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Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA
Efficient protocols based on Cu(I)-catalyzed azide–alkyne cycloaddition were developed for the synthesis of conjugates of pyrrole–imidazole polyamide minor groove binders (MGB) with fluorophores and with triplex-forming oligonucleotides (TFOs). Diverse bifunctional linkers were synthesized and used...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979877/ https://www.ncbi.nlm.nih.gov/pubmed/27559384 http://dx.doi.org/10.3762/bjoc.12.128 |
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author | Vasilyeva, Svetlana V Filichev, Vyacheslav V Boutorine, Alexandre S |
author_facet | Vasilyeva, Svetlana V Filichev, Vyacheslav V Boutorine, Alexandre S |
author_sort | Vasilyeva, Svetlana V |
collection | PubMed |
description | Efficient protocols based on Cu(I)-catalyzed azide–alkyne cycloaddition were developed for the synthesis of conjugates of pyrrole–imidazole polyamide minor groove binders (MGB) with fluorophores and with triplex-forming oligonucleotides (TFOs). Diverse bifunctional linkers were synthesized and used for the insertion of terminal azides or alkynes into TFOs and MGBs. The formation of stable triple helices by TFO-MGB conjugates was evaluated by gel-shift experiments. The presence of MGB in these conjugates did not affect the binding parameters (affinity and triplex stability) of the parent TFOs. |
format | Online Article Text |
id | pubmed-4979877 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-49798772016-08-24 Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA Vasilyeva, Svetlana V Filichev, Vyacheslav V Boutorine, Alexandre S Beilstein J Org Chem Full Research Paper Efficient protocols based on Cu(I)-catalyzed azide–alkyne cycloaddition were developed for the synthesis of conjugates of pyrrole–imidazole polyamide minor groove binders (MGB) with fluorophores and with triplex-forming oligonucleotides (TFOs). Diverse bifunctional linkers were synthesized and used for the insertion of terminal azides or alkynes into TFOs and MGBs. The formation of stable triple helices by TFO-MGB conjugates was evaluated by gel-shift experiments. The presence of MGB in these conjugates did not affect the binding parameters (affinity and triplex stability) of the parent TFOs. Beilstein-Institut 2016-06-30 /pmc/articles/PMC4979877/ /pubmed/27559384 http://dx.doi.org/10.3762/bjoc.12.128 Text en Copyright © 2016, Vasilyeva et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Vasilyeva, Svetlana V Filichev, Vyacheslav V Boutorine, Alexandre S Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
title | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
title_full | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
title_fullStr | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
title_full_unstemmed | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
title_short | Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA |
title_sort | application of cu(i)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded dna |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979877/ https://www.ncbi.nlm.nih.gov/pubmed/27559384 http://dx.doi.org/10.3762/bjoc.12.128 |
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