{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,7]],"date-time":"2026-08-07T15:47:51Z","timestamp":1786117671756,"version":"build-2736575974"},"reference-count":33,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/100006772","name":"Max and Minnie Tomerlin Voelcker Fund","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100006772","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["R37 GM076343"],"award-info":[{"award-number":["R37 GM076343"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Steroids"],"published-print":{"date-parts":[[2026,9]]},"DOI":"10.1016\/j.steroids.2026.109796","type":"journal-article","created":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T15:27:43Z","timestamp":1778858863000},"page":"109796","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":0,"special_numbering":"C","title":["Synthesis of steroids fused with a pyridine at C11-C12 to accommodate the active site ceiling of cytochrome P450 8B1"],"prefix":"10.1016","volume":"233-234","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-4625-8897","authenticated-orcid":false,"given":"Tu M.","family":"Ho","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1862-0529","authenticated-orcid":false,"given":"Elyse K.","family":"Frydendall","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiaying","family":"Zhou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6616-0718","authenticated-orcid":false,"given":"Samuel D.","family":"Offei","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9084-560X","authenticated-orcid":false,"given":"Hadi D.","family":"Arman","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5538-5716","authenticated-orcid":false,"given":"Emily E.","family":"Scott","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2308-2999","authenticated-orcid":false,"given":"Francis K.","family":"Yoshimoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.steroids.2026.109796_b0005","doi-asserted-by":"crossref","first-page":"8030","DOI":"10.1016\/S0021-9258(18)34292-3","article-title":"Purification and characterization of 7alpha-hydroxy-4-cholesten-3-one 12alpha-monooxygenase","volume":"257","author":"Murakami","year":"1982","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0010","doi-asserted-by":"crossref","first-page":"21319","DOI":"10.1016\/S0021-9258(19)36611-6","article-title":"Purification and characterization of 7alpha-hydroxy-4-cholesten-3-one 12alpha-hydroxylase","volume":"1992","author":"Ishida","year":"1992","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0015","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1080\/21623945.2020.1827519","article-title":"Increased whole body energy expenditure and protection against diet-induced obesity in Cyp8b1-deficient mice is accompanied by altered adipose tissue features","volume":"9","author":"Axling","year":"2020","journal-title":"Adipocyte"},{"key":"10.1016\/j.steroids.2026.109796_b0020","doi-asserted-by":"crossref","first-page":"1168","DOI":"10.2337\/db14-0716","article-title":"Loss of Cyp8b1 improves glucose homeostasis by increasing GLP-1","volume":"64","author":"Kaur","year":"2015","journal-title":"Diabetes"},{"key":"10.1016\/j.steroids.2026.109796_b0025","doi-asserted-by":"crossref","first-page":"E418","DOI":"10.1152\/ajpendo.00172.2017","article-title":"Genetic ablation of Cyp8b1 preserves host metabolic function by repressing steatohepatitis and altering gut microbiota composition","volume":"314","author":"Patankar","year":"2017","journal-title":"Am. J. Phys. Endocrinol. Metab."},{"key":"10.1016\/j.steroids.2026.109796_b0030","doi-asserted-by":"crossref","DOI":"10.1172\/JCI152961","article-title":"Haploinsufficiency of CYP8B1 associates with increased insulin sensitivity in humans","volume":"132","author":"Zhong","year":"2022","journal-title":"J. Clin. Investig."},{"key":"10.1016\/j.steroids.2026.109796_b0035","doi-asserted-by":"crossref","first-page":"1679","DOI":"10.1053\/j.gastro.2017.01.055","article-title":"Bile acid control of metabolism and inflammation in obesity, type 2 diabetes, dyslipidemia, and nonalcoholic fatty liver disease","volume":"152","author":"Chavez-Talavera","year":"2017","journal-title":"Gastroenterology"},{"key":"10.1016\/j.steroids.2026.109796_b0040","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1007\/s11892-018-1092-3","article-title":"Rethinking bile acid metabolism and signaling for type 2 diabetes treatment","volume":"18","author":"Zaborska","year":"2018","journal-title":"Curr. Diab. Rep."