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Special Issue: Sulfonamides
Article

A Chemical Genetics Strategy That Identifies Small Molecules Which Induce the Triple Response in Arabidopsis

1
Department of Biotechnology, Faculty of Bioresource Sciences, Akita Prefectural University, 241-438, Shimoshinjo Nakano, Akita 010-0195, Japan
2
Department of Biological Production, Faculty of Bioresource Sciences, Akita Prefectural University, 241-438, Shimoshinjo Nakano, Akita 010-0195, Japan
*
Author to whom correspondence should be addressed.
Molecules 2017, 22(12), 2270; https://doi.org/10.3390/molecules22122270
Received: 22 October 2017 / Revised: 10 December 2017 / Accepted: 13 December 2017 / Published: 19 December 2017
(This article belongs to the Special Issue Sulfonamides)
To explore small molecules with ethylene-like biological activity, we conducted a triple response-based assay system for chemical library screening. Among 9600 compounds, we found N-[(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-N-methyl-2-naphthalenesulfonamide (EH-1) displayed promising biological activity on inducing a triple response in Arabidopsis seedlings. Chemical synthesis and structure–activity relationship (SAR) analysis of EH-1 analogues with different substitution patterns on the phenyl ring structure of the sulfonamide group indicated that 3,4-dichloro-N-methyl-N-(1,3,5-trimethyl-1H-pyrazol-4-yl-methyl)benzenesulfonamide (8) exhibits the most potent biological activity. To determine the mechanism of action, we conducted RNA sequencing (RNA-Seq) analysis of the effect of EH-1 and 1-aminocyclopropane-1-carboxylate (ACC), the precursor of ethylene biosynthesis, following the quantitative real-time polymerase chain reaction (RT-PCR) confirmation. Data obtained from RNA-Seq analysis indicated that EH-1 and ACC significantly induced the expression of 39 and 48 genes, respectively (above 20 fold of control), among which five genes are up-regulated by EH-1 as well as by ACC. We also found 67 and 32 genes that are significantly down-regulated, respectively, among which seven genes are in common. For quantitative RT-PCR analysis. 12 up-regulated genes were selected from the data obtained from RNA-Seq analysis. We found a good correlation of quantitative RT-PCR analysis and RNA-Seq analysis. Based on these results, we conclude that the action mechanism of EH-1 on inducing triple response in Arabidopsis is different from that of ACC. View Full-Text
Keywords: ethylene; sulfonamide derivatives; pyrazole derivatives; plant growth regulator ethylene; sulfonamide derivatives; pyrazole derivatives; plant growth regulator
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MDPI and ACS Style

Oh, K.; Hoshi, T.; Tomio, S.; Ueda, K.; Hara, K. A Chemical Genetics Strategy That Identifies Small Molecules Which Induce the Triple Response in Arabidopsis. Molecules 2017, 22, 2270. https://doi.org/10.3390/molecules22122270

AMA Style

Oh K, Hoshi T, Tomio S, Ueda K, Hara K. A Chemical Genetics Strategy That Identifies Small Molecules Which Induce the Triple Response in Arabidopsis. Molecules. 2017; 22(12):2270. https://doi.org/10.3390/molecules22122270

Chicago/Turabian Style

Oh, Keimei; Hoshi, Tomoki; Tomio, Sumiya; Ueda, Kenji; Hara, Kojiro. 2017. "A Chemical Genetics Strategy That Identifies Small Molecules Which Induce the Triple Response in Arabidopsis" Molecules 22, no. 12: 2270. https://doi.org/10.3390/molecules22122270

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