Localization of Carbonic Anhydrase in Living Osteoclasts with Bodipy 558/568-modified Acetazolamide, a Thiadiazole Carbonic Anhydrase Inhibitor
We describe the synthesis of Bodipy 558/568-modified acetazolamide, a fluorescent inhibitor of carbonic anhydrase and its use to localize the enzyme in living cells. The modified acetazolamide, with its specific sulfonamide group intact, labeled cells at concentrations as low as 10−9 M, with a minim...
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| Veröffentlicht in: | The journal of histochemistry and cytochemistry 1999-04, Vol.47 (4), p.545-550 |
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| container_title | The journal of histochemistry and cytochemistry |
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| creator | Brubaker, Kristen D Mao, Fei Gay, Carol V |
| description | We describe the synthesis of Bodipy 558/568-modified acetazolamide, a fluorescent inhibitor of carbonic anhydrase and its use to localize the enzyme in living cells. The modified acetazolamide, with its specific sulfonamide group intact, labeled cells at concentrations as low as 10−9 M, with a minimal loading time of 5 min. The staining was decreased by 57.4% by preincubating cells with unaltered acetazolamide (1:100) or with trifluoromethane sulfonamide, 6-ethoxyzolamide, and 5-(3-hydroxybenzoyl)-thiophene-2-sulfonamide. The efficacy of the inhibitor was unchanged by the fluorescent label, as determined by an acridine orange assay that detects acidification of osteoclasts, the cell model used in this study. This compound should prove to be useful for studying carbonic anhydrase in many organisms because of the high degree of conservation of the active site of this enzyme. |
| doi_str_mv | 10.1177/002215549904700413 |
| format | Article |
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The modified acetazolamide, with its specific sulfonamide group intact, labeled cells at concentrations as low as 10−9 M, with a minimal loading time of 5 min. The staining was decreased by 57.4% by preincubating cells with unaltered acetazolamide (1:100) or with trifluoromethane sulfonamide, 6-ethoxyzolamide, and 5-(3-hydroxybenzoyl)-thiophene-2-sulfonamide. The efficacy of the inhibitor was unchanged by the fluorescent label, as determined by an acridine orange assay that detects acidification of osteoclasts, the cell model used in this study. This compound should prove to be useful for studying carbonic anhydrase in many organisms because of the high degree of conservation of the active site of this enzyme.</description><identifier>ISSN: 0022-1554</identifier><identifier>EISSN: 1551-5044</identifier><identifier>DOI: 10.1177/002215549904700413</identifier><identifier>PMID: 10082756</identifier><language>eng</language><publisher>Los Angeles, CA: Histochemical Soc</publisher><subject>Acetazolamide - metabolism ; Animals ; Binding, Competitive ; Boron Compounds - metabolism ; Carbonic Anhydrase Inhibitors - metabolism ; Carbonic Anhydrase Inhibitors - pharmacology ; Carbonic Anhydrases - metabolism ; Chickens ; Dose-Response Relationship, Drug ; Fluorescent Dyes - metabolism ; Male ; Osteoclasts - drug effects ; Osteoclasts - enzymology</subject><ispartof>The journal of histochemistry and cytochemistry, 1999-04, Vol.47 (4), p.545-550</ispartof><rights>1999 Authors</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c369t-63fd9ee3a1b901875b13af7938c511718bc184342907626b8648c64f93e671ac3</citedby><cites>FETCH-LOGICAL-c369t-63fd9ee3a1b901875b13af7938c511718bc184342907626b8648c64f93e671ac3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://journals.sagepub.com/doi/pdf/10.1177/002215549904700413$$EPDF$$P50$$Gsage$$H</linktopdf><linktohtml>$$Uhttps://journals.sagepub.com/doi/10.1177/002215549904700413$$EHTML$$P50$$Gsage$$H</linktohtml><link.rule.ids>315,781,785,21824,27929,27930,43626,43627</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10082756$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Brubaker, Kristen D</creatorcontrib><creatorcontrib>Mao, Fei</creatorcontrib><creatorcontrib>Gay, Carol V</creatorcontrib><title>Localization of Carbonic Anhydrase in Living Osteoclasts with Bodipy 558/568-modified Acetazolamide, a Thiadiazole Carbonic Anhydrase Inhibitor</title><title>The journal of histochemistry and cytochemistry</title><addtitle>J Histochem Cytochem</addtitle><description>We describe the synthesis of Bodipy 558/568-modified acetazolamide, a fluorescent inhibitor of carbonic anhydrase and its use to localize the enzyme in living cells. The modified acetazolamide, with its specific sulfonamide group intact, labeled cells at concentrations as low as 10−9 M, with a minimal loading time of 5 min. The staining was decreased by 57.4% by preincubating cells with unaltered acetazolamide (1:100) or with trifluoromethane sulfonamide, 6-ethoxyzolamide, and 5-(3-hydroxybenzoyl)-thiophene-2-sulfonamide. The efficacy of the inhibitor was unchanged by the fluorescent label, as determined by an acridine orange assay that detects acidification of osteoclasts, the cell model used in this study. This compound should prove to be useful for studying carbonic anhydrase in many organisms because of the high degree of conservation of the active site of this enzyme.