Design and synthesis of biotin-tagged photoaffinity probes of jasmonates.
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.
Gu
Min
M
Department of Chemistry and Institute of Medicinal Chemistry, East China Normal University, 3663 North Zhong Shan Road, Shanghai 200062, China.
Yan
Jianbin
J
Bai
Zhiyan
Z
Chen
Yue-Ting
YT
Lu
Wei
W
Tang
Jie
J
Duan
Liusheng
L
Xie
Daoxin
D
Nan
Fa-Jun
FJ
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
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