Synthesis and Biological Property of α-Human Atrial Natriuretic Peptide Analogs with a Constrained or Stereochemically Modified Cyclic Moiety
Conformationally restricted analogs of α-human atrial natriuretic peptide (α-hANP) containing L- or D-penicillamine, or D-cysteine in place of cysteine residues at positions 7 and 23 were synthesized by the liquid phase procedure. Their biological properties in the assays of receptor binding and cyc...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1990/07/25, Vol.38(7), pp.1920-1926 |
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| container_issue | 7 |
| container_start_page | 1920 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 38 |
| creator | MINAMITAKE, Yoshiharu FURUYA, Mayumi KITAJIMA, Yasuo TAKEHISA, Maki TANAKA, Shoji |
| description | Conformationally restricted analogs of α-human atrial natriuretic peptide (α-hANP) containing L- or D-penicillamine, or D-cysteine in place of cysteine residues at positions 7 and 23 were synthesized by the liquid phase procedure. Their biological properties in the assays of receptor binding and cyclic guanosine monophosphate (cGMP) accumulation employing rat vascular smooth muscle cells (VSMC), vasorelaxant activity using rat isolated aorta were evaluated. We found that the constrained and/or stereochemically altered ring moiety generally did not influence the receptor binding activity, however, cGMP accumulation and vasorelaxant activities were quite sensitive to conformational perturbation. Furthermore, a lack of correlation between cGMP acccumulation activity and vasorelaxant activity was observed. Dissociation between these activities was typical in the case of [DPen7, 23]-α-hANP(7-28), which showed quite weak vasorelaxant activity in spite of its full cGMP accumulation and receptor binding potencies. This result suggests that cGMP accumulation alone is not sufficient to promote AMP-induced vasorelaxation, and that the other second messenger (s) may mediate this activity. |
| doi_str_mv | 10.1248/cpb.38.1920 |
| format | Article |
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Their biological properties in the assays of receptor binding and cyclic guanosine monophosphate (cGMP) accumulation employing rat vascular smooth muscle cells (VSMC), vasorelaxant activity using rat isolated aorta were evaluated. We found that the constrained and/or stereochemically altered ring moiety generally did not influence the receptor binding activity, however, cGMP accumulation and vasorelaxant activities were quite sensitive to conformational perturbation. Furthermore, a lack of correlation between cGMP acccumulation activity and vasorelaxant activity was observed. Dissociation between these activities was typical in the case of [DPen7, 23]-α-hANP(7-28), which showed quite weak vasorelaxant activity in spite of its full cGMP accumulation and receptor binding potencies. This result suggests that cGMP accumulation alone is not sufficient to promote AMP-induced vasorelaxation, and that the other second messenger (s) may mediate this activity.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.38.1920</identifier><identifier>PMID: 2148506</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Amino Acid Sequence ; Animals ; Aorta, Thoracic - drug effects ; Atrial Natriuretic Factor - chemical synthesis ; Atrial Natriuretic Factor - pharmacology ; biological activity ; cyclic GMP ; Humans ; In Vitro Techniques ; liquid phase synthesis ; Male ; man ; Molecular Sequence Data ; Muscle Contraction - drug effects ; Muscle, Smooth, Vascular - drug effects ; Rats ; receptor binding ; Stereoisomerism ; vascular smooth muscle cells (VSMC) ; vasorelaxation ; α-human atrial natriuretic peptide analog</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1990/07/25, Vol.38(7), pp.1920-1926</ispartof><rights>The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c440t-e31a044f469b7d826db08e6bc7e91b16f37f4dcb6d5aa91e62ae4e78a3f5a0033</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2148506$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>MINAMITAKE, Yoshiharu</creatorcontrib><creatorcontrib>FURUYA, Mayumi</creatorcontrib><creatorcontrib>KITAJIMA, Yasuo</creatorcontrib><creatorcontrib>TAKEHISA, Maki</creatorcontrib><creatorcontrib>TANAKA, Shoji</creatorcontrib><title>Synthesis and Biological Property of α-Human Atrial Natriuretic Peptide Analogs with a Constrained or Stereochemically Modified Cyclic Moiety</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Conformationally restricted analogs of α-human atrial natriuretic peptide (α-hANP) containing L- or D-penicillamine, or D-cysteine in place of cysteine residues at positions 7 and 23 were synthesized by the liquid phase procedure. Their biological properties in the assays of receptor binding and cyclic guanosine monophosphate (cGMP) accumulation employing rat vascular smooth muscle cells (VSMC), vasorelaxant activity using rat isolated aorta were evaluated. We found that the constrained and/or stereochemically altered ring moiety generally did not influence the receptor binding activity, however, cGMP accumulation and vasorelaxant activities were quite sensitive to conformational perturbation. Furthermore, a lack of correlation between cGMP acccumulation activity and vasorelaxant activity was observed. Dissociation between these activities was typical in the case of [DPen7, 23]-α-hANP(7-28), which showed quite weak vasorelaxant activity in spite of its full cGMP accumulation and receptor binding potencies. This result suggests that cGMP accumulation alone is not sufficient to promote AMP-induced vasorelaxation, and that the other second messenger (s) may mediate this activity.</description><subject>Amino Acid Sequence</subject><subject>Animals</subject><subject>Aorta, Thoracic - drug effects</subject><subject>Atrial Natriuretic Factor - chemical synthesis</subject><subject>Atrial Natriuretic Factor - pharmacology</subject><subject>biological activity</subject><subject>cyclic GMP</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>liquid phase synthesis</subject><subject>Male</subject><subject>man</subject><subject>Molecular Sequence Data</subject><subject>Muscle Contraction - drug effects</subject><subject>Muscle, Smooth, Vascular - drug effects</subject><subject>Rats</subject><subject>receptor binding</subject><subject>Stereoisomerism</subject><subject>vascular smooth muscle cells (VSMC)</subject><subject>vasorelaxation</subject><subject>α-human atrial natriuretic peptide analog</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkctu1DAUhi0EKkNhxRrJKzYog29JnOUwXIrUQqXCOjpxTjqukjjYjlBeou_SF-GZcDSjsmRzzuL7z7c4PyGvOdtyofR7MzVbqbe8EuwJ2XCpyiwXQj4lG8ZYlQlZyOfkRQh3jImclfKMnAmudM6KDbm_WcZ4wGADhbGlH6zr3a010NNr7yb0caGuo38esot5gJHuoreJfYO0Z4_RGnqNU7Qt0t0I6TTQ3zYeKNC9G0P0YEdsqfP0JqJHZw44rPJ-oVeutZ1NcL-YPmmunMW4vCTPOugDvjrtc_Lz86cf-4vs8vuXr_vdZWaUYjFDyYEp1amiaspWi6JtmMaiMSVWvOFFJ8tOtaYp2hyg4lgIQIWlBtnlwJiU5-Tt0Tt592vGEOvBBoN9DyO6OdSaCZaXOv9vkOeaMa7LFHx3DBrvQvDY1ZO3A_il5qxea6pTTbXU9VpTSr85aedmwPYxe-ol8Y9Hfhci3OIjB59e3uPq4lWuV195HKv2Hz6Ar3GUfwEsUqj1</recordid><startdate>19900701</startdate><enddate>19900701</enddate><creator>MINAMITAKE, Yoshiharu</creator><creator>FURUYA, Mayumi</creator><creator>KITAJIMA, Yasuo</creator><creator>TAKEHISA, Maki</creator><creator>TANAKA, Shoji</creator><general>The Pharmaceutical Society of Japan</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>7QL</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M81</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>19900701</creationdate><title>Synthesis and Biological Property of α-Human Atrial Natriuretic Peptide Analogs with a Constrained or Stereochemically Modified Cyclic Moiety</title><author>MINAMITAKE, Yoshiharu ; FURUYA, Mayumi ; KITAJIMA, Yasuo ; TAKEHISA, Maki ; TANAKA, Shoji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c440t-e31a044f469b7d826db08e6bc7e91b16f37f4dcb6d5aa91e62ae4e78a3f5a0033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>Amino Acid Sequence</topic><topic>Animals</topic><topic>Aorta, Thoracic - drug effects</topic><topic>Atrial Natriuretic Factor - chemical synthesis</topic><topic>Atrial Natriuretic Factor - pharmacology</topic><topic>biological activity</topic><topic>cyclic GMP</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>liquid phase synthesis</topic><topic>Male</topic><topic>man</topic><topic>Molecular Sequence Data</topic><topic>Muscle Contraction - drug effects</topic><topic>Muscle, Smooth, Vascular - drug effects</topic><topic>Rats</topic><topic>receptor binding</topic><topic>Stereoisomerism</topic><topic>vascular smooth muscle cells (VSMC)</topic><topic>vasorelaxation</topic><topic>α-human atrial natriuretic peptide analog</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>MINAMITAKE, Yoshiharu</creatorcontrib><creatorcontrib>FURUYA, Mayumi</creatorcontrib><creatorcontrib>KITAJIMA, Yasuo</creatorcontrib><creatorcontrib>TAKEHISA, Maki</creatorcontrib><creatorcontrib>TANAKA, Shoji</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 3</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>MINAMITAKE, Yoshiharu</au><au>FURUYA, Mayumi</au><au>KITAJIMA, Yasuo</au><au>TAKEHISA, Maki</au><au>TANAKA, Shoji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Property of α-Human Atrial Natriuretic Peptide Analogs with a Constrained or Stereochemically Modified Cyclic Moiety</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1990-07-01</date><risdate>1990</risdate><volume>38</volume><issue>7</issue><spage>1920</spage><epage>1926</epage><pages>1920-1926</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Conformationally restricted analogs of α-human atrial natriuretic peptide (α-hANP) containing L- or D-penicillamine, or D-cysteine in place of cysteine residues at positions 7 and 23 were synthesized by the liquid phase procedure. Their biological properties in the assays of receptor binding and cyclic guanosine monophosphate (cGMP) accumulation employing rat vascular smooth muscle cells (VSMC), vasorelaxant activity using rat isolated aorta were evaluated. We found that the constrained and/or stereochemically altered ring moiety generally did not influence the receptor binding activity, however, cGMP accumulation and vasorelaxant activities were quite sensitive to conformational perturbation. Furthermore, a lack of correlation between cGMP acccumulation activity and vasorelaxant activity was observed. Dissociation between these activities was typical in the case of [DPen7, 23]-α-hANP(7-28), which showed quite weak vasorelaxant activity in spite of its full cGMP accumulation and receptor binding potencies. This result suggests that cGMP accumulation alone is not sufficient to promote AMP-induced vasorelaxation, and that the other second messenger (s) may mediate this activity.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>2148506</pmid><doi>10.1248/cpb.38.1920</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Amino Acid Sequence Animals Aorta, Thoracic - drug effects Atrial Natriuretic Factor - chemical synthesis Atrial Natriuretic Factor - pharmacology biological activity cyclic GMP Humans In Vitro Techniques liquid phase synthesis Male man Molecular Sequence Data Muscle Contraction - drug effects Muscle, Smooth, Vascular - drug effects Rats receptor binding Stereoisomerism vascular smooth muscle cells (VSMC) vasorelaxation α-human atrial natriuretic peptide analog |
| title | Synthesis and Biological Property of α-Human Atrial Natriuretic Peptide Analogs with a Constrained or Stereochemically Modified Cyclic Moiety |
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