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X-ray structural studies of quinone reductase 2 nanomolar range inhibitors.

Pegan SD, Sturdy M, Ferry G, Delagrange P, Boutin JA, Mesecar AD
Protein Sci 20 1182-95 (2011)
Related entries: 3ovm, 3owx, 3ox1, 3ox2, 3ox3

Cited: 24 times
EuropePMC logo PMID: 21538647

Abstract

Quinone reductase 2 (QR2) is one of two members comprising the mammalian quinone reductase family of enzymes responsible for performing FAD mediated reductions of quinone substrates. In contrast to quinone reductase 1 (QR1) which uses NAD(P)H as its co-substrate, QR2 utilizes a rare group of hydride donors, N-methyl or N-ribosyl nicotinamide. Several studies have linked QR2 to the generation of quinone free radicals, several neuronal degenerative diseases, and cancer. QR2 has been also identified as the third melatonin receptor (MT3) through in cellulo and in vitro inhibition of QR2 by traditional MT3 ligands, and through recent X-ray structures of human QR2 (hQR2) in complex with melatonin and 2-iodomelatonin. Several MT3 specific ligands have been developed that exhibit both potent in cellulo inhibition of hQR2 nanomolar, affinity for MT3. The potency of these ligands suggest their use as molecular probes for hQR2. However, no definitive correlation between traditionally obtained MT3 ligand affinity and hQR2 inhibition exists limiting our understanding of how these ligands are accommodated in the hQR2 active site. To obtain a clearer relationship between the structures of developed MT3 ligands and their inhibitory properties, in cellulo and in vitro IC₅₀ values were determined for a representative set of MT3 ligands (MCA-NAT, 2-I-MCANAT, prazosin, S26695, S32797, and S29434). Furthermore, X-ray structures for each of these ligands in complex with hQR2 were determined allowing for a structural evaluation of the binding modes of these ligands in relation to the potency of MT3 ligands.

Articles - 3owh mentioned but not cited (1)

  1. X-ray structural studies of quinone reductase 2 nanomolar range inhibitors. Pegan SD, Sturdy M, Ferry G, Delagrange P, Boutin JA, Mesecar AD. Protein Sci. 20 1182-1195 (2011)


Reviews citing this publication (3)

  1. Quinone reductase 2 as a promising target of melatonin therapeutic actions. Boutin JA. Expert Opin. Ther. Targets 20 303-317 (2016)
  2. Resveratrol derivatives: a patent review (2009 - 2012). Pezzuto JM, Kondratyuk TP, Ogas T. Expert Opin Ther Pat 23 1529-1546 (2013)
  3. Is There Sufficient Evidence that the Melatonin Binding Site MT3 Is Quinone Reductase 2? Boutin JA, Ferry G. J Pharmacol Exp Ther 368 59-65 (2019)

