Dataset Information

Two-step synthesis of a red-emissive warped nanographene derivative via a ten-fold C-H borylation.

ABSTRACT: The regioselective ten-fold borylation of warped nanographene (WNG: C₈₀H₃₀) was achieved by modifying the reaction conditions of a previously reported Ir-catalyzed C-H borylation, affording decaborylated WNG in high yield (75%) from pristine WNG. The solid-state structure of decaborylated WNG was confirmed by X-ray crystallography. Corresponding decaarylated WNGs containing electron-withdrawing and -donating groups were synthesized from decaborylated WNG using Suzuki-Miyaura cross-coupling reactions to afford the red-emissive warped nanographene derivative.

SUBMITTER: Kato K

PROVIDER: S-EPMC6857738 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Two-step synthesis of a red-emissive warped nanographene derivative via a ten-fold C-H borylation.

Kato Kenta K Lin Hsing-An HA Kuwayama Motonobu M Nagase Mai M Segawa Yasutomo Y Scott Lawrence T LT Itami Kenichiro K

Chemical science 20190809 39

The regioselective ten-fold borylation of warped nanographene (WNG: C80H30) was achieved by modifying the reaction conditions of a previously reported Ir-catalyzed C-H borylation, affording decaborylated WNG in high yield (75%) from pristine WNG. The solid-state structure of decaborylated WNG was confirmed by X-ray crystallography. Corresponding decaarylated WNGs containing electron-withdrawing and -donating groups were synthesized from decaborylated WNG using Suzuki-Miyaur ...[more]

PMID: 31762982

Similar Datasets

Project description:Optical microscopy techniques are ideal for live cell imaging for real-time nanoparticle tracking of nanoparticle localization. However, the quantification of nanoparticle uptake is usually evaluated by analytical methods that require cell isolation. Luminescent labeling of gold nanoparticles with transition metal probes yields particles with attractive photophysical properties, enabling cellular tracking using confocal and time-resolved microscopies. In the current study, gold nanoparticles coated with a red-luminescent ruthenium transition metal complex are used to quantify and track particle uptake and localization. Analysis of the red-luminescence signal from particles is used as a metric of cellular uptake, which correlates to total cellular gold and ruthenium content, independently measured and correlated by inductively coupled plasma mass spectrometry. Tracking of the luminescence signal provides evidence of direct diffusion of the nanoparticles across the cytoplasmic membrane with particles observed in the cytoplasm and mitochondria as nonclustered "free" nanoparticles. Electron microscopy and inhibition studies identified macropinocytosis of clusters of particles into endosomes as the major mechanism of uptake. Nanoparticles were tracked inside GFP-tagged cells by following the red-luminescence signal of the ruthenium complex. Tracking of the particles demonstrates their initial location in early endosomes and, later, in lysosomes and autophagosomes. Colocalization was quantified by calculating the Pearson's correlation coefficient between red and green luminescence signals and confirmed by electron microscopy. Accumulation of particles in autophagosomes correlated with biochemical evidence of active autophagy, but there was no evidence of detachment of the luminescent label or breakup of the gold core. Instead, accumulation of particles in autophagosomes caused organelle swelling, breakdown of the surrounding membranes, and endosomal release of the nanoparticles into the cytoplasm. The phenomenon of endosomal release has important consequences for the toxicity, cellular targeting, and therapeutic future applications of gold nanoparticles.

Dataset Information

Two-step synthesis of a red-emissive warped nanographene derivative via a ten-fold C-H borylation.

Publications

Two-step synthesis of a red-emissive warped nanographene derivative <i>via</i> a ten-fold C-H borylation.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets