Promising Luminescent Sensors Based on New Maleimide Derivatives of 1,8-Naphthalimide for the Selective Detection of Biogenic Thiols

Abstract

Cysteine, homocysteine, and glutathione are biogenic thiols. They perform important functions in the human body: they maintain the redox homeostasis of cells, regulate many signaling processes, etc. Changes in the concentration of these substances in the blood cause serious disturbances in the functioning of important body systems and can thus lead to the development of serious diseases. In this regard, the development of new sensor substances that are sensitive to these changes is an important task for modern bio-medical research. The article synthesizes two types of new 1,8-naphthalimide derivatives (fluorophores 8, 9, and 14, 17) that can be used for the detection of biogenic thiols. The first type contains a maleimide functional group in the 4th position of the aromatic ring, and the second has it at the imide nitrogen atom. For the target compounds, the effect of changing the concentration of cysteine on the spectral lumines-cence properties in a phosphate buffer solution was studied. Due to the presence of photoinduced electron transfer (PET), the initial fluorophores 8, 9, 14, and 17 have low brightness and fluorescence quantum yields. The addition of biogenic thiol to them leads to a significant increase in the fluorescence intensity of the dyes. The latter is due to the Michael reaction, accompanied by the formation of adducts with significantly more pronounced luminescent properties. For the lead compounds (fluorophores 8, and 17) detection concentration limits were calculated, which amounted to 5 and 13 nM. Their low values, combined with unique optical properties, allow the new maleimide derivatives of 1,8-naphthalimide to be considered as promising luminescent sensors for biogenic thiols

The work was carried out with support from the Ministry of Science and Higher Education of the Russian Federation as part of a State Assignment (FSSM-2025-0002)

Please cite this article in English as:

Yuriev D.Yu., Tkachenko S.V., Oshchepkov M.S., et al. Promising luminescent sensors based on new maleimide derivatives of 1,8-naphthalimide for the selective detection of biogenic thiols. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2026, no. 2 (125), pp. 111--131 (in Russ.). EDN: VVHNQZ

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