Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide–isozyme II adduct
Diuretics such as hydrochlorothiazide, hydroflumethiazide, quinethazone, metolazone, chlorthalidone, indapamide, furosemide, and bumetanide containing primary sulfamoyl moieties were reevaluated as inhibitors of 12 human carbonic anhydrases (hCAs, EC 4.2.1.1). These drugs considerably inhibit (low n...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2008-04, Vol.18 (8), p.2567-2573 |
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| creator | Temperini, Claudia Cecchi, Alessandro Scozzafava, Andrea Supuran, Claudiu T. |
| description | Diuretics such as hydrochlorothiazide, hydroflumethiazide, quinethazone, metolazone, chlorthalidone, indapamide, furosemide, and bumetanide containing primary sulfamoyl moieties were reevaluated as inhibitors of 12 human carbonic anhydrases (hCAs, EC 4.2.1.1). These drugs considerably inhibit (low nanomolar range) some CA isozymes involved in critical physiologic processes, among the 16 present in vertebrates, for example, metholazone against CA VII, XII, and XIII, chlorthalidone against CA VB, VII, IX, XII, and XIII, indapamide against CA VII, IX, XII, and XIII, furosemide against CA I, II, and XIV, and bumethanide against CA IX and XII. The X-ray crystal structure of the hCA II–indapamide adduct was also resolved at high resolution. |
| doi_str_mv | 10.1016/j.bmcl.2008.03.051 |
| format | Article |
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Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide–isozyme II adduct</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>Temperini, Claudia ; Cecchi, Alessandro ; Scozzafava, Andrea ; Supuran, Claudiu T.</creator><creatorcontrib>Temperini, Claudia ; Cecchi, Alessandro ; Scozzafava, Andrea ; Supuran, Claudiu T.</creatorcontrib><description>Diuretics such as hydrochlorothiazide, hydroflumethiazide, quinethazone, metolazone, chlorthalidone, indapamide, furosemide, and bumetanide containing primary sulfamoyl moieties were reevaluated as inhibitors of 12 human carbonic anhydrases (hCAs, EC 4.2.1.1). These drugs considerably inhibit (low nanomolar range) some CA isozymes involved in critical physiologic processes, among the 16 present in vertebrates, for example, metholazone against CA VII, XII, and XIII, chlorthalidone against CA VB, VII, IX, XII, and XIII, indapamide against CA VII, IX, XII, and XIII, furosemide against CA I, II, and XIV, and bumethanide against CA IX and XII. The X-ray crystal structure of the hCA II–indapamide adduct was also resolved at high resolution.</description><identifier>ISSN: 0960-894X</identifier><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3405</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmcl.2008.03.051</identifier><identifier>PMID: 18374572</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Animals ; Benzothiadiazine ; Carbonic anhydrase ; Carbonic Anhydrase Inhibitors - chemistry ; Carbonic Anhydrases - chemistry ; Carbonic Anhydrases - metabolism ; Computer Simulation ; Crystallography, X-Ray ; Diuretic ; Furosemide ; Humans ; Indapamide ; Indapamide - chemistry ; Isoenzymes - chemistry ; Isoenzymes - metabolism ; Isozyme ; Mice ; Models, Molecular ; Molecular Structure ; Sulfonamide ; X-ray crystallography</subject><ispartof>Bioorganic & medicinal chemistry, 2008-04, Vol.18 (8), p.2567-2573</ispartof><rights>2008 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-6029e3e1fca455d6796c168a255a2b198d9d9dbc077a28533e6b319ec54754d53</citedby><cites>FETCH-LOGICAL-c385t-6029e3e1fca455d6796c168a255a2b198d9d9dbc077a28533e6b319ec54754d53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X08003247$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18374572$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Temperini, Claudia</creatorcontrib><creatorcontrib>Cecchi, Alessandro</creatorcontrib><creatorcontrib>Scozzafava, Andrea</creatorcontrib><creatorcontrib>Supuran, Claudiu T.</creatorcontrib><title>Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide–isozyme II adduct</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Diuretics such as hydrochlorothiazide, hydroflumethiazide, quinethazone, metolazone, chlorthalidone, indapamide, furosemide, and bumetanide containing primary sulfamoyl moieties were reevaluated as inhibitors of 12 human carbonic anhydrases (hCAs, EC 4.2.1.1). These drugs considerably inhibit (low nanomolar range) some CA isozymes involved in critical physiologic processes, among the 16 present in vertebrates, for example, metholazone against CA VII, XII, and XIII, chlorthalidone against CA VB, VII, IX, XII, and XIII, indapamide against CA VII, IX, XII, and XIII, furosemide against CA I, II, and XIV, and bumethanide against CA IX and XII. The X-ray crystal structure of the hCA II–indapamide adduct was also resolved at high resolution.