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Nanosecond fluorescence studies of noncovalent interaction of monomeric and dimeric intercalators with DNA
The noncovalent interaction of 2-aminodipyrido[1,2-a:3',2'-d]imidazole (Glu-P-2) and its derivatives, which are potent mutagens isolated from L-glutamic acid pyrolysate, with calf thymus DNA was studied by steady-state and nanosecond fluorescence spectroscopies. The fluorescence of these c...
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Published in: | Biochemistry (Easton) 1985-11, Vol.24 (23), p.6401-6405 |
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container_title | Biochemistry (Easton) |
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creator | Itoh, Michiya Kurokawa, Hiroko Usui, Mayumi Ohno, Makiko Shimoda, Emiyo Hashimoto, Yuichi Shudo, Koichi |
description | The noncovalent interaction of 2-aminodipyrido[1,2-a:3',2'-d]imidazole (Glu-P-2) and its derivatives, which are potent mutagens isolated from L-glutamic acid pyrolysate, with calf thymus DNA was studied by steady-state and nanosecond fluorescence spectroscopies. The fluorescence of these compounds exhibits static quenching by noncovalent interaction with DNA. Fluorescence lifetimes of the free and intercalated states of these compounds were determined to be 9-10 and 0.5-1 ns, respectively. The bisintercalative effect of the dimeric analogue of Glu-P-2, bis(Glu-P-2)spermine (2GP-SP), to DNA was also investigated. This 2GP-SP, which has two Glu-P-2 moieties at each end of spermine, indicates a strong intramolecular interaction exhibiting remarkable quenching of fluorescence spectrum and lifetime (tau = 3.5 ns) in the absence of DNA. In the presence of DNA, however, the 3.5-ns lifetime component of fluorescence disappeared, and a two-exponential decay of fluorescence (t = approximately 10 and 1.5 ns) was observed at a DNA concentration of more than approximately 0.001 mM P, while the solution containing a very dilute DNA concentration (less than or equal to 0.001 mM P) exhibits a three-component decay of fluorescence (1.5, 3.5, and approximately 10 ns). The potent bis intercalation of two moieties in 2GP-SP with an identical DNA molecule was suggested by the DNA-concentration dependence of these fluorescence lifetimes and their intensity. |
doi_str_mv | 10.1021/bi00344a013 |
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The fluorescence of these compounds exhibits static quenching by noncovalent interaction with DNA. Fluorescence lifetimes of the free and intercalated states of these compounds were determined to be 9-10 and 0.5-1 ns, respectively. The bisintercalative effect of the dimeric analogue of Glu-P-2, bis(Glu-P-2)spermine (2GP-SP), to DNA was also investigated. This 2GP-SP, which has two Glu-P-2 moieties at each end of spermine, indicates a strong intramolecular interaction exhibiting remarkable quenching of fluorescence spectrum and lifetime (tau = 3.5 ns) in the absence of DNA. In the presence of DNA, however, the 3.5-ns lifetime component of fluorescence disappeared, and a two-exponential decay of fluorescence (t = approximately 10 and 1.5 ns) was observed at a DNA concentration of more than approximately 0.001 mM P, while the solution containing a very dilute DNA concentration (less than or equal to 0.001 mM P) exhibits a three-component decay of fluorescence (1.5, 3.5, and approximately 10 ns). The potent bis intercalation of two moieties in 2GP-SP with an identical DNA molecule was suggested by the DNA-concentration dependence of these fluorescence lifetimes and their intensity.</description><identifier>ISSN: 0006-2960</identifier><identifier>EISSN: 1520-4995</identifier><identifier>DOI: 10.1021/bi00344a013</identifier><identifier>PMID: 4084530</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Biological and medical sciences ; Carcinogens - pharmacology ; Cattle ; DNA - metabolism ; Fundamental and applied biological sciences. Psychology ; Imidazoles - pharmacology ; Interactions. Associations ; Intercalating Agents - pharmacology ; Intermolecular phenomena ; Kinetics ; Molecular biophysics ; Spectrometry, Fluorescence - methods ; Structure-Activity Relationship ; Thymus Gland</subject><ispartof>Biochemistry (Easton), 1985-11, Vol.24 (23), p.6401-6405</ispartof><rights>1986 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a383t-b6082474be60463b32ed5fc9d2f767078a7edf3dc537da1a90ae054268c465683</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bi00344a013$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bi00344a013$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,27064,27924,27925,56766,56816</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8793152$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/4084530$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Itoh, Michiya</creatorcontrib><creatorcontrib>Kurokawa, Hiroko</creatorcontrib><creatorcontrib>Usui, Mayumi</creatorcontrib><creatorcontrib>Ohno, Makiko</creatorcontrib><creatorcontrib>Shimoda, Emiyo</creatorcontrib><creatorcontrib>Hashimoto, Yuichi</creatorcontrib><creatorcontrib>Shudo, Koichi</creatorcontrib><title>Nanosecond fluorescence studies of noncovalent interaction of monomeric and dimeric intercalators with DNA</title><title>Biochemistry (Easton)</title><addtitle>Biochemistry</addtitle><description>The noncovalent interaction of 2-aminodipyrido[1,2-a:3',2'-d]imidazole (Glu-P-2) and its derivatives, which are potent mutagens isolated from L-glutamic acid pyrolysate, with calf thymus DNA was studied by steady-state and nanosecond fluorescence spectroscopies. The fluorescence of these compounds exhibits static quenching by noncovalent interaction with DNA. Fluorescence lifetimes of the free and intercalated states of these compounds were determined to be 9-10 and 0.5-1 ns, respectively. The bisintercalative effect of the dimeric analogue of Glu-P-2, bis(Glu-P-2)spermine (2GP-SP), to DNA was also investigated. This 2GP-SP, which has two Glu-P-2 moieties at each end of spermine, indicates a strong intramolecular interaction exhibiting remarkable quenching of fluorescence spectrum and lifetime (tau = 3.5 ns) in the absence of DNA. In the presence of DNA, however, the 3.5-ns lifetime component of fluorescence disappeared, and a two-exponential decay of fluorescence (t = approximately 10 and 1.5 ns) was observed at a DNA concentration of more than approximately 0.001 mM P, while the solution containing a very dilute DNA concentration (less than or equal to 0.001 mM P) exhibits a three-component decay of fluorescence (1.5, 3.5, and approximately 10 ns). The potent bis intercalation of two moieties in 2GP-SP with an identical DNA molecule was suggested by the DNA-concentration dependence of these fluorescence lifetimes and their intensity.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Carcinogens - pharmacology</subject><subject>Cattle</subject><subject>DNA - metabolism</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Imidazoles - pharmacology</subject><subject>Interactions. Associations</subject><subject>Intercalating Agents - pharmacology</subject><subject>Intermolecular phenomena</subject><subject>Kinetics</subject><subject>Molecular biophysics</subject><subject>Spectrometry, Fluorescence - methods</subject><subject>Structure-Activity Relationship</subject><subject>Thymus Gland</subject><issn>0006-2960</issn><issn>1520-4995</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1985</creationdate><recordtype>article</recordtype><recordid>eNptkE2P0zAQhi0EKqVw4oyUAxIHlGUSfyXHUmBZabUgbTlbE9sRLqld2Q7s_vtNN1XFYU8e6330auYh5G0FFxXU1afOAVDGECr6jCwrXkPJ2pY_J0sAEGXdCnhJXqW0m74MJFuQBYOGcQpLsrtBH5LVwZuiH8YQbdLWa1ukPBpnUxH6wgevw18crM-F89lG1NkFf4z2wYe9jU4XOBUYN8-PkMYBc4ip-Ofy7-LLzfo1edHjkOyb07siv7593W6-l9c_Lq826-sSaUNz2QloaiZZZwUwQTtaW8N73Zq6l0KCbFBa01OjOZUGK2wBLXBWi0YzwUVDV-Tj3KtjSCnaXh2i22O8VxWoozD1n7CJfjfTh7HbW3NmT4am_P0pxzSd1Ef02qUz1siWTsYnrJwxl7K9O8cY_yghqeRq-_NWbfmmrprPt-pY-2HmUSe1C2P0k5InF3wAW5OPHA</recordid><startdate>19851101</startdate><enddate>19851101</enddate><creator>Itoh, Michiya</creator><creator>Kurokawa, Hiroko</creator><creator>Usui, Mayumi</creator><creator>Ohno, Makiko</creator><creator>Shimoda, Emiyo</creator><creator>Hashimoto, Yuichi</creator><creator>Shudo, Koichi</creator><general>American Chemical Society</general><scope>BSCLL</scope><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></search><sort><creationdate>19851101</creationdate><title>Nanosecond fluorescence