New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion

Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained c...

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Autores principales: Laskova, Julia, Serdyukov, Alexander, Kosenko, Irina, Ananyev, Ivan, Titova, Ekaterina, Druzina, Anna, Sivaev, Igor, Antonets, Anastasia A., Nazarov, Alexey A., Bregadze, Vladimir I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738631/
https://www.ncbi.nlm.nih.gov/pubmed/36500667
http://dx.doi.org/10.3390/molecules27238575
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author Laskova, Julia
Serdyukov, Alexander
Kosenko, Irina
Ananyev, Ivan
Titova, Ekaterina
Druzina, Anna
Sivaev, Igor
Antonets, Anastasia A.
Nazarov, Alexey A.
Bregadze, Vladimir I.
author_facet Laskova, Julia
Serdyukov, Alexander
Kosenko, Irina
Ananyev, Ivan
Titova, Ekaterina
Druzina, Anna
Sivaev, Igor
Antonets, Anastasia A.
Nazarov, Alexey A.
Bregadze, Vladimir I.
author_sort Laskova, Julia
collection PubMed
description Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained coumarins have been tested with closo-dodecaborate derivative bearing terminal alkynyl group. Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction has led to fluorescent conjugates formation. The absorption–emission spectra of the formed conjugates have been presented. The antiproliferative activity and uptake of compounds against several human cell lines were evaluated.
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spelling pubmed-97386312022-12-11 New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion Laskova, Julia Serdyukov, Alexander Kosenko, Irina Ananyev, Ivan Titova, Ekaterina Druzina, Anna Sivaev, Igor Antonets, Anastasia A. Nazarov, Alexey A. Bregadze, Vladimir I. Molecules Article Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained coumarins have been tested with closo-dodecaborate derivative bearing terminal alkynyl group. Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction has led to fluorescent conjugates formation. The absorption–emission spectra of the formed conjugates have been presented. The antiproliferative activity and uptake of compounds against several human cell lines were evaluated. MDPI 2022-12-05 /pmc/articles/PMC9738631/ /pubmed/36500667 http://dx.doi.org/10.3390/molecules27238575 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Laskova, Julia
Serdyukov, Alexander
Kosenko, Irina
Ananyev, Ivan
Titova, Ekaterina
Druzina, Anna
Sivaev, Igor
Antonets, Anastasia A.
Nazarov, Alexey A.
Bregadze, Vladimir I.
New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion
title New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion
title_full New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion
title_fullStr New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion
title_full_unstemmed New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion
title_short New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with closo-Dodecaborate Anion
title_sort new azido coumarins as potential agents for fluorescent labeling and their “click” chemistry reactions for the conjugation with closo-dodecaborate anion
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738631/
https://www.ncbi.nlm.nih.gov/pubmed/36500667
http://dx.doi.org/10.3390/molecules27238575
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