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Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests

A potential hypoxia-sensitive system host-guest complex of three calixarenes (including two with four anionic carboxyl and sulphonate azo fragments on the upper rim and a newly synthesized bis-azo adduct of calixarene in the cone configuration with azo fragments on the lower rim with the most widesp...

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Autores principales: Mironova, Diana, Burilov, Vladimir, Galieva, Farida, Khalifa, Mohamed Ali Mohamed, Kleshnina, Sofia, Gazalieva, Alsu, Nugmanov, Ramil, Solovieva, Svetlana, Antipin, Igor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8469542/
https://www.ncbi.nlm.nih.gov/pubmed/34576922
http://dx.doi.org/10.3390/molecules26185451
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author Mironova, Diana
Burilov, Vladimir
Galieva, Farida
Khalifa, Mohamed Ali Mohamed
Kleshnina, Sofia
Gazalieva, Alsu
Nugmanov, Ramil
Solovieva, Svetlana
Antipin, Igor
author_facet Mironova, Diana
Burilov, Vladimir
Galieva, Farida
Khalifa, Mohamed Ali Mohamed
Kleshnina, Sofia
Gazalieva, Alsu
Nugmanov, Ramil
Solovieva, Svetlana
Antipin, Igor
author_sort Mironova, Diana
collection PubMed
description A potential hypoxia-sensitive system host-guest complex of three calixarenes (including two with four anionic carboxyl and sulphonate azo fragments on the upper rim and a newly synthesized bis-azo adduct of calixarene in the cone configuration with azo fragments on the lower rim with the most widespread cationic and zwitterionic rhodamine dyes (123, 6G and B)) was studied using UV-VIS spectrometry and fluorescence as well as 1D and 2D NMR techniques. It was found that all three calixarenes form a complex with rhodamine dyes with a 1:1 composition. The association constants of calixarene-dye complexes with sulfonate calixarenes, especially in the case of tetra-anionic calixarene, turned out to be higher compared with carboxyl calixarene due to the more intense electrostatic interactions. For the first time using an HRESI MS technique, it was shown that the treatment of rhodamine 6G and 123 with sodium dithionite (SDT) produces a non-fluorescent leuco form of the dye, and only rhodamine B can be used with SDT without the occurrence of a side reduction. Moreover, it was identified that in addition to the reduction in the azo groups, SDT causes partial cleavage of the aryl ether bonds. The found features of SDT should be taken into account when SDT is used as an azoreductase mimic.
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spelling pubmed-84695422021-09-27 Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests Mironova, Diana Burilov, Vladimir Galieva, Farida Khalifa, Mohamed Ali Mohamed Kleshnina, Sofia Gazalieva, Alsu Nugmanov, Ramil Solovieva, Svetlana Antipin, Igor Molecules Article A potential hypoxia-sensitive system host-guest complex of three calixarenes (including two with four anionic carboxyl and sulphonate azo fragments on the upper rim and a newly synthesized bis-azo adduct of calixarene in the cone configuration with azo fragments on the lower rim with the most widespread cationic and zwitterionic rhodamine dyes (123, 6G and B)) was studied using UV-VIS spectrometry and fluorescence as well as 1D and 2D NMR techniques. It was found that all three calixarenes form a complex with rhodamine dyes with a 1:1 composition. The association constants of calixarene-dye complexes with sulfonate calixarenes, especially in the case of tetra-anionic calixarene, turned out to be higher compared with carboxyl calixarene due to the more intense electrostatic interactions. For the first time using an HRESI MS technique, it was shown that the treatment of rhodamine 6G and 123 with sodium dithionite (SDT) produces a non-fluorescent leuco form of the dye, and only rhodamine B can be used with SDT without the occurrence of a side reduction. Moreover, it was identified that in addition to the reduction in the azo groups, SDT causes partial cleavage of the aryl ether bonds. The found features of SDT should be taken into account when SDT is used as an azoreductase mimic. MDPI 2021-09-07 /pmc/articles/PMC8469542/ /pubmed/34576922 http://dx.doi.org/10.3390/molecules26185451 Text en © 2021 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
Mironova, Diana
Burilov, Vladimir
Galieva, Farida
Khalifa, Mohamed Ali Mohamed
Kleshnina, Sofia
Gazalieva, Alsu
Nugmanov, Ramil
Solovieva, Svetlana
Antipin, Igor
Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests
title Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests
title_full Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests
title_fullStr Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests
title_full_unstemmed Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests
title_short Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests
title_sort azocalix[4]arene-rhodamine supramolecular hypoxia-sensitive systems: a search for the best calixarene hosts and rhodamine guests
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8469542/
https://www.ncbi.nlm.nih.gov/pubmed/34576922
http://dx.doi.org/10.3390/molecules26185451
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