{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T18:27:57Z","timestamp":1782930477038,"version":"3.54.5"},"reference-count":56,"publisher":"Elsevier BV","issue":"15","license":[{"start":{"date-parts":[[2010,8,1]],"date-time":"2010-08-01T00:00:00Z","timestamp":1280620800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2010,8,1]],"date-time":"2010-08-01T00:00:00Z","timestamp":1280620800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic & Medicinal Chemistry Letters"],"published-print":{"date-parts":[[2010,8]]},"DOI":"10.1016\/j.bmcl.2010.06.082","type":"journal-article","created":{"date-parts":[[2010,6,18]],"date-time":"2010-06-18T04:35:49Z","timestamp":1276835749000},"page":"4376-4381","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":71,"title":["Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors"],"prefix":"10.1016","volume":"20","author":[{"given":"Balendu Sankara","family":"Avvaru","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jason M.","family":"Wagner","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alfonso","family":"Maresca","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Scozzafava","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arthur H.","family":"Robbins","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"McKenna","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmcl.2010.06.082_bib1a","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1038\/nrd2467","volume":"7","author":"Supuran","year":"2008","journal-title":"Nat. Rev. Drug Disc."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref10","doi-asserted-by":"crossref","first-page":"4336","DOI":"10.1016\/j.bmc.2007.04.020","volume":"15","author":"Supuran","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref20","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1016\/j.bbapap.2009.12.015","volume":"1804","author":"Silverman","year":"2010","journal-title":"Biochim. Biophys. Acta"},{"key":"10.1016\/j.bmcl.2010.06.082_bib1d","doi-asserted-by":"crossref","first-page":"30766","DOI":"10.1074\/jbc.M805353200","volume":"283","author":"Domsic","year":"2008","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref30","doi-asserted-by":"crossref","first-page":"3467","DOI":"10.1016\/j.bmcl.2010.05.009","volume":"20","author":"Supuran","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref40","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1002\/med.10025","volume":"23","author":"Supuran","year":"2003","journal-title":"Med. Res. Rev."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref50","doi-asserted-by":"crossref","first-page":"667","DOI":"10.1517\/13543776.14.5.667","volume":"14","author":"Scozzafava","year":"2004","journal-title":"Expert Opin. Ther. Pat."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref60","doi-asserted-by":"crossref","first-page":"921","DOI":"10.2174\/138955706777934946","volume":"6","author":"Winum","year":"2006","journal-title":"Mini-Rev. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_bib3","doi-asserted-by":"crossref","first-page":"595","DOI":"10.1152\/physrev.1967.47.4.595","volume":"47","author":"Maren","year":"1967","journal-title":"Physiol. Rev."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref80","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1080\/14756360410001689540","volume":"19","author":"Pastorekova","year":"2004","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_bib4b","series-title":"Carbonic Anhydrase\u2014Its Inhibitors and Activators","first-page":"67","article-title":"Development of Sulfonamide Carbonic Anhydrase Inhibitors","author":"Supuran","year":"2004"},{"key":"10.1016\/j.bmcl.2010.06.082_sbref90","series-title":"Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications","first-page":"139","article-title":"Antiglaucoma Carbonic Anhydrase Inhibitors as Ophthalomologic Drugs","author":"Mincione","year":"2009"},{"key":"10.1016\/j.bmcl.2010.06.082_sbref100","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1089\/ham.2008.1029","volume":"9","author":"van Patot","year":"2008","journal-title":"High Alt. Med. Biol."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref110","doi-asserted-by":"crossref","first-page":"641","DOI":"10.2174\/138161208783877947","volume":"14","author":"Supuran","year":"2008","journal-title":"Curr. Pharm. Des."