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Utilization of Rhenium(I) Polypyridine Complexes Featuring a Dinitrophenylsulfonamide Moiety as Biothiol‐Selective Phosphorogenic Bioimaging Reagents and Photocytotoxic Agents
Author(s) -
Xu GuangXi,
Lee Lawrence ChoCheung,
Kwok Cyrus WingChing,
Leung Peter KamKeung,
Zhu JingHui,
Lo Kenneth KamWing
Publication year - 2021
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202100364
Subject(s) - chemistry , rhenium , moiety , diimine , pyridine , photochemistry , reagent , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
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)](CF 3 SO 3 ) (py‐DNPS=3‐((2,4‐dinitrophenylsulfonyl)aminomethyl)pyridine) and their DNPS‐free counterparts [Re(N^N)(CO) 3 (pyridine)](CF 3 SO 3 ) 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.