Dithiolane linked thiorhodamine dimer for Hg2+ recognition in living cells

Weimin Liu; Liwei Xu; Hongyan Zhang; Juanjuan You; Xiaoling Zhang; Ruilong Sheng; Huaping Li; Shikang Wu; Pengfei Wang

doi:10.1039/B815956D

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Dithiolane linked thiorhodamine dimer for Hg²⁺ recognition in living cells†

Weimin Liu,^a Liwei Xu,^ac Hongyan Zhang,^a Juanjuan You,^ab Xiaoling Zhang,*^c Ruilong Sheng,^a Huaping Li,*^d Shikang Wu^a and Pengfei Wang*^a

Author affiliations

* Corresponding authors

^a Laboratory of Organic Optoelectronic Functional Materials and Molecular Engineering, Technical Institute of Physics and Chemistry, the Chinese Academy of Sciences, Beijing, China
E-mail: wangpf@mail.ipc.ac.cn
Fax: +86-10-82543512
Tel: +86-10-82543512

^b Graduate School of the Chinese Academy of Sciences, Beijing, China

^c Department of Chemistry, School of Sciences, Beijing Institute of Technology
E-mail: zhangxl@bit.edu.cn

^d Center for Polymers and Organic Solids, Departments of Materials, Chemistry & Biochemistry, University of California, Santa Barbara
E-mail: hli@chem.ucsb.edu

Abstract

Thiorhodamine-based chemodosimeter A, a disulfide linked dimer, was designed for Hg²⁺ recognition by virtue of the strong affinity of mercury for sulfur. Spectroscopic results reveal that chemodosimeter A exhibits real-time responses, and high sensitivity and selectivity for Hg²⁺ in comparison to other cations. These properties are mechanistically ascribed to the transfer from rhodamine spirolactam to the thiazoline-derived open-ring rhodamineviaHg²⁺ induced desulfurization. The in vitro recognition of Hg²⁺ in living cells pretreated with A was examined, showing that the concentration of Hg²⁺ that could be imaged reaches the safety limit for human beings.

Download options Please wait...

Supplementary files

IR, ¹H NMR, ¹³C NMR and HRMS spectra of A, B, and C; the reversibility of compound A and B with DETA; the effect of different pH on the fluorescenceresponse of A and A + Hg²⁺; confocal images of living HK-2 cells in the presenceof compound A PDF (2173K)

Article information

DOI: https://doi.org/10.1039/B815956D
Article type: Paper
Submitted: 11 Sep 2008
Accepted: 21 Nov 2008
First published: 06 Jan 2009

Download Citation

Org. Biomol. Chem., 2009,7, 660-664

Permissions

Request permissions

Dithiolane linked thiorhodamine dimer for Hg²⁺ recognition in living cells

W. Liu, L. Xu, H. Zhang, J. You, X. Zhang, R. Sheng, H. Li, S. Wu and P. Wang, Org. Biomol. Chem., 2009, 7, 660 DOI: 10.1039/B815956D

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.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry