BENA435, a new cell-permeant photoactivated green fluorescent DNA probe
N′-(2,8-Dimethoxy-12-methyl-dibenzo [c,h] [1,5] naphthyridin-6-yl)-N,N-dimethyl-propane-1,3-diamine (BENA435) is a new cell-membrane permeant DNA dye with absorption/emission maxima in complex with DNA at 435 and 484 nm. This new reagent is unrelated to known DNA dyes, and shows a distinct preferenc...
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| Veröffentlicht in: | Nucleic acids research 2006-01, Vol.34 (5), p.e43-e43 |
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| container_title | Nucleic acids research |
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| creator | Erve, Alexandra Saoudi, Yasmina Thirot, Sylvie Guetta-Landras, Corinne Florent, Jean-Claude Nguyen, Chi-Hung Grierson, David S. Popov, Andrei V. |
| description | N′-(2,8-Dimethoxy-12-methyl-dibenzo [c,h] [1,5] naphthyridin-6-yl)-N,N-dimethyl-propane-1,3-diamine (BENA435) is a new cell-membrane permeant DNA dye with absorption/emission maxima in complex with DNA at 435 and 484 nm. This new reagent is unrelated to known DNA dyes, and shows a distinct preference to bind double-stranded DNA over RNA. Hydrodynamic studies suggest that BENA435 intercalates between the opposite DNA strands. BENA435 fluoresces much stronger when bound to dA/dT rather than dG/dC homopolymers. We evaluated 14 related dibenzonaphthyridine derivatives and found BENA435 to be superior in its in vivo DNA-binding properties. Molecular modelling was used to develop a model of BENA435 intercalation between base pairs of a DNA helix. BENA435 fluorescence in the nuclei of cells increases upon illumination, suggesting photoactivation. BENA435 represents thus the first known cell-permeant photoactivated DNA-binding dye. |
| doi_str_mv | 10.1093/nar/gkl011 |
| format | Article |
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This new reagent is unrelated to known DNA dyes, and shows a distinct preference to bind double-stranded DNA over RNA. Hydrodynamic studies suggest that BENA435 intercalates between the opposite DNA strands. BENA435 fluoresces much stronger when bound to dA/dT rather than dG/dC homopolymers. We evaluated 14 related dibenzonaphthyridine derivatives and found BENA435 to be superior in its in vivo DNA-binding properties. Molecular modelling was used to develop a model of BENA435 intercalation between base pairs of a DNA helix. BENA435 fluorescence in the nuclei of cells increases upon illumination, suggesting photoactivation. BENA435 represents thus the first known cell-permeant photoactivated DNA-binding dye.</description><identifier>ISSN: 0305-1048</identifier><identifier>EISSN: 1362-4962</identifier><identifier>DOI: 10.1093/nar/gkl011</identifier><identifier>PMID: 16547198</identifier><identifier>CODEN: NARHAD</identifier><language>eng</language><publisher>England: Oxford University Press</publisher><subject>Animals ; Biochemistry, Molecular Biology ; Cell Membrane Permeability ; Cell Nucleus ; Cell Nucleus - chemistry ; Cells, Cultured ; Color ; DNA ; DNA - analysis ; DNA - chemistry ; DNA Probes ; DNA Probes - chemistry ; DNA Probes - metabolism ; Fluorescent Dyes ; Fluorescent Dyes - chemistry ; Fluorescent Dyes - metabolism ; Humans ; Interphase ; Life Sciences ; Light ; Methods Online ; Mice ; Models, Molecular ; Naphthyridines ; Naphthyridines - chemistry ; Naphthyridines - metabolism ; Poly dA-dT ; Poly dA-dT - analysis ; Polydeoxyribonucleotides ; Polydeoxyribonucleotides - analysis ; RNA ; RNA - analysis ; Structure-Activity Relationship ; Xenopus</subject><ispartof>Nucleic acids research, 2006-01, Vol.34 (5), p.e43-e43</ispartof><rights>Copyright Oxford University Press(England) 2006</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><rights>The Author 2006. 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Acids Res</addtitle><description>N′-(2,8-Dimethoxy-12-methyl-dibenzo [c,h] [1,5] naphthyridin-6-yl)-N,N-dimethyl-propane-1,3-diamine (BENA435) is a new cell-membrane permeant DNA dye with absorption/emission maxima in complex with DNA at 435 and 484 nm. This new reagent is unrelated to known DNA dyes, and shows a distinct preference to bind double-stranded DNA over RNA. Hydrodynamic studies suggest that BENA435 intercalates between the opposite DNA strands. BENA435 fluoresces much stronger when bound to dA/dT rather than dG/dC homopolymers. We evaluated 14 related dibenzonaphthyridine derivatives and found BENA435 to be superior in its in vivo DNA-binding properties. Molecular modelling was used to develop a model of BENA435 intercalation between base pairs of a DNA helix. BENA435 fluorescence in the nuclei of cells increases upon illumination, suggesting photoactivation. BENA435 represents thus the first known cell-permeant photoactivated DNA-binding dye.