Phenyl- and benzylurea cytokinins as competitive inhibitors of cytokinin oxidase/dehydrogenase: A structural study

Kopečný, David; Briozzo, Pierre; Popelková, Hana; Šebela, Marek; Končitíková, Radka; Spíchal, Lukáš; Nisler, Jaroslav; Madzak, Catherine; Frébort, Ivo; Laloue, Michel; Houba-Hérin, Nicole

doi:10.1016/j.biochi.2010.05.006

Cited by 60 publications

(50 citation statements)

References 47 publications

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“…The enhanced fruit enlargement due to CPPU treatments is thought to be derived from a direct stimulation of cell division and/or activation of plant responses typically induced by naturally occurring adeninesubstituted cytokinins [2], combined with an inhibition of cytokinin oxidase/dehydrogenase enzymes that are responsible of cell homeostasis, thus increasing the effective concentration of the endogenous phytohormones [3]. CPPU is commercially available as 1% or 0.1% emulsifiable concentrates under different trade names, i.e.…”

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confidence: 99%

Development and validation of a direct competitive monoclonal antibody-based immunoassay for the sensitive and selective analysis of the phytoregulator forchlorfenuron

et al. 2012

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Forchlorfenuron is a synthetic phytohormone with cytokinin-like activity used worldwide as a plant growth regulator to increase fruit size in a number of crops, mostly in kiwifruit and grape vines. A monoclonal antibody-based enzyme-linked immunosorbent assay (ELISA) for the determination of forchlorfenuron has been characterized and optimized. The selected immunoreagents afforded a highly selective assay with a limit of detection of 10 ng L −1 in buffer.This direct competitive ELISA was validated in terms of trueness, precision, and robustness using both commercial juice and whole fruit samples. Recoveries from fortified kiwifruit juices and white and red musts were between 97 and 131%, with relative standard deviations below 16%. When homogenized whole fruits were analysed after acetonitrile extraction, recoveries between 96 and 113% were found, with a limit of quantification of 5 µg kg −1. The proposed immunoassay was validated by comparison with a reference chromatographic method using fruits from in-field treated grape and kiwifruit vines. Linear regression analysis of ELISA and HPLC-UV determinationsshowed an excellent correlation (r 2 = 0.998), whereas analysis of the slope (0.99 ± 0.01) and of the intercept (−1 ± 3) clearly proved that the developed competitive immunoassay provided results that were statistically comparable to those obtained by the instrumental method for the analysis of CPPU in fruits at trace levels.

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confidence: 99%

Development and validation of a direct competitive monoclonal antibody-based immunoassay for the sensitive and selective analysis of the phytoregulator forchlorfenuron

et al. 2012

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“…It is worth noting that FCF targets at least three distinct proteins in plants (23,63), and it may be naive to imagine that for none of these would there be a nonplant protein sharing high structural similarity at the site of FCF binding. In principle, the same kind of biochemical approach used to identify CSBP as the major FCF-binding protein in plants (63,64) could be applied to other organisms to isolate FCF-binding proteins.…”

Section: Discussionmentioning

confidence: 99%

“…FCF binds and competitively inhibits the catabolic cytokinin dehydrogenase CKO (23), resulting in prolonged elevation of intracellular cytokinin levels and, ultimately, larger fruits (23). In 2004, Iwase et al reported that treatment of the budding yeast Saccharomyces cerevisiae with FCF inhibits growth and causes the formation of ectopic septin structures (24).…”

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Off-Target Effects of the Septin Drug Forchlorfenuron on Nonplant Eukaryotes

2014

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“…Several synthetic urea-derived CKs that competitively inhibit CKX activity have been reported, including thidiazuron, CPPU, and CBPU (Hare and Van Staden 1994;Laloue and Fox 1989;Burch and Horgan 1989;Kopečný et al 2010). In the most cases, their modes of binding to CKX have been clarified by structural analysis (Kopečný et al 2010).…”

Section: Chemical Tools To Modulate Cytokinin Statusmentioning

confidence: 99%

“…In the most cases, their modes of binding to CKX have been clarified by structural analysis (Kopečný et al 2010). The activity of CKX was shown to be strongly inhibited by unsaturated allenic (HA-1, HA-8) and alkyne substrate analogues (Houba-Hérin et al 1999;Suttle and Mornet 2005;Kopečný et al 2008).…”

Section: Chemical Tools To Modulate Cytokinin Statusmentioning

confidence: 99%

The Biotechnological Potential of Cytokinin Status Manipulation

Šmehilová

Spíchal

2013

Plant Cell Monographs

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Cytokinins are highly conserved plant hormones with a long evolutionary history that regulate various aspects of plant growth and development. The genetic background of the mechanisms involved in the regulation of plants' cytokinin status has recently been elucidated. Studies on transgenic plants with altered cytokinin biosynthesis, metabolism, degradation, or signaling revealed interesting consequences of cytokinin deficiency or disruption of cytokinin perception that can be applied in plant biotechnology and agriculture. Cytokinin levels and the sensing thereof can be manipulated using transgenic approaches and by treating plants with novel exogenous compounds in order to promote root system development, biomass formation, yield-forming traits, nutrient uptake, and tolerance of biotic and abiotic stresses. This chapter provides an overview of recent findings concerning the molecular basis and genetic background of cytokinin signaling and metabolism and the ways in which they can be manipulated to tailor plants' traits to meet specific requirements.

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Phenyl- and benzylurea cytokinins as competitive inhibitors of cytokinin oxidase/dehydrogenase: A structural study

Cited by 60 publications

References 47 publications

Development and validation of a direct competitive monoclonal antibody-based immunoassay for the sensitive and selective analysis of the phytoregulator forchlorfenuron

Development and validation of a direct competitive monoclonal antibody-based immunoassay for the sensitive and selective analysis of the phytoregulator forchlorfenuron

Off-Target Effects of the Septin Drug Forchlorfenuron on Nonplant Eukaryotes

The Biotechnological Potential of Cytokinin Status Manipulation

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