A Novel Fluorescent Conjugate Applicable To Visualize the Translocation of Glucose–Fipronil

Wang, Jie; Lei, Zhiwei; Wen, Yingjie; Mao, Genlin; Wu, Hongya; Xu, Hanhong

doi:10.1021/jf502838m

Cited by 21 publications

(26 citation statements)

References 32 publications

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“…Additional glucoside carriers may have transported these compounds, or they may have simply been able to diffuse more readily into the phloem. The addition of Glc to fluorescent compounds has been shown previously to facilitate phloem transport (Wang et al, 2014) and may provide a generic means of enhancing the transport (Wolfbeis et al, 1983). e Quantum yield after acetate cleavage (Mineno et al, 2006).…”

Section: Discussionmentioning

confidence: 99%

Multispectral Phloem-Mobile Probes: Properties and Applications

et al. 2015

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Using Arabidopsis (Arabidopsis thaliana) seedlings, we identified a range of small fluorescent probes that entered the translocation stream and were unloaded at the root tip. These probes had absorbance/emission maxima ranging from 367/454 to 546/576 nm and represent a versatile toolbox for studying phloem transport. Of the probes that we tested, naturally occurring fluorescent coumarin glucosides (esculin and fraxin) were phloem loaded and transported in oocytes by the sucrose transporter, AtSUC2. Arabidopsis plants in which AtSUC2 was replaced with barley (Hordeum vulgare) sucrose transporter (HvSUT1), which does not transport esculin in oocytes, failed to load esculin into the phloem. In wild-type plants, the fluorescence of esculin decayed to background levels about 2 h after phloem unloading, making it a suitable tracer for pulse-labeling studies of phloem transport. We identified additional probes, such as carboxytetraethylrhodamine, a red fluorescent probe that, unlike esculin, was stable for several hours after phloem unloading and could be used to study phloem transport in Arabidopsis lines expressing green fluorescent protein.

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Section: Discussionmentioning

confidence: 99%

Multispectral Phloem-Mobile Probes: Properties and Applications

et al. 2015

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“…Glucose and amino acid promoieties were introduced into insecticides to develop phloem‐targeted proinsecticides (Table ). The resulting derivatives included glycinyl fipronil conjugate, sugar‐fipronil conjugates, D‐glucose‐rotenone conjugates, glycinergic‐fipronil conjugate, and amino acid‐chlorantraniliprole conjugates . Despite their parent compounds lack of mobility in the phloem, several of the above mentioned insecticide conjugates had good phloem systemicity .…”

Section: Carrier‐mediated Propesticide Strategies For Improving Agrocmentioning

confidence: 99%

“…The vacuolar sequestration of sugar and glutathione conjugates via ABC transporters which occurs in planta during the final detoxification process of agrochemicals may reduce the phloem loading of these synthetic conjugates. Data from short time experiments using a fluorescent insecticide sugar conjugate indicate that the dye accumulates dramatically in epidermal cells and phloem, more specifically in sieve tubes after incubation of Ricinus cotyledons in an incubation solution containing N‐[3‐cyano‐1‐[2,6‐dichloro‐4‐(trifluoromethyl)phenyl]‐4‐[(trifluoromethyl)sulfinyl]‐1H‐pyrazol‐5‐yl]‐1‐(2‐[N‐(7‐nitrobenz‐2‐oxa‐1,3‐diazol‐4‐yl)amino]‐2‐deoxy‐β‐D‐glucopyranosyl)‐1H‐1,2,3‐triazole‐4‐methanamine (2‐NBDGTF) . The fluorescence in the mesophyll cells is moderate and localized mainly at their external part.…”

Section: Carrier‐mediated Propesticide Strategies For Improving Agrocmentioning

confidence: 99%

“…56,62 The vacuolar sequestration of sugar and glutathione conjugates via ABC transporters which occurs in planta during the final detoxification process of agrochemicals 67 may reduce the phloem loading of these synthetic conjugates. Data from short time experiments using a fluorescent insecticide sugar conjugate indicate that the dye accumulates dramatically in epidermal cells and phloem, more specifically in sieve tubes after incubation of Ricinus cotyledons in an incubation solution containing N- 65 The fluorescence in the mesophyll cells is moderate and localized mainly at their external wileyonlinelibrary.com/journal/ps part. Therefore, there is no clear evidence of an accumulation of 2-NBDGTF in the vacuoles under these experimental conditions.…”

