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Design and visualization of second generation cyanoisoindole based fluorescent strigolactone analogs

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Abstract
Strigolactones (SLs) are a family of terpenoid allelochemicals that were recognized as plant hormones only a decade ago. They influence a myriad of both above- and belowground 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, where the original tricyclic lactone moiety of natural SLs 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 (CISA) to be comparable to the commonly accepted standard GR24. Additionally, via a SMXL6 protein degradation assay, we provided molecular evidence that the compounds elicit SL-like responses through the natural signaling cascade. All CISA analogs 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 SLs, which renders the analog a promising tracer to investigate the spatiotemporal distribution of SLs in plants and fungi.
Keywords
Arabidopsis thaliana, Phelipanche ramosa, SMXL6 degradation, fluorescence labeling, hypocotyl elongation, isoindole, parasitic seed germination, pyrroloindole, strigolactone

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Chicago
Van Overtveldt, Melissa, Lukas Braem, Sylwia Magdalena Struk, Anna Kaczmarek, François‐Didier Boyer, Rik Van Deun, Kris Gevaert, Sofie Goormachtig, Thomas Heugebaert, and Christian Stevens. 2019. “Design and Visualization of Second Generation Cyanoisoindole Based Fluorescent Strigolactone Analogs.” Plant Journal.
APA
Van Overtveldt, M., Braem, L., Struk, S. M., Kaczmarek, A., Boyer, F., Van Deun, R., Gevaert, K., et al. (2019). Design and visualization of second generation cyanoisoindole based fluorescent strigolactone analogs. PLANT JOURNAL.
Vancouver
1.
Van Overtveldt M, Braem L, Struk SM, Kaczmarek A, Boyer F, Van Deun R, et al. Design and visualization of second generation cyanoisoindole based fluorescent strigolactone analogs. PLANT JOURNAL. 2019;
MLA
Van Overtveldt, Melissa, Lukas Braem, Sylwia Magdalena Struk, et al. “Design and Visualization of Second Generation Cyanoisoindole Based Fluorescent Strigolactone Analogs.” PLANT JOURNAL (2019): n. pag. Print.
@article{8586053,
  abstract     = {Strigolactones (SLs) are a family of terpenoid allelochemicals that were recognized as plant hormones only a decade ago. They influence a myriad of both above- and belowground 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, where the original tricyclic lactone moiety of natural SLs 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 (CISA) to be comparable to the commonly accepted standard GR24. Additionally, via a SMXL6 protein degradation assay, we provided molecular evidence that the compounds elicit SL-like responses through the natural signaling cascade. All CISA analogs 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 SLs, which renders the analog a promising tracer to investigate the spatiotemporal distribution of SLs in plants and fungi.},
  author       = {Van Overtveldt, Melissa and Braem, Lukas and Struk, Sylwia Magdalena and Kaczmarek, Anna and Boyer, Fran\c{c}ois\unmatched{2010}Didier and Van Deun, Rik and Gevaert, Kris and Goormachtig, Sofie and Heugebaert, Thomas and Stevens, Christian},
  issn         = {0960-7412},
  journal      = {PLANT JOURNAL},
  keyword      = {Arabidopsis thaliana,Phelipanche ramosa,SMXL6 degradation,fluorescence labeling,hypocotyl elongation,isoindole,parasitic seed germination,pyrroloindole,strigolactone},
  language     = {eng},
  title        = {Design and visualization of second generation cyanoisoindole based fluorescent strigolactone analogs},
  url          = {http://dx.doi.org/10.1111/tpj.14197},
  year         = {2019},
}

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