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Design, Synthesis and Evaluation of Fluorescent Analogues of Abscisic Acid
Author(s) -
González Florenci V.,
BouIserte Lledó,
MiguelLópez Borja,
HozRodríguez Sergio,
Kersten Christian,
SánchezSarasúa Sandra,
EspinosaFernández Verónica,
SánchezPérez Ana María
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002294
Subject(s) - abscisic acid , chemistry , fluorescence , fluorophore , linker , isomerization , stereochemistry , amine gas treating , biochemistry , biophysics , combinatorial chemistry , catalysis , organic chemistry , biology , physics , quantum mechanics , computer science , gene , operating system
A fluorescent analogue of abscisic acid has been prepared by combining (S)‐abscisic acid (ABA) with nitrobenzoxadiazole (NBD) fluorophore using ethanol amine as a linker. Isomerization of the double bond at the side chain of abscisic acid happened during the synthesis. The resulting fluorophore analogues derived from both isomeric compounds entered cells suggesting a wide applicability of the ABA‐NBD conjugates as fluorescent probes to study ABA mechanism of action. The functional properties of the isomeric ABA‐NBD conjugates were tested in vitro, by measuring TNFα expression and nitrite concentration in LPS‐stimulated macrophages and compared with their non‐fluorescent ABA isomers. Rationalization of the results is given as supported by docking studies of the compounds with LANCL2 and PPARγ targets.