Mono- and bis-edaravone adducts formed in the presence of vanillin in an aqueous solution

Regnault, Romain; Kouach, Mostafa; Goossens, Laurence; Thuru, Xavier; Bailly, Christian; Goossens, Jean-Francois

Document type :

Article dans une revue scientifique: Article original

DOI :

10.1002/sscp.202200031

Permalink :

http://hdl.handle.net/20.500.12210/82573

Title :

Mono- and bis-edaravone adducts formed in the presence of vanillin in an aqueous solution

Author(s) :

Regnault, Romain [Auteur]
Groupe de Recherche sur les formes Injectables et les Technologies Associées - ULR 7365 [GRITA]
Kouach, Mostafa [Auteur]

Groupe de Recherche sur les formes Injectables et les Technologies Associées (GRITA) - ULR 7365
Goossens, Laurence [Auteur]

Groupe de Recherche sur les formes Injectables et les Technologies Associées (GRITA) - ULR 7365
Thuru, Xavier [Auteur]

Cancer Heterogeneity, Plasticity and Resistance to Therapies (CANTHER) - UMR 9020 - UMR 1277
Bailly, Christian [Auteur]
Oncowitan [Wasquehal]
Goossens, Jean-Francois [Auteur]

Groupe de Recherche sur les formes Injectables et les Technologies Associées (GRITA) - ULR 7365

Journal title :

SEPARATION SCIENCE PLUS

Abbreviated title :

Sep. Sci. Plus

Publication date :

2022-05-06

ISSN :

2573-1815

Keyword(s) :

aldehyde reactivity
drug adducts
edaravone
pyrazolone
vanillin

HAL domain(s) :

Sciences du Vivant [q-bio]

English abstract : [en]

Edaravone is an antioxidant drug used for the treatment of amyotrophic lateral sclerosis. Edaravone has been shown to react with aldehydes, such as 6-formylpterin. We investigated the reaction of edaravone with vanillin ...
Show more >Edaravone is an antioxidant drug used for the treatment of amyotrophic lateral sclerosis. Edaravone has been shown to react with aldehydes, such as 6-formylpterin. We investigated the reaction of edaravone with vanillin (used as a model aromatic aldehyde) to evidence the reaction products formed in an aqueous solution. Mono- and bis-adducts vanillin-(edaravone)1-2 were characterized by high-performance liquid chromatography coupled to high-resolution mass spectrometry. Kinetic analysis revealed that the bis-adduct vanillin-(edaravone)2 formed more intensely and more rapidly than the mono-adduct vanillin-(edaravone)1. Decay rates of 2.4 and 3.4 μM/min were calculated for vanillin and edaravone, respectively. The Michael addition of a second edaravone molecule onto the vanillin-(edaravone)1 hybrid corresponds to a facile reaction compared to the initial Knoevenagel-type condensation between edaravone and vanillin. However, the bis-adduct vanillin-(edaravone)2 can decompose in solution to provide the mono-adduct and regenerate small amounts of edaravone and vanillin. The regeneration of vanillin from vanillin-(edaravone)2 was kinetically characterized. We compared the condensation of edaravone with fifteen aromatic aldehydes, to show that only vanillin and 3-methoxy-benzaldehyde can react easily with edaravone, the other aromatic aldehydes being less or not reactive. The study opens perspectives to apprehend the reactivity of edaravone with biologically relevant aldehydes.Show less >

Language :

Anglais

Audience :

Internationale

Popular science :

Non

Administrative institution(s) :

Université de Lille
CHU Lille

Collections :

Groupe de Recherche sur les formes Injectables et les Technologies Associées (GRITA) - ULR 7365

Submission date :

2023-05-25T04:09:11Z
2023-09-11T06:52:41Z

Version	Link	Modification date
2	20.500.12210/82573*	2023-09-11T06:48:14Z
1	20.500.12210/82573.1	2023-05-25T04:09:11Z

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Mono- and bis-edaravone adducts formed in ...

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