ArticlePlant molecular biology2016
Novel thidiazuron-derived inhibitors of cytokinin oxidase/dehydrogenase.
Article in Plant molecular biology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 65 citations in OpenAlex.
- Micropropagation and ex vitro acclimatization of Lonicera caerulea var. altaica: molecular identification and protocol optimization.Scientific reports · 2026Article
- Effect of Light and Cytokinin Modulators on Adventitious Shooting inPlants (Basel, Switzerland) · 2026Article
- Cytokinin derivatives as tools to enhance plant stress resilience.Frontiers in plant science · 2026Review
- Discovery and Biological Evaluation of 3‑(1,2,3-Thiadiazol-5-yl)-1-arylimidazolidine-2,4-diones as Potential Plant Growth Regulators.ACS omega · 2025Article
- Genomic Insights intoInternational journal of molecular sciences · 2025Article
- Small chemical molecules regulating the phytohormone signalling alter the plant's physiological processes to improve stress adaptation, growth and productivity.Physiology and molecular biology of plants : an international journal of functional plant biology · 2024Review
- New Insights into the Enhancement of Adventitious Root Formation Using N,N'-Bis(2,3-methylenedioxyphenyl)urea.Plants (Basel, Switzerland) · 2023Article
- Characterization, Preparation, and Promotion of Plant Growth of 1,3-Diphenylurea/β-Cyclodextrin Derivatives Inclusion Complexes.ACS omega · 2023Article
- Comprehensive Phytohormone Profiling of Kohlrabi during In Vitro Growth and Regeneration: The Interplay with Cytokinin and Sucrose.Life (Basel, Switzerland) · 2022Article
- Cytokinin Oxygenase/Dehydrogenase Inhibitors: An Emerging Tool in Stress Biotechnology Employed for Crop Improvement.Frontiers in genetics · 2022Review
- Killing two birds with a single stone-genetic manipulation of cytokinin oxidase/dehydrogenase (Frontiers in genetics · 2022Review
- Plant Growth Regulators INCYDE and TD-K Underperform in Cereal Field Trials.Plants (Basel, Switzerland) · 2021Article
- A synthetic cytokinin influences the accumulation of leaf soluble sugars and sugar transporters, and enhances the drought adaptability in rice.3 Biotech · 2021Article
- Sucrose interferes with endogenous cytokinin homeostasis and expression of organogenesis-related genes during de novo shoot organogenesis in kohlrabi.Scientific reports · 2021Article
- Targeting Cytokinin Homeostasis in Rapid CyclingPlants (Basel, Switzerland) · 2020Article
- A Synthetic Cytokinin Improves Photosynthesis in Rice under Drought Stress by Modulating the Abundance of Proteins Related to Stomatal Conductance, Chlorophyll Contents, and Rubisco Activity.Plants (Basel, Switzerland) · 2020Article
- Chemical Defoliant Promotes Leaf Abscission by Altering ROS Metabolism and Photosynthetic Efficiency inInternational journal of molecular sciences · 2020Article
- Article
- Role of Cytokinins in Senescence, Antioxidant Defence and Photosynthesis.International journal of molecular sciences · 2018Review
- Thidiazuron-induced abnormalities in plant tissue cultures.Plant cell reports · 2018Review
Corrections and comments
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Authors and funding
10 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
key messageTwo new TDZ derivatives (HETDZ and 3FMTDZ) are very potent inhibitors of CKX and are promising candidates for in vivo studies. Cytokinin hormones regulate a wide range of essential processes in plants. Thidiazuron (N-phenyl-N'-1,2,3-thiadiazol-5-yl urea, TDZ), formerly registered as a cotton defoliant, is a well known inhibitor of cytokinin oxidase/dehydrogenase (CKX), an enzyme catalyzing the degradation of cytokinins. TDZ thus increases the lifetime of cytokinins and their effects in plants. We used in silico modeling to design, synthesize and characterize twenty new TDZ derivatives with improved inhibitory properties. Two compounds, namely 1-[1,2,3]thiadiazol-5-yl-3-(3-trifluoromethoxy-phenyl)urea (3FMTDZ) and 1-[2-(2-hydroxyethyl)phenyl]-3-(1,2,3-thiadiazol-5-yl)urea (HETDZ), displayed up to 15-fold lower IC 50 values compared with TDZ for AtCKX2 from Arabidopsis thaliana and ZmCKX1 and ZmCKX4a from Zea mays. Binding modes of 3FMTDZ and HETDZ were analyzed by X-ray crystallography. Crystal structure complexes, solved at 2.0 Å resolution, revealed that HETDZ and 3FMTDZ bound differently in the active site of ZmCKX4a: the thiadiazolyl ring of 3FMTDZ was positioned over the isoalloxazine ring of FAD, whereas that of HETDZ had the opposite orientation, pointing toward the entrance of the active site. The compounds were further tested for cytokinin activity in several cytokinin bioassays. We suggest that the combination of simple synthesis, lowered cytokinin activity, and enhanced inhibitory effects on CKX isoforms, makes 3FMTDZ and HETDZ suitable candidates for in vivo studies.
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