Issue 47, 2022

A turn-on bis-BODIPY chemosensor for copper recognition based on the in situ generation of a benzimidazole–triazole receptor and its applications in bioimaging

Abstract

A highly sensitive and selective off–on bis-BODIPY fluorescent sensor, BODIPY-NN, could be used to detect Cu2+ ions in aqueous solutions and to image intracellular Cu2+ ions in living cells. Upon addition of Cu2+ ions, BODIPY-NN showed a turn-on fluorescence response with 4-fold enhancement at 529 nm, indicating the inhibition of photo-induced electron transfer (PET) from the phenylenediamine–triazole unit to the BODIPY skeleton. This was triggered by oxidative C–N cyclization of phenylenediamine–triazole to in situ form a benzimidazole–triazole receptor providing an appropriate coordination environment that enhances metal ion binding efficiency. A mechanistic study revealed that Cu2+ acts as both a catalyst for oxidative C–N cyclization and a coordination center. The detection limit was determined to be 85 nM. Importantly, BODIPY-NN has been successfully utilized for fluorescence imaging of Cu2+ ions in MCF-7 cells and showed no toxicity toward MCF-7 cells. The non-cytotoxic nature and high sensitivity of BODIPY-NN pave a way for its use in in vivo studies as a promising fluorescent probe for high-performance sensing and bioimaging.

Graphical abstract: A turn-on bis-BODIPY chemosensor for copper recognition based on the in situ generation of a benzimidazole–triazole receptor and its applications in bioimaging

Supplementary files

Article information

Article type
Paper
Submitted
10 Sep 2022
Accepted
07 Nov 2022
First published
22 Nov 2022

New J. Chem., 2022,46, 22525-22532

A turn-on bis-BODIPY chemosensor for copper recognition based on the in situ generation of a benzimidazole–triazole receptor and its applications in bioimaging

W. Saiyasombat, S. Nuchpun, K. P. Katewongsa, S. Pornsuwan, J. J. Weigand and S. Kiatisevi, New J. Chem., 2022, 46, 22525 DOI: 10.1039/D2NJ04508G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements