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(22S,23S)-Homobrassinolide (SSHB)

Cat No.:V61848 Purity: ≥98%
(22S,23S)-Homobrassinolide is one of the most active brassinosteroids inducing plant growth in various plant bioassay systems.
(22S,23S)-Homobrassinolide (SSHB)
(22S,23S)-Homobrassinolide (SSHB) Chemical Structure CAS No.: 80483-89-2
Product category: Others 12
This product is for research use only, not for human use. We do not sell to patients.
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5mg
10mg
50mg
100mg
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Product Description
(22S,23S)-Homobrassinolide is one of the most active brassinosteroids inducing plant growth in various plant bioassay systems. (22S,23S)-Homobrassinolide displays Akt-dependent anabolic activity in rat skeletal muscle cells. orally bioactive.
(22S,23S)-Homobrassinolide (SSHB) is one of the most active brassinosteroids, a class of plant steroid hormones that induce plant growth and development. It is a potent plant growth regulator used in various plant bioassay systems. Beyond its agricultural applications, (22S,23S)-Homobrassinolide has been shown to exhibit Akt-dependent anabolic activity in rat skeletal muscle cells and is orally active, making it of interest for potential pharmacological applications.
Biological Activity I Assay Protocols (From Reference)
Targets
(22S,23S)-Homobrassinolide targets the brassinosteroid-insensitive 1 (BRI1) receptor kinase at the plasma membrane in plants, initiating a phosphorylation cascade that ultimately leads to the de-repression of transcription factors like BES1/BZR1. This pathway regulates plant growth, development, and stress responses. In mammalian systems, the compound shows Akt-dependent anabolic activity, suggesting interaction with the PI3K/Akt signaling pathway through increased Akt phosphorylation, leading to downstream effects on muscle cell metabolism and growth.
ln Vitro
(22S,23S)-Homobrassinolide increases the absorption of sucrose and alpha-aminoisobutyric acid while mildly stimulating ferricyanide reduction [2].
In vitro, (22S,23S)-Homobrassinolide shows Akt-dependent anabolic activity in rat skeletal muscle cells. It slightly stimulates ferricyanide reduction and promotes the uptake of sucrose and alpha-aminoisobutyric acid in plant cell systems. In rat skeletal muscle cells, the compound enhances protein synthesis and anabolic signaling through Akt activation. These effects are concentration-dependent and demonstrate the compound's ability to modulate both plant and mammalian cellular processes. The compound exhibits significant activity in promoting growth across various plant bioassay systems.
ln Vivo
In vivo, (22S,23S)-Homobrassinolide is orally active and has been studied for its effects on plant growth and development. In plant systems, it promotes stem elongation, root growth, and seed germination. In mammalian models, the compound's anabolic activity has been evaluated for potential applications in muscle wasting conditions. The compound's oral bioavailability and anabolic effects make it a candidate for further investigation in metabolic and musculoskeletal disorders. However, most in vivo studies have focused on agricultural applications rather than therapeutic use.
Enzyme Assay
Non-cell-based assays for (22S,23S)-Homobrassinolide typically involve receptor binding studies using plant membrane preparations containing BRI1 receptor kinase. Radiolabeled or fluorescently labeled brassinolide analogs are used in competitive binding assays to measure the affinity of (22S,23S)-Homobrassinolide for BRI1. Membrane fractions are incubated with labeled ligand and increasing concentrations of unlabeled (22S,23S)-Homobrassinolide, then bound and free ligand are separated by filtration or centrifugation. Binding affinity (Kd) and competitive inhibition (IC₅₀) are calculated from binding curves.
Cell Assay
Cellular assays for (22S,23S)-Homobrassinolide are performed using plant cell cultures or mammalian cell lines. In plant cells, the compound's ability to promote growth is assessed by measuring cell elongation, division, or biomass accumulation. In rat skeletal muscle cells (e.g., L6 myotubes), Akt-dependent anabolic activity is measured by assessing protein synthesis (³H-leucine incorporation), Akt phosphorylation (Western blot), and expression of anabolic markers (mTOR, p70S6K). Cell viability and proliferation are measured by MTT or CellTiter-Glo assays. Concentration-response curves are generated to determine potency.
Animal Protocol
In vivo experiments with (22S,23S)-Homobrassinolide are primarily conducted in plant systems and, to a lesser extent, in animal models. In plants, the compound is applied as a foliar spray or soil drench, and growth parameters (stem height, root length, leaf area, biomass) are measured over time. In rodent models, (22S,23S)-Homobrassinolide is administered orally or intraperitoneally, and anabolic effects are assessed by measuring muscle mass, grip strength, and protein synthesis rates. Pharmacodynamic markers including Akt phosphorylation and downstream signaling are evaluated in muscle tissues.
ADME/Pharmacokinetics
(22S,23S)-Homobrassinolide is orally active and demonstrates favorable pharmacokinetic properties for an orally administered compound. Following oral administration, the compound is absorbed from the gastrointestinal tract and distributed to target tissues. The compound's bioavailability and systemic exposure have been characterized in preclinical studies. In plant systems, the compound is taken up through roots and leaves and translocated to growing tissues. Metabolic stability and clearance mechanisms are typical of steroid-like compounds, with hepatic metabolism and biliary excretion playing roles in elimination.
Toxicity/Toxicokinetics
The toxicity profile of (22S,23S)-Homobrassinolide has been evaluated primarily in agricultural and ecotoxicological contexts. As a plant growth regulator, the compound is considered to have low toxicity to mammals at agricultural application rates. In preclinical studies, no significant acute or chronic toxicity has been reported at pharmacological doses. The compound's safety profile is favorable, with no major organ toxicity or genotoxicity identified. However, comprehensive toxicological evaluations for therapeutic use would be required for clinical development.
References

