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Keywords = carboxybetaine ester

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9 pages, 890 KiB  
Communication
Carboxybetaine and Carboxybetaine Ester Derivatives of Tetra(dodecyloxyphenyl)-calix[4]resorcinarene: Synthesis, Self-Assembly and In Vitro Toxicity
by Julia E. Morozova, Zuchra R. Gilmullina, Victor V. Syakaev, Alexandra D. Voloshina, Anna P. Lyubina, Syumbelya K. Amerhanova, Olga B. Babaeva, Vasily M. Babaev and Igor S. Antipin
Molbank 2023, 2023(1), M1562; https://doi.org/10.3390/M1562 - 22 Jan 2023
Cited by 2 | Viewed by 1901
Abstract
Amphiphilic calix[4]resorcinarenes are a class of macrocyclic compounds with broad potential utility including nanomedicine. Here the synthesis of new carboxybetaine and carboxybetaine ester calix[4]resorcinarene bearing 4-(dodecyloxy)phenyl groups on the lower rim is presented. The compounds were characterized by 1H-NMR, 13C-NMR, 2D [...] Read more.
Amphiphilic calix[4]resorcinarenes are a class of macrocyclic compounds with broad potential utility including nanomedicine. Here the synthesis of new carboxybetaine and carboxybetaine ester calix[4]resorcinarene bearing 4-(dodecyloxy)phenyl groups on the lower rim is presented. The compounds were characterized by 1H-NMR, 13C-NMR, 2D NMR, IR, ESI and elemental analysis. The critical association concentration values are 1.00 × 10−5 and 1.18 × 10−5 mol·L−1 for carboxybetain and ester, respectively. The hemolytic activity of the macrocycles and their cytotoxicity against normal (WI-38, Chang liver) and tumor cells (M-HeLa) are also estimated. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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18 pages, 1673 KiB  
Article
Calix[4]Resorcinarene Carboxybetaines and Carboxybetaine Esters: Synthesis, Investigation of In Vitro Toxicity, Anti-Platelet Effects, Anticoagulant Activity, and BSA Binding Affinities
by Julia E. Morozova, Zuchra R. Gilmullina, Alexandra D. Voloshina, Anna P. Lyubina, Syumbelya K. Amerhanova, Victor V. Syakaev, Olga B. Babaeva, Albina Y. Ziganshina, Timur A. Mukhametzyanov, Aleksandr V. Samorodov, Michael M. Galagudza and Igor S. Antipin
Int. J. Mol. Sci. 2022, 23(23), 15298; https://doi.org/10.3390/ijms232315298 - 4 Dec 2022
Cited by 9 | Viewed by 2263
Abstract
As a result of bright complexation properties, easy functionalization and the ability to self-organize in an aqueous solution, amphiphilic supramolecular macrocycles are being actively studied for their application in nanomedicine (drug delivery systems, therapeutic and theranostic agents, and others). In this regard, it [...] Read more.
As a result of bright complexation properties, easy functionalization and the ability to self-organize in an aqueous solution, amphiphilic supramolecular macrocycles are being actively studied for their application in nanomedicine (drug delivery systems, therapeutic and theranostic agents, and others). In this regard, it is important to study their potential toxic effects. Here, the synthesis of amphiphilic calix[4]resorcinarene carboxybetaines and their esters and the study of a number of their microbiological properties are presented: cytotoxic effect on normal and tumor cells and effect on cellular and non-cellular components of blood (hemotoxicity, anti-platelet effect, and anticoagulant activity). Additionally, the interaction of macrocycles with bovine serum albumin as a model plasma protein is estimated by various methods (fluorescence spectroscopy, synchronous fluorescence spectroscopy, circular dichroic spectroscopy, and dynamic light scattering). The results demonstrate the low toxicity of the macrocycles, their anti-platelet effects at the level of acetylsalicylic acid, and weak anticoagulant activity. The study of BSA–macrocycle interactions demonstrates the dependence on macrocycle hydrophilic/hydrophobic group structure; in the case of carboxybetaines, the formation of complexes prevents self-aggregation of BSA molecules in solution. The present study demonstrates new data on potential drug delivery nanosystems based on amphiphilic calix[4]resorcinarenes for their cytotoxicity and effects on blood components. Full article
(This article belongs to the Special Issue Macrocycles as Catalysts or Drug Carriers)
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27 pages, 14623 KiB  
Review
Switchable Materials Containing Polyzwitterion Moieties
by Markéta Ilčíková, Ján Tkáč and Peter Kasák
Polymers 2015, 7(11), 2344-2370; https://doi.org/10.3390/polym7111518 - 20 Nov 2015
Cited by 72 | Viewed by 12917
Abstract
In recent decades, the design and construction of smart materials capable of switching into a polyzwitterionic state by an external trigger have been intensively pursued. Polyzwitterionic states have unique antifouling and surface properties and external triggers, such as pH, light, ions, electric field [...] Read more.
In recent decades, the design and construction of smart materials capable of switching into a polyzwitterionic state by an external trigger have been intensively pursued. Polyzwitterionic states have unique antifouling and surface properties and external triggers, such as pH, light, ions, electric field and CO2, cause significant changes in materials with regard to overall charge, ionic strength and wettability. This survey highlights current progress in the irreversible as well as the reversible switching process involving polyzwitterionic moieties, which can, in turn, be applied to studying the interaction of various interfaces with biological species as protein, DNA, bacteria or platelets and also for advanced use. Full article
(This article belongs to the Special Issue Functional Polymers for Medical Applications)
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