Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives
An investigation of the interactions of two novel and several known DBTAA–adenine conjugates with double-stranded DNA and RNA has revealed the DNA/RNA groove as the dominant binding site, which is in contrast to the majority of previously studied DBTAA analogues (DNA/RNA intercalators). Only DBTAA–p...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.10.225 |
| _version_ | 1818874927750578176 |
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| author | Marijana Radić Stojković Marko Škugor Łukasz Dudek Jarosław Grolik Julita Eilmes Ivo Piantanida |
| author_facet | Marijana Radić Stojković Marko Škugor Łukasz Dudek Jarosław Grolik Julita Eilmes Ivo Piantanida |
| author_sort | Marijana Radić Stojković |
| collection | DOAJ |
| description | An investigation of the interactions of two novel and several known DBTAA–adenine conjugates with double-stranded DNA and RNA has revealed the DNA/RNA groove as the dominant binding site, which is in contrast to the majority of previously studied DBTAA analogues (DNA/RNA intercalators). Only DBTAA–propyladenine conjugates revealed the molecular recognition of AT-DNA by an ICD band pattern > 300 nm, whereas significant ICD bands did not appear for other ds-DNA/RNA. A structure–activity relation for the studied series of compounds showed that the essential structural features for the ICD recognition are a) the presence of DNA-binding appendages (adenine side chain and positively charged side chain) on both DBTAA side chains, and b) the presence of a short propyl linker, which does not support intramolecular aromatic stacking between DBTAA and adenine. The observed AT-DNA-ICD pattern differs from previously reported ss-DNA (poly dT) ICD recognition by a strong negative ICD band at 350 nm, which allows for the dynamic differentiation between ss-DNA (poly dT) and coupled ds-AT-DNA. |
| first_indexed | 2024-12-19T13:18:23Z |
| format | Article |
| id | doaj.art-ea0f7c61a33840afa9d0ac08ecf11e41 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T13:18:23Z |
| publishDate | 2014-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-ea0f7c61a33840afa9d0ac08ecf11e412022-12-21T20:19:46ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-09-011012175218510.3762/bjoc.10.2251860-5397-10-225Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivativesMarijana Radić Stojković0Marko Škugor1Łukasz Dudek2Jarosław Grolik3Julita Eilmes4Ivo Piantanida5Laboratory for Study of Interactions of Biomacromolecules, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, PO Box 180, HR-10002 Zagreb, CroatiaLaboratory for Study of Interactions of Biomacromolecules, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, PO Box 180, HR-10002 Zagreb, CroatiaDepartment of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, PolandDepartment of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, PolandDepartment of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, PolandLaboratory for Study of Interactions of Biomacromolecules, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, PO Box 180, HR-10002 Zagreb, CroatiaAn investigation of the interactions of two novel and several known DBTAA–adenine conjugates with double-stranded DNA and RNA has revealed the DNA/RNA groove as the dominant binding site, which is in contrast to the majority of previously studied DBTAA analogues (DNA/RNA intercalators). Only DBTAA–propyladenine conjugates revealed the molecular recognition of AT-DNA by an ICD band pattern > 300 nm, whereas significant ICD bands did not appear for other ds-DNA/RNA. A structure–activity relation for the studied series of compounds showed that the essential structural features for the ICD recognition are a) the presence of DNA-binding appendages (adenine side chain and positively charged side chain) on both DBTAA side chains, and b) the presence of a short propyl linker, which does not support intramolecular aromatic stacking between DBTAA and adenine. The observed AT-DNA-ICD pattern differs from previously reported ss-DNA (poly dT) ICD recognition by a strong negative ICD band at 350 nm, which allows for the dynamic differentiation between ss-DNA (poly dT) and coupled ds-AT-DNA.https://doi.org/10.3762/bjoc.10.225AT-DNA recognitioncircular dichroismDBTAA-adenine conjugateds-DNA/RNAminor groove bindingnucleic acids |
| spellingShingle | Marijana Radić Stojković Marko Škugor Łukasz Dudek Jarosław Grolik Julita Eilmes Ivo Piantanida Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives Beilstein Journal of Organic Chemistry AT-DNA recognition circular dichroism DBTAA-adenine conjugate ds-DNA/RNA minor groove binding nucleic acids |
| title | Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives |
| title_full | Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives |
| title_fullStr | Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives |
| title_full_unstemmed | Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives |
| title_short | Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives |
| title_sort | molecular recognition of at dna sequences by the induced cd pattern of dibenzotetraaza 14 annulene dbtaa adenine derivatives |
| topic | AT-DNA recognition circular dichroism DBTAA-adenine conjugate ds-DNA/RNA minor groove binding nucleic acids |
| url | https://doi.org/10.3762/bjoc.10.225 |
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