Utilization of Rhenium(I) Polypyridine Complexes Featuring a Dinitrophenylsulfonamide Moiety as Biothiol-Selective Phosphorogenic Bioimaging Reagents and Photocytotoxic Agents

Guang-Xi Xu; Lawrence Cho-Cheung Lee; Cyrus Wing-Ching Kwok; Peter Kam-Keung Leung; Jing-Hui Zhu; Kenneth Kam-Wing Lo

doi:10.1002/ejic.202100364

Author(s)

Cyrus Wing-Ching Kwok

Related Research Unit(s)

Detail(s)

Original language	English
Pages (from-to)	3432-3442
Journal / Publication	European Journal of Inorganic Chemistry
Volume	2021
Issue number	34
Online published	15 Jun 2021
Publication status	Published - 14 Sept 2021

Link(s)

DOI	DOI https://doi.org/10.1002/ejic.202100364 Final Published version
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Attachment(s)	Documents 80194509.pdf Post-print, 2.25 MB, PDF Publisher's Copyright Statement COPYRIGHT TERMS OF DEPOSITED POSTPRINT FILE: This is the peer reviewed version of the following article: Xu, G-X., Lee, L. C-C., Kwok, C. W-C., Leung, P. K-K., Zhu, J-H., & Lo, K. K-W. (2021). Utilization of Rhenium(I) Polypyridine Complexes Featuring a Dinitrophenylsulfonamide Moiety as Biothiol-Selective Phosphorogenic Bioimaging Reagents and Photocytotoxic Agents. European Journal of Inorganic Chemistry, 2021(34), 3432-3442, which has been published in final form at https://doi.org/10.1002/ejic.202100364. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
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Permanent Link	https://scholars.cityu.edu.hk/en/publications/publication(bbad34c9-db3e-40b3-9968-3b81efd82cb3).html

Abstract

We report herein a series of rhenium(I) polypyridine complexes featuring a 2,4-dinitrophenylsulfonamide (DNPS) unit as phosphorogenic bioimaging reagents and photocytotoxic agents. The biothiol-selective rhenium(I) polypyridine complexes [Re(N^N)(CO)₃(py-DNPS)](CF₃SO₃) (py-DNPS=3-((2,4-dinitrophenylsulfonyl)aminomethyl)pyridine) and their DNPS-free counterparts [Re(N^N)(CO)₃(pyridine)](CF₃SO₃) were synthesized and characterized. Upon photoexcitation, the DNPS complexes exhibited very weak luminescence as a result of photoinduced electron transfer (PET) from the excited rhenium(I) diimine moiety to the DNPS quenching unit. However, upon treatment with glutathione (GSH), the DNPS moiety was removed, resulting in emission enhancement of the solutions (I/I_o=12.6–22.2). After reaction of the DNPS complexes with GSH in living cells, intense intracellular emission and potent photocytotoxicity were both observed. Additionally, the modification of the diimine ligand with a tosylamide unit conferred on the complexes an endoplasmic reticulum (ER)-targeting ability, which can be exploited for selective bioimaging and photocytotoxic applications.