Elucidating the Structural Isomerism of Fluorescent Strigolactone Analogue CISA‐1

Goossens, Hannelore; Heugebaert, Thomas S. A.; Dereli, Büşra; Overtveldt, Melissa Van; Karahan, Özlem; Doğan, İlknur; Waroquier, Michel; Speybroeck, Véronique Van; Avi̇yente, Vi̇ktorya; Çatak, Şaron; Stevens, Christian V.

doi:10.1002/ejoc.201403457

Cited by 5 publications

(3 citation statements)

References 30 publications

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“…This likely arises from steric hindrance between the fluorescent core and the lactone D‐ring. Indeed, computations of interconversion barriers and 1 H‐NMR chemical shifts indicated the enol double‐bond to solely prevail as the ( Z ) isomer, which was also determined to be the more stable configuration (Goossens et al ., ). The unequivocal proof for the ( Z ) configuration also supports the previous structure assignment of formyl esters 22 , as the chemical shift of the olefinic proton (H o ) of their minor isomers ( 22 ) corresponds well to the shifts observed in the CISAs 6a–f (H o’ δ 8.09–8.19, major atropisomer).…”

Section: Resultsmentioning

confidence: 97%

Design and visualization of second‐generation cyanoisoindole‐based fluorescent strigolactone analogs

et al. 2019

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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 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 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 (CISAs) 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 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 SLs, which renders the analog a promising tracer to investigate the spatiotemporal distribution of SLs in plants and fungi.

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Section: Resultsmentioning

confidence: 97%

Design and visualization of second‐generation cyanoisoindole‐based fluorescent strigolactone analogs

et al. 2019

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“…Previous efforts at generating fluorescently labelled strigolactone analogues have concentrated on substituting the A/B ring system with an indole or isoindole unit. [20][21][22][23] We felt that a more flexible strategy would be to append a fluorophore directly to the GR24 scaffold, allowing for tailored molecules for individual assays. We therefore targeted 6-Br-(þ)-GR24 (18) as a proof of concept.…”

Section: Synthetic Studiesmentioning

confidence: 99%

Chemistry of the Synthetic Strigolactone Mimic GR24

2015

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“…In fungal plant pathogen Cryphonectria parasitica, CpD14, a structural homolog of plant receptor D14, is involved in the SL response. Many fluorescent SL analogs or mimics, most of which bear known fluorophore molecules, have already been prepared to reveal all protein receptors and the distribution of SLs in plants, and to elucidate their mode of action [49,50,[62][63][64][65][66].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Properties of Fluorescent Strigolactone Mimics Derived from 1,8-Naphthalimide

Bala,

Nicolescu,

Georgescu

et al. 2024

Molecules

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Strigolactones (SLs) have potential to be used in sustainable agriculture to mitigate various stresses that plants have to deal with. The natural SLs, as well as the synthetic analogs, are difficult to obtain in sufficient amounts for practical applications. At the same time, fluorescent SLs would be useful for the mechanistic understanding of their effects based on bio-imaging or spectroscopic techniques. In this study, new fluorescent SL mimics containing a substituted 1,8-naphthalimide ring system connected through an ether link to a bioactive furan-2-one moiety were prepared. The structural, spectroscopic, and biological activity of the new SL mimics on phytopathogens were investigated and compared with previously synthetized fluorescent SL mimics. The chemical group at the C-6 position of the naphthalimide ring influences the fluorescence parameters. All SL mimics showed effects similar to GR24 on phytopathogens, indicating their suitability for practical applications. The pattern of the biological activity depended on the fungal species, SL mimic and concentration, and hyphal order. This dependence is probably related to the specificity of each fungal receptor–SL mimic interaction, which will have to be analyzed in-depth. Based on the biological properties and spectroscopic particularities, one SL mimic could be a good candidate for microscopic and spectroscopic investigations.

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Elucidating the Structural Isomerism of Fluorescent Strigolactone Analogue CISA‐1

Cited by 5 publications

References 30 publications

Design and visualization of second‐generation cyanoisoindole‐based fluorescent strigolactone analogs

Design and visualization of second‐generation cyanoisoindole‐based fluorescent strigolactone analogs

Chemistry of the Synthetic Strigolactone Mimic GR24

Synthesis and Biological Properties of Fluorescent Strigolactone Mimics Derived from 1,8-Naphthalimide

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