Immunochemical Evidence Supporting 2-Pentylpyrrole Formation on Proteins Exposed to 4-Hydroxy-2-nonenal
Previous model studies suggested the formation of lysine-based 2-pentylpyrroles as novel late adduction products formed upon exposure of proteins to the lipid peroxidation product 4-hydroxy-2-nonenal (HNE). Two 2-pentylpyrrole immunogens were prepared, one by treating keyhole limpet hemocyanin (KLH)...
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| Veröffentlicht in: | Chemical research in toxicology 1996-10, Vol.9 (7), p.1194-1201 |
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| container_title | Chemical research in toxicology |
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| creator | Sayre, Lawrence M Sha, Wei Xu, Guozhang Kaur, Kamaljit Nadkarni, Durgesh Subbanagounder, Ganesamoorthy Salomon, Robert G |
| description | Previous model studies suggested the formation of lysine-based 2-pentylpyrroles as novel late adduction products formed upon exposure of proteins to the lipid peroxidation product 4-hydroxy-2-nonenal (HNE). Two 2-pentylpyrrole immunogens were prepared, one by treating keyhole limpet hemocyanin (KLH) directly with 4-oxononanal and the other by preformation of 6-(2-pentylpyrrol-1-yl)hexanoic acid from 6-aminocaproic acid and 4-oxononanal, followed by carbodiimide coupling to KLH. Pyrrole content and lysine modification in KLH were assayed independently. Following immunization of rabbits, antibody titer increased and plateaued over a 4 month period. The structural specificity of the IgG fractions of the antisera was evaluated through comprehensive competitive ELISA studies. These antibodies were used to verify the time-dependent appearance of the 2-pentylpyrrole epitope in protein exposed to HNE. Potential advantages of antibodies recognizing “advanced lipid peroxidation end products” over those recognizing "early" HNE adduction products are discussed. |
| doi_str_mv | 10.1021/tx960094j |
| format | Article |
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Res. Toxicol</addtitle><description>Previous model studies suggested the formation of lysine-based 2-pentylpyrroles as novel late adduction products formed upon exposure of proteins to the lipid peroxidation product 4-hydroxy-2-nonenal (HNE). Two 2-pentylpyrrole immunogens were prepared, one by treating keyhole limpet hemocyanin (KLH) directly with 4-oxononanal and the other by preformation of 6-(2-pentylpyrrol-1-yl)hexanoic acid from 6-aminocaproic acid and 4-oxononanal, followed by carbodiimide coupling to KLH. Pyrrole content and lysine modification in KLH were assayed independently. Following immunization of rabbits, antibody titer increased and plateaued over a 4 month period. The structural specificity of the IgG fractions of the antisera was evaluated through comprehensive competitive ELISA studies. These antibodies were used to verify the time-dependent appearance of the 2-pentylpyrrole epitope in protein exposed to HNE. Potential advantages of antibodies recognizing “advanced lipid peroxidation end products” over those recognizing "early" HNE adduction products are discussed.</description><subject>Aldehydes - chemistry</subject><subject>Aldehydes - immunology</subject><subject>Aldehydes - toxicity</subject><subject>Animals</subject><subject>Antibodies - chemistry</subject><subject>Cross-Linking Reagents</subject><subject>Epitopes - chemistry</subject><subject>Immunochemistry</subject><subject>Proteins - chemistry</subject><subject>Proteins - drug effects</subject><subject>Proteins - immunology</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Rabbits</subject><issn>0893-228X</issn><issn>1520-5010</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFq3DAQhkVoSDdpDnmAgi8t9KBEkmVLPpawyQYWuiQLzU3I8jj11pZcSS7rt6_CLnsqDDOH_2Nm-BC6oeSWEkbv4r4qCan47gwtaMEILgglH9CCyCrHjMnXj-gyhB0hNOHiAl3IijAmygV6exqGyTrzC4bO6D5b_u0asAayl2kcnY-dfcsY3oCNcz_O3rsesgfnBx07Z7NUG-8idDZky_3oAjRZdBnHq7nxbj9jhq2zYHX_CZ23ug9wfZxXaPuw3N6v8PrH49P99zXWnBcR53VdGcNo6gVnraYi_VxxqAtBDVDRiLYtoBKtlMI0eckTZGRLTV1qWfP8Cn09rB29-zNBiGrogoG-1xbcFBQtZMnyXCbw2wE03oXgoVWj7wbtZ0WJeneqTk4T-_m4dKoHaE7kUWLK8SHvQoT9Kdb-typFLgq13byoZ_5ztc43a_WY-C8HXpugdm7yyU_4z91_-RWOlg</recordid><startdate>19961001</startdate><enddate>19961001</enddate><creator>Sayre, Lawrence