{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,16]],"date-time":"2026-06-16T18:32:07Z","timestamp":1781634727428,"version":"3.54.5"},"reference-count":55,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2024,7,1]],"date-time":"2024-07-01T00:00:00Z","timestamp":1719792000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2024,7,1]],"date-time":"2024-07-01T00:00:00Z","timestamp":1719792000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T00:00:00Z","timestamp":1715644800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Archives of Biochemistry and Biophysics"],"published-print":{"date-parts":[[2024,7]]},"DOI":"10.1016\/j.abb.2024.110025","type":"journal-article","created":{"date-parts":[[2024,5,11]],"date-time":"2024-05-11T06:36:48Z","timestamp":1715409408000},"page":"110025","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":4,"special_numbering":"C","title":["Sequence similarity network analysis of drug- and dye-modifying azoreductase enzymes found in the human gut microbiome"],"prefix":"10.1016","volume":"757","author":[{"given":"Audrey R.","family":"Long","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emma L.","family":"Mortara","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brisa N.","family":"Mendoza","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emma C.","family":"Fink","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francis X.","family":"Sacco","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthew J.","family":"Ciesla","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1422-784X","authenticated-orcid":false,"given":"Tyler M.M.","family":"Stack","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.abb.2024.110025_bib1","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1038\/nature08821","article-title":"A human gut microbial gene catalogue established by metagenomic sequencing","volume":"464","author":"Qin","year":"2010","journal-title":"Nature"},{"key":"10.1016\/j.abb.2024.110025_bib2","doi-asserted-by":"crossref","DOI":"10.1126\/science.aag2770","article-title":"Chemical transformation of xenobiotics by the human gut microbiota","volume":"356","author":"Koppel","year":"2017","journal-title":"Science"},{"key":"10.1016\/j.abb.2024.110025_bib3","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1016\/j.cell.2016.01.013","article-title":"Are we really vastly outnumbered? Revisiting the ratio of bacterial to host cells in humans","volume":"164","author":"Sender","year":"2016","journal-title":"Cell"},{"key":"10.1016\/j.abb.2024.110025_bib4","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1038\/nrmicro.2016.17","article-title":"The microbial pharmacists within us: a metagenomic view of xenobiotic metabolism","volume":"14","author":"Spanogiannopoulos","year":"2016","journal-title":"Nat. Rev. Microbiol."},{"key":"10.1016\/j.abb.2024.110025_bib5","doi-asserted-by":"crossref","first-page":"204","DOI":"10.1016\/j.trsl.2016.08.002","article-title":"Gut microbiome interactions with drug metabolism, efficacy, and toxicity","volume":"179","author":"Wilson","year":"2017","journal-title":"Transl. Res."},{"key":"10.1016\/j.abb.2024.110025_bib6","doi-asserted-by":"crossref","first-page":"1661","DOI":"10.1016\/j.cell.2020.05.001","article-title":"Personalized mapping of drug metabolism by the human gut microbiome","volume":"181","author":"Javdan","year":"2020","journal-title":"Cell"},{"key":"10.1016\/j.abb.2024.110025_bib7","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1038\/s41586-019-1291-3","article-title":"Mapping human microbiome drug metabolism by gut bacteria and their genes","volume":"570","author":"Zimmermann","year":"2019","journal-title":"Nature"},{"key":"10.1016\/j.abb.2024.110025_bib8","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1126\/science.1235872","article-title":"Predicting and manipulating cardiac drug inactivation by the human gut bacterium eggerthella lenta","volume":"341","author":"Haiser","year":"2013","journal-title":"Science."},{"key":"10.1016\/j.abb.2024.110025_bib9","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1016\/S0140-6736(00)97447-6","article-title":"IS p-AMINOBENZENESULPHONAMIDE THE ACTIVE AGENT IN PRONTOSIL THERAPY","volume":"229","author":"Fuller","year":"1937","journal-title":"Lancet"},{"key":"10.1016\/j.abb.2024.110025_bib10","doi-asserted-by":"crossref","first-page":"3171","DOI":"10.1002\/jps.24103","article-title":"On the colonic bacterial metabolism of azo-bonded prodrugsof 5-aminosalicylic acid","volume":"103","author":"Sousa","year":"2014","journal-title":"J. Pharmaceut. Sci."},{"key":"10.1016\/j.abb.2024.110025_bib11","doi-asserted-by":"crossref","first-page":"142","DOI":"10.1124\/dmd.122.000898","article-title":"Gut microbiome\u2013wide search for bacterial azoreductases reveals potentially uncharacterized azoreductases encoded in the human gut microbiome","volume":"51","author":"Braccia","year":"2023","journal-title":"Drug Metab. Dispos."},{"key":"10.1016\/j.abb.2024.110025_bib12","doi-asserted-by":"crossref","DOI":"10.1080\/19490976.2023.2203963","article-title":"Diverse but desolate landscape of gut microbial azoreductases: a rationale for idiopathic IBD drug response","volume":"15","author":"Simpson","year":"2023","journal-title":"Gut Microb."},{"key":"10.1016\/j.abb.2024.110025_bib13","doi-asserted-by":"crossref","first-page":"1260","DOI":"10.1038\/s42255-022-00656-z","article-title":"Bacterial hydrogen sulfide drives cryptic redox chemistry in gut microbial communities","volume":"4","author":"Wolfson","year":"2022","journal-title":"Nat. Metab."},{"key":"10.1016\/j.abb.2024.110025_bib14","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1186\/s12866-017-1033-3","article-title":"Identification of Enterococcus faecalis enzymes with azoreductases and\/or nitroreductase activity","volume":"17","author":"Chalansonnet","year":"2017","journal-title":"BMC Microbiol."},{"key":"10.1016\/j.abb.2024.110025_bib15","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1016\/j.anaerobe.2011.12.006","article-title":"Identification, Isolation and characterization of a novel azoreductase from Clostridium perfringens","volume":"18","author":"Morrison","year":"2012","journal-title":"Anaerobe"},{"key":"10.1016\/j.abb.2024.110025_bib16","doi-asserted-by":"crossref","first-page":"5508","DOI":"10.1038\/s41598-019-41894-8","article-title":"Azoreductase activity of dye-decolorizing bacteria isolated from the human gut microbiota","volume":"9","author":"Zahran","year":"2019","journal-title":"Sci. Rep."},{"key":"10.1016\/j.abb.2024.110025_bib17","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1042\/BJ20150856","article-title":"Identification of novel members of the bacterial azoreductase family in Pseudomonas aeruginosa","volume":"473","author":"Crescente","year":"2016","journal-title":"Biochem. J."},{"key":"10.1016\/j.abb.2024.110025_bib18","doi-asserted-by":"crossref","first-page":"3965","DOI":"10.1007\/s00253-019-09775-2","article-title":"Remarkable diversification of bacterial azoreductases: primary sequences, structures, substrates, physiological roles, and biotechnological applications","volume":"103","author":"Suzuki","year":"2019","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"10.1016\/j.abb.2024.110025_bib19","doi-asserted-by":"crossref","first-page":"780","DOI":"10.1007\/s13238-010-0090-2","article-title":"Reaction mechanism of azoreductases suggests convergent evolution with quinone oxidoreductases","volume":"1","author":"Ryan","year":"2010","journal-title":"Protein Cell"},{"key":"10.1016\/j.abb.2024.110025_bib20","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/j.freeradbiomed.2019.04.026","article-title":"Reaction of quinones with proteins: kinetics of adduct formation, effects on enzymatic activity and protein structure, and potential reversibility of modifications","volume":"137","author":"Shu","year":"2019","journal-title":"Free Radic. Biol. Med."},{"key":"10.1016\/j.abb.2024.110025_bib21","doi-asserted-by":"crossref","DOI":"10.1371\/journal.pone.0098551","article-title":"Identification of NAD(P)H quinone oxidoreductase activity in azoreductases from P. aeruginosa: azoreductases and NAD(P)H quinone oxidoreductases belong to the same FMN-dependent superfamily of enzymes","volume":"9","author":"Ryan","year":"2014","journal-title":"PLoS One"},{"key":"10.1016\/j.abb.2024.110025_bib22","doi-asserted-by":"crossref","first-page":"6394","DOI":"10.1128\/JB.00552-09","article-title":"The Escherichia coli azoreductase AzoR is involved in resistance to thiol-specific stress caused by electrophilic quinones","volume":"191","author":"Liu","year":"2009","journal-title":"J. Bacteriol."},{"key":"10.1016\/j.abb.2024.110025_bib23","doi-asserted-by":"crossref","DOI":"10.1128\/mbio.01573-23","article-title":"The global anaerobic metabolism regulator fnr is necessary for the degradation of food dyes and drugs by Escherichia coli","volume":"14","author":"Pieper","year":"2023","journal-title":"mBio"},{"key":"10.1016\/j.abb.2024.110025_bib24","doi-asserted-by":"crossref","first-page":"4146","DOI":"10.1099\/ijsem.0.002268","volume":"67","author":"Ueki","year":"2017","journal-title":"Int. J. Syst. Evol. Microbiol."},{"key":"10.1016\/j.abb.2024.110025_bib25","doi-asserted-by":"crossref","first-page":"e4345","DOI":"10.1371\/journal.pone.0004345","article-title":"Using sequence similarity networks for visualization of relationships across diverse protein superfamilies","volume":"4","author":"Atkinson","year":"2009","journal-title":"PLoS One"},{"key":"10.1016\/j.abb.2024.110025_bib26","doi-asserted-by":"crossref","DOI":"10.1016\/j.jmb.2023.168018","article-title":"EFI-EST, EFI-GNT, and EFI-CGFP: enzyme function initiative (EFI) web resource for genomic enzymology tools","volume":"435","author":"Oberg","year":"2023","journal-title":"J. Mol. Biol."},{"key":"10.1016\/j.abb.2024.110025_bib27","article-title":"A prominent glycyl radical enzyme in human gut microbiomes metabolizes trans-4-hydroxy-l-proline","author":"Levin","year":"2017","journal-title":"Science"},{"key":"10.1016\/j.abb.2024.110025_bib28","doi-asserted-by":"crossref","first-page":"4169","DOI":"10.1021\/acs.biochem.9b00735","article-title":"The EFI web resource for genomic enzymology tools: leveraging protein, genome, and metagenome databases to discover novel enzymes and metabolic pathways","volume":"58","author":"Zallot","year":"2019","journal-title":"Biochemistry"},{"key":"10.1016\/j.abb.2024.110025_bib29","doi-asserted-by":"crossref","first-page":"1209","DOI":"10.1271\/bbb.80872","article-title":"Comparative enzymatic analysis of azoreductases from Bacillus sp. B29","volume":"73","author":"Ooi","year":"2009","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"10.1016\/j.abb.2024.110025_bib30","doi-asserted-by":"crossref","first-page":"1431","DOI":"10.1007\/s00253-009-2351-7","article-title":"Characterization of thermostable FMN-dependent NADH azoreductase from the moderate thermophile Geobacillus stearothermophilus","volume":"86","author":"Matsumoto","year":"2010","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"10.1016\/j.abb.2024.110025_bib31","doi-asserted-by":"crossref","first-page":"504","DOI":"10.1021\/acschembio.9b00970","article-title":"Mechanistic and crystallographic studies of azoreductase AzoA from Bacillus wakoensis A01","volume":"15","author":"Romero","year":"2020","journal-title":"ACS Chem. Biol."},{"key":"10.1016\/j.abb.2024.110025_bib32","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1016\/j.ijbiomac.2015.12.065","article-title":"Isolation, cloning and characterization of an azoreductase from the halophilic bacterium Halomonas elongata","volume":"85","author":"Eslami","year":"2016","journal-title":"Int. J. Biol. Macromol."