Discovering selective antiferroptotic inhibitors of the 15LOX/PEBP1 complex noninterfering with biosynthesis of lipid mediators.


Journal

Proceedings of the National Academy of Sciences of the United States of America
ISSN: 1091-6490
Titre abrégé: Proc Natl Acad Sci U S A
Pays: United States
ID NLM: 7505876

Informations de publication

Date de publication:
20 Jun 2023
Historique:
pmc-release: 16 12 2023
medline: 19 6 2023
pubmed: 16 6 2023
entrez: 16 6 2023
Statut: ppublish

Résumé

Programmed ferroptotic death eliminates cells in all major organs and tissues with imbalanced redox metabolism due to overwhelming iron-catalyzed lipid peroxidation under insufficient control by thiols (Glutathione (GSH)). Ferroptosis has been associated with the pathogenesis of major chronic degenerative diseases and acute injuries of the brain, cardiovascular system, liver, kidneys, and other organs, and its manipulation offers a promising new strategy for anticancer therapy. This explains the high interest in designing new small-molecule-specific inhibitors against ferroptosis. Given the role of 15-lipoxygenase (15LOX) association with phosphatidylethanolamine (PE)-binding protein 1 (PEBP1) in initiating ferroptosis-specific peroxidation of polyunsaturated PE, we propose a strategy of discovering antiferroptotic agents as inhibitors of the 15LOX/PEBP1 catalytic complex rather than 15LOX alone. Here we designed, synthesized, and tested a customized library of 26 compounds using biochemical, molecular, and cell biology models along with redox lipidomic and computational analyses. We selected two lead compounds, FerroLOXIN-1 and 2, which effectively suppressed ferroptosis in vitro and in vivo without affecting the biosynthesis of pro-/anti-inflammatory lipid mediators in vivo. The effectiveness of these lead compounds is not due to radical scavenging or iron-chelation but results from their specific mechanisms of interaction with the 15LOX-2/PEBP1 complex, which either alters the binding pose of the substrate [eicosatetraenoyl-PE (ETE-PE)] in a nonproductive way or blocks the predominant oxygen channel thus preventing the catalysis of ETE-PE peroxidation. Our successful strategy may be adapted to the design of additional chemical libraries to reveal new ferroptosis-targeting therapeutic modalities.

Identifiants

pubmed: 37327313
doi: 10.1073/pnas.2218896120
pmc: PMC10288584
doi:

Substances chimiques

Glutathione GAN16C9B8O
Iron E1UOL152H7
Lipids 0
Phosphatidylethanolamine Binding Protein 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e2218896120

Subventions

Organisme : NCI NIH HHS
ID : R01 CA165065
Pays : United States
Organisme : NIAID NIH HHS
ID : U01 AI156924
Pays : United States
Organisme : NINDS NIH HHS
ID : R01 NS076511
Pays : United States
Organisme : NIDDK NIH HHS
ID : P01 DK096990
Pays : United States
Organisme : NIAID NIH HHS
ID : U01 AI156923
Pays : United States
Organisme : NHLBI NIH HHS
ID : P01 HL114453
Pays : United States
Organisme : NINDS NIH HHS
ID : R37 NS061817
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM139297
Pays : United States
Organisme : NINDS NIH HHS
ID : R01 NS061817
Pays : United States
Organisme : NIGMS NIH HHS
ID : P41 GM103712
Pays : United States

Commentaires et corrections

Type : CommentIn

Références

J Biol Chem. 2021 Jan-Jun;296:100105
pubmed: 33219130
Biochim Biophys Acta. 2000 Apr 12;1484(2-3):298-306
pubmed: 10760478
ACS Chem Biol. 2016 Feb 19;11(2):530-40
pubmed: 26697918
Radiat Res. 2018 Jan;189(1):68-83
pubmed: 29140165
Nat Chem Biol. 2020 Mar;16(3):278-290
pubmed: 32080625
Cell. 2017 Oct 5;171(2):273-285
pubmed: 28985560
Prog Lipid Res. 2019 Jan;73:28-45
pubmed: 30472260
Nat Chem Biol. 2017 Jan;13(1):81-90
pubmed: 27842066
Nat Chem Biol. 2021 Jun;17(6):665-674
pubmed: 33686292
Cell. 2022 Jul 7;185(14):2401-2421
pubmed: 35803244
J Immunother Cancer. 2021 Dec;9(12):
pubmed: 34903554
Adv Mater. 2019 Dec;31(51):e1904197
pubmed: 31595562
Int J Radiat Biol. 2011 Aug;87(8):851-68
pubmed: 21417595
Antioxidants (Basel). 2021 Sep 29;10(10):
pubmed: 34679687
J Chem Theory Comput. 2016 Apr 12;12(4):2079-90
pubmed: 26918937
J Biol Chem. 2004 Jul 9;279(28):29023-30
pubmed: 15123652
Front Genet. 2019 May 03;10:260
pubmed: 31130979
Radiat Res. 1987 Jun;110(3):340-52
pubmed: 3588842
Front Endocrinol (Lausanne). 2021 Feb 19;11:628079
pubmed: 33679610
Redox Biol. 2015 Dec;6:297-310
pubmed: 26298204
Health Phys. 2012 Oct;103(4):383-99
pubmed: 23091876
Cell Res. 2019 May;29(5):347-364
pubmed: 30948788
J Hematol Oncol. 2019 Mar 29;12(1):34
pubmed: 30925886
Radiat Res. 2015 Nov;184(5):545-53
pubmed: 26495870
Science. 2020 Oct 30;370(6516):
pubmed: 33122357
Trends Pharmacol Sci. 2017 May;38(5):489-498
pubmed: 28363764
Proc Natl Acad Sci U S A. 2022 Mar 8;119(10):e2111537119
pubmed: 35238643
Cell Death Dis. 2022 Jul 26;13(7):649
pubmed: 35882850
Methods Mol Biol. 1998;108:277-84
pubmed: 9921537
Cell Death Dis. 2020 Oct 27;11(10):922
pubmed: 33110056
Cell Chem Biol. 2020 Apr 16;27(4):387-408
pubmed: 32275865
Bioorg Med Chem. 2021 Sep 15;46:116349
pubmed: 34500187
Nat Rev Mol Cell Biol. 2021 Apr;22(4):266-282
pubmed: 33495651
Ann Intern Med. 2004 Jun 15;140(12):1037-51
pubmed: 15197022
Nat Commun. 2022 Jun 27;13(1):3676
pubmed: 35760796
Front Pharmacol. 2022 Mar 02;13:838782
pubmed: 35308198
Radiat Res. 2010 Apr;173(4):469-78
pubmed: 20334519
Bioinformatics. 2021 Oct 25;37(20):3657-3659
pubmed: 33822884
Essays Biochem. 2020 Sep 23;64(3):401-421
pubmed: 32618335
Int J Mol Sci. 2021 May 17;22(10):
pubmed: 34067535
J Clin Invest. 2018 Oct 1;128(10):4639-4653
pubmed: 30198910
Phytochemistry. 2009 Sep;70(13-14):1504-10
pubmed: 19767040
Biochim Biophys Acta. 2015 Apr;1851(4):331-9
pubmed: 25152163
Cell Death Differ. 2021 Oct;28(10):2843-2856
pubmed: 34465893
PLoS One. 2014 Aug 11;9(8):e104094
pubmed: 25111178
Nat Chem Biol. 2021 Apr;17(4):465-476
pubmed: 33542532
J Chem Inf Model. 2019 May 28;59(5):2496-2508
pubmed: 30762363
Nature. 2015 Apr 2;520(7545):57-62
pubmed: 25799988
J Am Chem Soc. 2018 Dec 26;140(51):17835-17839
pubmed: 30525572
Redox Biol. 2021 Jan;38:101744
pubmed: 33126055
Nature. 2021 May;593(7860):586-590
pubmed: 33981038
Front Pharmacol. 2019 Jul 04;10:719
pubmed: 31333453
IUBMB Life. 2017 Jun;69(6):423-434
pubmed: 28276141
Phys Chem Chem Phys. 2013 Apr 7;15(13):4642-50
pubmed: 23423333
Cell. 2017 Oct 19;171(3):628-641.e26
pubmed: 29053969
Int J Mol Sci. 2020 Nov 20;21(22):
pubmed: 33233496
Cell Metab. 2008 Sep;8(3):237-48
pubmed: 18762024
JCI Insight. 2022 Feb 22;7(4):
pubmed: 35041620
Cell. 2012 May 25;149(5):1060-72
pubmed: 22632970

Auteurs

Haider H Dar (HH)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Karolina Mikulska-Ruminska (K)

Department of Biophysics, Faculty of Physics Astronomy and Informatics, Institute of Physics, Nicolaus Copernicus University in Toruń, Toruń, Poland.

Yulia Y Tyurina (YY)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Diane K Luci (DK)

National Center for Advancing Translational Sciences, Rockville, MD 20892.

Adam Yasgar (A)

National Center for Advancing Translational Sciences, Rockville, MD 20892.

Svetlana N Samovich (SN)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Alexander A Kapralov (AA)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Austin B Souryavong (AB)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Vladimir A Tyurin (VA)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Andrew A Amoscato (AA)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Michael W Epperly (MW)

Department of Radiation Oncology, University of Pittsburgh, Pittsburgh, PA 15260.

Galina V Shurin (GV)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Melissa Standley (M)

Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, CA 95064.

Theodore R Holman (TR)

Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, CA 95064.

Claudette M St Croix (CM)

Department of Cell Biology, University of Pittsburgh, Pittsburgh, PA 15260.

Simon C Watkins (SC)

Department of Cell Biology, University of Pittsburgh, Pittsburgh, PA 15260.

Andrew P VanDemark (AP)

Department of Biological Sciences, University of Pittsburgh, Pittsburgh, PA 15260.

Sandeep Rana (S)

National Center for Advancing Translational Sciences, Rockville, MD 20892.

Alexey V Zakharov (AV)

National Center for Advancing Translational Sciences, Rockville, MD 20892.

Anton Simeonov (A)

National Center for Advancing Translational Sciences, Rockville, MD 20892.

Juan Marugan (J)

National Center for Advancing Translational Sciences, Rockville, MD 20892.

Rama K Mallampalli (RK)

Department of Internal Medicine, The Ohio State University, Columbus, OH 43210.

Sally E Wenzel (SE)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

Joel S Greenberger (JS)

Department of Radiation Oncology, University of Pittsburgh, Pittsburgh, PA 15260.

Ganesha Rai (G)

National Center for Advancing Translational Sciences, Rockville, MD 20892.

Hülya Bayir (H)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.
Department of Pediatrics, Division of Critical Care and Hospital Medicine, Redox Health Center, Vagelos College of Physicians and Surgeons, Columbia University Irving Medical Center, New York, NY 10032.

Ivet Bahar (I)

Laufer Center for Physical Quantitative Biology and Department of Biochemistry and Cell Biology, School of Medicine, Stony Brook University, NY 11794.

Valerian E Kagan (VE)

Department of Environmental and Occupational Health, Center for Free Radical and Antioxidant Health, University of Pittsburgh, Pittsburgh, PA 15260.

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Classifications MeSH