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Hardeland","year":"2009","journal-title":"J Pineal Res"},{"key":"ref39","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1002\/da.22084","article-title":"Cytokine targets in the brain: impact on neurotransmitters and neurocircuits","volume":"30","author":"AH Miller","year":"2013","journal-title":"Depress Anxiety"},{"key":"ref40","doi-asserted-by":"crossref","first-page":"12","DOI":"10.3389\/fnins.2014.00012","article-title":"Kynurenines in CNS disease: regulation by inflammatory cytokines","volume":"8","author":"BM Campbell","year":"2014","journal-title":"Front Neurosci"},{"key":"ref41","doi-asserted-by":"crossref","first-page":"116","DOI":"10.3389\/fpsyt.2015.00116","article-title":"Kynurenine 3-monooxygenase: an influential mediator of neuropathology","volume":"6","author":"JM Parrott","year":"2015","journal-title":"Front Psychiatry"},{"key":"ref42","doi-asserted-by":"crossref","first-page":"67","DOI":"10.21519\/0234-2758-2018-34-3-67-77","article-title":"Effect of antioxidants on medium-term memory formation in <italic>Drosophila melanogaster cardinal<\/italic> mutant","volume":"34","author":"EA Nikitina","year":"2018","journal-title":"Biotekhnologiya"},{"key":"ref43","article-title":"Ommochromes in invertebrates: biochemistry and cell biology","author":"F Figon","year":"2018","journal-title":"Biol Rev Camb Philos Soc"},{"key":"ref44","doi-asserted-by":"crossref","first-page":"1101","DOI":"10.1007\/BF01101711","article-title":"The role of hydrogen peroxide in the in vitro cytotoxicity of 3-hydroxykynurenine","volume":"15","author":"CL Eastman","year":"1990","journal-title":"Neurochem Res"},{"key":"ref45","doi-asserted-by":"crossref","first-page":"12553","DOI":"10.1073\/pnas.93.22.12553","article-title":"Hydrogen peroxide-mediated neuronal cell death induced by an endogenous neurotoxin, 3-hydroxykynurenine","volume":"93","author":"S Okuda","year":"1996","journal-title":"Proc Natl Acad Sci U S A"},{"key":"ref46","doi-asserted-by":"crossref","first-page":"7266","DOI":"10.1021\/bi992997s","article-title":"3-Hydroxykynurenine and 3-hydroxyanthranilic acid generate hydrogen peroxide and promote alpha-crystallin cross-linking by metal ion reduction","volume":"39","author":"LE Goldstein","year":"2000","journal-title":"Biochemistry"},{"key":"ref47","doi-asserted-by":"crossref","first-page":"1108","DOI":"10.1016\/j.freeradbiomed.2007.12.003","article-title":"Tryptophan-derived ultraviolet filter compounds covalently bound to lens proteins are photosensitizers of oxidative damage","volume":"44","author":"J Mizdrak","year":"2008","journal-title":"Free Radic Biol Med"},{"key":"ref48","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.freeradbiomed.2015.02.006","article-title":"Antioxidant activity of dopamine and L-DOPA in lipid micelles and their cooperation with an analogue of \u03b1-tocopherol","volume":"83","author":"K Jodko-Piorecka","year":"2015","journal-title":"Free Radic Biol Med"},{"key":"ref49","doi-asserted-by":"crossref","first-page":"429","DOI":"10.18388\/abp.2006_3314","article-title":"Melanin synthesis in microorganisms\u2013biotechnological and medical aspects","volume":"53","author":"PM Plonka","year":"2006","journal-title":"Acta Biochim Pol"},{"key":"ref50","doi-asserted-by":"crossref","first-page":"898","DOI":"10.1111\/jnc.12686","article-title":"Protective and toxic roles of dopamine in Parkinson&apos;s disease","volume":"129","author":"J Segura-Aguilar","year":"2014","journal-title":"J Neurochem"},{"key":"ref51","first-page":"19","article-title":"AIDS and the historian","author":"O. Augusto","year":"2011"},{"key":"ref52","doi-asserted-by":"crossref","first-page":"2717","DOI":"10.1021\/bi101732n","article-title":"Structure and reaction mechanism in the heme dioxygenases","volume":"50","author":"I Efimov","year":"2011","journal-title":"Biochemistry"},{"key":"ref53","first-page":"363","article-title":"Probing dioxygen activation mechanisms in heme-containing enzymes by heme models","volume":"50A","author":"JG Liu","year":"2011","journal-title":"Indian journal of chemistry"},{"key":"ref54","doi-asserted-by":"crossref","first-page":"33","DOI":"10.3109\/03630268609072469","article-title":"Reactions of oxy- and methemoglobin with tryptophan metabolites, 3-hydroxyanthranilic acid and 3-hydroxykynurenine","volume":"10","author":"A Tomoda","year":"1986","journal-title":"Hemoglobin"},{"key":"ref55","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1620\/tjem.192.301","article-title":"Oscillatory oxido-reductive reaction of intracellular hemoglobin in human erythrocyte incubated with o-aminophenol","volume":"192","author":"M Akazawa","year":"2000","journal-title":"Tohoku J Exp Med"},{"key":"ref56","doi-asserted-by":"crossref","first-page":"142","DOI":"10.1126\/science.1256754","article-title":"Biochemistry. Fishing for peroxidase protons","volume":"345","author":"JT Groves","year":"2014","journal-title":"Science"},{"key":"ref57","unstructured":"PubChem Compound database [Internet]. Available from: <ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" ext-link-type=\"uri\" xlink:href=\"https:\/\/pubchem.ncbi.nlm.nih.gov\" xlink:type=\"simple\">https:\/\/pubchem.ncbi.nlm.nih.gov<\/ext-link>"},{"key":"ref58","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1023\/B:JCAM.0000035186.90683.f2","article-title":"VEGA\u2013an open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming","volume":"18","author":"A Pedretti","year":"2004","journal-title":"J Comput Aided Mol Des"},{"key":"ref59","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/1758-2946-4-17","article-title":"Avogadro: an advanced semantic chemical editor, visualization, and analysis platform","volume":"4","author":"MD Hanwell","year":"2012","journal-title":"J Cheminformatics"},{"key":"ref60","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1186\/1758-2946-3-8","article-title":"Confab\u2014Systematic generation of diverse low-energy conformers","volume":"3","author":"NM O'Boyle","year":"2011","journal-title":"J Cheminform"},{"key":"ref61","doi-asserted-by":"crossref","first-page":"490","DOI":"10.1002\/(SICI)1096-987X(199604)17:5\/6<490::AID-JCC1>3.0.CO;2-P","article-title":"Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94","volume":"17","author":"TA Halgren","year":"1996","journal-title":"J Comput Chem"},{"key":"ref62","unstructured":"Chemicalize [Internet]. Available from: <ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" ext-link-type=\"uri\" xlink:href=\"http:\/\/www.chemicalize.org\" xlink:type=\"simple\">http:\/\/www.chemicalize.org<\/ext-link>"},{"key":"ref63","doi-asserted-by":"crossref","first-page":"1347","DOI":"10.1002\/jcc.540141112","article-title":"General atomic and molecular electronic structure system","volume":"14","author":"MW Schmidt","year":"1993","journal-title":"J Comput Chem"},{"key":"ref64","unstructured":"Granovsky A. Firefly [Internet]. Available: <ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" ext-link-type=\"uri\" xlink:href=\"http:\/\/classic.chem.msu.su\/gran\/firefly\/index.html\" xlink:type=\"simple\">http:\/\/classic.chem.msu.su\/gran\/firefly\/index.html<\/ext-link>."},{"key":"ref65","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1007\/BF00533485","article-title":"The influence of polarization functions on molecular orbital hydrogenation energies","volume":"28","author":"PC Hariharan","year":"1973","journal-title":"Theor Chim Acta"},{"key":"ref66","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1063\/1.438955","article-title":"Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions","volume":"72","author":"R Krishnan","year":"1980","journal-title":"J Chem Phys"},{"key":"ref67","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"C Lee","year":"1988","journal-title":"Phys Rev B"},{"key":"ref68","doi-asserted-by":"crossref","first-page":"386","DOI":"10.1002\/wcms.1086","article-title":"Polarizable continuum model","volume":"2","author":"B Mennucci","year":"2012","journal-title":"Wiley Interdiscip Rev Comput Mol Sci"},{"issue":"33","key":"ref69","doi-asserted-by":"crossref","first-page":"11987","DOI":"10.1039\/c3dt50908g","article-title":"Mechanistic insights into iron catalyzed dehydrogenation of formic acid: \u03b2-hydride elimination vs. direct hydride transfer","volume":"42","author":"X Yang","year":"2013","journal-title":"Dalton Trans"},{"key":"ref70","doi-asserted-by":"crossref","first-page":"258","DOI":"10.1002\/qua.24757","article-title":"Intrinsic reaction coordinate: Calculation, bifurcation, and automated search","volume":"115","author":"S Maeda","year":"2015","journal-title":"Int J Quantum Chem"},{"key":"ref71","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1002\/qua.24518","article-title":"Thermodynamic and kinetic study of ibuprofen with hydroxyl radical: a density functional theory approach","volume":"114","author":"R Xiao","year":"2014","journal-title":"Int J Quantum Chem"},{"key":"ref72","first-page":"203","article-title":"Zeitschrift fur physikalische chemie-abteilung b-chemie der elementarprozesse","volume":"19","author":"E Wigner","year":"1932","journal-title":"Aufbau der Materie"},{"key":"ref73","doi-asserted-by":"crossref","first-page":"707","DOI":"10.1063\/1.556020","article-title":"Energetics of the O\u2013H bond in phenol and substituted phenols: a critical evaluation of literature data","volume":"27","author":"RM Borges dos Santos","year":"1998","journal-title":"J Phys Chem Ref