Synthesis of 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid: Photoaffinity labeling of human red blood cell ghosts with A 5-nitro-2-(3-phenylpropylamino)-benzoic acid analog
A photoaffinity analog of the potent epithelial chloride channel blocker 5-nitro-2-(3-phenylpropylamino)-benzoic acid has been synthesized and characterized. In the dark, this reagent, 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid, and the parent compound reversibly inhibited chloride eff...
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| Veröffentlicht in: | Biochemical and biophysical research communications 1991-04, Vol.176 (1), p.459-465 |
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| creator | Branchini, Bruce R. Murtiashaw, Martha H. Egan, Laura A. |
| description | A photoaffinity analog of the potent epithelial chloride channel blocker 5-nitro-2-(3-phenylpropylamino)-benzoic acid has been synthesized and characterized. In the dark, this reagent, 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid, and the parent compound reversibly inhibited chloride efflux in human red blood cell ghosts. Irradiation of ghost membranes with 350 μM arylazide analog reduced the rate of chloride efflux to 33% of the control value. The photoinactivation process was not reversed by exhaustive washing of ghost membranes. Covalent incorporation of the photoaffinity reagent was supported by difference ultraviolet spectroscopy, which indicated the attachment of the substituted 2-amino-5-nitrobenzoic acid chromophore to ghost membranes. The novel photolabeling agent described here should be a useful structural probe for chloride channels in erythrocyte membranes and epithelial cells. |
| doi_str_mv | 10.1016/0006-291X(91)90946-5 |
| format | Article |
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In the dark, this reagent, 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid, and the parent compound reversibly inhibited chloride efflux in human red blood cell ghosts. Irradiation of ghost membranes with 350 μM arylazide analog reduced the rate of chloride efflux to 33% of the control value. The photoinactivation process was not reversed by exhaustive washing of ghost membranes. Covalent incorporation of the photoaffinity reagent was supported by difference ultraviolet spectroscopy, which indicated the attachment of the substituted 2-amino-5-nitrobenzoic acid chromophore to ghost membranes. The novel photolabeling agent described here should be a useful structural probe for chloride channels in erythrocyte membranes and epithelial cells.</description><identifier>ISSN: 0006-291X</identifier><identifier>EISSN: 1090-2104</identifier><identifier>DOI: 10.1016/0006-291X(91)90946-5</identifier><identifier>PMID: 2018534</identifier><identifier>CODEN: BBRCA9</identifier><language>eng</language><publisher>San Diego, CA: Elsevier Inc</publisher><subject>Affinity Labels - chemical synthesis ; Azides - chemical synthesis ; Azides - pharmacology ; Biological and medical sciences ; Chlorides - blood ; Darkness ; Diverse techniques ; Erythrocyte Membrane - drug effects ; Erythrocyte Membrane - metabolism ; Erythrocyte Membrane - radiation effects ; Fundamental and applied biological sciences. 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In the dark, this reagent, 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid, and the parent compound reversibly inhibited chloride efflux in human red blood cell ghosts. Irradiation of ghost membranes with 350 μM arylazide analog reduced the rate of chloride efflux to 33% of the control value. The photoinactivation process was not reversed by exhaustive washing of ghost membranes. Covalent incorporation of the photoaffinity reagent was supported by difference ultraviolet spectroscopy, which indicated the attachment of the substituted 2-amino-5-nitrobenzoic acid chromophore to ghost membranes. The novel photolabeling agent described here should be a useful structural probe for chloride channels in erythrocyte membranes and epithelial cells.</description><subject>Affinity Labels - chemical synthesis</subject><subject>Azides - chemical synthesis</subject><subject>Azides - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Chlorides - blood</subject><subject>Darkness</subject><subject>Diverse techniques</subject><subject>Erythrocyte Membrane - drug effects</subject><subject>Erythrocyte Membrane - metabolism</subject><subject>Erythrocyte Membrane - radiation effects</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Humans</subject><subject>Indicators and Reagents</subject><subject>Kinetics</subject><subject>Light</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Molecular and cellular biology</subject><subject>Molecular Structure</subject><subject>Nitrobenzoates - chemical synthesis</subject><subject>Nitrobenzoates - pharmacology</subject><subject>Spectrophotometry</subject><issn>0006-291X</issn><issn>1090-2104</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kd2KFDEQhYMo67j6Bgq5UWYuopVOd6azF8Ky-AeLCioIIqE6P9ORnmTs9Ci9L-br2e0M63rjVV3UV-dU1SHkIYenHLh8BgCSFYp_Xiq-UqBKyapbZMFBASs4lLfJ4hq5S-7l_A2A81KqE3JSAK8rUS7Irw9jHFqXQ6bJ04rFMPSJFezLWybYsmR4FWzatS6O3Yrt-rQbO9yGmL6yxsWrFAxFE-wZfd-mIaH3YRIYaYeN60LczJrtfouR9s7SpkvJUuO6jm7alIdMf4ahpec3bJeCHcxuWK3-saIYsUub--SOxy67B8d6Sj69fPHx4jW7fPfqzcX5JTOiXg8MaxBS-qaoQRaNMr4BL2XjrKkKbOoKizV4j2UNSlj0RolijVVphQBlS1WKU_LkoDst9H3v8qC3Ic8nYHRpn3UNVcFrVU9geQBNn3Lunde7PmyxHzUHPeel5zD0HIZWXP_JS1fT2KOj_r7ZOns9dAxo6j8-9jEb7HyP0YT8V1tJUSvgE_f8wLnpGT-C63U2wUXjbOidGbRN4f-L_AZxI7OL</recordid><startdate>19910415</startdate><enddate>19910415</enddate><creator>Branchini, Bruce R.