Efficient Separation of C-Tetramethylcalix[4]resorcinarene Conformers by Means of Reversed-Phase Solid-Phase Extraction

Pineda-Castañeda, Héctor Manuel; Maldonado, Mauricio; Rivera‐Monroy, Zuly Jenny

doi:10.1021/acsomega.2c03218

Cited by 2 publications

(3 citation statements)

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“…It has been reported that a single conformer or a conformational mixture can be obtained as a reaction product in the synthesis of this type of resorcinarene derivative [ 28 , 29 ]. To characterize the two principal products, a purification/separation and recrystallization process was carried out [ 30 ], and then each purified product was characterized via RP-HPLC, 1 H-NMR, and 13 C-NMR. A white solid was obtained, and its chromatographic profile shows a single species at 9.6 min with a purity of 96.4% ( Figure 2 b).…”

Section: Resultsmentioning

confidence: 99%

Peptide-Resorcinarene Conjugates Obtained via Click Chemistry: Synthesis and Antimicrobial Activity

et al. 2023

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Antimicrobial resistance (AMR) is one of the top ten threats to public health, as reported by the World Health Organization (WHO). One of the causes of the growing AMR problem is the lack of new therapies and/or treatment agents; consequently, many infectious diseases could become uncontrollable. The need to discover new antimicrobial agents that are alternatives to the existing ones and that allow mitigating this problem has increased, due to the rapid and global expansion of AMR. Within this context, both antimicrobial peptides (AMPs) and cyclic macromolecules, such as resorcinarenes, have been proposed as alternatives to combat AMR. Resorcinarenes present multiple copies of antibacterial compounds in their structure. These conjugate molecules have exhibited antifungal and antibacterial properties and have also been used in anti-inflammatory, antineoplastic, and cardiovascular therapies, as well as being useful in drug and gene delivery systems. In this study, it was proposed to obtain conjugates that contain four copies of AMP sequences over a resorcinarene core. Specifically, obtaining (peptide)4-resorcinarene conjugates derived from LfcinB (20–25): RRWQWR and BF (32–34): RLLR was explored. First, the synthesis routes that allowed obtaining: (a) alkynyl-resorcinarenes and (b) peptides functionalized with the azide group were established. These precursors were used to generate (c) (peptide)4-resorcinarene conjugates by azide-alkyne cycloaddition CuAAC, a kind of click chemistry. Finally, the conjugates’ biological activity was evaluated: antimicrobial activity against reference strains and clinical isolates of bacteria and fungi, and the cytotoxic activity over erythrocytes, fibroblast, MCF-7, and HeLa cell lines. Our results allowed establishing a new synthetic route, based on click chemistry, for obtaining macromolecules derived from resorcinarenes functionalized with peptides. Moreover, it was possible to identify promising antimicrobial chimeric molecules that may lead to advances in the development of new therapeutic agents.

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Section: Resultsmentioning

confidence: 99%

Peptide-Resorcinarene Conjugates Obtained via Click Chemistry: Synthesis and Antimicrobial Activity

et al. 2023

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“…Each single crystal example was grown with slow evaporation from the relevant isomer solution (1 mM). It should be noted that the corresponding macrocycle isomer has the structure that is similar to meso-substituted resorcinarene with chair ( 1 ), kite ( 2 ), or crown ( 3 ) comformation 35 . With the NMR spectroscopic study, the similarities were further verified.…”

Section: Resultsmentioning

confidence: 99%

“…Additionally, it is used as a slipping technique in the production of rotaxane 17 , 27 , 33 . Some examples of thermal-induced conversion between two forms are achieved 28 , 34 , 35 . However, some biomacromolecules have been found to have more than two distinct stable or metastable folding configurations.…”

Section: Introductionmentioning

confidence: 99%

Thermally-induced atropisomerism promotes metal-organic cage construction

Liang,

Lu,

Yang

et al. 2023

Nat Commun

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Molecular folding regulation with environmental stimuli is critical in living and artificial molecular machine systems. Herein, we described a macrocycle, cyclo[4] (1,3-(4,6-dimethyl)benzene)[4](1,3-(4,6-dimethyl)benzene)(4-pyridine). Under 298 K, it has three stable stiff atropisomers with names as 1 (Cs symmetry), 2 (Cs symmetry), and 3 (C4v symmetry). At 393 K, 1 can reversibly transform into 2, but at 473 K, it can irrevocably transform into 3. At 338 K, 3 and (PhCN)2PdCl2 complex to produce the metal-organic cage 4. Only at 338 K does the combination of 1 or 2 and (PhCN)2PdCl2 create a gel-like structure. Heating both gels to 473 K transforms them into 4. In addition to offering a thermally accelerated method for modifying self-assembled systems using macrocyclic building blocks, this study also has the potential to develop the nanoscale transformation material with a thermal response.

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Efficient Separation of C-Tetramethylcalix[4]resorcinarene Conformers by Means of Reversed-Phase Solid-Phase Extraction

Cited by 2 publications

References 24 publications

Peptide-Resorcinarene Conjugates Obtained via Click Chemistry: Synthesis and Antimicrobial Activity

Peptide-Resorcinarene Conjugates Obtained via Click Chemistry: Synthesis and Antimicrobial Activity

Thermally-induced atropisomerism promotes metal-organic cage construction

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