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  1. Design, synthesis, and biological evaluation of potent quinoline and pyrroloquinoline ammosamide analogues as inhibitors of quinone reductase 2. Reddy PV, Jensen KC, Mesecar AD, Fanwick PE, Cushman M. J. Med. Chem. 55 367-377 (2012)
  2. Role of melatonin receptor MT(2) and quinone reductase II in the regulation of the redox status of 3T3-L1 preadipocytes in vitro. Adamczyk-Sowa M, Sowa P, Zwirska-Korczala K, Pierzchala K, Bartosz G, Sadowska-Bartosz I. Cell Biol. Int. 37 835-842 (2013)
  3. In cellulo monitoring of quinone reductase activity and reactive oxygen species production during the redox cycling of 1,2 and 1,4 quinones. Cassagnes LE, Perio P, Ferry G, Moulharat N, Antoine M, Gayon R, Boutin JA, Nepveu F, Reybier K. Free Radic. Biol. Med. 89 126-134 (2015)
  4. Divergent C-H Annulation for Multifused N-Heterocycles: Regio- and Stereospecific Cyclizations of N-Alkynylindoles. Alam K, Hong SW, Oh KH, Park JK. Angew. Chem. Int. Ed. Engl. 56 13387-13391 (2017)
  5. The melatonin analog 5-MCA-NAT increases endogenous dopamine levels by binding NRH:quinone reductase enzyme in the developing chick retina. Sampaio Lde F, Mesquita FP, de Sousa PR, Silva JL, Alves CN. Int. J. Dev. Neurosci. 38 119-126 (2014)
  6. Flavin-adenine-dinucleotide gold complex nanoparticles: chemical modeling design, physico-chemical assessment and perspectives in nanomedicine. Arib C, Bouchemal N, Barile M, Paleni D, Djaker N, Dupont N, Spadavecchia J. Nanoscale Adv 3 6144-6156 (2021)
  7. Synthesis of novel МТ3 receptor ligands via an unusual Knoevenagel condensation. Volkova MS, Jensen KC, Lozinskaya NA, Sosonyuk SE, Proskurnina MV, Mesecar AD, Zefirov NS. Bioorg. Med. Chem. Lett. 22 7578-7581 (2012)
  8. Contribution of Sigma-1 receptor to cytoprotective effect of afobazole. Voronin MV, Kadnikov IA. Pharmacol Res Perspect 4 e00273 (2016)
  9. Expression of Quinone Reductase-2 in the Cortex Is a Muscarinic Acetylcholine Receptor-Dependent Memory Consolidation Constraint. Rappaport AN, Jacob E, Sharma V, Inberg S, Elkobi A, Ounallah-Saad H, Pasmanik-Chor M, Edry E, Rosenblum K. J. Neurosci. 35 15568-15581 (2015)
  10. Eye and heart morphogenesis are dependent on melatonin signaling in chick embryos. Nogueira RC, Sampaio LFS. J. Exp. Biol. 220 3826-3835 (2017)
  11. Neuroprotective Properties of Quinone Reductase 2 Inhibitor M-11, a 2-Mercaptobenzimidazole Derivative. Voronin MV, Kadnikov IA, Zainullina LF, Logvinov IO, Verbovaya ER, Antipova TA, Vakhitova YV, Seredenin SB. Int J Mol Sci 22 13061 (2021)
  12. Quantitative phosphoproteomic analysis identifies the potential therapeutic target EphA2 for overcoming sorafenib resistance in hepatocellular carcinoma cells. Chen CT, Liao LZ, Lu CH, Huang YH, Lin YK, Lin JH, Chow LP. Exp Mol Med 52 497-513 (2020)
  13. S29434, a Quinone Reductase 2 Inhibitor: Main Biochemical and Cellular Characterization. Boutin JA, Bouillaud F, Janda E, Gacsalyi I, Guillaumet G, Hirsch EC, Kane DA, Nepveu F, Reybier K, Dupuis P, Bertrand M, Chhour M, Le Diguarher T, Antoine M, Brebner K, Da Costa H, Ducrot P, Giganti A, Goswami V, Guedouari H, Michel PP, Patel A, Paysant J, Stojko J, Viaud-Massuard MC, Ferry G. Mol Pharmacol 95 269-285 (2019)
  14. 3-Arylidene-2-oxindoles as Potent NRH:Quinone Oxidoreductase 2 Inhibitors. Lozinskaya NA, Bezsonova EN, Dubar M, Melekhina DD, Bazanov DR, Bunev AS, Grigor'eva OB, Klochkov VG, Sokolova EV, Babkov DA, Spasov AA, Sosonyuk SE. Molecules 28 1174 (2023)
  15. Cloning, Expression, Purification, Crystallization, and X-Ray Structural Determination of the Human NQO2 in Complex with Melatonin. Calamini B, Ferry G, Boutin JA. Methods Mol Biol 2550 291-304 (2022)
  16. Measurement of NQO2 Catalytic Activity and of Its Inhibition by Melatonin. Ferry G, Boutin JA. Methods Mol Biol 2550 315-321 (2022)
  17. Measuring the NQO2: Melatonin Complex by Native Nano-Electrospray Ionization Mass Spectrometry. Boutin JA, Stojko J, Ferry G, Cianferani S. Methods Mol Biol 2550 323-328 (2022)
  18. Melatonin Binding to Human NQO2 by Isothermal Titration Calorimetry. Calamini B, Ferry G, Boutin JA. Methods Mol Biol 2550 305-314 (2022)
  19. Preparation of pyrrolizinone derivatives via sequential transformations of cyclic allyl imides: synthesis of quinolactacide and marinamide. Simic M, Tasic G, Jovanovic P, Petkovic M, Savic V. Org. Biomol. Chem. 16 2125-2133 (2018)
  20. Role of Quinone Reductase 2 in the Antimalarial Properties of Indolone-Type Derivatives. Cassagnes LE, Rakotoarivelo N, Sirigu S, Pério P, Najahi E, Chavas LM, Thompson A, Gayon R, Ferry G, Boutin JA, Valentin A, Reybier K, Nepveu F. Molecules 22 (2017)


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