title: A novel fluorescent conjugate applicable to visualize the translocation of glucose-fipronil.
abstract: The ability to visualize the movement of glycosyl insecticides contributes to learning their translocation and distribution in plants. In our present work, a novel fluorescent glucose-fipronil conjugate 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), was obtained via click chemistry. Disk uptake experiments showed that an active carrier-mediated system was involved in the 2-NBDGTF uptake process. Meanwhile, 2-NBDGTF exhibited comparable phloem mobility with GTF in castor bean seedlings. Visualization of 2-NBDGTF uptake and transport experiment showed that this fluorescent glucose-fipronil conjugate could be loaded into sieve tubes after transiting through epidermal cells and mesophyll cells and then translocate from cotyledon to hypocotyl via phloem in castor bean seedlings. The results above determined that it is a promising fluorescence tagging approach for revealing the activities of glycosyl insecticides and 2-NBDGTF is a reasonable and feasible fluorescent surrogate of GTF for tracing the distribution of glucose-fipronil conjugates.
authors.affiliation: State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources and ‡Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University , Guangzhou, 510642, Guangdong China.
authors.forename: Jie
authors.initials: J
authors.lastname: Wang
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Lei
authors.forename: Yingjie
authors.initials: Y
authors.lastname: Wen
authors.forename: Genlin
authors.initials: G
authors.lastname: Mao
authors.forename: Hanxiang
authors.initials: H
authors.lastname: Wu
authors.forename: Hanhong
authors.initials: H
authors.lastname: Xu
mesh_terms: D001692:Biological Transport; D002367:Ricinus communis / Q000737:chemistry / Q000196:embryology / Q000378:metabolism*; D018548:Cotyledon / Q000737:chemistry / Q000378:metabolism; D005456:Fluorescent Dyes; D005947:Glucose / Q000737:chemistry* / Q000378:metabolism; D007306:Insecticides / Q000737:chemistry* / Q000378:metabolism; D018613:Microscopy, Confocal; D052585:Phloem / Q000737:chemistry / Q000378:metabolism; D011720:Pyrazoles / Q000737:chemistry* / Q000378:metabolism*; D036226:Seedlings / Q000737:chemistry / Q000378:metabolism
chemical_list: D005456:Fluorescent Dyes; D007306:Insecticides; D011720:Pyrazoles; D005947:Glucose; C082360:fipronil