Delta(2)-oxazolines-1,3 and N-acylaziridines as potential proinsecticides of carboxylic acids. V. Direct thin-layer chromatography monitoring of the metabolism in locust tissues. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Chromatography B Biomedical Sciences and Applications Année : 2001

Delta(2)-oxazolines-1,3 and N-acylaziridines as potential proinsecticides of carboxylic acids. V. Direct thin-layer chromatography monitoring of the metabolism in locust tissues.

J.C Cherton
  • Fonction : Auteur
A Carlin-Sinclair
  • Fonction : Auteur
S Hamm
  • Fonction : Auteur

Résumé

Modern thin-layer chromatography (TLC) was used for the evaluation of delta2-oxazolines-1,3 I and N-acylaziridine VII structures, as potential proinsecticides of carboxylic acids III. Thus the unmasking2 of the active principles III from delta2-oxazolines-1,3 Ia-c and N-acylaziridine VIIc was monitored by spotting aliquots directly onto RP-18 TLC plates, without any sample pretreatment during in vitro assays performed in concentrated locust tissues. To achieve a good separation of carboxylate IIIa from endogenous components of the tissues, a short preliminary development with methanol or ion-pairing was necessary. From UV-TLC chromatograms (densitograms) it appeared that in a phosphate buffer at pH 7.4, the oxazoline Ia with a C2 substituent devoid of alpha-ramification or alpha,beta-insaturation hydrolysed slowly into the corresponding beta-hydroxylamide VIa and intermediate aminoester Va. Significantly, locust mesenteron (or fat body) efficiently triggered the unmasking of IIIa, a transformation which corresponds to the expected proinsecticide behavior of Ia. Conducting TLC monitoring in the same locust tissues also revealed that the oxazolines Ib and Ic with an alpha-ramification and an alpha,beta-insaturation, respectively, cannot be considered as proinsecticides of the corresponding carboxylic acids IIIb and IIIc. In contrast, the N-acylaziridine VIIc appeared as a convenient proinsecticide structure for masking the carboxylic acid IIIc.

Dates et versions

hal-02149591 , version 1 (06-06-2019)

Identifiants

Citer

M. Beaufour, J.C Cherton, A Carlin-Sinclair, S Hamm. Delta(2)-oxazolines-1,3 and N-acylaziridines as potential proinsecticides of carboxylic acids. V. Direct thin-layer chromatography monitoring of the metabolism in locust tissues.. Journal of Chromatography B Biomedical Sciences and Applications, 2001, 761 (1), pp.35-45. ⟨10.1016/S0378-4347(01)00295-X⟩. ⟨hal-02149591⟩

Collections

CNRS UVSQ
8 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Mastodon Facebook X LinkedIn More