Macrocyclic Coordination Chemistry of Resorcin[4]arenes and Pyrogallol[4]arenes

Kumari, Harshita; Deakyne, Carol A.; Atwood, Jerry L.

doi:10.1002/9781119053859.ch15

Cited by 7 publications

(4 citation statements)

References 78 publications

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“…The chemical structure of PgC1 is very similar to that of RsC1, only possessing an additional hydroxyl group per aromatic ring, as it is polymerised from the monomer pyrogallol. Alkylpyrogallol [4]arenes (PgCn) have demonstrated the ability to undergo self-assembly to create a number of architectures in the solid state as well as in the solution state (8,32). Amphiphilic PgCn with longer alkyl groups are active in membranes and can also function as ion channels in bilayer membranes (33).…”

Section: Introductionmentioning

confidence: 99%

Assessment of the in vitro toxicity of calixarenes and a metal-seamed calixarene: a chemical pathway for clinical application

Dawn

Yao

et al. 2019

Supramolecular Chemistry

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Calixarenes are known to form host-guest complexes and supramolecular nanoassemblies with well-defined architectures. However, the use of these materials in conjunction with drug moieties is still under explored. One reason is the insuffcient biocompatibility studies. Our present study represents a systematic in vitro investigation of the cytotoxicity associated with Cmethylresorcin[4]arene, C-methylpyrogallol[4]arene, p-phosphonated calix[8]arene and a metalseamed calixarene-copper(II) complex, using human HEK293 and rat C6G cell lines and two different cell viability assays (MTT and CellTiter-Glo) to avoid species-biased results. All compounds showed low to moderate toxicity. The trend in the CC 50 values indicated that the suppression of the coordination ability and the presence of phosphonate groups decrease the overall cytotoxicity of the compounds. The results of this study not only establish calixarenes and their immediate families as potential drug carriers and drug modifiers, but also reveal a pathway for fine-tuning their toxicological behaviour by appropriate chemical modification.

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Section: Introductionmentioning

confidence: 99%

Assessment of the in vitro toxicity of calixarenes and a metal-seamed calixarene: a chemical pathway for clinical application

Dawn

Yao

et al. 2019

Supramolecular Chemistry

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“…Cyclophanes serve as key structural components of various host molecules not only by themselves, [1][2][3][4][5][6][7][8] but also as their phenolic derivatives such as calixarenes, [9,10] calixresorcinarenes, [11] and pillararenes, [12,13] because of their ability to create cavities of defined size and shape, which are requisite for selective guest binding, by aromatic rings and bridging units. Among them, chiral cyclophanes have attracted intense interest in view of their capability in chiral recognition.…”

Section: Introductionmentioning

confidence: 99%

[2.2.2.2](2,7)‐1‐Bromonaphthalenophane from a Desymmetrized Building Block Bearing Electrophilic and Masked Nucleophilic Functionalities

Cai

Chatterjee

Hisaki

et al. 2019

Helvetica Chimica Acta

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In search of 2,7‐ethylene‐bridged naphthalenophanes with desymmetrized naphthalene cores as inherently chiral cyclophanes, nucleophilic substitution of 1‐bromo‐7‐(bromomethyl)‐2‐[(trimethylsilyl)methyl]naphthalene, a desymmetrized building block bearing an electrophilic group (CH2Br) and a masked nucleophilic functionality (CH2TMS) which can be activated by fluoride anion, was examined. As a result, in contrast to the case of parent naphthalenophanes wherein the smallest [2.2]naphthalenophane was obtained as the major product, only [2.2.2.2](2,7)‐1‐bromonaphthalenophane was obtained albeit in low yields, whereas the corresponding [2.2]‐ or [2.2.2]naphthalenophanes were not obtained. Though the [2.2.2.2]‐1‐bromonaphthalenophane can adopt four idealized geometries of different symmetry, among which three are inherently chiral, theoretical calculations predict that three conformers have almost equal energy and may equilibrate in solution. The X‐ray crystallographic study shows that it adopts a C2 conformation with anti,anti,anti orientation of the C−Br bonds at least as a major component in crystal.

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“…7 Among macrocycles, the calixarene family has garnered significant interest because the bowl-shaped conformation 8 is considered an ideal model for host−guest binding and selfassembly. Calixarenes are repeating units of phenol, whereas their derivatives 9 (resorcinarenes and pyrogalloarenes) have polyphenol (resorcinol and pyrogallol) as repeating units.…”

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confidence: 99%

“…Resorcinarenes (Figure ) are a class of cyclic polyphenolic compounds obtained by the condensation of resorcinol with different aldehydes in acidic solutions. Interestingly, owing to the flexibility in changing the electron-rich upper-rim groups and lower-rim alkyl chains with distinctive substituents, a wide assortment of tunable host molecules can be obtained. , For instance, water-soluble anionic and cationic resorcinarene receptors disrupt the aggregation of the peptide associated with cataracts, which highlights the potential of tunable resorcinarenes in therapeutics. Among cyclic polyphenolic cavitands, resorcinarenes have been studied extensively in host–guest chemistry, as their conical shape has the potential for the development of useful (bio)materials and sensors .…”

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confidence: 99%

Supramolecule-Driven Host–Guest Co-Crystallization of Cyclic Polyphenols with Anti-Fibrotic Pharmaceutical Drug

Panigrahi

Mayhan

Dar

et al. 2023

Crystal Growth & Design

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Host–guest complexes are of interest as supramolecular drugs in pharmaceutical sciences because the activity of antibacterial agents can be enhanced upon complexation with various cyclic oligomers or metal ions, with some complexes possessing higher healing properties than the parent drugs. Herein, to develop a microbiologically potent supramolecular drug, we investigated the complexation of macrocyclic hosts (resorcinarenes and β-cyclodextrin) with pirfenidone (PFD), an FDA-approved antifibrotic drug containing an antibacterial pyridone core. Electronic structure calculations gave insights into the interactions in the host–PFD complexes. Further, complex formation and clinical activities were investigated using spectroscopic techniques and in vitro measurements of antibacterial activity against Gram-positive and Gram-negative bacteria. An unprecedented interplay between the antibacterial activity of the polyphenolic resorcinarene hosts and their ability to interact chemically with PFD was found to improve the overall antibacterial activity of PFD. These results could revolutionize the use of synthetically modifiable resorcinarene and their analogues for fine-tuning the clinical behavior of drugs.

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Macrocyclic Coordination Chemistry of Resorcin[4]arenes and Pyrogallol[4]arenes

Cited by 7 publications

References 78 publications

Assessment of the in vitro toxicity of calixarenes and a metal-seamed calixarene: a chemical pathway for clinical application

Assessment of the in vitro toxicity of calixarenes and a metal-seamed calixarene: a chemical pathway for clinical application

[2.2.2.2](2,7)‐1‐Bromonaphthalenophane from a Desymmetrized Building Block Bearing Electrophilic and Masked Nucleophilic Functionalities

Supramolecule-Driven Host–Guest Co-Crystallization of Cyclic Polyphenols with Anti-Fibrotic Pharmaceutical Drug

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