},{"key":"10.1016\/j.abb.2024.110025_bib33","doi-asserted-by":"crossref","first-page":"46394","DOI":"10.1074\/jbc.M104483200","article-title":"Putative ACP phosphodiesterase gene (acpD) encodes an azoreductase","volume":"276","author":"Nakanishi","year":"2001","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.abb.2024.110025_bib34","doi-asserted-by":"crossref","first-page":"611","DOI":"10.1271\/bbb.60548","article-title":"Characterization of a NADH:dichloroindophenol oxidoreductase from Bacillus subtilis","volume":"71","author":"Nishiya","year":"2007","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"10.1016\/j.abb.2024.110025_bib35","doi-asserted-by":"crossref","first-page":"1213","DOI":"10.1016\/j.jmb.2007.08.048","article-title":"Molecular cloning, characterisation and ligand-bound structure of an azoreductase from Pseudomonas aeruginosa","volume":"373","author":"Wang","year":"2007","journal-title":"J. Mol. Biol."},{"key":"10.1016\/j.abb.2024.110025_bib36","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1016\/j.biortech.2013.09.124","article-title":"Characterization of a new oxygen-insensitive azoreductase from Brevibacillus laterosporus TISTR1911: toward dye decolorization using a packed-bed metal affinity reactor","volume":"150","author":"Lang","year":"2013","journal-title":"Bioresour. Technol."},{"key":"10.1016\/j.abb.2024.110025_bib37","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.jmb.2010.04.023","article-title":"A novel mechanism for azoreduction","volume":"400","author":"Ryan","year":"2010","journal-title":"J. Mol. Biol."},{"key":"10.1016\/j.abb.2024.110025_bib38","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1007\/s00253-011-3366-4","article-title":"Molecular determinants of azo reduction activity in the strain Pseudomonas putida MET94","volume":"92","author":"Mendes","year":"2011","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"10.1016\/j.abb.2024.110025_bib39","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1007\/s00253-006-0836-1","article-title":"An azoreductase, aerobic NADH-dependent flavoprotein discovered from Bacillus sp.: functional expression and enzymatic characterization","volume":"75","author":"Ooi","year":"2007","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"10.1016\/j.abb.2024.110025_bib40","doi-asserted-by":"crossref","first-page":"302","DOI":"10.1016\/j.pep.2003.12.016","article-title":"Molecular cloning, overexpression, purification, and characterization of an aerobic FMN-dependent azoreductase from Enterococcus faecalis","volume":"34","author":"Chen","year":"2004","journal-title":"Protein Expr. Purif."},{"key":"10.1016\/j.abb.2024.110025_bib41","doi-asserted-by":"crossref","first-page":"3232","DOI":"10.1007\/s11356-012-1221-5","article-title":"Characterization of an efficient catalytic and organic solvent-tolerant azoreductase toward methyl red from Shewanella oneidensis MR-1","volume":"20","author":"Yang","year":"2013","journal-title":"Environ. Sci. Pollut. Res."},{"key":"10.1016\/j.abb.2024.110025_bib42","doi-asserted-by":"crossref","first-page":"9171","DOI":"10.1007\/s00253-018-9284-y","article-title":"Azoreductase from alkaliphilic Bacillus sp. AO1 catalyzes indigo reduction","volume":"102","author":"Suzuki","year":"2018","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"10.1016\/j.abb.2024.110025_bib43","doi-asserted-by":"crossref","first-page":"46394","DOI":"10.1074\/jbc.M104483200","article-title":"Putative ACP phosphodiesterase gene (acpD) encodes an azoreductase","volume":"276","author":"Nakanishi","year":"2001","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.abb.2024.110025_bib44","article-title":"A rare but important clinical presentation of induced methemoglobinemia","author":"Banimahd","year":"2016","journal-title":"West. J. Emerg. Med. Integrating Emerg. Care Popul. Health"},{"key":"10.1016\/j.abb.2024.110025_bib45","doi-asserted-by":"crossref","first-page":"773","DOI":"10.1139\/o67-088","article-title":"The metabolism and toxicity of 2,3,6-triaminopyridine, a metabolite of pyridium","volume":"45","author":"Burba","year":"1967","journal-title":"Can. J. Biochem."