pH-Responsive Molecular Tweezers

Leblond, Jeanne; Gao, Hui; Petitjean, Anne; Leroux, Jean‐Christophe

doi:10.1021/ja103153t

Cited by 85 publications

(52 citation statements)

References 27 publications

(10 reference statements)

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“…[14] We previously reported ap H-responsive molecular tweezer able to bind and release asubstrate in apH-dependent fashion. [15] In this study,w ec onstructed lipidlike switches that can integrate into the structure of liposomes ( Figure 1A). It was hypothesized that, upon protonation, hydrogen-bonding opportunities would favor achange in the relative orientation of the hydrocarbon chains of the switchable lipids,w hich would disturb the lipid packing of the liposomes,provoke the release of their cargo,a nd confer endosomal-escape properties ( Figure 1B).…”

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confidence: 99%

Switchable Lipids: Conformational Change for Fast pH‐Triggered Cytoplasmic Delivery

2015

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We report the use of switchable lipids to improve the endosomal escape and cytosolic delivery of cell-impermeable compounds. The system is based on a conformational reorganization of the lipid structure upon acidification, as demonstrated by NMR spectroscopic studies. When incorporated in a liposome formulation, the switchable lipids triggered bilayer destabilization through fusion even in the presence of poly(ethylene glycol). We observed 88 % release of sulforhodamine B in 15 min at pH 5, and the liposome formulations demonstrated high stability at pH 7.4 for several months. By using sulforhodamine B as a model of a highly polar drug, we demonstrated fast cytosolic delivery mediated by endosomal escape in HeLa cells, and no toxicity.

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confidence: 99%

Switchable Lipids: Conformational Change for Fast pH‐Triggered Cytoplasmic Delivery

2015

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“…However, the emission of 8 – 10 was quenched differently to that of 7 . To avoid emission quenching, phenyl groups were introduced at the 3,5‐positions of the 4‐pyridyl group (entry 4) . Thus, thiazole 6 displayed visually confirmed fluorescence at 609 nm, but the presence of phenyl groups at the 3,5‐positions of the 4‐pyridyl group in 6 inhibited the protonation of the pyridyl group of 6 with TfOH.…”

Section: Methodsmentioning

confidence: 99%

Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid

et al. 2016

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Solutions of 5‐N‐arylaminothiazoles containing pyridyl groups exhibited clear halochromism and halofluorism upon addition of Brønsted and Lewis acids. The addition of triflic acid to solutions of 5‐N‐arylaminothiazoles in Et2O induced bathochromic shifts of the absorption and emission bands. DFT calculations suggested that the spectral changes arise from the protonation of the pyridyl group of the thiazoles in Et2O. Single‐crystal X‐ray diffraction analysis of a thiazole and its protonated form revealed the change of the conformation around the thiazole ring. The emission of white light was accomplished from a single fluorescent dye by adjusting the ratio of dye and B(C6F5)3, whereby the International Commission on Illumination coordinates showed a linear change from blue to orange.

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“…This versatility in design, structure and function makes molecular tweezers suitable candidates for the fabrication of nanoscale molecular devices 1a,1c. Consequently, molecular tweezers are beginning to find applications in targeted drug delivery and controlled release,2c and in the determination of enantiomeric purity or absolute configuration of chiral guest compounds 7…”

Section: Introductionmentioning

confidence: 99%

Organocatalysed Asymmetric Direct Mannich Reaction of Acetophenone Derivatives and Dibenzo[b,f][1,4]oxazepines with Azetidine‐2‐carboxylic Acid

et al. 2014

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An enantioselective direct Mannich reaction of different acetophenone derivatives with various substituted seven‐membered cyclic imines using (S)‐azetidine‐2‐carboxylic acid as an organocatalyst is described, which provides an efficient access to optically active 11‐substituted‐10,11‐dihydrodibenzo[b,f][1,4]oxazepine derivatives with 87–95 % ee. For α,β‐unsaturated ketone benzalacetone, the desired Mannich product was obtained with 72 % ee. A plausible transition state is established to explain the observed absolute stereochemistry of the Mannich products. The reaction can also be performed on a gram scale with no adverse effects on the yield and enantioselectivity. Furthermore, some simple transformations involving the Wittig olefination and the decarboxylative reduction of the Mannich products were performed.

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pH-Responsive Molecular Tweezers

Cited by 85 publications

References 27 publications

Switchable Lipids: Conformational Change for Fast pH‐Triggered Cytoplasmic Delivery

Switchable Lipids: Conformational Change for Fast pH‐Triggered Cytoplasmic Delivery

Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid

Organocatalysed Asymmetric Direct Mannich Reaction of Acetophenone Derivatives and Dibenzo[b,f][1,4]oxazepines with Azetidine‐2‐carboxylic Acid

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