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| 5mg |
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| Other Sizes |
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| Targets |
Brassinosteroid (BR) biosynthesis[1]
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| ln Vitro |
The morphology of seedlings significantly resembled that of BR-deficient mutants because to the considerable deformity caused by brassinazole (0.5, 1, 5 μM). Brassinazole induces cress dwarfism, which modifies leaf morphology. For example, Arabidopsis BR-deficient mutants' distinctive downward curling and dark green look. On the other hand, dwarfism is reversed by administering 10 nM BR [1].
Screening for brassinosteroid (BR) biosynthesis inhibitors was performed to find chemicals that induce dwarfism in Arabidopsis, mutants that resembled BR biosynthesis mutants that can be rescued by BR. Through this screening experiment, the compound brassinazole was selected as the most potent chemical. In dark-grown Arabidopsis, brassinazole-induced morphological changes were nearly restored to those of wild type by treatment with brassinolide. The structure of brassinazole is similar to pacrobutrazol, a gibberellin biosynthesis inhibitor. However, in assays with cress (Lepidium sativum) plants, brassinazole-treated plants did not show recovery after the addition of gibberellin but showed good recovery after the addition of brassinolide. These data demonstrate that brassinazole is a specific BR biosynthesis inhibitor. Brassinazole-treated cress also showed dwarfism, with altered leaf morphology, including the downward curling and dark green color typical of Arabidopsis BR-deficient mutants, and this dwarfism was reversed by the application of 10 nM brassinolide. This result suggests that BRs are essential for plant growth, and that brassinazole can be used to clarify the function of BRs in plants as a complement to BR-deficient mutants. The brassinazole action site was also investigated by feeding BR biosynthesis intermediates to cress grown in the light [2]. |
| References |
[1]. Preparation of (1,2,4-triazolyl)alkanols as specific inhibitors of brassinosteroid biosynthesis: Japan, JP2000053657. 2000-02-22.
[2]. Mode of action of brassinazole: a specific inhibitor of brassinosteroid biosynthesis[M]. 2000. Agrochemical Discovery Chapter 23pp 269-280. DOI: 10.1021/bk-2001-0774.ch023 [3]. Characterization of Brassinazole, a Triazole-Type Brassinosteroid Biosynthesis Inhibitor. Plant Physiol. 2000 May;123(1):93-100. |
| Additional Infomation |
Inhibitors of phytohormone have proven to be useful tools for understanding hormonal function. Recently, brassinolide has been designated as a new class of phytohormone based on the physiological responses of brassinolide-deficient mutants. However, information on other roles of this hormone is limited because studies have been confined to mutants in a limited number of plant species. Therefore, specific inhibitors of brassinosteroid biosynthesis would be valuable tools for investigating their roles at various stages of plant development, such as germination, leaf expansion and flowering. Recent advances in developing brassinosteroid biosynthesis inhibitor, brassinazole (Brz), have shown the importance of brassinosteroids in broad aspects of plant growth and development. This inhibitor induced drastic morphological changes in treated plants, almost identical to those found in brassinosteroid-deficient mutants. The normal phenotype of inhibitor-treated plants could be recovered by the addition of brassinolide. This result suggests that brassinosteroids are essential for plant growth, and that specific brassinosteroid biosynthesis inhibitors can be used to clarify the functions of brassinosteroids in plants when used as a complement to brassinosteroid-deficient mutants. The action site of brassinazole was an oxidative processes from 6-oxo-campestanol to teasterone. [1]
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| Molecular Formula |
C18H18CLN3O
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|---|---|
| Molecular Weight |
327.808022975922
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| Exact Mass |
327.113
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| Elemental Analysis |
C, 65.95; H, 5.53; Cl, 10.81; N, 12.82; O, 4.88
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| CAS # |
259200-31-2
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| Related CAS # |
Brassinazole;280129-83-1;(2R,3S)-Brassinazole;259200-30-1
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| PubChem CID |
92846666
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| Appearance |
White to off-white solid powder
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| LogP |
3.6
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
23
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| Complexity |
369
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| Defined Atom Stereocenter Count |
2
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| SMILES |
ClC1C=CC(=CC=1)C[C@H]([C@](C)(C1C=CC=CC=1)O)N1C=NC=N1
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| InChi Key |
YULDTPKHZNKFEY-MSOLQXFVSA-N
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| InChi Code |
InChI=1S/C18H18ClN3O/c1-18(23,15-5-3-2-4-6-15)17(22-13-20-12-21-22)11-14-7-9-16(19)10-8-14/h2-10,12-13,17,23H,11H2,1H3/t17-,18+/m1/s1
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| Chemical Name |
(2S,3R)-4-(4-chlorophenyl)-2-phenyl-3-(1,2,4-triazol-1-yl)butan-2-ol
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| Synonyms |
(2S,3R)-Brassinazole; 280129-83-1; 259200-31-2; (2S,3R)-4-(4-CHLOROPHENYL)-2-PHENYL-3-(1,2,4-TRIAZOL-1-YL)BUTAN-2-OL; Brassinazole, >=98% (HPLC)
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 20 mg/mL (61.01 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0505 mL | 15.2527 mL | 30.5055 mL | |
| 5 mM | 0.6101 mL | 3.0505 mL | 6.1011 mL | |
| 10 mM | 0.3051 mL | 1.5253 mL | 3.0505 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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