Section: Carrier-mediated Propesticide Strategies For Improving Agrocmentioning

confidence: 99%

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Vectorizing agrochemicals: enhancing bioavailability via carrier‐mediated transport

Marivingt-Mounir

et al. 2019

Pest Management Science

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Systemicity of agrochemicals is an advantageous property for controlling phloem sucking insects, as well as pathogens and pests not accessible to contact products. After the penetration of the cuticle, the plasma membrane constitutes the main barrier to the entry of an agrochemical into the sap flow. The current strategy for developing systemic agrochemicals is to optimize the physicochemical properties of the molecules so that they can cross the plasma membrane by simple diffusion or ion trapping mechanisms. The main problem with current systemic compounds is that they move everywhere within the plant, and this non‐controlled mobility results in the contamination of the plant parts consumed by vertebrates and pollinators. To achieve the site‐targeted distribution of agrochemicals, a carrier‐mediated propesticide strategy is proposed in this review. After conjugating a non‐systemic agrochemical with a nutrient (α‐amino acids or sugars), the resulting conjugate may be actively transported across the plasma membrane by nutrient‐specific carriers. By applying this strategy, non‐systemic active ingredients are expected to be delivered into the target organs of young plants, thus avoiding or minimizing subsequent undesirable redistribution. The development of this innovative strategy presents many challenges, but opens up a wide range of exciting possibilities. © 2018 Society of Chemical Industry

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“…It has been demonstrated that coupling existing nonphloem mobile pesticide structures with endogenous substances, such as amino acids and saccharides, was effective on improving their phloem mobility [3][4][5][6][7][8][9][10][11][12][13][14]. For example, a series of phloem mobile glucose-fipronil conjugates (GTF and GOF), glycinergic-fipronil conjugate (GlyF) and alanine ester-chlorantraniliprole conjugate were synthesized in our previous work, and their uptake process was proven to be mediated by active transport systems [5,6,8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, bioactivities and phloem uptake of dipeptide-chlorantraniliprole derivatives

Zheng

Lin

et al. 2020

BMC Chemistry

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Phloem systemicity is a desirable property for insecticides to control sucking insects. However, the development of phloem systemic insecticides is challenging. One possible strategy is to link existed insecticides with endogenous substances so that the resulting conjugates can be transported by specific transporters into the phloem. In this study, novel dipeptide promoieties were introduced into chlorantraniliprole, which is an efficient and broad-spectrum anthranilic diamide insecticide without phloem mobility. Twenty-two new dipeptide-chlorantraniliprole conjugates have been synthesized. Systemic tests showed that all conjugates exhibited phloem mobility in Ricinus communis. In particular, compound 4g with alanyl-alanine dipeptide fragment was able to accumulate in phloem sap (114.49 ± 11.10 μM) in the form of its hydrolysis product 5g. Results of bioassay showed that conjugates 4g and 5g were able to exhibit comparable insecticidal activity against Plutella xylostella L. and Spodoptera exigua compared to its parent compound chlorantraniliprole. This work demonstrated that the dipeptide structures were able to contribute to the improvement of the uptake and phloem mobility of chlorantraniliprole, and two phloem mobile conjugates with satisfactory in vivo insecticidal effect was obtained as new candidates for high-efficient insecticides.

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A Novel Fluorescent Conjugate Applicable To Visualize the Translocation of Glucose–Fipronil

Cited by 21 publications

References 32 publications

Multispectral Phloem-Mobile Probes: Properties and Applications

Multispectral Phloem-Mobile Probes: Properties and Applications

Vectorizing agrochemicals: enhancing bioavailability via carrier‐mediated transport

Synthesis, bioactivities and phloem uptake of dipeptide-chlorantraniliprole derivatives

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