Efficient Cleavage of pUC19 DNA by Tetraaminonaphthols
Abstract In an attempt to create models of phosphodiesterases, we previously investigated bis(guanidinium) naphthols. Such metal‐free anion receptors cleaved aryl phosphates and also plasmid DNA. Observed reaction rates, however, could not compete with those of highly reactive metal complexes. In th...
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Wiley-VCH
2025-02-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202400157 |
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| author | Catharina Kost Ute Scheffer Elisabeth Kalden Michael Wilhelm Göbel |
| author_facet | Catharina Kost Ute Scheffer Elisabeth Kalden Michael Wilhelm Göbel |
| author_sort | Catharina Kost |
| collection | DOAJ |
| description | Abstract In an attempt to create models of phosphodiesterases, we previously investigated bis(guanidinium) naphthols. Such metal‐free anion receptors cleaved aryl phosphates and also plasmid DNA. Observed reaction rates, however, could not compete with those of highly reactive metal complexes. In the present study, we have replaced the guanidines by ethylene diamine side chains which accelerates the plasmid cleavage by compound 13 significantly (1 mM 13: t1/2=22 h). Further gains in reactivity are achieved by azo coupling of the naphthol unit. The electron accepting azo group decreases the pKa of the hydroxy group. It can also serve as a dye label and a handle for attaching DNA binding moieties. The resulting azo naphthol 17 not only nicks (1 mM 17: t1/2~1 h) but also linearizes pUC19 DNA. Although the high reactivity of 17 seems to result in part from aggregation, in the presence of EDTA azo naphthol 17 obeys first order kinetics (1 mM 17: t1/2=4.8 h), reacts four times faster than naphthol 13 and surpasses by far the former bis(guanidinium) naphthols 4 and 5. |
| format | Article |
| id | doaj-art-d0c4e9d7b0b54dc5af19a11e8831ce9a |
| institution | Kabale University |
| issn | 2191-1363 |
| language | English |
| publishDate | 2025-02-01 |
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| spelling | doaj-art-d0c4e9d7b0b54dc5af19a11e8831ce9a2025-08-20T03:49:37ZengWiley-VCHChemistryOpen2191-13632025-02-01142n/an/a10.1002/open.202400157Efficient Cleavage of pUC19 DNA by TetraaminonaphtholsCatharina Kost0Ute Scheffer1Elisabeth Kalden2Michael Wilhelm Göbel3Institut für Organische Chemie und Chemische Biologie Goethe-Universität, Frankfurt am Main Max-von-Laue-Str. 7 D-60438 Frankfurt am Main GermanyInstitut für Organische Chemie und Chemische Biologie Goethe-Universität, Frankfurt am Main Max-von-Laue-Str. 7 D-60438 Frankfurt am Main GermanyInstitut für Organische Chemie und Chemische Biologie Goethe-Universität, Frankfurt am Main Max-von-Laue-Str. 7 D-60438 Frankfurt am Main GermanyInstitut für Organische Chemie und Chemische Biologie Goethe-Universität, Frankfurt am Main Max-von-Laue-Str. 7 D-60438 Frankfurt am Main GermanyAbstract In an attempt to create models of phosphodiesterases, we previously investigated bis(guanidinium) naphthols. Such metal‐free anion receptors cleaved aryl phosphates and also plasmid DNA. Observed reaction rates, however, could not compete with those of highly reactive metal complexes. In the present study, we have replaced the guanidines by ethylene diamine side chains which accelerates the plasmid cleavage by compound 13 significantly (1 mM 13: t1/2=22 h). Further gains in reactivity are achieved by azo coupling of the naphthol unit. The electron accepting azo group decreases the pKa of the hydroxy group. It can also serve as a dye label and a handle for attaching DNA binding moieties. The resulting azo naphthol 17 not only nicks (1 mM 17: t1/2~1 h) but also linearizes pUC19 DNA. Although the high reactivity of 17 seems to result in part from aggregation, in the presence of EDTA azo naphthol 17 obeys first order kinetics (1 mM 17: t1/2=4.8 h), reacts four times faster than naphthol 13 and surpasses by far the former bis(guanidinium) naphthols 4 and 5.https://doi.org/10.1002/open.202400157Anion receptorAzo naphtholDNA cleavageEnzyme mimicOrganocatalysis |
| spellingShingle | Catharina Kost Ute Scheffer Elisabeth Kalden Michael Wilhelm Göbel Efficient Cleavage of pUC19 DNA by Tetraaminonaphthols ChemistryOpen Anion receptor Azo naphthol DNA cleavage Enzyme mimic Organocatalysis |
| title | Efficient Cleavage of pUC19 DNA by Tetraaminonaphthols |
| title_full | Efficient Cleavage of pUC19 DNA by Tetraaminonaphthols |
| title_fullStr | Efficient Cleavage of pUC19 DNA by Tetraaminonaphthols |
| title_full_unstemmed | Efficient Cleavage of pUC19 DNA by Tetraaminonaphthols |
| title_short | Efficient Cleavage of pUC19 DNA by Tetraaminonaphthols |
| title_sort | efficient cleavage of puc19 dna by tetraaminonaphthols |
| topic | Anion receptor Azo naphthol DNA cleavage Enzyme mimic Organocatalysis |
| url | https://doi.org/10.1002/open.202400157 |
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