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Design and visualization of second‐generation cyanoisoindole‐based fluorescent strigolactone analogs
Author(s) -
Van Overtveldt Melissa,
Braem Lukas,
Struk Sylwia,
Kaczmarek Anna M.,
Boyer FrançoisDidier,
Van Deun Rik,
Gevaert Kris,
Goormachtig Sofie,
Heugebaert Thomas S. A.,
Stevens Christian V.
Publication year - 2019
Publication title -
the plant journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 3.058
H-Index - 269
eISSN - 1365-313X
pISSN - 0960-7412
DOI - 10.1111/tpj.14197
Subject(s) - strigolactone , fluorescence , chemistry , natural product , moiety , computational biology , biology , biochemistry , stereochemistry , mutant , arabidopsis , physics , quantum mechanics , gene
Summary Strigolactones ( SL s) are a family of terpenoid allelochemicals that were recognized as plant hormones only a decade ago. They influence a myriad of both above‐ and below‐ground developmental processes, and are an important survival strategy for plants in nutrient‐deprived soils. A rapidly emerging approach to gain knowledge on hormone signaling is the use of traceable analogs. A unique class of labeled SL analogs was constructed, in which the original tricyclic lactone moiety of natural SL s is replaced by a fluorescent cyanoisoindole ring system. Biological evaluation as parasitic seed germination stimulant and hypocotyl elongation repressor proved the potency of the cyanoisoindole strigolactone analogs ( CISAs ) to be comparable to the commonly accepted standard GR 24. Additionally, via a SMXL 6 protein degradation assay, we provided molecular evidence that the compounds elicit SL ‐like responses through the natural signaling cascade. All CISAs were shown to exhibit fluorescent properties, and the high quantum yield and Stokes shift of the pyrroloindole derivative CISA ‐7 also enabled in vivo visualization in plants. In contrast to the previously reported fluorescent analogs, CISA ‐7 displays a large similarity in shape and structure with natural SL s, which renders the analog a promising tracer to investigate the spatiotemporal distribution of SL s in plants and fungi.

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