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref120","doi-asserted-by":"crossref","first-page":"5544","DOI":"10.1021\/jm060531j","volume":"49","author":"De Simone","year":"2006","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref130","doi-asserted-by":"crossref","first-page":"2315","DOI":"10.1016\/j.bmcl.2005.03.032","volume":"15","author":"De Simone","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref140","doi-asserted-by":"crossref","first-page":"7024","DOI":"10.1021\/jm060807n","volume":"49","author":"Winum","year":"2006","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref150","doi-asserted-by":"crossref","first-page":"8329","DOI":"10.1021\/ja061574s","volume":"128","author":"Alterio","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref160","doi-asserted-by":"crossref","first-page":"841","DOI":"10.1016\/S0960-894X(03)00029-5","volume":"13","author":"Casini","year":"2003","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bmcl.2010.06.082_bib7c","doi-asserted-by":"crossref","first-page":"550","DOI":"10.1021\/jm030912m","volume":"47","author":"Weber","year":"2004","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_bib7d","doi-asserted-by":"crossref","first-page":"5721","DOI":"10.1021\/jm050333c","volume":"48","author":"Menchise","year":"2005","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref170","doi-asserted-by":"crossref","first-page":"383","DOI":"10.1517\/14728214.13.2.383","volume":"13","author":"Supuran","year":"2008","journal-title":"Expert Opin. Emerg. Drugs."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref180","doi-asserted-by":"crossref","first-page":"655","DOI":"10.2174\/138161208783877820","volume":"14","author":"De Simone","year":"2008","journal-title":"Curr. Pharm. Des."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref190","doi-asserted-by":"crossref","first-page":"439","DOI":"10.1016\/j.febslet.2004.10.043","volume":"577","author":"Svastova","year":"2004","journal-title":"FEBS Lett."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref200","doi-asserted-by":"crossref","first-page":"566","DOI":"10.1016\/j.tips.2006.09.002","volume":"27","author":"Thiry","year":"2006","journal-title":"Trends Pharmacol. Sci."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref210","doi-asserted-by":"crossref","first-page":"16233","DOI":"10.1073\/pnas.0908301106","volume":"106","author":"Alterio","year":"2009","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"10.1016\/j.bmcl.2010.06.082_bib10","series-title":"Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications","first-page":"73","article-title":"X-ray Crystallography of CA Inhibitors and Its Importance in Drug Design","author":"Alterio","year":"2009"},{"key":"10.1016\/j.bmcl.2010.06.082_bib11","doi-asserted-by":"crossref","first-page":"3174","DOI":"10.1021\/bi702385k","volume":"47","author":"Barrese","year":"2008","journal-title":"Biochemistry"},{"key":"10.1016\/j.bmcl.2010.06.082_sbref240","doi-asserted-by":"crossref","first-page":"3057","DOI":"10.1021\/ja809683v","volume":"131","author":"Maresca","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref250","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1021\/jm901287j","volume":"53","author":"Maresca","year":"2010","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_bib13","doi-asserted-by":"crossref","first-page":"850","DOI":"10.1021\/jm901524f","volume":"53","author":"Temperini","year":"2010","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_bib14","doi-asserted-by":"crossref","first-page":"2822","DOI":"10.1016\/j.bmc.2010.03.026","volume":"18","author":"Innocenti","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref280","doi-asserted-by":"crossref","first-page":"739","DOI":"10.1016\/S0223-5234(98)80042-1","volume":"33","author":"Supuran","year":"1998","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref290","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1016\/0223-5234(96)85163-4","volume":"31","author":"Supuran","year":"1996","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref300","doi-asserted-by":"crossref","first-page":"4542","DOI":"10.1021\/jm000296j","volume":"43","author":"Scozzafava","year":"2000","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref310","doi-asserted-by":"crossref","first-page":"2397","DOI":"10.1016\/S0968-0896(99)00190-X","volume":"7","author":"Borras","year":"1999","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_bib15e","doi-asserted-by":"crossref","first-page":"2187","DOI":"10.1021\/jm021123s","volume":"46","author":"Ilies","year":"2003","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_bib16a","doi-asserted-by":"crossref","first-page":"2717","DOI":"10.1016\/j.bmc.2004.03.008","volume":"12","author":"Ilies","year":"2004","