},{"key":"10.1016\/j.steroids.2026.109796_b0045","doi-asserted-by":"crossref","first-page":"3485","DOI":"10.1096\/fj.201701084RR","article-title":"Therapeutic modulation of the bile acid pool by Cyp8b1 knockdown protects against nonalcoholic fatty liver disease in mice","volume":"32","author":"Chevre","year":"2018","journal-title":"FASEB J."},{"key":"10.1016\/j.steroids.2026.109796_b0050","doi-asserted-by":"crossref","DOI":"10.1016\/j.steroids.2021.108952","article-title":"A synthesis of a rationally designed inhibitor of cytochrome P450 8B1, a therapeutic target to treat obesity","volume":"178","author":"Chung","year":"2022","journal-title":"Steroids"},{"key":"10.1016\/j.steroids.2026.109796_b0055","doi-asserted-by":"crossref","unstructured":"T.M. Ho, F.K. Yoshimoto, Strategies to inhibit steroid cytochrome P450 enzymes to benefit human health: development of steroid ligands for P450s 17A1, 19A1, and 8B1 to treat cancer and obesity, RSC Med. Chem., (2026), In press.","DOI":"10.1039\/D5MD00954E\/v3\/response1"},{"key":"10.1016\/j.steroids.2026.109796_b0060","doi-asserted-by":"crossref","first-page":"116","DOI":"10.1038\/nature10743","article-title":"Structures of cytochrome P450 17A1 with prostate cancer drugs abiraterone and TOK-001","volume":"482","author":"DeVore","year":"2012","journal-title":"Nature"},{"key":"10.1016\/j.steroids.2026.109796_b0065","article-title":"Pyridine-containing substrate analogs are restricted from accessing the human cytochrome P450 8B1 active site by tryptophan 281","volume":"299","author":"Liu","year":"2023","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0070","unstructured":"CrysAlisPro 1.171.40.63a, Rigaku Oxford Diffraction, (2019)."},{"key":"10.1016\/j.steroids.2026.109796_b0075","unstructured":"SCALE3 ABSPACK -An Oxford Diffraction program(1.0.4,gui:1.0.3), Oxford Diffraction Ltd., (2005)."},{"key":"10.1016\/j.steroids.2026.109796_b0080","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: a complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"10.1016\/j.steroids.2026.109796_b0085","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT \u2013 integrated space-group and crystal-structure determination","volume":"A71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. A"},{"key":"10.1016\/j.steroids.2026.109796_b0090","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"A64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. A"},{"key":"10.1016\/j.steroids.2026.109796_b0095","doi-asserted-by":"crossref","DOI":"10.1016\/j.jbc.2022.102344","article-title":"The structure and characterization of human cytochrome P450 8B1 supports future drug design for nonalcoholic fatty liver disease and diabetes","volume":"298","author":"Liu","year":"2022","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0100","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/j.steroids.2018.10.010","article-title":"Chemical synthesis of 7-oxygenated 12alpha-hydroxy steroid derivatives to enable the biochemical characterization of cytochrome P450 8B1, the oxysterol 12alpha-hydroxylase enzyme implicated in cardiovascular health and obe","volume":"140","author":"Offei","year":"2018","journal-title":"Steroids"},{"key":"10.1016\/j.steroids.2026.109796_b0105","doi-asserted-by":"crossref","DOI":"10.1016\/j.steroids.2023.109287","article-title":"Synthesis and biological activities of bicyclic pyridines integrated steroid hybrid","volume":"199","author":"Hammouda","year":"2023","journal-title":"Steroids"},{"key":"10.1016\/j.steroids.2026.109796_b0110","doi-asserted-by":"crossref","first-page":"9618","DOI":"10.1039\/D5OB01218J","article-title":"A synthesis of 1\u03b2-hydroxytestosterone, a metabolite of xenobiotic human cytochrome P450 enzymes, beginning with a borylation of boldione","volume":"23","author":"Elizondo","year":"2025","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0115","doi-asserted-by":"crossref","first-page":"7315","DOI":"10.1021\/acs.joc.0c03038","article-title":"Cu-catalyzed pyridine synthesis via oxidative annulation of cyclic ketons with propargylamine","volume":"86","author":"Sotnik","year":"2021","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0120","doi-asserted-by":"crossref","first-page":"6959","DOI":"10.1021\/jo0347260","article-title":"Sequential amination\/annulation\/aromatization reaction of carbonyl compounds and propargylamine: a new one-pot approach to functionalized pyridines","volume":"68","author":"Abbiati","year":"2003","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0125","doi-asserted-by":"crossref","first-page":"4725","DOI":"10.3390\/molecules28124725","article-title":"Synthesis of nitrogen-containing hetrocyclic scaffolds through sequential reactions of aminoalkynes with carbonyls","volume":"28","author":"Arcadi","year":"2023","journal-title":"Molecules"},{"key":"10.1016\/j.steroids.2026.109796_b0130","doi-asserted-by":"crossref","first-page":"23","DOI":"10.24959\/ophcj.23.289263","article-title":"The synthesis of diverse annulated pyridines with 6-membered functionalized saturated cycles for medical chemistry research","volume":"21","author":"Yehorov","year":"2023","journal-title":"J. Organ. Pharm. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0135","doi-asserted-by":"crossref","first-page":"12561","DOI":"10.1002\/chem.201102710","article-title":"Copper(I)-catalyzed deacetylenative coupling of propargylic amines: an efficient synthesis of symmetric 1,4-diamino-2-butynes","volume":"17","author":"Kim","year":"2011","journal-title":"Chem. Eur. J."},{"key":"10.1016\/j.steroids.2026.109796_b0140","doi-asserted-by":"crossref","first-page":"3172","DOI":"10.1039\/D3OB00054K","article-title":"Synthesis of menarandroside A from dehydroepiandrosterone","volume":"21","author":"Offei","year":"2023","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0145","doi-asserted-by":"crossref","DOI":"10.1016\/j.steroids.2019.108449","article-title":"Chemical synthesis of 7\u03b1-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption","volume":"151","author":"Offei","year":"2019","journal-title":"Steroids"},{"key":"10.1016\/j.steroids.2026.109796_b0150","doi-asserted-by":"crossref","first-page":"5092","DOI":"10.1074\/jbc.M114.627661","article-title":"Contributions of ionic interactions and protein dynamics to cytochrome P450 2D6 (CYP2D6) substrate and inhibitor binding","volume":"290","author":"Wang","year":"2015","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0155","doi-asserted-by":"crossref","first-page":"38617","DOI":"10.1074\/jbc.M505974200","article-title":"Why is quinidine an inhibitor of cytochrome P450 2D6?","volume":"280","author":"McLaughlin","year":"2005","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.steroids.2026.109796_b0160","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1124\/dmd.30.8.869","article-title":"Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen","volume":"30","author":"Crewe","year":"2002","journal-title":"Drug Metab. Dispos."},{"key":"10.1016\/j.steroids.2026.109796_b0165","unstructured":"T.M. Ho, S.D. Offei, H.D. Arman, F.K. Yoshimoto, Synthesis of steroids fused with a pyridine at C11-C12 to accommodate the active site ceiling of cytochrome P450 8B1 - NMR Data https:\/\/doi.org\/10.57992\/NMRXIV.P155 (accessed December 25. 2025)."}],"container-title":["Steroids"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0039128X26000589?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0039128X26000589?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T14:26:45Z","timestamp":1786026405000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0039128X26000589"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9]]},"references-count":33,"alternative-id":["S0039128X26000589"],"URL":"https:\/\/doi.org\/10.1016\/j.steroids.2026.109796","relation":{"is-supplemented-by":[{"id-type":"uri","id":"https:\/\/drive.google.com\/file\/d\/1f_GIZEmdJaNp_4os1HZD2CpqEJsHF-Ou\/view","asserted-by":"subject"}],"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv-2025-6l4pf","asserted-by":"object"}]},"ISSN":["0039-128X"],"issn-type":[{"value":"0039-128X","type":"print"}],"subject":[],"published":{"date-parts":[[2026,9]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis of steroids fused with a pyridine at C11-C12 to accommodate the active site ceiling of cytochrome P450 8B1","name":"articletitle","label":"Article Title"},{"value":"Steroids","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.steroids.2026.109796","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2026 Published by Elsevier Inc.","name":"copyright","label":"Copyright"}],"article-number":"109796"}}