Inhibition of tyrosine hydroxylase in vitro and in vivo by 3-amino-pyrrolo[3,4c]isoxazole and derivatives
Tyrosine hydroxylase was shown to be inhibited in vitro by a series of 3-amino-pyrrolo[3,4c]isoxazoles. Greatest inhibition was observed with ethyl 3-amino-4H-pyrrolo[3,4c]isoxazole-5(6H) carboxylate and other 5-carboxylates. Acylation of the 3-amine group greatly decreased inhibition. Inhibition by...
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| Veröffentlicht in: | Biochemical pharmacology 1968-09, Vol.17 (9), p.1779-1788 |
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| container_end_page | 1788 |
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| container_issue | 9 |
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| container_title | Biochemical pharmacology |
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| creator | Taylor, R.J. Stubbs, C.S. Ellenbogen, Leon |
| description | Tyrosine hydroxylase was shown to be inhibited
in vitro by a series of 3-amino-pyrrolo[3,4c]isoxazoles. Greatest inhibition was observed with ethyl 3-amino-4H-pyrrolo[3,4c]isoxazole-5(6H) carboxylate and other 5-carboxylates. Acylation of the 3-amine group greatly decreased inhibition. Inhibition by ethyl 3-amino-4H-pyrrolo[3,4c]isoxazole carboxylate was noncompetitive with tyrosine or pteridine cofactor, but could be reversed by addition of iron or copper. 3-Amino-pyrroloisoxazoles were found to form metal complexes with Fe
2+, suggesting that their inhibition may be due to chelation. Tyrosine hydroxylase activity of adrenal extracts was decreased in rats treated with ethyl-3-amino-4H-pyrrolo[3,4c]isoxazole carboxylate and its -acetylated derivative. |
| doi_str_mv | 10.1016/0006-2952(68)90093-2 |
| format | Article |
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2+, suggesting that their inhibition may be due to chelation. Tyrosine hydroxylase activity of adrenal extracts was decreased in rats treated with ethyl-3-amino-4H-pyrrolo[3,4c]isoxazole carboxylate and its -acetylated derivative.</description><identifier>ISSN: 0006-2952</identifier><identifier>EISSN: 1873-2968</identifier><identifier>DOI: 10.1016/0006-2952(68)90093-2</identifier><identifier>PMID: 5688266</identifier><language>eng</language><publisher>England: Elsevier Inc</publisher><subject>Adrenal Medulla - enzymology ; Animals ; Carbon Isotopes ; Copper - pharmacology ; Hydrogen-Ion Concentration ; Iron - pharmacology ; Kinetics ; Male ; Metals - pharmacology ; Mixed Function Oxygenases - antagonists & inhibitors ; Oxazoles - pharmacology ; Rats ; Spectrophotometry ; Tritium ; Tyrosine</subject><ispartof>Biochemical pharmacology, 1968-09, Vol.17 (9), p.1779-1788</ispartof><rights>1968</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c357t-22ff4e6a923e12b667b8e409a4ee586cf92ffa692422a869b9883855e704b2f83</citedby><cites>FETCH-LOGICAL-c357t-22ff4e6a923e12b667b8e409a4ee586cf92ffa692422a869b9883855e704b2f83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0006295268900932$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/5688266$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Taylor, R.J.</creatorcontrib><creatorcontrib>Stubbs, C.S.</creatorcontrib><creatorcontrib>Ellenbogen, Leon</creatorcontrib><title>Inhibition of tyrosine hydroxylase in vitro and in vivo by 3-amino-pyrrolo[3,4c]isoxazole and derivatives</title><title>Biochemical pharmacology</title><addtitle>Biochem Pharmacol</addtitle><description>Tyrosine hydroxylase was shown to be inhibited
in vitro by a series of 3-amino-pyrrolo[3,4c]isoxazoles. Greatest inhibition was observed with ethyl 3-amino-4H-pyrrolo[3,4c]isoxazole-5(6H) carboxylate and other 5-carboxylates. Acylation of the 3-amine group greatly decreased inhibition. Inhibition by ethyl 3-amino-4H-pyrrolo[3,4c]isoxazole carboxylate was noncompetitive with tyrosine or pteridine cofactor, but could be reversed by addition of iron or copper. 3-Amino-pyrroloisoxazoles were found to form metal complexes with Fe