studies of noncovalent interaction of monomeric and dimeric intercalators with DNA</title><author>Itoh, Michiya ; Kurokawa, Hiroko ; Usui, Mayumi ; Ohno, Makiko ; Shimoda, Emiyo ; Hashimoto, Yuichi ; Shudo, Koichi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a383t-b6082474be60463b32ed5fc9d2f767078a7edf3dc537da1a90ae054268c465683</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1985</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Carcinogens - pharmacology</topic><topic>Cattle</topic><topic>DNA - metabolism</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Imidazoles - pharmacology</topic><topic>Interactions. Associations</topic><topic>Intercalating Agents - pharmacology</topic><topic>Intermolecular phenomena</topic><topic>Kinetics</topic><topic>Molecular biophysics</topic><topic>Spectrometry, Fluorescence - methods</topic><topic>Structure-Activity Relationship</topic><topic>Thymus Gland</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Itoh, Michiya</creatorcontrib><creatorcontrib>Kurokawa, Hiroko</creatorcontrib><creatorcontrib>Usui, Mayumi</creatorcontrib><creatorcontrib>Ohno, Makiko</creatorcontrib><creatorcontrib>Shimoda, Emiyo</creatorcontrib><creatorcontrib>Hashimoto, Yuichi</creatorcontrib><creatorcontrib>Shudo, Koichi</creatorcontrib><collection>Istex</collection><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><jtitle>Biochemistry (Easton)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Itoh, Michiya</au><au>Kurokawa, Hiroko</au><au>Usui, Mayumi</au><au>Ohno, Makiko</au><au>Shimoda, Emiyo</au><au>Hashimoto, Yuichi</au><au>Shudo, Koichi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nanosecond fluorescence studies of noncovalent interaction of monomeric and dimeric intercalators with DNA</atitle><jtitle>Biochemistry (Easton)</jtitle><addtitle>Biochemistry</addtitle><date>1985-11-01</date><risdate>1985</risdate><volume>24</volume><issue>23</issue><spage>6401</spage><epage>6405</epage><pages>6401-6405</pages><issn>0006-2960</issn><eissn>1520-4995</eissn><abstract>The noncovalent interaction of 2-aminodipyrido[1,2-a:3',2'-d]imidazole (Glu-P-2) and its derivatives, which are potent mutagens isolated from L-glutamic acid pyrolysate, with calf thymus DNA was studied by steady-state and nanosecond fluorescence spectroscopies. The fluorescence of these compounds exhibits static quenching by noncovalent interaction with DNA. Fluorescence lifetimes of the free and intercalated states of these compounds were determined to be 9-10 and 0.5-1 ns, respectively. The bisintercalative effect of the dimeric analogue of Glu-P-2, bis(Glu-P-2)spermine (2GP-SP), to DNA was also investigated. This 2GP-SP, which has two Glu-P-2 moieties at each end of spermine, indicates a strong intramolecular interaction exhibiting remarkable quenching of fluorescence spectrum and lifetime (tau = 3.5 ns) in the absence of DNA. In the presence of DNA, however, the 3.5-ns lifetime component of fluorescence disappeared, and a two-exponential decay of fluorescence (t = approximately 10 and 1.5 ns) was observed at a DNA concentration of more than approximately 0.001 mM P, while the solution containing a very dilute DNA concentration (less than or equal to 0.001 mM P) exhibits a three-component decay of fluorescence (1.5, 3.5, and approximately 10 ns). The potent bis intercalation of two moieties in 2GP-SP with an identical DNA molecule was suggested by the DNA-concentration dependence of these fluorescence lifetimes and their intensity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>4084530</pmid><doi>10.1021/bi00344a013</doi><tpages>5</tpages></addata></record> |
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subjects | Animals Biological and medical sciences Carcinogens - pharmacology Cattle DNA - metabolism Fundamental and applied biological sciences. Psychology Imidazoles - pharmacology Interactions. Associations Intercalating Agents - pharmacology Intermolecular phenomena Kinetics Molecular biophysics Spectrometry, Fluorescence - methods Structure-Activity Relationship Thymus Gland |
title | Nanosecond fluorescence studies of noncovalent interaction of monomeric and dimeric intercalators with DNA |
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