},{"key":"10.1016\/j.abb.2024.110025_bib46","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1038\/srep00063","article-title":"Activation of nitrofurazone by azoreductases: multiple activities in one enzyme","volume":"1","author":"Ryan","year":"2011","journal-title":"Sci. Rep."},{"key":"10.1016\/j.abb.2024.110025_bib47","doi-asserted-by":"crossref","first-page":"20567","DOI":"10.1074\/jbc.M513345200","article-title":"Three-dimensional structure of AzoR from Escherichia coli: an OXIDEREDUCTASE conserved in microorganisms","volume":"281","author":"Ito","year":"2006","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.abb.2024.110025_bib48","doi-asserted-by":"crossref","first-page":"13889","DOI":"10.1074\/jbc.M710070200","article-title":"Expansion of substrate specificity and catalytic mechanism of azoreductase by X-ray crystallography and site-directed mutagenesis","volume":"283","author":"Ito","year":"2008","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.abb.2024.110025_bib49","doi-asserted-by":"crossref","first-page":"1188","DOI":"10.1101\/gr.849004","article-title":"WebLogo: a sequence logo generator","volume":"14","author":"Crooks","year":"2004","journal-title":"Genome Res."},{"key":"10.1016\/j.abb.2024.110025_bib50","doi-asserted-by":"crossref","first-page":"16009","DOI":"10.1073\/pnas.1920483117","article-title":"Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives","volume":"117","author":"Zou","year":"2020","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"10.1016\/j.abb.2024.110025_bib51","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/j.pep.2005.01.016","article-title":"Protein production by auto-induction in high-density shaking cultures","volume":"41","author":"Studier","year":"2005","journal-title":"Protein Expr. Purif."},{"key":"10.1016\/j.abb.2024.110025_bib52","doi-asserted-by":"crossref","first-page":"16","DOI":"10.3762\/bjoc.15.2","article-title":"New standards for collecting and fitting steady state kinetic data","volume":"15","author":"Johnson","year":"2019","journal-title":"Beilstein J. Org. Chem."},{"key":"10.1016\/j.abb.2024.110025_bib53","doi-asserted-by":"crossref","DOI":"10.1371\/journal.pcbi.1004557","article-title":"High-specificity targeted functional profiling in microbial communities with ShortBRED","volume":"11","author":"Kaminski","year":"2015","journal-title":"PLoS Comput. Biol."},{"key":"10.1016\/j.abb.2024.110025_bib54","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1186\/s13059-015-0611-7","article-title":"Average genome size estimation improves comparative metagenomics and sheds light on the functional ecology of the human microbiome","volume":"16","author":"Nayfach","year":"2015","journal-title":"Genome Biol."},{"key":"10.1016\/j.abb.2024.110025_bib55","series-title":"A Virtual and Mixed Reality Platform for Molecular Design & Drug Discovery - Nanome Version 1.24","author":"Bennie","year":"2023"}],"container-title":["Archives of Biochemistry and Biophysics"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0003986124001449?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0003986124001449?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2024,6,12]],"date-time":"2024-06-12T22:02:14Z","timestamp":1718229734000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0003986124001449"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7]]},"references-count":55,"alternative-id":["S0003986124001449"],"URL":"https:\/\/doi.org\/10.1016\/j.abb.2024.110025","relation":{},"ISSN":["0003-9861"],"issn-type":[{"value":"0003-9861","type":"print"}],"subject":[],"published":{"date-parts":[[2024,7]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Sequence similarity network analysis of drug- and dye-modifying azoreductase enzymes found in the human gut microbiome","name":"articletitle","label":"Article Title"},{"value":"Archives of Biochemistry and Biophysics","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.abb.2024.110025","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2024 The Authors. Published by Elsevier Inc.","name":"copyright","label":"Copyright"}],"article-number":"110025"}}