</creator><creator>Murtiashaw, Martha H.</creator><creator>Egan, Laura A.</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>IQODW</scope><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>19910415</creationdate><title>Synthesis of 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid: Photoaffinity labeling of human red blood cell ghosts with A 5-nitro-2-(3-phenylpropylamino)-benzoic acid analog</title><author>Branchini, Bruce R. ; Murtiashaw, Martha H. ; Egan, Laura A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c387t-a80366fb28062b9cfb0f66bedc52ab85a270ffa48093dafc9327a54d3309d4943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>Affinity Labels - chemical synthesis</topic><topic>Azides - chemical synthesis</topic><topic>Azides - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Chlorides - blood</topic><topic>Darkness</topic><topic>Diverse techniques</topic><topic>Erythrocyte Membrane - drug effects</topic><topic>Erythrocyte Membrane - metabolism</topic><topic>Erythrocyte Membrane - radiation effects</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Humans</topic><topic>Indicators and Reagents</topic><topic>Kinetics</topic><topic>Light</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Molecular and cellular biology</topic><topic>Molecular Structure</topic><topic>Nitrobenzoates - chemical synthesis</topic><topic>Nitrobenzoates - pharmacology</topic><topic>Spectrophotometry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Branchini, Bruce R.</creatorcontrib><creatorcontrib>Murtiashaw, Martha H.</creatorcontrib><creatorcontrib>Egan, Laura A.</creatorcontrib><collection>Pascal-Francis</collection><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 and biophysical research communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Branchini, Bruce R.</au><au>Murtiashaw, Martha H.</au><au>Egan, Laura A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid: Photoaffinity labeling of human red blood cell ghosts with A 5-nitro-2-(3-phenylpropylamino)-benzoic acid analog</atitle><jtitle>Biochemical and biophysical research communications</jtitle><addtitle>Biochem Biophys Res Commun</addtitle><date>1991-04-15</date><risdate>1991</risdate><volume>176</volume><issue>1</issue><spage>459</spage><epage>465</epage><pages>459-465</pages><issn>0006-291X</issn><eissn>1090-2104</eissn><coden>BBRCA9</coden><abstract>A photoaffinity analog of the potent epithelial chloride channel blocker 5-nitro-2-(3-phenylpropylamino)-benzoic acid has been synthesized and characterized. In the dark, this reagent, 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid, and the parent compound reversibly inhibited chloride efflux in human red blood cell ghosts. Irradiation of ghost membranes with 350 μM arylazide analog reduced the rate of chloride efflux to 33% of the control value. The photoinactivation process was not reversed by exhaustive washing of ghost membranes. Covalent incorporation of the photoaffinity reagent was supported by difference ultraviolet spectroscopy, which indicated the attachment of the substituted 2-amino-5-nitrobenzoic acid chromophore to ghost membranes. The novel photolabeling agent described here should be a useful structural probe for chloride channels in erythrocyte membranes and epithelial cells.</abstract><cop>San Diego, CA</cop><pub>Elsevier Inc</pub><pmid>2018534</pmid><doi>10.1016/0006-291X(91)90946-5</doi><tpages>7</tpages></addata></record> |
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| subjects | Affinity Labels - chemical synthesis Azides - chemical synthesis Azides - pharmacology Biological and medical sciences Chlorides - blood Darkness Diverse techniques Erythrocyte Membrane - drug effects Erythrocyte Membrane - metabolism Erythrocyte Membrane - radiation effects Fundamental and applied biological sciences. Psychology Humans Indicators and Reagents Kinetics Light Magnetic Resonance Spectroscopy Mass Spectrometry Molecular and cellular biology Molecular Structure Nitrobenzoates - chemical synthesis Nitrobenzoates - pharmacology Spectrophotometry |
| title | Synthesis of 5-nitro-2-[N-3-(4-azidophenyl)-propylamino]-benzoic acid: Photoaffinity labeling of human red blood cell ghosts with A 5-nitro-2-(3-phenylpropylamino)-benzoic acid analog |
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