemistry 2017, 82, 10523-10536
The Potency of Diarylamine Radical-Trapping Antioxidants as Inhibitors of Ferroptosis Underscores
the Role of Autoxidation in Cell Death
Ron Shah, Kaitlyn D. Margison & Derek A. Pratt*
ACS Chemical Biology 2017, 12, 2538-2545
Hydroperosulfides: H-atom Transfer Agents Par Excellence
Jean-Philippe R. Chauvin, Markus Griesser & Derek A. Pratt*
Journal of the American Chemical Society 2017, 139, 6484-6493
(selected for a JACS ‘Spotlight’)
Diazaphenoxazines and Diazaphenothiazines: Synthesis of the ‘Correct’ Isomers Reveals They are
Highly Reactive Radical-Trapping Antioxidants
Evan A. Haidasz & Derek A. Pratt*
Organic Letters 2017, 19, 1854-1857
Lipid Peroxidation: Kinetics, Mechanisms and Products
Zosia A. M. Zielinski & Derek A. Pratt*
Journal of Organic Chemistry 2017, 82, 2817-2825
(invited ‘Synopsis’)
Aminyl Radical Generation via Tandem Norrish Type I Photocleavage, b-Fragmentation:
Independent Generation and Reactivity of the 2'-Deoxyadenosin-N6-yl Radical
Liwei Zheng, Markus Griesser, Derek A. Pratt* & Marc M. Greenberg*
Journal of Organic Chemistry 2017, 82, 3571-3580
Ferroptosis Inhibition: Mechanisms and Opportunities
José Pedro Friedmann Angeli,* Ron Shah, Derek A. Pratt & Marcus Conrad
Trends in Pharmaceutical Sciences 2017, 38, 489-498
The Radical-Trapping Antioxidant Activity of Ferrostatin-1 and Liproxstatin-1 Suggests that
Lipid Peroxidation (Autoxidation) Drives Ferroptotic Cell Death
Omkar Zilka, Ron Shah, Bo Li, José Pedro Friedmann Angeli, Markus Griesser, Marcus Conrad & Derek A. Pratt*
ACS Central Science 2017, 3, 232-243
(highlighted in Cell Chemical Biology)
On the Mechanism of Thiol, Sulfenic and Sulfinic Acid Oxidation by Hydrogen Peroxide
Jean-Philippe R. Chauvin & Derek A. Pratt*
Angewandte Chemie International Edition 2017, 56, 6255-6259
(highlighted in Nature Reviews Chemistry)
2016
Synthesis of Resveratrol Tetramers via a Stereoconvergent Radical Equilibrium
Mitchell H. Keylor, Bryan S. Matsuura, Markus Griesser, Jean-Philippe R. Chauvin, Ryan A. Harding,
Mariia S. Kirillova, Oliver J. Fischer, Derek A. Pratt* & Corey R. J. Stephenson*
Science 2016, 354, 1260-1265
(highlighted in the American Chemical Society’s Chemical & Engineering News)
Rapid Determination of Key Hydrocarbon Autoxidation Products by Fluorescence
Ron Shah & Derek A. Pratt*
Journal of Organic Chemistry 2016, 81, 6649-6656
Polysulfide-1-Oxides React with Peroxyl Radicals as Quickly as Hindered Phenolic Antioxidants and
Do So By a Surprising Concerted Homolytic Substitution
Jean-Philippe R. Chauvin, Evan A. Haidasz, Markus Griesser & Derek A. Pratt*
Chemical Science 2016, 7, 6347-6356
Cholesterol Autoxidation Revisited: Debunking the Dogma Associated with the Most Vilified of Lipids
Zosia Zielinski & Derek A. Pratt*
Journal of the American Chemical Society 2016, 138, 6932-6935
(selected for a JACS ‘Spotlight’; selected as one of twelve ‘JACS Editors’ Choice’ articles for 2016)
Acid is Key to the Radical-Trapping Antioxidant Activity of Nitroxides
Evan A. Haidasz, Derek Meng, Riccardo Amorati, Keith U. Ingold, Luca Valgimigli* & Derek A. Pratt*
Journal of the American Chemical Society 2016, 138, 5290-5298
A Continuous Visible Light Spectrophotometric Approach to Accurately Determine the Reactivity of
Radical-Trapping Antioxidants
Evan A. Haidasz, Antonius T. M. Van Kessel & Derek A. Pratt*
Journal of Organic Chemistry 2016, 81, 737-744
(selected as a ‘Featured Article’ and ‘Cover Article’)
Inspired by Garlic: Insights on the Chemistry of Sulfenic Acids and the Radical-Trapping Antioxidant Activity of
Organsulfur Compounds
Jean-Philippe R. Chauvin, Zosia Zielinski & Derek A. Pratt*
Canadian Journal of Chemistry 2016, 94, 1-8
(invited minireview in recognition of the 2015 CSC Fagnou Award in Organic Chemistry)
2015
Molecular Mechanisms of the Medicinal Thiosulfinates from Garlic and Anamu: They Are Not Radical-Trapping Antioxidants
Bo Li, Feng Zheng, Jean-Philippe R. Chauvin & Derek A. Pratt*
Chemical Science 2015, 6, 6165-6178
(highlighted in the Royal Society of Chemistry’s Chemistry World)
Maximizing the Reactivity of Phenolic and Aminic Radical-Trapping Antioxidants: Just Add Nitrogen!
Luca Valgimigli* & Derek A. Pratt*
Accounts of Chemical Research 2015, 48, 966-975
(invited review)
Determining the Efficacy of Radical-Trapping Antioxidants
Bo Li & Derek A. Pratt*
Free Radical Biology and Medicine 2015, 82, 187-202
(invited review)
Unprecedented Inhibition of Hydrocarbon Autoxidation by Diarylamine Radical-Trapping Antioxidants
Ron Shah, Evan A. Haidasz, Luca Valgimigli & Derek A. Pratt*
Journal of the American Chemical Society 2015, 137, 2440-2443
(selected for a JACS ‘Spotlight’)
A Scalable Biomimetic Synthesis of Resveratrol and Systematic Evaluation of their Antioxidant Activities
Byran S. Matsuura, Mitchell H. Keylor, Bo Li, YuXuan Lin, Shelby Allison, Derek A. Pratt* & Corey R. J. Stephenson*
Angewandte Chemie International Edition 2015, 54, 3754-3757
(selected as a ‘Hot Article’; highlighted in Nature Chemistry)