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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.

Author information

1
School of Chemical Engineering, Yeungnam University, Gyeongsan, 38541, Republic of Korea.
2
Shandong University-Helmholtz Institute of Biotechnology, School of Life Science, Shandong University, Jinan, P. R. China.
3
Department of Agricultural Chemistry, Institute of Environmentally Friendly Agriculture, College of Agriculture and Life Sciences, Chonnam National University, Gwangju, Republic of Korea.
4
Advanced Bio Convergence Center, Pohang Technopark Foundation, Pohang, 37668, Republic of Korea.
5
School of Chemical Engineering, Yeungnam University, Gyeongsan, 38541, Republic of Korea. jtlee@ynu.ac.kr.

Abstract

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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