The interaction of multiply charged intercalating heterocycles with DNA
The interaction with DNA of two aromatic nitrogen heterocycles, 1 and 2, which at pH 6 have two positive charges on their ring systems and two cationic side chains, have been determined. A third similar compound, 3, with a single side chain and reduced ring charge, was analyzed as a control. Viscome...
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| Veröffentlicht in: | Biopolymers 1988-09, Vol.27 (9), p.1433-1447 |
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| container_title | Biopolymers |
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| creator | Fairley, Terri Molock, Frank Boykin, David W. Wilson, W. David |
| description | The interaction with DNA of two aromatic nitrogen heterocycles, 1 and 2, which at pH 6 have two positive charges on their ring systems and two cationic side chains, have been determined. A third similar compound, 3, with a single side chain and reduced ring charge, was analyzed as a control. Viscometric titrations with sonicated DNA indicated that all three compounds bind to DNA by intercalation. Spectrophotometric binding studies as a function of ionic strength indicated that both 1 and 2 bind to DNA as tetracations at pH 6. These are the first examples of intercalators with two charges directly on the intercalating ring system. Dissociation kinetics experiments as a function of ionic strength confirmed that 1 and 2 bind to DNA as tetracations. Compound 1 has a G · C base‐pair binding preference, 2 seems to prefer binding to alternating pyrimidine–purine sequences regardless of the composition, and 3 has no significant binding specificity. |
| doi_str_mv | 10.1002/bip.360270909 |
| format | Article |
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Compound 1 has a G · C base‐pair binding preference, 2 seems to prefer binding to alternating pyrimidine–purine sequences regardless of the composition, and 3 has no significant binding specificity.</description><identifier>ISSN: 0006-3525</identifier><identifier>EISSN: 1097-0282</identifier><identifier>DOI: 10.1002/bip.360270909</identifier><identifier>PMID: 3219405</identifier><identifier>CODEN: BIPMAA</identifier><language>eng</language><publisher>Hoboken: Wiley Subscription Services, Inc., A Wiley Company</publisher><subject>Analytical, structural and metabolic biochemistry ; Biological and medical sciences ; DNA - metabolism ; Dna, deoxyribonucleoproteins ; Fundamental and applied biological sciences. 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David</creatorcontrib><title>The interaction of multiply charged intercalating heterocycles with DNA</title><title>Biopolymers</title><addtitle>Biopolymers</addtitle><description>The interaction with DNA of two aromatic nitrogen heterocycles, 1 and 2, which at pH 6 have two positive charges on their ring systems and two cationic side chains, have been determined. A third similar compound, 3, with a single side chain and reduced ring charge, was analyzed as a control. Viscometric titrations with sonicated DNA indicated that all three compounds bind to DNA by intercalation. Spectrophotometric binding studies as a function of ionic strength indicated that both 1 and 2 bind to DNA as tetracations at pH 6. These are the first examples of intercalators with two charges directly on the intercalating ring system. Dissociation kinetics experiments as a function of ionic strength confirmed that 1 and 2 bind to DNA as tetracations. Compound 1 has a G · C base‐pair binding preference, 2 seems to prefer binding to alternating pyrimidine–purine sequences regardless of the composition, and 3 has no significant binding specificity.