{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T14:33:11Z","timestamp":1791383591300,"version":"4.3.3"},"reference-count":32,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2006,9,25]],"date-time":"2006-09-25T00:00:00Z","timestamp":1159142400000},"content-version":"vor","delay-in-days":55,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chem Biol Drug Des"],"published-print":{"date-parts":[[2006,8]]},"abstract":"<jats:p>Enzyme inhibition assays often require deviations from physiological conditions. For carbonic anhydrases, procedures involving native CO<jats:sub>2<\/jats:sub> and non\u2010native substrates have been used. We compared a native and a non\u2010native substrate in the context of inhibition of human carbonic anhydrases I and II by examining various sulfamate and sulfamide compounds in two kinetic assays: hydration of CO<jats:sub>2<\/jats:sub> and hydrolysis of 4\u2010nitrophenylacetate. For carbonic anhydrase II, the two assays consistently generated similar <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values, with the relative difference between the assays never exceeding 2.5\u2010fold. However, for carbonic anhydrase I there was more variability between the two assays, with <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values for three compounds differing by more than 2.5\u2010fold, up to eightfold. In the CO<jats:sub>2<\/jats:sub> hydration assay, some sulfamates and sulfamides exhibited mixed kinetics or partial inhibition. Our results indicate that <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> or <jats:italic>K<\/jats:italic><jats:sub>d<\/jats:sub> values from carbonic anhydrase assays involving non\u2010native substrates should be confirmed by assays that use CO<jats:sub>2<\/jats:sub> (or HCO<jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/CBDD_423_mu1.gif\" xlink:title=\"inline image\"\/>), to establish pharmacological relevance. From structure\u2013activity comparisons, the sulfamate is more effective than the sulfamide in inhibiting carbonic anhydrase I and II, but the sulfamate does not confer selectivity. In contrast, the sulfonamide confers selectivity for carbonic anhydrase I (10\u2010 to 30\u2010fold). Selectivity for carbonic anhydrase II occurred with the substituted fructose moiety, especially the <jats:sc>d<\/jats:sc>\u2010enantiomer (&gt;100\u2010fold).<\/jats:p>","DOI":"10.1111\/j.1747-0285.2006.00423.x","type":"journal-article","created":{"date-parts":[[2006,9,25]],"date-time":"2006-09-25T15:37:01Z","timestamp":1159198621000},"page":"113-119","source":"Crossref","is-referenced-by-count":15,"title":["Examination of Two Independent Kinetic Assays for Determining the Inhibition of Carbonic Anhydrases I and II: Structure\u2013Activity Comparison of Sulfamates and Sulfamides"],"prefix":"10.1111","volume":"68","author":[{"given":"Richard P","family":"Shank","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David F","family":"McComsey","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Virginia L","family":"Smith\u2010Swintosky","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bruce E","family":"Maryanoff","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,9,25]]},"reference":[{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01167a012"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1152\/physrev.1967.47.4.595"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-0348-8446-4_21"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-0348-8446-4_3"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-0348-8446-4_31"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/med.10025"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.14.5.667"},{"key":"e_1_2_5_9_2","first-page":"283","volume-title":"Carbonic Anhydrase: Its Inhibitors and Activators","author":"Parkkila S.","year":"2004"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756360410001689540"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-0348-8446-4_15"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00388a023"},{"issue":"1","key":"e_1_2_5_13_2","doi-asserted-by":"crossref","first-page":"S35","DOI":"10.1111\/j.1528-1157.2000.tb06047.x","article-title":"Topiramate as an inhibitor of carbonic anhydrase isozymes","volume":"41","author":"Dodgson S.J.","year":"2000","journal-title":"Epilepsia"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.eplepsyres.2005.01.001"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm970790w"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(03)00029-5"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm021124k"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.02.091"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(03)00028-3"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.04.058"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm040124c"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm058279n"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1967.tb19504.x"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-0348-8446-4_22"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1471-4159.1976.tb01559.x"},{"key":"e_1_2_5_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00855a005"},{"key":"e_1_2_5_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(73)90196-2"},{"key":"e_1_2_5_28_2","first-page":"161","article-title":"A study of the release of carbon dioxide gas from carbonated beverages","volume":"46","author":"Talbot A.","year":"1998","journal-title":"Microscope"},{"key":"e_1_2_5_29_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1748-1716.1981.tb06918.x"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4899-0750-9_4"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.97.26.14212"},{"key":"e_1_2_5_32_2","doi-asserted-by":"crossref","first-page":"26233","DOI":"10.1016\/S0021-9258(19)74305-1","article-title":"A new class of carbonic anhydrase inhibitor","volume":"268","author":"Maren T.H.","year":"1993","journal-title":"J Biol Chem"},{"key":"e_1_2_5_33_2","first-page":"416","article-title":"Inhibitory effect of zonisamide on human carbonic anhydrase in vitro","volume":"43","author":"Masuda Y.","year":"1993","journal-title":"Arzneim-Forsch"}],"container-title":["Chemical Biology &amp; 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