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2024-09-16

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cc by-nc (c) Camerin, Luisa et al, 2024
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/215169

Photoswitchable Carbamazepine Analogs for Non-Invasive Neuroinhibition In Vivo

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https://doi.org/10.1002/anie.202403636

Abstract

A problem of systemic pharmacotherapy is off-target activity, which causes adverse effects. Outstanding examples include neuroinhibitory medications like antiseizure drugs, which are used against epilepsy and neuropathic pain but cause systemic side effects. There is a need of drugs that inhibit nerve signals locally and on-demand without affecting other regions of the body. Photopharmacology aims to address this problem with light-activated drugs and localized illumination in the target organ. Here, we have developed photoswitchable derivatives of the widely prescribed antiseizure drug carbamazepine. For that purpose, we expanded our method of ortho azologization of tricyclic drugs to meta/para and to N-bridged diazocine. Our results validate the concept of ortho cryptoazologs (uniquely exemplified by Carbazopine-1) and bring to light Carbadiazocine (8), which can be photoswitched between 400-590 nm light (using violet LEDs and halogen lamps) and shows good drug-likeness and predicted safety. Both compounds display photoswitchable activity in vitro and in translucent zebrafish larvae. Carbadiazocine (8) also offers in vivo analgesic efficacy (mechanical and thermal stimuli) in a rat model of neuropathic pain and a simple and compelling treatment demonstration with non-invasive illumination.

Subject

Epilèpsia, Fotofarmacologia

Subject (English)

Epilepsy, Photopharmacology

Citation

Camerin, Luisa; Maleeva, Galyna; Gomila, Alexandre M J; Suarez-Pereira, Irene; Matera, Carlo; Prischich, Davia; Opar, Ekin; Riefolo, Fabio; Berrocoso, (2024). Photoswitchable Carbamazepine Analogs for Non-Invasive Neuroinhibition In Vivo. Angewandte Chemie (International Ed. Print), (), e202403636-. DOI: 10.1002/anie.202403636

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Articles publicats en revistes (Institut de Bioenginyeria de Catalunya (IBEC))

Citation

CAMERIN, Luisa, et al. Photoswitchable Carbamazepine Analogs for Non-Invasive Neuroinhibition In Vivo. Angewandte Chemie (International Ed. Print). 2024. Vol. 63, num. 38. ISSN 1521-3773. [consulted: 11 of June of 2026]. Available at: https://hdl.handle.net/2445/215169

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