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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MDPI AG
2021-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/18/5451 |
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| author | Diana Mironova Vladimir Burilov Farida Galieva Mohamed Ali Mohamed Khalifa Sofia Kleshnina Alsu Gazalieva Ramil Nugmanov Svetlana Solovieva Igor Antipin |
| author_facet | Diana Mironova Vladimir Burilov Farida Galieva Mohamed Ali Mohamed Khalifa Sofia Kleshnina Alsu Gazalieva Ramil Nugmanov Svetlana Solovieva Igor Antipin |
| author_sort | Diana Mironova |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T07:24:08Z |
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| id | doaj.art-6b180a2b1cfd4ca6aa5ee8d8ea20fc83 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T07:24:08Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6b180a2b1cfd4ca6aa5ee8d8ea20fc832023-11-22T14:23:16ZengMDPI AGMolecules1420-30492021-09-012618545110.3390/molecules26185451Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine GuestsDiana Mironova0Vladimir Burilov1Farida Galieva2Mohamed Ali Mohamed Khalifa3Sofia Kleshnina4Alsu Gazalieva5Ramil Nugmanov6Svetlana Solovieva7Igor Antipin8Alexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaAlexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaAlexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaAlexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaA.E.Arbuzov Institute of Organic & Physical Chemistry, 8 Arbuzov Street, 420088 Kazan, RussiaAlexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaAlexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaA.E.Arbuzov Institute of Organic & Physical Chemistry, 8 Arbuzov Street, 420088 Kazan, RussiaAlexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, RussiaA 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.https://www.mdpi.com/1420-3049/26/18/5451calixarenehypoxia sensinghost-guest complex |
| spellingShingle | Diana Mironova Vladimir Burilov Farida Galieva Mohamed Ali Mohamed Khalifa Sofia Kleshnina Alsu Gazalieva Ramil Nugmanov Svetlana Solovieva Igor Antipin Azocalix[4]arene-Rhodamine Supramolecular Hypoxia-Sensitive Systems: A Search for the Best Calixarene Hosts and Rhodamine Guests Molecules calixarene hypoxia sensing host-guest complex |
| 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 | calixarene hypoxia sensing host-guest complex |
| url | https://www.mdpi.com/1420-3049/26/18/5451 |
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