An easily accessible, lower rim substituted calix[4]arene selectively binds <i>N</i>,<i>N</i>-dimethyllysine

Shaurya, Alok; Garnett, Graham A. E.; Starke, Melissa J.; Grasdal, Mark; Dewar, Charlotte C.; Kliuchynskyi, Anton Y.; Hof, Fraser

doi:10.1039/d1ob00524c

Cited by 2 publications

(2 citation statements)

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“…The 1 H NMR results of both compounds in CD 3 OD (Figures S1 and S6) show two pairs of doublets for the four methylene bridges indicating that, in this solvent, 1 and 2 adopt the cone conformation . In D 2 O, the 1 H NMR spectra of 1 and 2 (Figures S2 and S7) are substantially different from those observed in CD 3 OD, showing broader resonances, which can be tentatively assigned to intermediate conformational and/or aggregation exchange dynamics on the NMR chemical shift timescale …”

Section: Resultsmentioning

confidence: 88%

“…40 In D 2 O, the 1 H NMR spectra of 1 and 2 (Figures S2 and S7) are substantially different from those observed in CD 3 OD, showing broader resonances, which can be tentatively assigned to intermediate conformational and/or aggregation exchange dynamics on the NMR chemical shift timescale. 41 The photochromic properties of 1 and 2 were investigated in diluted aqueous solution by UV−vis absorption spectroscopy and in CD 3 OD by 1 H NMR. Photochemical irradiation using a UV-light wavelength (λ irr ) of 366 nm led to quantitative conversion of the E isomers into the respective Z-forms (Φ 1E → Z = 0.4 and Φ 2E → Z = 0.4) (see Figure 1 and Figure S23).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Photoswitchable Calixarene Activators for Controlled Peptide Transport across Lipid Membranes

et al. 2023

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Supramolecular synthetic transporters are crucial to understand and activate the passage across lipid membranes of hydrophilic effector molecules. Herein, we introduce photoswitchable calixarenes for the light-controlled transport activation of cationic peptide cargos across model lipid bilayers and inside living cells. Our approach was based on rationally designed p-sulfonatocalix[4]arene receptors equipped with a hydrophobic azobenzene arm, which recognize cationic peptide sequences at the nM range. Activation of membrane peptide transport is confirmed, in synthetic vesicles and living cells, for calixarene activators featuring the azobenzene arm in the E configuration. Therefore, this method allows the modulation of the transmembrane transport of peptide cargos upon Z–E photoisomerization of functionalized calixarenes using 500 nm visible light. These results showcase the potential of photoswitchable counterion activators for the light-triggered delivery of hydrophilic biomolecules and pave the way for potential applications in remotely controlled membrane transport and photopharmacology applications of hydrophilic functional biomolecules.

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Section: Resultsmentioning

confidence: 88%

Section: ■ Results and Discussionmentioning

confidence: 99%