Calixarenes in Bio-Medical Researches

Rodik, Roman V.; Boyko, Vyacheslav M.; Kаlchеnkо, Vitaly I.

doi:10.2174/092986709788186219

Cited by 149 publications

(154 citation statements)

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“…One such macrocyclic scaffold is calixarene. [11][12][13][14][15][16][17][18][19][20] Calix [n]arenes are one of the most exciting synthetic macrocycles known to date besides cyclodextrins, crown ethers, cryptands, and cucurbiturils having diverse applications in supramolecular chemistry. [21][22][23] They can easily be synthesized by the reaction of p-tert-butyl phenol and formaldehyde in the presence of a base.…”

Section: S P E C I a L I S S U E A R T I C L E Functionalized Calix[4mentioning

confidence: 99%

Functionalized calix[4]arenes as potential therapeutic agents

2017

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Calixarenes, composed of phenolic units linked by methylene bridges at the 2,6-positions, represent a versatile class of macrocyclic compounds in supramolecular chemistry that can host small molecules or ions in their well-defined hydrophobic cavities. In recent years, it has been recognized that this class of compounds has the potential to serve as platform for the design of biological active compounds. Therefore, the calixarenes functionalized with different pharmacophoric groups have been synthesized as target structure by many researchers and were further evaluated for their biological activities. Owing to their promising biological activities such as antiviral, antibacterial, antifungal, and anticancer, the functionalized calixarenes are recently receiving increased attention from pharmaceutical/medicinal chemistry community. In this review, we summarize and discuss the synthetic approaches and the biological potential of functionalized calixarenes, mainly focusing on the selected recent studies for a comprehensive and target-oriented information, which could help in the design and synthesis of new therapeutic agents leading to the development of clinically viable drugs based on these macrocyles. K E Y W O R D Sbiological activity, calixarenes, cone conformation, functionalization, upper/lower rim/annulus

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Section: S P E C I a L I S S U E A R T I C L E Functionalized Calix[4mentioning

confidence: 99%

Functionalized calix[4]arenes as potential therapeutic agents

2017

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“…Among carcerands, as inclusion compounds the most deeply studied and most widely spread are carcerands based on various derivatives of calix[n]arenes, cyclodextrins, etc. [2][3][4]. They are known under the general name -"hostguest" complexes.…”

Section: Introductionmentioning

confidence: 99%

Double-layer silicene-based carcerands: molecular containers for unstable compounds

Mykhailenko¹,

Prylutskyy²,

Komarov³

et al. 2017

Him. Fiz. Tehnol. Poverhni

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We have studied the formation of a "host-guest" type сarcerand with a double-layer silicene (DL-S) When initially heated from 0 to ∼273 K, the systems energy grows gradually, then rises sharply between 273-300 K and 350-400 K, then, with the temperature growth, it reaches a plateau which proves its high stability up to ~420 K. In the temperature range 0-273 K there appears physical sorption while chemisorption is observed at higher temperature (∼300 K) which is peculiar of π-π interactions of classical aromatic and quasiaromatic cyclic and heterocyclic systems.There have been calculated the UV-spectra of the DL-S depending on the intercalate concentration in terms of the modified Benes-Hilderbrand method. There has been shown that the association constant of the system studied is 380 l·mol -1 , with computation accuracy ≥ 0.977.

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“…Owing to the persistent conical shape, calixarenes are powerful building blocks for micelles, [18] nanoparticles, nanocages, supramolecular polymers, etc. [19] They already found applications as antiviral, bactericidal and anticancer agents [20] as well as sensors [21] and vehicles for gene delivery. [22] Here, using a calixarene amphiphile bearing four alkyne groups, we prepared 7 nm micellar NPs shell-cross-linked with cyanine corona (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Protein‐Sized Bright Fluorogenic Nanoparticles Based on Cross‐Linked Calixarene Micelles with Cyanine Corona

et al. 2016

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The key challenge in the field of fluorescent nanoparticles (NPs) for biological applications is to achieve superior brightness for sizes equivalent to single proteins (3-7 nm). We propose a concept of shell-cross-linked fluorescent micelles, where PEGylated cyanine 3 and 5 bis-azides form a covalently attached "corona" on micelles of amphiphilic calixarene bearing four alkyne groups. The obtained monodisperse NPs of 7 nm size increase their fluorescence quantum yield as a function of viscosity reaching 15% in glycerol. In the on-state they are ~2-fold brighter than quantum dots (QD-585), being the smallest PEGylated organic NPs of this high brightness. FRET between cyanine 3 and 5 cross-linkers at the surface of NPs suggests their integrity in physiological media, organic solvents and living cells, where they rapidly internalize showing excellent imaging contrast. Calixarene micelles with cyanine corona constitute a new platform for development of protein-sized ultrabright fluorescent NPs.* andrey.klymchenko@unistra.fr. Presently, we propose a concept of protein-sized fluorescent NPs based on calixarene micelles that are shell-cross-linked by fluorescent bi-functional dyes via Cu-catalysed "click" chemistry. In one recent report, a surfactant bearing three acetylene groups was polymerized using non-fluorescent cross-linker, while the non-reacted alkynes were further modified with fluorescent mono-functional dyes. Europe PMC Funders Group[15] In our strategy, we designed fluorescent cross-linkers to enable both micelle cross-linking and introduction of the fluorescent units. To this end, we selected cyanine 3 and 5 dyes, because of their excellent optical properties [16] and symmetric structure ( Figure 1). They were modified with two azide groups for crosslinking of the micelle and two hydrophilic PEG(8) chains to create its biocompatible shell. We call this design "cyanine corona", similarly to well-known protein corona that modifies the surfaces of a variety of NPs. (Figure 1). They are the first protein-sized NPs combining fluorogenic response to viscosity with superior brightness compared to quantum dots (QD-585).The calixarene amphiphile CX8TP at 150 μM concentration in aqueous solution (75 mM sodium sulfate) forms micelles of 5 nm according to dynamic light scattering (DLS) ( Figure S1). These micelles were further reacted with 2 eq of the cross-linkers Cy3L or Cy5L in the presence of copper catalyst for 24h at 30 °C. Then these reaction mixtures were dialyzed and their pick absorbance was compared to that before the dialysis. We found that after the reaction only a fraction (≤50%) of the cross-linkers was removed, whereas the control samples without added Cu-catalyst lost nearly all cross-linkers after the dialysis ( Figure 1A). These results provide an evidence for the successful cross-linking of micellar NPs with Cy3L and Cy5L. The absorption data suggested the cross-linking yields of 59 and 49% for Cy3L and Cy5L dyes, respectively. Moreover, the IR spectrum of the cross-linked micelles (CX/C...

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Calixarenes in Bio-Medical Researches

Cited by 149 publications

References 0 publications

Functionalized calix[4]arenes as potential therapeutic agents

Functionalized calix[4]arenes as potential therapeutic agents

Double-layer silicene-based carcerands: molecular containers for unstable compounds

Protein‐Sized Bright Fluorogenic Nanoparticles Based on Cross‐Linked Calixarene Micelles with Cyanine Corona

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