Naphthalimide-based macrophage nucleus imaging probes

The photophysical properties of naphthalimide-based fluorophores can be easily tuned by chemical manipulation of the substituents on that privileged scaffold. Replacement of a OMe group at position 6 in 2-(hydroxyl)ethyl-naphthalimide derivatives by diverse amines, including 2-(hydroxyl)ethylamine,...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2020-08, Vol.200, p.112407-112407, Article 112407
Main Authors: Fueyo-González, Francisco, Fernández-Gutiérrez, Mar, García-Puentes, Diego, Orte, Angel, González-Vera, Juan A., Herranz, Rosario
Format: Article
Language:English
Subjects:
DNA intercalants
Fluorescence probes
Macrophage imaging probes
Naphthalimide derivatives
Quinolimide derivatives
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Summary:The photophysical properties of naphthalimide-based fluorophores can be easily tuned by chemical manipulation of the substituents on that privileged scaffold. Replacement of a OMe group at position 6 in 2-(hydroxyl)ethyl-naphthalimide derivatives by diverse amines, including 2-(hydroxyl)ethylamine, trans-(4-acetamido)cyclohexylamine and azetidine increases the solvatochromic (ICT) character, while this replacement in 2-(dimethylamino)ethyl-naphthalimide analogues (PET fluorophores) decrease their solvent polarity sensitivity or even reversed them to solvatochromic fluorophores. These fluorophores resulted macrophage nucleus imaging probes, which bind DNA as intercalants and showed low cytotoxicity in human cancer cells. [Display omitted] •New naphthalimide and quinolimide-based fluorophores are described.•Properties of naphthalimide-based fluorophores have been tuned by substituent manipulation.•DNA intercalating properties provide macrophage nucleus fluorescence imaging.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2020.112407