Cytokinin receptor antagonists derived from 6-benzylaminopurine
Language English Country Great Britain, England Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
20189204
DOI
10.1016/j.phytochem.2010.01.018
PII: S0031-9422(10)00045-2
Knihovny.cz E-resources
- MeSH
- Arabidopsis MeSH
- Benzyl Compounds MeSH
- Biological Assay MeSH
- Cytokinins metabolism MeSH
- Mass Spectrometry MeSH
- Kinetin pharmacology MeSH
- Purines MeSH
- Receptors, Cell Surface antagonists & inhibitors metabolism MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- benzylaminopurine MeSH Browser
- Benzyl Compounds MeSH
- Cytokinins MeSH
- Kinetin MeSH
- Purines MeSH
- Receptors, Cell Surface MeSH
Recently we reported 6-(2-hydroxy-3-methylbenzylamino)purine (PI-55) as the first molecule to antagonize cytokinin activity at the receptor level. Here we report the synthesis and in vitro biological testing of eleven BAP derivatives substituted in the benzyl ring and in the C2, N7 and N9 positions of the purine moiety. The ability of the compounds to interact with Arabidopsis cytokinin receptors AHK3 and CRE1/AHK4 was tested in bacterial receptor and in live-cell binding assays, and in an Arabidopsis ARR5:GUS (Arabidopsis response regulator 5) reporter gene assay. Cytokinin activity of the compounds was determined in classical cytokinin biotests (tobacco callus, wheat leaf senescence and Amaranthus bioassays). 6-(2,5-Dihydroxybenzylamino)purine (LGR-991) was identified as a cytokinin receptor antagonist. At the molecular level LGR-991 blocks the cytokinin receptor CRE1/AHK4 with the same potency as PI-55. Moreover, LGR-991 acts as a competitive inhibitor of AHK3, and importantly shows reduced agonistic effects in comparison to PI-55 in the ARR5:GUS reporter gene assay and in cytokinin bioassays. LGR-991 causes more rapid germination of Arabidopsis seeds and increases hypocotyl length of dark-grown seedlings, which are characteristics of plants with a reduced cytokinin status. LGR-991 exhibits a structural motive that might lead to preparation of cytokinin antagonists with a broader specificity and reduced agonistic properties.
References provided by Crossref.org
Sucrose promotes stem branching through cytokinin
Cytokinins Are Initial Targets of Light in the Control of Bud Outgrowth
Novel thidiazuron-derived inhibitors of cytokinin oxidase/dehydrogenase
