The pH-responsive calix[4]resorcinarene-mPEG conjugates bearing acylhydrazone bonds: Synthesis and study of the potential as supramolecular drug delivery systems

Shumatbaeva, Alina M.; Morozova, Julia E.; Syakaev, Victor V.; Shalaeva, Yana V.; Sapunova, Аnastasiia S.; Voloshina, Alexandra D.; Gubaidullin, А. Т.; Bazanova, Olga B.; Babaev, Vasily M.; Nizameev, Irek R.; Kadirov, Marsil K.; Антипин, И. С.

doi:10.1016/j.colsurfa.2020.124453

Cited by 27 publications

(7 citation statements)

References 46 publications

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“…A slight decrease in drug toxicity against the normal human hepatocytes cells was attributed to the conjugate‐self‐associates’ successful cloaking of the drug, whereas the encapsulated drug shows a more toxic effect on the M‐HeLa cells than in its free form. Photodynamic therapy study of a photosensitizer loaded conjugate with M‐HeLa cells displayed an increase in tumor cells death after irradiation [59] . Raval et al.…”

Section: Macrocyclesmentioning

confidence: 99%

Recent Updates on Supramolecular‐Based Drug Delivery – Macrocycles and Supramolecular Gels

Saji

2022

The Chemical Record

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Supramolecules‐based drug delivery has attracted significant recent research attention as it could enhance drug solubility, retention time, targeting, and stimuli responsiveness. Among the different supramolecules and assemblies, the macrocycles and the supramolecular hydrogels are the two important categories investigated to a greater extent. Here, we provide the most recent advancements in these categories. Under macrocycles, reports on drug delivery by cyclodextrins, cucurbiturils, calixarenes/pillararenes, crown ethers and porphyrins are detailed. The second category discusses the supramolecular hydrogels of macrocycles/polymers and low molecular weight gelators. The updated information provided could be helpful to advance R & D in this vital area.

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Section: Macrocyclesmentioning

confidence: 99%

Recent Updates on Supramolecular‐Based Drug Delivery – Macrocycles and Supramolecular Gels

Saji

2022

The Chemical Record

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“…The high hemolytic activity was observed with the use of amino derivatives of calix[4]arenes [ 16 ] and calix[4]resorcinarenes [ 17 ], as well as calix[4]resorcinarene cavitands with lipophilic cationic groups [ 18 ]. Calix[4]resorcinarene bearing N-methyl-D-glucamine groups [ 19 ] and pegylated calix[4]resorcinarenes [ 20 , 21 , 22 , 23 ] has zero or low effect on red blood cells. It was found that the hemolytic activity of carboxy calix[4]resorcinarenes depends on the hydrophobicity of macrocycles: basically, macrocycles demonstrate low hemolysis (0.34–3.42% at C = 5 × 10 −4 M) except for the macrocycle with octyl groups on the lower rim (34.1% at C = 5 × 10 −4 M) [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

Calix[4]Resorcinarene Carboxybetaines and Carboxybetaine Esters: Synthesis, Investigation of In Vitro Toxicity, Anti-Platelet Effects, Anticoagulant Activity, and BSA Binding Affinities

Morozova

Gilmullina

Voloshina

et al. 2022

IJMS

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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.

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“…Finally, the cavity of the molecule is non-polar in nature and surrounded by the polar wide rim, a feature that equips resorcin [4]arenes for micellar behavior. [20,21] Looking at these properties it is not surprising that these compounds have found their way into a number of applications such as molecular receptor systems, [22,23] photo resists, [24,25] selective membranes, molecular sensing, [26,27] drug delivery, [28,29] ion channel mimics, [30] metal ion extraction agents, [31,32] molecular switches, [33,34] stationary phases in GC and HPLC, [35][36][37][38] ligands for organometallic catalysts, [39][40][41] host-guest chemistry, [14,42] and starting materials in synthesis of supramolecular compounds. [43] Several relatives of these molecules have been developed and studied such as the closely related cavitands, [44] carcerands and hemicarcerands; [45] also pyrogallol [4]arenes, [46] catechol [4]arenes, [47] pillar [4]arenes, [48] pyridin [4]arenes; [49] calix [4]arenes, [50] and other structurally similar compounds.…”

Section: Introductionmentioning

confidence: 99%

Methodologies for the Derivatization of Resorcin[4]arenes at the Upper Rim ortho‐Positions

et al. 2022

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Resorcin[4]arenes are not as extensively studied as their sister compounds, calix[4]arenes, owing to challenges in synthetic methodologies for their derivatization from the perceptive of molecular economy. In this tutorial review, we briefly illustrate the summary of their access methodologies together with their limitations, focusing at the derivatization of the ortho‐positions in the upper rim. We hope to spark a refreshed surge in the development of these derivatization strategies, allowing access to novel molecules and futuristic applications, putting resorcin[4]arenes at the center stage of research for which they were meant.

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The pH-responsive calix[4]resorcinarene-mPEG conjugates bearing acylhydrazone bonds: Synthesis and study of the potential as supramolecular drug delivery systems

Cited by 27 publications

References 46 publications

Recent Updates on Supramolecular‐Based Drug Delivery – Macrocycles and Supramolecular Gels

Recent Updates on Supramolecular‐Based Drug Delivery – Macrocycles and Supramolecular Gels

Calix[4]Resorcinarene Carboxybetaines and Carboxybetaine Esters: Synthesis, Investigation of In Vitro Toxicity, Anti-Platelet Effects, Anticoagulant Activity, and BSA Binding Affinities

Methodologies for the Derivatization of Resorcin[4]arenes at the Upper Rim ortho‐Positions

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