Citation: Lei Shen, Hongmei Liu, Ming Jin, Jinchao Zhang, Caixia Yin, Shuxiang Wang, Yutao Yang. “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone[J]. Chinese Chemical Letters, ;2024, 35(10): 109572. doi: 10.1016/j.cclet.2024.109572 shu

“Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone

Lei Shen ^a ,
Hongmei Liu ^a ,
Ming Jin ^a ,
Jinchao Zhang ^a ,
Caixia Yin ^{b, *,} ,
Shuxiang Wang ^{a, *,} ,
Yutao Yang ^{a, *,}

a.
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Chemical Biology Key Laboratory of Hebei Province, State Key Laboratory of New Pharmaceutical Preparations and Excipients, College of Chemistry and Materials Science, Hebei University, Baoding 071002, China
b.
Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China

yincx@sxu.edu.cn

wsx@hbu.edu.cn

yutaoyang2016@163.com

Received Date: 13 December 2023
Revised Date: 24 January 2024
Accepted Date: 25 January 2024
Available Online: 2 February 2024

Figures(4)

Epilepsy, as a chronic neurological disease of the brain, is closely related to oxidative stress, and the peroxynitrite (ONOO⁻) significantly rise up in this event. Therefore, ONOO⁻ is considered as a potential biomarker for early prediction of epilepsy. However, some potential diagnostic reagents for epilepsy are hindered by the blood-brain barrier (BBB). Meanwhile, “drug repurposing” is attracting a growing interest. Edaravone (EDA), as a first-line drug in the clinical treatment of cerebral ischemia, plays antioxidant roles in scavenging free radicals, promising potential antiepileptic activity. Thus, it is imperative to develop fluorescent probes for monitoring ONOO⁻ fluctuations in the epileptic brain. Hence, we proposed a novel fluorescent probe with the thiocarbonate as the promising recognition unit for ONOO⁻ and dicyanoisophorone derivative as the fluorophore. Moreover, by the “three-in-one” strategy, the introduction of trifluoromethyl into DCI-ONOO-3 can extend the emission wavelength of the fluorophore, shorten the response and increase lipophilicity. Consequently, DCI-ONOO-3 was used for monitoring ONOO⁻ fluxes in brain of epileptic mice and evaluating the antiepileptic efficacy of EDA. It opens up a new way for the design of BBB permeable fluorescent probes, and provides a convincing new method for the diagnosis and treatment of epilepsy.
- Fluorescent probe,
- Blood-brain barrier,
- Peroxynitrite,
- Epilepsy,
- Drug repurposing
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