title: Synthesis, resolution and biological evaluation of cyclopropyl analogs of abscisic acid.
abstract: cis-2,3-Cyclopropanated abscisic acid (cis-CpABA) has high photostability and good ABA-like activity. To further investigate its activity and action mechanism, 2S,3S-2,3-cyclopropanated ABA (3a) and 2R,3R-2,3-cyclopropanated ABA (3b) were synthesized. Bioassay showed that 3a displayed higher inhibitory activity in germination than that of 3b and ABA at the concentration of 3.0 μM, but 3a and 3b had much weaker inhibitory activity in inhibition seedling growth compared to ABA. The study of photostability revealed that 3a and 3b showed high stability under UV light exposure, which were 4 times and 3 times greater than (±)-ABA, respectively. Action mechanism study showed that 3a presented higher inhibition on phosphatase activity of HAB1 than 3b, although they all inferior to ABA. Molecular docking studies of 3a, 3b and ABA receptor PYL10 were agreement with the bioassay data and confirmed the importance of the configuration of the 2,3-cyclopropyl ABA analogs for their bioactivity in somewhat. This study provides a new approach for the design of ABA analogs, and the results validated structure-based design for this target class.
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Xiaoqiang
authors: X
authors: Han
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Jinlong
authors: J
authors: Fan
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Huizhe
authors: H
authors: Lu
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Chuan
authors: C
authors: Wan
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Xiuyun
authors: X
authors: Li
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Hong
authors: H
authors: Li
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Dongyan
authors: D
authors: Yang
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Yuanzhi
authors: Y
authors: Zhang
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. Electronic address: xiaoyumei@cau.edu.cn.
authors: Yumei
authors: Y
authors: Xiao
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. Electronic address: qinzhaohai@263.net.
authors: Zhaohai
authors: Z
authors: Qin
mesh_terms: D000040:Abscisic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D017360:Arabidopsis / Q000254:growth & development / Q000378:metabolism; D029681:Arabidopsis Proteins / Q000037:antagonists & inhibitors / Q000235:genetics / Q000378:metabolism; D001665:Binding Sites; D003521:Cyclopropanes / Q000737:chemistry; D018525:Germination / Q000187:drug effects; D062105:Molecular Docking Simulation; D000081222:Monocyclic Sesquiterpenes; D010749:Phosphoprotein Phosphatases / Q000037:antagonists & inhibitors / Q000235:genetics / Q000378:metabolism; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017434:Protein Structure, Tertiary; D011994:Recombinant Proteins / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification; D012639:Seeds / Q000254:growth & development
chemical_list: C000588996:2,3-cyclopropanated abscisic acid; D029681:Arabidopsis Proteins; D003521:Cyclopropanes; D000081222:Monocyclic Sesquiterpenes; D010937:Plant Growth Regulators; D011994:Recombinant Proteins; D000040:Abscisic Acid; C514757:HAB1 protein, Arabidopsis; D010749:Phosphoprotein Phosphatases
keywords: 2,3-Cyclopropanated abscisic acid; Abscisic acid; Bioactivity; Molecular docking; Photostability