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Sci Rep. 2019 Feb 14;9(1):2010. doi: 10.1038/s41598-019-38561-3.

Nematicidal and insecticidal activities of halogenated indoles.

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School of Chemical Engineering, Yeungnam University, Gyeongsan, 38541, Republic of Korea.
Shandong University-Helmholtz Institute of Biotechnology, School of Life Science, Shandong University, Jinan, P. R. China.
Department of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Sciences, Chonnam National University, Gwangju, Republic of Korea.
Advanced Bio Convergence Center, Pohang Technopark Foundation, Pohang, 37668, Republic of Korea.
School of Chemical Engineering, Yeungnam University, Gyeongsan, 38541, Republic of Korea.


Parasite death via ion channel activations is the hallmark of anthelmintic and antiparasitic drugs. Glutamate gated chloride channel (GluCl) is a prominent targets for drug selection and design in parasitology. We report several iodine-fluorine based lead activators of GluCl by computational studies and structure-activity relationship analysis. 5-Fluoro-4-iodo-1H-pyrrolo [2, 3-b] pyridine and 5-iodoindole were bioactive hits that displayed in vitro anthelmintic and insecticidal activities against Bursaphelenchus xylophilus, Meloidogyne incognita, and Tenebrio molitor. Two important findings stood out: (i) 5F4IPP induced parasite death, and interacted proficiently with Gln219 amino acid of pentameric GluCl in docking analysis, and (ii) 5-iodoindole appeared to act by forming giant vacuoles in nematodes, which led to a form of non-apoptotic death known as methuosis. The study suggests halogenated-indoles and 1H-pyrrolo [2, 3-b] pyridine derivatives be regarded potential biocides for plant-parasitic nematodes and insects, and warrants further research on the mode of actions, and field investigations.

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