Elmes, Robert B. P. and Ryan, Gary J. and Erby, Maria Luisa and Frimannsson, Daniel O. and Kitchen, Jonathan A. and Lawler, Mark and Williams, D. Clive and Quinn, Susan J. and Gunnlaugsson, Thorfinnur (2020) Synthesis, Characterization, and Biological Profiling of Ruthenium(II)-Based 4-Nitro- and 4-Amino-1,8-naphthalimide Conjugates. Inorganic Chemistry, 59 (15). pp. 10874-10893. ISSN 0020-1669

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Abstract

We report the synthesis, photophysical characterization, and biological evaluation of four DNA-binding ruthenium(II) polypyridyl 4-nitro- and 4-amino-1,8-naphthalimide conjugates. A meta arrangement around the ring connecting the 1,8-naphthalimide to a bipyridine ligand creates a cleft, the result of which renders the shape of the complex complementary to that of DNA. We have demonstrated that each complex exhibits water solubility and a distinctive set of photophysical properties that has allowed the nature of their interaction with DNA to be probed by various ground- and excited-state titrations. Furthermore, by varying the ancillary ligands, we also demonstrate their ability to act as DNA photocleavers, where all compounds have been found to cleave supercoiled DNA with high efficiency. Detailed cellular uptake experiments revealed that the conjugates accumulate in the cytoplasm and nucleus of HeLa cells, showing characteristic red metal-to-ligand charge-transfer emission, and also exhibit photoactivated cytotoxicity within the cells upon irradiation at 450 nm. A comparison between the meta and para arrangements of the 1,8-naphthalimide moiety relative to the Ru(II) center suggests increased DNA binding in the case of the meta arrangement; however, bipyridine–4-amino-1,8-naphthalimide conjugates appear to show superior phototoxicity in comparison to their 4-nitro derivatives.

Item Type:	Article
Keywords:	Synthesis; Characterization; Biological Profiling; Ruthenium(II)-Based 4-Nitro; 4-Amino-1; 8-naphthalimide; Conjugates;
Academic Unit:	Faculty of Science and Engineering > Chemistry Faculty of Science and Engineering > Research Institutes > Human Health Institute
Item ID:	16164
Identification Number:	https://doi.org/10.1021/acs.inorgchem.0c01395
Depositing User:	Robert Elmes
Date Deposited:	21 Jun 2022 11:50
Journal or Publication Title:	Inorganic Chemistry
Refereed:	Yes
URI:	Publisher
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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