Synthesis and Biological Activity of 2′,3′-iso-Aryl-abscisic Acid Analogs

Abstract

2′,3′-iso-Benzoabscisic acid (iso-PhABA), an excellent selective abscisic acid (ABA) analog, was developed in our previous work. In order to find its more structure-activity information, some structural modifications were completed in this paper, including the substitution of phenyl ring and replacing the ring with heterocycles. Thus, 16 novel analogs of iso-PhABA were synthesized and screened with three bioassays, Arabidopsis and lettuce seed germination and rice seedling elongation. Some of them, i.e., 2′,3′-iso-pyridoabscisic acid (iso-PyABA) and 2′,3′-iso-franoabscisic acid (iso-FrABA), displayed good bioactivities that closed to iso-PhABA and natural (+)-ABA. Some others, for instance, substituted-iso-PhABA, exhibited certain selectivity to different physiological process when compared to iso-PhABA or (+)-ABA. These analogs not only provided new candidates of ABA-like synthetic plant growth regulators (PGRs) for practical application, but also new potential selective agonist/antagonist for probing the specific function of ABA receptors.

APAn, a Class of ABA Receptor Agonism/Antagonism Switching Probes

“…Microscale Thermophoresis (MST). 29 The ABA receptor PYLs (PYR1, PYL2, and PYL5) were labeled with the red fluorescent dye NT-647-NHS, using the Monolith NT Protein Labeling Kit according to the user's instructions. Compounds were dissolved in DMSO, and a dilution series of the compounds (16 concentrations, 0.015−1000 μM) were prepared using the PBS buffer.…”

“…Phosphatase HAB1 Inhibition Assay. 29 The phosphatase HAB1 activity assay was performed using a Promega's Serine/Threonine Phosphatase Assay System kit. PYLs (3 μM) and 1 μM HAB1 were dissolved and incubated in Tris buffer at room temperature for 20 min.…”

Function and Mechanism of Abscisic Acid on Microglia-Induced Neuroinflammation in Parkinson’s Disease

“…Compared with left-handed compounds, right-handed compounds have stronger biological activity but degrade faster [139]. Its physiological activity depends on the presence of free carboxyl groups, a double bond at alpha-or beta-on the cyclohexane ring, and a double bond at C-2 [140]. The biosynthesis of ABA in plants consists of two pathways: the terpenoid pathway, which directly syntheses ABA from mevalonate (MVA); and the carotenoid pathway, where ABA is indirectly synthesized through the subsequent oxidative cleavage of all-trans C40 carotenoid precursors [141].…”

Synthesis of All Stereoisomers of RK460 and Evaluation of Their Activity and Selectivity as Abscisic Acid Receptor Antagonists

“…Following the discovery of pyrabactin ( 2 ), a potent PYR1 (and weak PYL1) agonist and an antagonist of PYL2 and PYL3, several ABA ligands have recently been developed . Focusing on the antagonists, the ABA derivative PBI‐51 was first identified, and then DFPM ([5‐(3,4‐dichlorophenyl)furan‐2‐yl]‐piperidine‐1‐ylmethanethione) derivatives, AS (3′‐alkylsulfanyl ABA) derivatives, PAO (propenyl‐ABA with an O ‐alkyl chain) derivatives, 6‐ or 7′‐nor‐ABA, AA1, 2′,3′‐ iso ‐aryl‐ABA analogues, JFA1, JFA2, and PANMe were obtained by screening or rational design based on the crystal structures of complexes of these receptors with ABA or pyrabactin . However, antagonists with high subtype selectivity are needed for functional analysis of ABA receptor subtypes.…”