</description><subject>Animals</subject><subject>Benzothiadiazine</subject><subject>Carbonic anhydrase</subject><subject>Carbonic Anhydrase Inhibitors - chemistry</subject><subject>Carbonic Anhydrases - chemistry</subject><subject>Carbonic Anhydrases - metabolism</subject><subject>Computer Simulation</subject><subject>Crystallography, X-Ray</subject><subject>Diuretic</subject><subject>Furosemide</subject><subject>Humans</subject><subject>Indapamide</subject><subject>Indapamide - chemistry</subject><subject>Isoenzymes - chemistry</subject><subject>Isoenzymes - metabolism</subject><subject>Isozyme</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Sulfonamide</subject><subject>X-ray crystallography</subject><issn>0960-894X</issn><issn>0968-0896</issn><issn>1464-3405</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc2q1DAUx4Mo3vHqC7iQrNy1Js1HW3Ajgx8DF9wo3F04TU6dDG0zJqmXuvIdfBTfyCex4wzoSjmLLM7v_zuQPyFPOSs54_rFoexGO5QVY03JRMkUv0c2XGpZCMnUfbJhrWZF08rbK_IopQNjXDIpH5Ir3ohaqrrakB9biF2YvKUw7RcXISH10953PoeYSrqbMkaw2YeJhn5dOTjC6B2uvKMRB8joqPNzxOxtonc-7ymv6AjjCIOHifoUvi4jpt-B2yLCQm1cUoZhCJ8iHPfr7ZRn51ekD5HmPf515ue37xcB3e0oODfb_Jg86GFI-OTyXpOPb15_2L4rbt6_3W1f3RRWNCoXmlUtCuS9BamU03WrLdcNVEpB1fG2ce06nWV1DVWjhEDdCd6iVbJW0ilxTZ6fvccYPs-Yshl9sjgMMGGYk9Eta6VuxH9B3gqheH0yVmfQxpBSxN4cox8hLoYzc-rUHMypU3Pq1DBh1k7X0LOLfe5GdH8ilxJX4OUZwPUzvniMJlmPk0XnI9psXPD_8v8C0WC3bA</recordid><startdate>20080415</startdate><enddate>20080415</enddate><creator>Temperini, Claudia</creator><creator>Cecchi, Alessandro</creator><creator>Scozzafava, Andrea</creator><creator>Supuran, Claudiu T.</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20080415</creationdate><title>Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide–isozyme II adduct</title><author>Temperini, Claudia ; Cecchi, Alessandro ; Scozzafava, Andrea ; Supuran, Claudiu T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-6029e3e1fca455d6796c168a255a2b198d9d9dbc077a28533e6b319ec54754d53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Animals</topic><topic>Benzothiadiazine</topic><topic>Carbonic anhydrase</topic><topic>Carbonic Anhydrase Inhibitors - chemistry</topic><topic>Carbonic Anhydrases - chemistry</topic><topic>Carbonic Anhydrases - metabolism</topic><topic>Computer Simulation</topic><topic>Crystallography, X-Ray</topic><topic>Diuretic</topic><topic>Furosemide</topic><topic>Humans</topic><topic>Indapamide</topic><topic>Indapamide - chemistry</topic><topic>Isoenzymes - chemistry</topic><topic>Isoenzymes - metabolism</topic><topic>Isozyme</topic><topic>Mice</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Sulfonamide</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Temperini, Claudia</creatorcontrib><creatorcontrib>Cecchi, Alessandro</creatorcontrib><creatorcontrib>Scozzafava, Andrea</creatorcontrib><creatorcontrib>Supuran, Claudiu T.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Temperini, Claudia</au><au>Cecchi, Alessandro</au><au>Scozzafava, Andrea</au><au>Supuran, Claudiu T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide–isozyme II adduct</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2008-04-15</date><risdate>2008</risdate><volume>18</volume><issue>8</issue><spage>2567</spage><epage>2573</epage><pages>2567-2573</pages><issn>0960-894X</issn><issn>0968-0896</issn><eissn>1464-3405</eissn><eissn>1464-3391</eissn><abstract>Diuretics such as hydrochlorothiazide, hydroflumethiazide, quinethazone, metolazone, chlorthalidone, indapamide, furosemide, and bumetanide containing primary sulfamoyl moieties were reevaluated as inhibitors of 12 human carbonic anhydrases (hCAs, EC 4.2.1.1). These drugs considerably inhibit (low nanomolar range) some CA isozymes involved in critical physiologic processes, among the 16 present in vertebrates, for example, metholazone against CA VII, XII, and XIII, chlorthalidone against CA VB, VII, IX, XII, and XIII, indapamide against CA VII, IX, XII, and XIII, furosemide against CA I, II, and XIV, and bumethanide against CA IX and XII. The X-ray crystal structure of the hCA II–indapamide adduct was also resolved at high resolution.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>18374572</pmid><doi>10.1016/j.bmcl.2008.03.051</doi><tpages>7</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2008-04, Vol.18 (8), p.2567-2573 |
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| subjects | Animals Benzothiadiazine Carbonic anhydrase Carbonic Anhydrase Inhibitors - chemistry Carbonic Anhydrases - chemistry Carbonic Anhydrases - metabolism Computer Simulation Crystallography, X-Ray Diuretic Furosemide Humans Indapamide Indapamide - chemistry Isoenzymes - chemistry Isoenzymes - metabolism Isozyme Mice Models, Molecular Molecular Structure Sulfonamide X-ray crystallography |
| title | Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide–isozyme II adduct |
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