title: Triazolyl phenyl disulfides: 8-Amino-7-oxononanoate synthase inhibitors as potential herbicides.
abstract: The chemical validation of a potential herbicide target was investigated with 8-amino-7-oxononanoate synthase (AONS, also known as 7-keto-8-aminopelargonate synthase, KAPAS) and triazolyl phenyl disulfide derivatives in vitro and in vivo. AONS activity was completely inhibited by these synthesized compounds, with an IC50 of 48 to 592μM in vitro. Forty five-day old Arabidopsis thaliana plants were completely killed by representative compound KHG23844 {N-(2-fluorophenyl)-3-(phenyldisulphanyl)-1H-1,2,4-triazole-1-carboxamide} at the application rate of 250gha(-1) of foliar treatment in greenhouse conditions. Foliar application of 1000gha(-1) KHG23844 induced 2.3-fold higher l-alanine accumulation in the treated A. thaliana plants. Foliar supplement of 1mM biotin at 1 and 2days before KHG23844 application effectively recovered the growth inhibition of A. thaliana plant treated with KHG23844. The results strongly suggested that representative compound KHG23844 and its derivatives are potential AONS inhibitors.
authors.affiliation: Korea Institute of Science and Technology, 39-1, Wolsong-Gil 5, Seongbuk-gu, Seoul 136-791, Republic of Korea.
authors.forename: Hoh-Gyu
authors.initials: HG
authors.lastname: Hahn
authors.affiliation: Korea Research Institute of Chemical Technology, P.O. Box 107, Yuseong, Daejon, 305-600, Republic of Korea.
authors.forename: Jung-Sup
authors.initials: JS
authors.lastname: Choi
authors.affiliation: Korea Research Institute of Chemical Technology, P.O. Box 107, Yuseong, Daejon, 305-600, Republic of Korea.
authors.forename: Hee Kyung
authors.initials: HK
authors.lastname: Lim
authors.affiliation: Korea Research Institute of Chemical Technology, P.O. Box 107, Yuseong, Daejon, 305-600, Republic of Korea; Department of Green Chemistry and Environmental Biotechnology, University of Science & Technology, 217 Gajungro, Yuseong-gu, Daejon 305-350, Republic of Korea.
authors.forename: Kee-In
authors.initials: KI
authors.lastname: Lee
authors.affiliation: Korea Research Institute of Chemical Technology, P.O. Box 107, Yuseong, Daejon, 305-600, Republic of Korea; Department of Green Chemistry and Environmental Biotechnology, University of Science & Technology, 217 Gajungro, Yuseong-gu, Daejon 305-350, Republic of Korea. Electronic address: ithwang@krict.re.kr.
authors.forename: In Taek
authors.initials: IT
authors.lastname: Hwang
mesh_terms: D000217:Acyltransferases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D017360:Arabidopsis / Q000187:drug effects* / Q000201:enzymology; D029681:Arabidopsis Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D004220:Disulfides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006540:Herbicides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D029681:Arabidopsis Proteins; D004220:Disulfides; D006540:Herbicides; D014230:Triazoles; C045575:1,2,4-triazole; D000217:Acyltransferases; C021929:8-amino-7-oxononanoate synthase
keywords: 8-Amino-7-oxononanoate synthase (AONS); Herbicide; Recover; Target enzyme; Triazolyl phenyl disulfide; l-Alanine