</description><subject>Animals</subject><subject>Biochemistry, Molecular Biology</subject><subject>Cell Membrane Permeability</subject><subject>Cell Nucleus</subject><subject>Cell Nucleus - chemistry</subject><subject>Cells, Cultured</subject><subject>Color</subject><subject>DNA</subject><subject>DNA - analysis</subject><subject>DNA - chemistry</subject><subject>DNA Probes</subject><subject>DNA Probes - chemistry</subject><subject>DNA Probes - metabolism</subject><subject>Fluorescent Dyes</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Fluorescent Dyes - metabolism</subject><subject>Humans</subject><subject>Interphase</subject><subject>Life Sciences</subject><subject>Light</subject><subject>Methods Online</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Naphthyridines</subject><subject>Naphthyridines - chemistry</subject><subject>Naphthyridines - metabolism</subject><subject>Poly dA-dT</subject><subject>Poly dA-dT - analysis</subject><subject>Polydeoxyribonucleotides</subject><subject>Polydeoxyribonucleotides - analysis</subject><subject>RNA</subject><subject>RNA - analysis</subject><subject>Structure-Activity Relationship</subject><subject>Xenopus</subject><issn>0305-1048</issn><issn>1362-4962</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkc1u1DAUhS0EokNhwwOgiAUL1NB7_ZtsKg2ldEBDqSqQqm4sJ3Fm0mbiYCcDvD0eZVSg3nhxPx_fcw4hLxHeIeTsuDP-eHXXAuIjMkMmacpzSR-TGTAQKQLPDsizEG4BkKPgT8kBSsEV5tmMnL8_u5hzJo4Sk3T2Z1Latk176zfWdEPSr93gTDk0WzPYKll5a7ukbkfnbShtBD5czJPeu8I-J09q0wb7Yn8fku8fz76dLtLl1_NPp_NlWnKVDakQtuCIgmaMUwqUYQ4KeM1kQfMCykqwysSjpOKqqupCZKy2xggqmEFU7JCcTLr9WGxstVvCm1b3vtkY_1s70-j_J12z1iu31cghlyqLAkeTwPrBs8V8qZsuROsagGUAIt9ixN_s__Pux2jDoDdN2IVkOuvGoKVSMsYHEXz9ALx1o-9iFpoCSIh-dmpvJ6j0LgRv6_sNEPSuSx271FOXEX71r9W_6L68CKQT0ITB_rqfG38X12JK6MX1jb65_MIvr66u9Wf2BxdkqGo</recordid><startdate>20060101</startdate><enddate>20060101</enddate><creator>Erve, Alexandra</creator><creator>Saoudi, Yasmina</creator><creator>Thirot, Sylvie</creator><creator>Guetta-Landras, Corinne</creator><creator>Florent, Jean-Claude</creator><creator>Nguyen, Chi-Hung</creator><creator>Grierson, David S.</creator><creator>Popov, Andrei V.</creator><general>Oxford University Press</general><general>Oxford Publishing Limited (England)</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>7QL</scope><scope>7QO</scope><scope>7QP</scope><scope>7QR</scope><scope>7SS</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><scope>5PM</scope></search><sort><creationdate>20060101</creationdate><title>BENA435, a new cell-permeant photoactivated green fluorescent DNA probe</title><author>Erve, Alexandra ; 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Acids Res</addtitle><date>2006-01-01</date><risdate>2006</risdate><volume>34</volume><issue>5</issue><spage>e43</spage><epage>e43</epage><pages>e43-e43</pages><issn>0305-1048</issn><eissn>1362-4962</eissn><coden>NARHAD</coden><abstract>N′-(2,8-Dimethoxy-12-methyl-dibenzo [c,h] [1,5] naphthyridin-6-yl)-N,N-dimethyl-propane-1,3-diamine (BENA435) is a new cell-membrane permeant DNA dye with absorption/emission maxima in complex with DNA at 435 and 484 nm. This new reagent is unrelated to known DNA dyes, and shows a distinct preference to bind double-stranded DNA over RNA. Hydrodynamic studies suggest that BENA435 intercalates between the opposite DNA strands. BENA435 fluoresces much stronger when bound to dA/dT rather than dG/dC homopolymers. We evaluated 14 related dibenzonaphthyridine derivatives and found BENA435 to be superior in its in vivo DNA-binding properties. Molecular modelling was used to develop a model of BENA435 intercalation between base pairs of a DNA helix. BENA435 fluorescence in the nuclei of cells increases upon illumination, suggesting photoactivation. BENA435 represents thus the first known cell-permeant photoactivated DNA-binding dye.</abstract><cop>England</cop><pub>Oxford University Press</pub><pmid>16547198</pmid><doi>10.1093/nar/gkl011</doi><oa>free_for_read</oa></addata></record> |
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| subjects | Animals Biochemistry, Molecular Biology Cell Membrane Permeability Cell Nucleus Cell Nucleus - chemistry Cells, Cultured Color DNA DNA - analysis DNA - chemistry DNA Probes DNA Probes - chemistry DNA Probes - metabolism Fluorescent Dyes Fluorescent Dyes - chemistry Fluorescent Dyes - metabolism Humans Interphase Life Sciences Light Methods Online Mice Models, Molecular Naphthyridines Naphthyridines - chemistry Naphthyridines - metabolism Poly dA-dT Poly dA-dT - analysis Polydeoxyribonucleotides Polydeoxyribonucleotides - analysis RNA RNA - analysis Structure-Activity Relationship Xenopus |
| title | BENA435, a new cell-permeant photoactivated green fluorescent DNA probe |
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