2+, suggesting that their inhibition may be due to chelation. Tyrosine hydroxylase activity of adrenal extracts was decreased in rats treated with ethyl-3-amino-4H-pyrrolo[3,4c]isoxazole carboxylate and its -acetylated derivative.</description><subject>Adrenal Medulla - enzymology</subject><subject>Animals</subject><subject>Carbon Isotopes</subject><subject>Copper - pharmacology</subject><subject>Hydrogen-Ion Concentration</subject><subject>Iron - pharmacology</subject><subject>Kinetics</subject><subject>Male</subject><subject>Metals - pharmacology</subject><subject>Mixed Function Oxygenases - antagonists & inhibitors</subject><subject>Oxazoles - pharmacology</subject><subject>Rats</subject><subject>Spectrophotometry</subject><subject>Tritium</subject><subject>Tyrosine</subject><issn>0006-2952</issn><issn>1873-2968</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1968</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1Lw0AQQBdRaq3-A4WcRMHoZpNsdi-CFD8KBS96Elk2yYSOJNm6m4bGX2_SFI-eZoZ5M8M8Qs4DehvQgN9RSrnPZMyuuLiWlMrQZwdkGoikTyQXh2T6hxyTE-e-hlLwYEImMReCcT4luKhXmGKDpvZM4TWdNQ5r8FZdbs22K7UDD2uvxcYaT9f5WLTGSzsv9HWFtfHXnbWmNB_hTZR9ojNb_WNK2NE5WGx1gy24U3JU6NLB2T7OyPvT49v8xV--Pi_mD0s_C-Ok8Rkrigi4liyEgKWcJ6mAiEodAcSCZ4XsAc0lixjTgstUChGKOIaERikrRDgjl-PetTXfG3CNqtBlUJa6BrNxSsQ0kLGUPRiNYNb_7CwUam2x0rZTAVWDYTX4UoM-xYXaGVasH7vY79-kFeR_Q3ulff9-7EP_ZItglcsQ6gxytJA1Kjf4_4Ff22uLUg</recordid><startdate>196809</startdate><enddate>196809</enddate><creator>Taylor, R.J.</creator><creator>Stubbs, C.S.</creator><creator>Ellenbogen, Leon</creator><general>Elsevier Inc</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>196809</creationdate><title>Inhibition of tyrosine hydroxylase in vitro and in vivo by 3-amino-pyrrolo[3,4c]isoxazole and derivatives</title><author>Taylor, R.J. ; Stubbs, C.S. ; Ellenbogen, Leon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c357t-22ff4e6a923e12b667b8e409a4ee586cf92ffa692422a869b9883855e704b2f83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1968</creationdate><topic>Adrenal Medulla - enzymology</topic><topic>Animals</topic><topic>Carbon Isotopes</topic><topic>Copper - pharmacology</topic><topic>Hydrogen-Ion Concentration</topic><topic>Iron - pharmacology</topic><topic>Kinetics</topic><topic>Male</topic><topic>Metals - pharmacology</topic><topic>Mixed Function Oxygenases - antagonists & inhibitors</topic><topic>Oxazoles - pharmacology</topic><topic>Rats</topic><topic>Spectrophotometry</topic><topic>Tritium</topic><topic>Tyrosine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Taylor, R.J.</creatorcontrib><creatorcontrib>Stubbs, C.S.</creatorcontrib><creatorcontrib>Ellenbogen, Leon</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>Biochemical pharmacology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Taylor, R.J.</au><au>Stubbs, C.S.</au><au>Ellenbogen, Leon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibition of tyrosine hydroxylase in vitro and in vivo by 3-amino-pyrrolo[3,4c]isoxazole and derivatives</atitle><jtitle>Biochemical pharmacology</jtitle><addtitle>Biochem Pharmacol</addtitle><date>1968-09</date><risdate>1968</risdate><volume>17</volume><issue>9</issue><spage>1779</spage><epage>1788</epage><pages>1779-1788</pages><issn>0006-2952</issn><eissn>1873-2968</eissn><abstract>Tyrosine hydroxylase was shown to be inhibited
in vitro by a series of 3-amino-pyrrolo[3,4c]isoxazoles. Greatest inhibition was observed with ethyl 3-amino-4H-pyrrolo[3,4c]isoxazole-5(6H) carboxylate and other 5-carboxylates. Acylation of the 3-amine group greatly decreased inhibition. Inhibition by ethyl 3-amino-4H-pyrrolo[3,4c]isoxazole carboxylate was noncompetitive with tyrosine or pteridine cofactor, but could be reversed by addition of iron or copper. 3-Amino-pyrroloisoxazoles were found to form metal complexes with Fe
2+, suggesting that their inhibition may be due to chelation. Tyrosine hydroxylase activity of adrenal extracts was decreased in rats treated with ethyl-3-amino-4H-pyrrolo[3,4c]isoxazole carboxylate and its -acetylated derivative.</abstract><cop>England</cop><pub>Elsevier Inc</pub><pmid>5688266</pmid><doi>10.1016/0006-2952(68)90093-2</doi><tpages>10</tpages></addata></record> |
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| ispartof | Biochemical pharmacology, 1968-09, Vol.17 (9), p.1779-1788 |
| issn | 0006-2952 1873-2968 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Adrenal Medulla - enzymology Animals Carbon Isotopes Copper - pharmacology Hydrogen-Ion Concentration Iron - pharmacology Kinetics Male Metals - pharmacology Mixed Function Oxygenases - antagonists & inhibitors Oxazoles - pharmacology Rats Spectrophotometry Tritium Tyrosine |
| title | Inhibition of tyrosine hydroxylase in vitro and in vivo by 3-amino-pyrrolo[3,4c]isoxazole and derivatives |
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