4-Azido-7-nitrobenzoxadiazole as innovative clickable fluorescence probe for trace and selective quantification of ethinylestradiol in human plasma.

Autor: Aref HA; Medicinal Chemistry Department, Faculty of Pharmacy, El Mounufia University, El Mounufia, Egypt., Salama I; Medicinal Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt., Aboukhatwa SM; Medicinal Chemistry Department, Faculty of Pharmacy, Tanta University, Tanta, Egypt., Helal MA; Biomedical Sciences Program, University of Science and Technology, Zewail City of Science and Technology, Giza, Egypt., Kishk SM; Medicinal Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt., Elgawish MS; Medicinal Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt.
Jazyk: angličtina
Zdroj: Luminescence : the journal of biological and chemical luminescence [Luminescence] 2023 Nov; Vol. 38 (11), pp. 1848-1856. Date of Electronic Publication: 2023 Aug 27.
DOI: 10.1002/bio.4571
Abstrakt: Quantification of ethinylestradiol (EE) in biological matrices is challenging as it is a very potent drug with a very low C max (75 pg.ml -1 ). Despite the high sensitivity of fluorometric methods, the detection of EE was confined because its structure exhibited very limited fluorescence. Therefore, it must be derivatized first using a fluorogenic agent to produce a more potent fluorescence derivative to achieve the desired ultrasensitive bioanalysis. Here, for the first time, we proposed a promising click fluorescent probe, 4-azido-7-nitrobenzoxadiazole (NBD-AZ) to react with the alkyne group of EE, with the help of copper sulphate and l-ascorbic acid to give a highly fluorescent and stable 1,2,3-triazole derivative. Density functional theory calculation revealed how the triazole formation affects the quantum yield and fluorescence of click reaction product when compared with NBD-AZ. The resulting triazole exhibited a strong signal at a wavelength of 540 nm after excitation at 470 nm. Reaction parameters impacting the intensity of fluorescence were cautiously studied and optimized. The suggested approach has shown outstanding performance, high linearity (25-300 pg.ml -1 ) and a low detection limit of 7.5 pg.ml -1 . The enhanced sensitivity and selectivity were exploited for analyzing EE in plasma using liquid-liquid extraction for samples cleaning up without interference from any biological components and with a mean % recovery of 100.13 ± 0.39. Accuracy, sensitivity, selectivity, simplicity, and cost-effectiveness make this approach a convincing, promising, and appealing alternative to the reported analytical methods for EE bioanalysis in different matrices.
(© 2023 John Wiley & Sons Ltd.)
Databáze: MEDLINE
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