</description><subject>Analytical, structural and metabolic biochemistry</subject><subject>Biological and medical sciences</subject><subject>DNA - metabolism</subject><subject>Dna, deoxyribonucleoproteins</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Heterocyclic Compounds - metabolism</subject><subject>Intercalating Agents - metabolism</subject><subject>Kinetics</subject><subject>Nucleic acids</subject><subject>Polydeoxyribonucleotides</subject><issn>0006-3525</issn><issn>1097-0282</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFv0zAUhy3ENMrgyBEpB8Qt23u2Y8fHMaCbNA2EOm3iYrnOy2pIk85ONfrfY9So4gQny_p97-fnj7E3CKcIwM-WYXMqFHANBswzNkMwugRe8-dsBgCqFBWvXrCXKf0AkFIgHLNjwdFIqGZsvlhREfqRovNjGPpiaIv1thvDptsVfuXiAzX73LvOjaF_KFaUb4Pf-Y5S8RTGVfHx5vwVO2pdl-j1dJ6w28-fFheX5fWX-dXF-XXppZCmXGpBXjtwxqCTVLfKVEJ43Yqaa8Rlo5XnRkmHhhOilBXmscZXDYFETuKEvd_3buLwuKU02nVInrrO9TRsk9W1kjJ__r8gVqCxRpXBcg_6OKQUqbWbGNYu7iyC_WPYZsP2YDjzb6fi7XJNzYGelOb83ZS7lJ210fU-pAOmtJI11BnTe-wpdLT795v2w9XXvxeYFg5ppF-HSRd_5nKhK3t3M7fV3QK-4_03eyl-A8IIoV8</recordid><startdate>198809</startdate><enddate>198809</enddate><creator>Fairley, Terri</creator><creator>Molock, Frank</creator><creator>Boykin, David W.</creator><creator>Wilson, W. 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David</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4349-b73ec7a0a991a4e8f69533c7f382711bd76c2964a192e114451349dc5de0412e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Analytical, structural and metabolic biochemistry</topic><topic>Biological and medical sciences</topic><topic>DNA - metabolism</topic><topic>Dna, deoxyribonucleoproteins</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Heterocyclic Compounds - metabolism</topic><topic>Intercalating Agents - metabolism</topic><topic>Kinetics</topic><topic>Nucleic acids</topic><topic>Polydeoxyribonucleotides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fairley, Terri</creatorcontrib><creatorcontrib>Molock, Frank</creatorcontrib><creatorcontrib>Boykin, David W.</creatorcontrib><creatorcontrib>Wilson, W. 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David</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The interaction of multiply charged intercalating heterocycles with DNA</atitle><jtitle>Biopolymers</jtitle><addtitle>Biopolymers</addtitle><date>1988-09</date><risdate>1988</risdate><volume>27</volume><issue>9</issue><spage>1433</spage><epage>1447</epage><pages>1433-1447</pages><issn>0006-3525</issn><eissn>1097-0282</eissn><coden>BIPMAA</coden><abstract>The interaction with DNA of two aromatic nitrogen heterocycles, 1 and 2, which at pH 6 have two positive charges on their ring systems and two cationic side chains, have been determined. A third similar compound, 3, with a single side chain and reduced ring charge, was analyzed as a control. Viscometric titrations with sonicated DNA indicated that all three compounds bind to DNA by intercalation. Spectrophotometric binding studies as a function of ionic strength indicated that both 1 and 2 bind to DNA as tetracations at pH 6. These are the first examples of intercalators with two charges directly on the intercalating ring system. Dissociation kinetics experiments as a function of ionic strength confirmed that 1 and 2 bind to DNA as tetracations. Compound 1 has a G · C base‐pair binding preference, 2 seems to prefer binding to alternating pyrimidine–purine sequences regardless of the composition, and 3 has no significant binding specificity.</abstract><cop>Hoboken</cop><pub>Wiley Subscription Services, Inc., A Wiley Company</pub><pmid>3219405</pmid><doi>10.1002/bip.360270909</doi><tpages>15</tpages></addata></record> |
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| ispartof | Biopolymers, 1988-09, Vol.27 (9), p.1433-1447 |
| issn | 0006-3525 1097-0282 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Analytical, structural and metabolic biochemistry Biological and medical sciences DNA - metabolism Dna, deoxyribonucleoproteins Fundamental and applied biological sciences. Psychology Heterocyclic Compounds - metabolism Intercalating Agents - metabolism Kinetics Nucleic acids Polydeoxyribonucleotides |
| title | The interaction of multiply charged intercalating heterocycles with DNA |
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