</description><subject>Acetazolamide - metabolism</subject><subject>Animals</subject><subject>Binding, Competitive</subject><subject>Boron Compounds - metabolism</subject><subject>Carbonic Anhydrase Inhibitors - metabolism</subject><subject>Carbonic Anhydrase Inhibitors - pharmacology</subject><subject>Carbonic Anhydrases - metabolism</subject><subject>Chickens</subject><subject>Dose-Response Relationship, Drug</subject><subject>Fluorescent Dyes - metabolism</subject><subject>Male</subject><subject>Osteoclasts - drug effects</subject><subject>Osteoclasts - enzymology</subject><issn>0022-1554</issn><issn>1551-5044</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc-O0zAQxi0EYkvhBTggX-C0oXb8_1gqFlaqtJflbDmO08wqiYudbtR9CV6ZVNkDEojTaEa_7xvNNwi9p-QzpUptCClLKgQ3hnBFCKfsBVrNA1oIwvlLtLoAxYW4Qm9yfiCEci70a3RFCdGlEnKFfu2jdx08uRHigGODdy5VcQCPt0N7rpPLAcOA9_AIwwHf5TFE37k8ZjzB2OIvsYbjGQuhN0Lqop_bBkKNtz6M7il2roc6XGOH71twNVxG4V8rbocWKhhjeoteNa7L4d1zXaMfN1_vd9-L_d232912X3gmzVhI1tQmBOZoZQjVSlSUuUYZpr2Ys6G68lRzxktDlCxlpSXXXvLGsCAVdZ6t0afF95jiz1PIo-0h-9B1bgjxlK00kik2G65RuYA-xZxTaOwxQe_S2VJiL2-wf79hFn14dj9Vfaj_kCy5z8BmAbI7BPsQT2mYr_2_5cdF0cKhnSAFm3vXdfMCaqdp4spyK7hgvwGi1Jyg</recordid><startdate>19990401</startdate><enddate>19990401</enddate><creator>Brubaker, Kristen D</creator><creator>Mao, Fei</creator><creator>Gay, Carol V</creator><general>Histochemical Soc</general><general>SAGE Publications</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>7X8</scope></search><sort><creationdate>19990401</creationdate><title>Localization of Carbonic Anhydrase in Living Osteoclasts with Bodipy 558/568-modified Acetazolamide, a Thiadiazole Carbonic Anhydrase Inhibitor</title><author>Brubaker, Kristen D ; Mao, Fei ; Gay, Carol V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c369t-63fd9ee3a1b901875b13af7938c511718bc184342907626b8648c64f93e671ac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Acetazolamide - metabolism</topic><topic>Animals</topic><topic>Binding, Competitive</topic><topic>Boron Compounds - metabolism</topic><topic>Carbonic Anhydrase Inhibitors - metabolism</topic><topic>Carbonic Anhydrase Inhibitors - pharmacology</topic><topic>Carbonic Anhydrases - metabolism</topic><topic>Chickens</topic><topic>Dose-Response Relationship, Drug</topic><topic>Fluorescent Dyes - metabolism</topic><topic>Male</topic><topic>Osteoclasts - drug effects</topic><topic>Osteoclasts - enzymology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Brubaker, Kristen D</creatorcontrib><creatorcontrib>Mao, Fei</creatorcontrib><creatorcontrib>Gay, Carol V</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>The journal of histochemistry and cytochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Brubaker, Kristen D</au><au>Mao, Fei</au><au>Gay, Carol V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Localization of Carbonic Anhydrase in Living Osteoclasts with Bodipy 558/568-modified Acetazolamide, a Thiadiazole Carbonic Anhydrase Inhibitor</atitle><jtitle>The journal of histochemistry and cytochemistry</jtitle><addtitle>J Histochem Cytochem</addtitle><date>1999-04-01</date><risdate>1999</risdate><volume>47</volume><issue>4</issue><spage>545</spage><epage>550</epage><pages>545-550</pages><issn>0022-1554</issn><eissn>1551-5044</eissn><abstract>We describe the synthesis of Bodipy 558/568-modified acetazolamide, a fluorescent inhibitor of carbonic anhydrase and its use to localize the enzyme in living cells. The modified acetazolamide, with its specific sulfonamide group intact, labeled cells at concentrations as low as 10−9 M, with a minimal loading time of 5 min. The staining was decreased by 57.4% by preincubating cells with unaltered acetazolamide (1:100) or with trifluoromethane sulfonamide, 6-ethoxyzolamide, and 5-(3-hydroxybenzoyl)-thiophene-2-sulfonamide. The efficacy of the inhibitor was unchanged by the fluorescent label, as determined by an acridine orange assay that detects acidification of osteoclasts, the cell model used in this study. This compound should prove to be useful for studying carbonic anhydrase in many organisms because of the high degree of conservation of the active site of this enzyme.</abstract><cop>Los Angeles, CA</cop><pub>Histochemical Soc</pub><pmid>10082756</pmid><doi>10.1177/002215549904700413</doi><tpages>6</tpages></addata></record> |
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| ispartof | The journal of histochemistry and cytochemistry, 1999-04, Vol.47 (4), p.545-550 |
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| subjects | Acetazolamide - metabolism Animals Binding, Competitive Boron Compounds - metabolism Carbonic Anhydrase Inhibitors - metabolism Carbonic Anhydrase Inhibitors - pharmacology Carbonic Anhydrases - metabolism Chickens Dose-Response Relationship, Drug Fluorescent Dyes - metabolism Male Osteoclasts - drug effects Osteoclasts - enzymology |
| title | Localization of Carbonic Anhydrase in Living Osteoclasts with Bodipy 558/568-modified Acetazolamide, a Thiadiazole Carbonic Anhydrase Inhibitor |
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