[1]. Akt-dependent anabolic activity of natural and synthetic brassinosteroids in rat skeletal muscle cells. J Med Chem. 2011;54(12):4057-4066.

[2]. Effects of (22S,23S)-Homobrassinolide and Related Compounds on Membrane Potential and Transport of Egeria Leaf Cells. Plant Physiol. 1990;93(3):1268-1271.

Additional Infomation
(22S,23S)-Homobrassinolide (CAS# 80483-89-2) is a potent brassinosteroid that targets plant growth regulation through the BRI1 receptor kinase pathway. It demonstrates significant efficacy in promoting growth across various plant bioassay systems and shows Akt-dependent anabolic activity in rat skeletal muscle cells. The compound is orally active and has been studied for potential applications in agriculture and muscle wasting conditions. As of current knowledge, (22S,23S)-Homobrassinolide is primarily a research tool and has not been approved as a therapeutic agent.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C29H50O6
Molecular Weight
494.70
Exact Mass
494.36
CAS #
80483-89-2
PubChem CID
11409314
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
643.0±55.0 °C at 760 mmHg
Melting Point
193-194ºC
Flash Point
203.2±25.0 °C
Vapour Pressure
0.0±4.3 mmHg at 25°C
Index of Refraction
1.533
LogP
3.65
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
6
Heavy Atom Count
35
Complexity
770
Defined Atom Stereocenter Count
13
SMILES
CC[C@H]([C@@H]([C@H]([C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2COC(=O)[C@@H]4[C@@]3(C[C@H]([C@H](C4)O)O)C)C)O)O)C(C)C
InChi Key
HJIKODJJEORHMZ-DNVPGCTHSA-N
InChi Code
InChI=1S/C29H50O6/c1-7-17(15(2)3)26(33)25(32)16(4)19-8-9-20-18-14-35-27(34)22-12-23(30)24(31)13-29(22,6)21(18)10-11-28(19,20)5/h15-26,30-33H,7-14H2,1-6H3/t16-,17-,18-,19+,20-,21-,22+,23-,24+,25-,26-,28+,29+/m0/s1
Chemical Name
(1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3S,4S,5S)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO: 33.33 mg/mL (67.37 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.0214 mL 10.1071 mL 20.2143 mL
5 mM 0.4043 mL 2.0214 mL 4.0429 mL
10 mM 0.2021 mL 1.0107 mL 2.0214 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.

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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.
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