Bohemine

Names

[ Name ]:
Bohemine

[Synonym ]:
purine deriv. 1
3-{[6-(Benzylamino)-9-isopropyl-9H-purin-2-yl]amino}-1-propanol
2-[(3-hydroxypropyl)amino]-6-benzylamino-9-isopropylpurine
HMS3229C10
3-{[6-(benzylamino)-9-(propan-2-yl)-9H-purin-2-yl]amino}propan-1-ol
[6-Benzylamino-2-(3-hydroxypropylamino)-9-isopropylpurine
1-Propanol, 3-[[9-(1-methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-
bohemine
2-(3-Hydroxypropylamino)-6-benzylamino-9-isopropylpurine

Biological Activity

[Description]:

Bohemine is a purine analogue and is a synthetic and selective CDK inhibitor with IC50s of 4.6 μM, 83 μM, and 2.7 μM for Cdk2/cyclin E, Cdk2/cyclin A, and Cdk9/cyclin T1, respectively. Bohemine also inhibits ERK2 with an IC50 of 52 μM and has less inhibitory effect on CDK1, CDK4 and CDK6. Bohemine has a broad spectrum anti-cancer activities[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> CDK

Signaling Pathways >> MAPK/ERK Pathway >> ERK

Signaling Pathways >> Stem Cell/Wnt >> ERK

[Target]

CDK2/cyclinE:4.6 μM (IC50)

cdk2/cyclin A:83 μM (IC50)

CDK9/cyclinT1:2.7 μM (IC50)

ERK2:52 μM (IC50)

[In Vitro]

Bohemine (0-30 µM; 72 hours; ME-750 cells) treatment inhibits cell growth. Addition of Bohemine at concentrations in the range of 1-10 µM results in a short-term arrest of growth and of monoclonal antibody production. The short-term suppression of cell functions is followed by a significant temporary increase of specific growth rate and of specific production rate[1]. Hybridoma cells are retarded both at the G1/S boundary and at the G2/M boundary, depending on Bohemine (0-30 µM) concentration[1]. T-lymphoblastic cell line CEM is treated by Bohemine, five proteins are found to be downregulated, namely α-enolase, triosephosphate isomerase, initiation factor 5A, and α- and β-subunits of Rho GDP-dissociation inhibitor 1. These proteins play significant roles in glycolysis, proteosynthesis, and in cytoskeleton rearrangement[1]. Bohemine inhibits growth of human tumor cell lines with an IC50 of 27 µM[2]. Cell Viability Assay[1] Cell Line: Mouse hybridoma ME-750 cells Concentration: 0 µM, 1 µM, 3 µM, 10 µM and 30 µM Incubation Time: 72 hours Result: At 10 µM and 30 µM concentrations, the viable cell count was significantly lower with respect to control, i.e., 77% and 48%, respectively.

[In Vivo]

Bohemine (50 mg/kg; intravenous injection; BALB/c mice) treatment shows Cmax is 72,308 nM, observed clearance is 0.23 L/h and T1/2 is 1.39 h[2]. Animal Model: BALB/c mice bearing the colon 26 murine tumor[2] Dosage: 50 mg/kg Administration: Intravenous injection (Pharmacokinetic Analysis) Result: Cmax is 72,308 nM, observed clearance is 0.23 L/h and T1/2 is 1.39 h.

[References]

[1]. Franek F, et al. 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]. Raynaud FI, et al. 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.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
589.4±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₈H₂₄N₆O

[ Molecular Weight ]:
340.423

[ Flash Point ]:
310.3±32.9 °C

[ Exact Mass ]:
340.201172

[ PSA ]:
91.12000

[ LogP ]:
1.02

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.653

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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