Design of a New Glutamine-Fipronil Conjugate with alpha-Amino Acid Function and Its Uptake by A-thaliana Lysine Histidine Transporter 1 (AtLHT1)

Sammanfattning

Creating novel pesticides with phloem mobility is essential for controlling insects in vascular tissue and root, and conjugating existing pesticides with amino acid is an effective approach. In order to obtain a highly phloem-mobile candidate for efficient pesticides, an electro-neutral L-glutamine-fipronil conjugate (L-GlnF) retaining alpha-amino acid function was designed and synthesized to fit the substrate specificity of an amino acid transporter. Cotyledon uptake and phloem loading tests with Ricinus communis have verified that L-GlnF was phloem mobile, and its phloem mobility was higher than that of its enantiomer D-GlnF and other previously reported amino acid-fipronil conjugates. Inhibition experiments then suggested that the uptake of L-GlnF was, at least partially, mediated by an active transport mechanism. This inference was further strengthened by assimilation experiments with Xenopus oocytes and genetically modified Arabidopsis thaliana, which showed a direct correlation between the uptake of L-GlnF and the expression of amino acid transporter AtLHT1. Thus, conjugation with L-Gln appears to be a potential strategy to ensure the uptake of pesticides via an endogenous amino acid transport system.

Nyckelord

glutamine; fipronil; amino acid transporter; AtLHT1

Publicerad i

Journal of Agricultural and Food Chemistry
2018, volym: 66, nummer: 29, sidor: 7597-7605
Utgivare: AMER CHEMICAL SOC

SLU författare

• Ganeteg, Ulrika

  • Institutionen för skoglig genetik och växtfysiologi, Sveriges lantbruksuniversitet
    

Associerade SLU-program

SLU Nätverk växtskydd

UKÄ forskningsämne

Biokemi och molekylärbiologi
Jordbruksvetenskap

Publikationens identifierare

• DOI: https://doi.org/10.1021/acs.jafc.8b02287

Permanent länk till denna sida (URI)

https://res.slu.se/id/publ/96335