M</creator><creator>Sha, Wei</creator><creator>Xu, Guozhang</creator><creator>Kaur, Kamaljit</creator><creator>Nadkarni, Durgesh</creator><creator>Subbanagounder, Ganesamoorthy</creator><creator>Salomon, Robert G</creator><general>American Chemical Society</general><scope>BSCLL</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>7U7</scope><scope>C1K</scope></search><sort><creationdate>19961001</creationdate><title>Immunochemical Evidence Supporting 2-Pentylpyrrole Formation on Proteins Exposed to 4-Hydroxy-2-nonenal</title><author>Sayre, Lawrence M ; Sha, Wei ; Xu, Guozhang ; Kaur, Kamaljit ; Nadkarni, Durgesh ; Subbanagounder, Ganesamoorthy ; Salomon, Robert G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-3bb9cc21b9c542fa1700194eb571ce17d7ff5e97f887cd36442fc8f1cb6a8b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Aldehydes - chemistry</topic><topic>Aldehydes - immunology</topic><topic>Aldehydes - toxicity</topic><topic>Animals</topic><topic>Antibodies - chemistry</topic><topic>Cross-Linking Reagents</topic><topic>Epitopes - chemistry</topic><topic>Immunochemistry</topic><topic>Proteins - chemistry</topic><topic>Proteins - drug effects</topic><topic>Proteins - immunology</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Rabbits</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sayre, Lawrence M</creatorcontrib><creatorcontrib>Sha, Wei</creatorcontrib><creatorcontrib>Xu, Guozhang</creatorcontrib><creatorcontrib>Kaur, Kamaljit</creatorcontrib><creatorcontrib>Nadkarni, Durgesh</creatorcontrib><creatorcontrib>Subbanagounder, Ganesamoorthy</creatorcontrib><creatorcontrib>Salomon, Robert G</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Chemical research in toxicology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sayre, Lawrence M</au><au>Sha, Wei</au><au>Xu, Guozhang</au><au>Kaur, Kamaljit</au><au>Nadkarni, Durgesh</au><au>Subbanagounder, Ganesamoorthy</au><au>Salomon, Robert G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Immunochemical Evidence Supporting 2-Pentylpyrrole Formation on Proteins Exposed to 4-Hydroxy-2-nonenal</atitle><jtitle>Chemical research in toxicology</jtitle><addtitle>Chem. Res. Toxicol</addtitle><date>1996-10-01</date><risdate>1996</risdate><volume>9</volume><issue>7</issue><spage>1194</spage><epage>1201</epage><pages>1194-1201</pages><issn>0893-228X</issn><eissn>1520-5010</eissn><abstract>Previous model studies suggested the formation of lysine-based 2-pentylpyrroles as novel late adduction products formed upon exposure of proteins to the lipid peroxidation product 4-hydroxy-2-nonenal (HNE). Two 2-pentylpyrrole immunogens were prepared, one by treating keyhole limpet hemocyanin (KLH) directly with 4-oxononanal and the other by preformation of 6-(2-pentylpyrrol-1-yl)hexanoic acid from 6-aminocaproic acid and 4-oxononanal, followed by carbodiimide coupling to KLH. Pyrrole content and lysine modification in KLH were assayed independently. Following immunization of rabbits, antibody titer increased and plateaued over a 4 month period. The structural specificity of the IgG fractions of the antisera was evaluated through comprehensive competitive ELISA studies. These antibodies were used to verify the time-dependent appearance of the 2-pentylpyrrole epitope in protein exposed to HNE. Potential advantages of antibodies recognizing “advanced lipid peroxidation end products” over those recognizing "early" HNE adduction products are discussed.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>8902276</pmid><doi>10.1021/tx960094j</doi><tpages>8</tpages></addata></record> |
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| subjects | Aldehydes - chemistry Aldehydes - immunology Aldehydes - toxicity Animals Antibodies - chemistry Cross-Linking Reagents Epitopes - chemistry Immunochemistry Proteins - chemistry Proteins - drug effects Proteins - immunology Pyrroles - chemical synthesis Pyrroles - chemistry Rabbits |
| title | Immunochemical Evidence Supporting 2-Pentylpyrrole Formation on Proteins Exposed to 4-Hydroxy-2-nonenal |
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