Data"},{"key":"ref74","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1080\/00268977000101561","article-title":"The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors","volume":"19","author":"SF Boys","year":"1970","journal-title":"Mol Phys"},{"key":"ref75","doi-asserted-by":"crossref","first-page":"779","DOI":"10.1006\/jmbi.1993.1626","article-title":"Comparative protein modelling by satisfaction of spatial restraints","volume":"234","author":"A Sali","year":"1993","journal-title":"J Mol Biol"},{"key":"ref76","doi-asserted-by":"crossref","first-page":"1881","DOI":"10.1110\/ps.036061.108","article-title":"How well can the accuracy of comparative protein structure models be predicted?","volume":"17","author":"D Eramian","year":"2008","journal-title":"Protein Sci"},{"key":"ref77","doi-asserted-by":"crossref","first-page":"2507","DOI":"10.1110\/ps.062416606","article-title":"Statistical potential for assessment and prediction of protein structures","volume":"15","author":"MY Shen","year":"2006","journal-title":"Protein Sci"},{"key":"ref78","doi-asserted-by":"crossref","first-page":"430","DOI":"10.1002\/pro.110430","article-title":"Sali A. Statistical potentials for fold assessment","volume":"11","author":"F Melo","year":"2002","journal-title":"Protein Sci"},{"key":"ref79","doi-asserted-by":"crossref","first-page":"810","DOI":"10.1016\/S0006-3495(95)79955-6","article-title":"Thermodynamics of water mediating protein-ligand interactions in cytochrome P450cam: a molecular dynamics study","volume":"69","author":"V Helms","year":"1995","journal-title":"Biophys J"},{"key":"ref80","doi-asserted-by":"crossref","first-page":"2785","DOI":"10.1002\/jcc.21256","article-title":"Autodock4 and AutoDockTools4: automated docking with selective receptor flexiblity","volume":"16","author":"GM Morris","year":"2009","journal-title":"J Comput Chem"},{"key":"ref81","doi-asserted-by":"crossref","first-page":"1639","DOI":"10.1002\/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B","article-title":"Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function","volume":"19","author":"GM Morris","year":"1998","journal-title":"J Comput Chem"},{"key":"ref82","doi-asserted-by":"crossref","first-page":"905","DOI":"10.1021\/ed074p905","article-title":"ACD\/ChemSketch 1.0 (freeware); ACD\/ChemSketch 2.0 and its tautomers, dictionary, and 3D plug-ins; ACD\/HNMR 2.0; ACD\/CNMR 2.0","volume":"74","author":"AD Hunter","year":"1997","journal-title":"J Chem Educ"},{"key":"ref83","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","article-title":"VMD: visual molecular dynamics","volume":"14","author":"W Humphrey","year":"1996","journal-title":"J Mol Graph"},{"key":"ref84","first-page":"568","article-title":"Gen. Neurochem. Tech.","author":"G de LA Rodrigues","year":"1986"},{"key":"ref85","doi-asserted-by":"crossref","first-page":"4290","DOI":"10.1021\/jf0502698","article-title":"Standarized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements","volume":"53","author":"RL Prior","year":"2005","journal-title":"J Agric Food Chem"},{"key":"ref86","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1134\/S1819712409030052","article-title":"Changes in lipid peroxidation in the hippocampus and neocortex after severe hypobaric hypoxia","volume":"3","author":"MS Kislin","year":"2009","journal-title":"Neurochem J"},{"key":"ref87","unstructured":"Social Science Statistics [Internet]. Available from: <ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" ext-link-type=\"uri\" xlink:href=\"http:\/\/www.socscistatistics.com\" xlink:type=\"simple\">http:\/\/www.socscistatistics.com<\/ext-link>."},{"key":"ref88","article-title":"Biometry","author":"RR Sokal","year":"1995"}],"updated-by":[{"DOI":"10.1371\/journal.pcbi.1006672","type":"new_version","label":"New version","source":"publisher","updated":{"date-parts":[[2018,12,20]],"date-time":"2018-12-20T00:00:00Z","timestamp":1545264000000}}],"container-title":["PLOS Computational Biology"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/dx.plos.org\/10.1371\/journal.pcbi.1006672","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,9,7]],"date-time":"2022-09-07T19:39:19Z","timestamp":1662579559000},"score":1,"resource":{"primary":{"URL":"https:\/\/dx.plos.org\/10.1371\/journal.pcbi.1006672"}},"subtitle":[],"editor":[{"given":"James M.","family":"Briggs","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"editor"}]}],"short-title":[],"issued":{"date-parts":[[2018,12,10]]},"references-count":88,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2018,12,10]]}},"URL":"https:\/\/doi.org\/10.1371\/journal.pcbi.1006672","relation":{},"ISSN":["1553-7358"],"issn-type":[{"value":"1553-7358","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,12,10]]}}}