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref320","doi-asserted-by":"crossref","first-page":"1466","DOI":"10.1021\/jm0108202","volume":"45","author":"Scozzafava","year":"2002","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref330","doi-asserted-by":"crossref","first-page":"2641","DOI":"10.1021\/jm9900523","volume":"42","author":"Scozzafava","year":"1999","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref340","doi-asserted-by":"crossref","first-page":"1005","DOI":"10.1016\/S0960-894X(03)00091-X","volume":"13","author":"Vullo","year":"2003","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bmcl.2010.06.082_sbref350","doi-asserted-by":"crossref","first-page":"963","DOI":"10.1016\/j.bmcl.2004.12.053","volume":"15","author":"Vullo","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bmcl.2010.06.082_bib19","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1111\/j.1747-0285.2009.00857.x","volume":"74","author":"De Simone","year":"2009","journal-title":"Chem. Biol. Drug Des."},{"key":"10.1016\/j.bmcl.2010.06.082_bib21","doi-asserted-by":"crossref","first-page":"2930","DOI":"10.1021\/bi062066y","volume":"42","author":"Fisher","year":"2007","journal-title":"Biochemistry"},{"key":"10.1016\/j.bmcl.2010.06.082_bib22","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1016\/S0076-6879(97)76066-X","volume":"276","author":"Otwinowski","year":"1997","journal-title":"Methods Enzymol."},{"key":"10.1016\/j.bmcl.2010.06.082_bib23","doi-asserted-by":"crossref","first-page":"1192","DOI":"10.1016\/0022-2836(92)90531-N","volume":"227","author":"Hakansson","year":"1992","journal-title":"J. Mol. Biol."},{"key":"10.1016\/j.bmcl.2010.06.082_bib24","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1107\/S0907444909052925","volume":"66","author":"Adams","year":"2010","journal-title":"Acta Cryst., Sect. D"},{"key":"10.1016\/j.bmcl.2010.06.082_bib25","doi-asserted-by":"crossref","first-page":"472","DOI":"10.1038\/355472a0","volume":"355","author":"Brunger","year":"1992","journal-title":"Nature"},{"key":"10.1016\/j.bmcl.2010.06.082_bib26","doi-asserted-by":"crossref","first-page":"2126","DOI":"10.1107\/S0907444904019158","volume":"60","author":"Emsley","year":"2004","journal-title":"Acta Crystallogr., Sect. D"},{"key":"10.1016\/j.bmcl.2010.06.082_bib27","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1107\/S0021889892009944","volume":"26","author":"Laskowski","year":"1993","journal-title":"J. Appl. Cryst."},{"key":"10.1016\/j.bmcl.2010.06.082_bib28","doi-asserted-by":"crossref","first-page":"7598","DOI":"10.1021\/ja8091938","volume":"131","author":"Maupin","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.bmcl.2010.06.082_bib29","doi-asserted-by":"crossref","first-page":"6204","DOI":"10.1016\/j.bmcl.2006.09.022","volume":"16","author":"Menchise","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bmcl.2010.06.082_bib30","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1093\/nar\/28.1.235","volume":"28","author":"Berman","year":"2000","journal-title":"Nucl. Acids Res."},{"key":"10.1016\/j.bmcl.2010.06.082_bib31","doi-asserted-by":"crossref","first-page":"1270","DOI":"10.1073\/pnas.032673399","volume":"99","author":"Grzybowski","year":"2002","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"10.1016\/j.bmcl.2010.06.082_bib32","doi-asserted-by":"crossref","first-page":"3011","DOI":"10.1021\/ja057257n","volume":"128","author":"Jude","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.bmcl.2010.06.082_bib33","doi-asserted-by":"crossref","first-page":"672","DOI":"10.2174\/138161208783877811","volume":"14","author":"Hilvo","year":"2008","journal-title":"Curr. Pharm. Des."}],"container-title":["Bioorganic & Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X10008565?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X10008565?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T06:15:02Z","timestamp":1760768102000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X10008565"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,8]]},"references-count":56,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2010,8]]}},"alternative-id":["S0960894X10008565"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2010.06.082","relation":{},"ISSN":["0960-894X"],"issn-type":[{"value":"0960-894X","type":"print"}],"subject":[],"published":{"date-parts":[[2010,8]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2010.06.082","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"Copyright \u00a9 2010 Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}]}}