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Bohemine

Alias: Bohemine
Cat No.:V5209 Purity: ≥98%
Bohemine, structurally similar to Olomoucine and Roscovitine, is a novel, potent, selective, and cell-permeable cyclin-dependent kinase (CDK) with IC50s of 4.6, 83, and 2.7 μM for Cdk2/cyclin E, Cdk2/cyclin A, and Cdk9/cyclin T1, respectively.
Bohemine
Bohemine Chemical Structure CAS No.: 189232-42-6
Product category: CDK
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Bohemine, structurally similar to Olomoucine and Roscovitine, is a novel, potent, selective, and cell-permeable cyclin-dependent kinase (CDK) with IC50s of 4.6, 83, and 2.7 μM for Cdk2/cyclin E, Cdk2/cyclin A, and Cdk9/cyclin T1, respectively. Bohemine exhibits a 52 μM IC50 for ERK2 inhibition, while its impact on CDK1, CDK4, and CDK6 is lessened. The anti-cancer effects of bohemine are wide-ranging.

Biological Activity I Assay Protocols (From Reference)
Targets
CDK2/cyclinE (IC50 = 4.6 μM); cdk2/cyclin A (IC50 = 83 μM); CDK9/cyclinT1 (IC50 = 2.7 μM); ERK2 (IC50 = 52 μM)
ln Vitro
Bohemine treatment inhibits cell growth. When bohemine is added at concentrations between 1 and 10 µM, growth and the production of monoclonal antibodies are temporarily stopped. Following the brief suppression of cell functions, there is a notable, transient increase in both the rate of specific growth and production[1].
The G1/S and G2/M boundaries of hybridoma cells are retarded, based on the concentration of bohemine (0-30 µM)[1].
T-cell lymphoblastic line Five proteins are shown to be downregulated when bohemine is used to treat CEM: α-enolase, triosephosphate isomerase, initiation factor 5A, and the α- and β-subunits of Rho GDP-dissociation inhibitor 1. These proteins are important for the processes of glycolysis, proteosynthesis, and cytoskeleton rearrangement[1].
With an IC50 of 27 µM, bohemine inhibits the growth of human tumor cell lines[2].
ln Vivo
Bohemine (50 mg/kg; intravenous injection; BALB/c mice) treatment reveals a T1/2 of 1.39 hours, an observed clearance of 0.23 L/h, and a Cmax of 72,308 nM[2].
Animal Protocol
BALB/c mice bearing the colon 26 murine tumor[2]
50 mg/kg
Intravenous injection (Pharmacokinetic Analysis)
References

[1]. Diverse effects of the cyclin-dependent kinase inhibitor bohemine: Concentration- and time-dependent suppression or stimulation of hybridoma culture. Cytotechnology. 2001 Jul;36(1-3):117-23.

[2]. In vitro and in vivo pharmacokinetic-pharmacodynamic relationships for the trisubstituted aminopurine cyclin-dependent kinase inhibitors olomoucine, bohemine and CYC202. Clin Cancer Res. 2005 Jul 1;11(13):4875-87.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H24N6O
Molecular Weight
340.42276
Exact Mass
340.20
Elemental Analysis
C, 63.51; H, 7.11; N, 24.69; O, 4.70
CAS #
189232-42-6
Related CAS #
189232-42-6
Appearance
Solid powder
SMILES
CC(C)N1C=NC2=C(N=C(N=C21)NCCCO)NCC3=CC=CC=C3
InChi Key
OPQGFIAVPSXOBO-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H24N6O/c1-13(2)24-12-21-15-16(20-11-14-7-4-3-5-8-14)22-18(23-17(15)24)19-9-6-10-25/h3-5,7-8,12-13,25H,6,9-11H2,1-2H3,(H2,19,20,22,23)
Chemical Name
3-[[6-(benzylamino)-9-propan-2-ylpurin-2-yl]amino]propan-1-ol
Synonyms
Bohemine
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: 68~100 mg/mL (199.8~293.8 mM)
Ethanol: ~68 mg/mL (199.8 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.34 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.34 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.34 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 2.9375 mL 14.6877 mL 29.3755 mL
5 mM 0.5875 mL 2.9375 mL 5.8751 mL
10 mM 0.2938 mL 1.4688 mL 2.9375 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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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

Biological Data
  • Chemical structures of olomoucine, bohemine, and CYC202. Clin Cancer Res . 2005 Jul 1;11(13):4875-87.
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