title: Design and synthesis of biotin-tagged photoaffinity probes of jasmonates.
abstract: Jasmonates (JAs) are a class of oxylipin compounds that play diverse roles in plant defense and development. The F-box protein coronatine insensitive 1 (COI1) plays a crucial role in the JA signaling pathway. To determine whether COI1 binds directly to jasmonates, three biotin-tagged photoaffinity probes for JAs, a jasmonic acid photoaffinity probe (PAJA), a JAIle photoaffinity probe (PAJAIle), and a coronatine photoaffinity probe (PACOR), were designed and synthesized based on analysis of JA structure-activity relationships and molecular modeling of the interaction between COI1 and JAs. Among them, PACOR exhibited the most significant biological activity in inhibiting root growth, promoting accumulation of JA-responsive proteins, and triggering COI1-JAZ1 interaction in Arabidopsis seedlings. PACOR is an effective tool for elucidating the interaction between COI1 and JA.
authors.affiliation: Department of Chemistry and Institute of Medicinal Chemistry, East China Normal University, 3663 North Zhong Shan Road, Shanghai 200062, China.
authors.forename: Min
authors.initials: M
authors.lastname: Gu
authors.forename: Jianbin
authors.initials: J
authors.lastname: Yan
authors.forename: Zhiyan
authors.initials: Z
authors.lastname: Bai
authors.forename: Yue-Ting
authors.initials: YT
authors.lastname: Chen
authors.forename: Wei
authors.initials: W
authors.lastname: Lu
authors.forename: Jie
authors.initials: J
authors.lastname: Tang
authors.forename: Liusheng
authors.initials: L
authors.lastname: Duan
authors.forename: Daoxin
authors.initials: D
authors.lastname: Xie
authors.forename: Fa-Jun
authors.initials: FJ
authors.lastname: Nan
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism; D029681:Arabidopsis Proteins / Q000737:chemistry / Q000378:metabolism; D001710:Biotin; D003517:Cyclopentanes / Q000737:chemistry* / Q000378:metabolism; D015195:Drug Design; D007192:Indenes / Q000737:chemistry / Q000378:metabolism; D008027:Light; D008958:Models, Molecular; D015394:Molecular Structure; D054883:Oxylipins / Q000737:chemistry* / Q000378:metabolism; D019920:Photoaffinity Labels / Q000138:chemical synthesis / Q000737:chemistry; D010777:Photochemistry; D015398:Signal Transduction; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D029681:Arabidopsis Proteins; C112279:COI1 protein, Arabidopsis; D003517:Cyclopentanes; D007192:Indenes; D054883:Oxylipins; D019920:Photoaffinity Labels; C058487:coronatine; C011006:jasmonic acid; D001710:Biotin