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Cationic styryl dyes for DNA labelling and selectivity toward cancer cells and Gram-negative bacteria
Fluorescence-based methods are important tools for the analysis of nucleic acids in vitro and in cells. In this study, two cationic cyanine–styryl derivatives were produced using a two-step synthesis. Their optical properties were evaluated in different solvents, and frontier molecular orbital theor...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9832362/ https://www.ncbi.nlm.nih.gov/pubmed/36712646 http://dx.doi.org/10.1039/d2ra07601b |
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author | Wangngae, Sirilak Ngivprom, Utumporn Khrootkaew, Tunyawat Worakaensai, Suphanida Lai, Rung-Yi Kamkaew, Anyanee |
author_facet | Wangngae, Sirilak Ngivprom, Utumporn Khrootkaew, Tunyawat Worakaensai, Suphanida Lai, Rung-Yi Kamkaew, Anyanee |
author_sort | Wangngae, Sirilak |
collection | PubMed |
description | Fluorescence-based methods are important tools for the analysis of nucleic acids in vitro and in cells. In this study, two cationic cyanine–styryl derivatives were produced using a two-step synthesis. Their optical properties were evaluated in different solvents, and frontier molecular orbital theory was utilized to interpret the findings. The DNA binding of these molecules was investigated to show fluorescence intensification. The molecular docking of both dyes in DNA illustrated the relevance of the electrostatic interaction between the quaternary ammonium of both dyes and the phosphate of the DNA backbone. Last but not least, applications of the synthesized styryl dyes were demonstrated to be selective towards cancer cells and particular kinds of bacteria. |
format | Online Article Text |
id | pubmed-9832362 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-98323622023-01-26 Cationic styryl dyes for DNA labelling and selectivity toward cancer cells and Gram-negative bacteria Wangngae, Sirilak Ngivprom, Utumporn Khrootkaew, Tunyawat Worakaensai, Suphanida Lai, Rung-Yi Kamkaew, Anyanee RSC Adv Chemistry Fluorescence-based methods are important tools for the analysis of nucleic acids in vitro and in cells. In this study, two cationic cyanine–styryl derivatives were produced using a two-step synthesis. Their optical properties were evaluated in different solvents, and frontier molecular orbital theory was utilized to interpret the findings. The DNA binding of these molecules was investigated to show fluorescence intensification. The molecular docking of both dyes in DNA illustrated the relevance of the electrostatic interaction between the quaternary ammonium of both dyes and the phosphate of the DNA backbone. Last but not least, applications of the synthesized styryl dyes were demonstrated to be selective towards cancer cells and particular kinds of bacteria. The Royal Society of Chemistry 2023-01-11 /pmc/articles/PMC9832362/ /pubmed/36712646 http://dx.doi.org/10.1039/d2ra07601b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Wangngae, Sirilak Ngivprom, Utumporn Khrootkaew, Tunyawat Worakaensai, Suphanida Lai, Rung-Yi Kamkaew, Anyanee Cationic styryl dyes for DNA labelling and selectivity toward cancer cells and Gram-negative bacteria |
title | Cationic styryl dyes for DNA labelling and selectivity toward cancer cells and Gram-negative bacteria |
title_full | Cationic styryl dyes for DNA labelling and selectivity toward cancer cells and Gram-negative bacteria |
title_fullStr | Cationic styryl dyes for DNA labelling and selectivity toward cancer cells and Gram-negative bacteria |
title_full_unstemmed | Cationic styryl dyes for DNA labelling and selectivity toward cancer cells and Gram-negative bacteria |
title_short | Cationic styryl dyes for DNA labelling and selectivity toward cancer cells and Gram-negative bacteria |
title_sort | cationic styryl dyes for dna labelling and selectivity toward cancer cells and gram-negative bacteria |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9832362/ https://www.ncbi.nlm.nih.gov/pubmed/36712646 http://dx.doi.org/10.1039/d2ra07601b |
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