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Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties
A series of new 5‐mono‐ and 5,5′‐bisamino‐substituted azothiazole derivatives was synthesized from the readily available diethyl azothiazole‐4,4′‐dicarboxylate. This reaction most likely comprises an initial Michael‐type addition by the respective primary alkyl and aromatic amines at the carbon atom...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6973281/ https://www.ncbi.nlm.nih.gov/pubmed/31523866 http://dx.doi.org/10.1002/chem.201903657 |
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author | Pithan, Phil M. Kuhlmann, Christopher Engelhard, Carsten Ihmels, Heiko |
author_facet | Pithan, Phil M. Kuhlmann, Christopher Engelhard, Carsten Ihmels, Heiko |
author_sort | Pithan, Phil M. |
collection | PubMed |
description | A series of new 5‐mono‐ and 5,5′‐bisamino‐substituted azothiazole derivatives was synthesized from the readily available diethyl azothiazole‐4,4′‐dicarboxylate. This reaction most likely comprises an initial Michael‐type addition by the respective primary alkyl and aromatic amines at the carbon atom C5 of the substrate. Subsequently, the resulting intermediates are readily oxidized by molecular oxygen to afford the amino‐substituted azothiazole derivatives. The latter exhibit remarkably red‐shifted absorption bands (λ (abs)=507–661 nm) with high molar extinction coefficients and show a strong positive solvatochromism. As revealed by spectrometric titrations and circular and linear dichroism studies, the water‐soluble, bis‐(dimethylaminopropylamino)‐substituted azo dye associates with duplex DNA by formation of aggregates along the phosphate backbone at high ligand–DNA ratios (LDR) and by intercalation at low LDR, which also leads to a significant increase of the otherwise low emission intensity at 671 nm. |
format | Online Article Text |
id | pubmed-6973281 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-69732812020-01-28 Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties Pithan, Phil M. Kuhlmann, Christopher Engelhard, Carsten Ihmels, Heiko Chemistry Full Papers A series of new 5‐mono‐ and 5,5′‐bisamino‐substituted azothiazole derivatives was synthesized from the readily available diethyl azothiazole‐4,4′‐dicarboxylate. This reaction most likely comprises an initial Michael‐type addition by the respective primary alkyl and aromatic amines at the carbon atom C5 of the substrate. Subsequently, the resulting intermediates are readily oxidized by molecular oxygen to afford the amino‐substituted azothiazole derivatives. The latter exhibit remarkably red‐shifted absorption bands (λ (abs)=507–661 nm) with high molar extinction coefficients and show a strong positive solvatochromism. As revealed by spectrometric titrations and circular and linear dichroism studies, the water‐soluble, bis‐(dimethylaminopropylamino)‐substituted azo dye associates with duplex DNA by formation of aggregates along the phosphate backbone at high ligand–DNA ratios (LDR) and by intercalation at low LDR, which also leads to a significant increase of the otherwise low emission intensity at 671 nm. John Wiley and Sons Inc. 2019-11-08 2019-12-13 /pmc/articles/PMC6973281/ /pubmed/31523866 http://dx.doi.org/10.1002/chem.201903657 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Full Papers Pithan, Phil M. Kuhlmann, Christopher Engelhard, Carsten Ihmels, Heiko Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties |
title | Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties |
title_full | Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties |
title_fullStr | Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties |
title_full_unstemmed | Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties |
title_short | Synthesis of 5‐Alkyl‐ and 5‐Phenylamino‐Substituted Azothiazole Dyes with Solvatochromic and DNA‐Binding Properties |
title_sort | synthesis of 5‐alkyl‐ and 5‐phenylamino‐substituted azothiazole dyes with solvatochromic and dna‐binding properties |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6973281/ https://www.ncbi.nlm.nih.gov/pubmed/31523866 http://dx.doi.org/10.1002/chem.201903657 |
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