Flavopiridol

Modify Date: 2024-01-02 17:53:53

Flavopiridol Structure
Flavopiridol structure
Common Name Flavopiridol
CAS Number 146426-40-6 Molecular Weight 401.840
Density 1.4±0.1 g/cm3 Boiling Point 603.6±55.0 °C at 760 mmHg
Molecular Formula C21H20ClNO5 Melting Point N/A
MSDS N/A Flash Point 318.8±31.5 °C

 Use of Flavopiridol


Flavopiridol is a broad spectrum and competitive inhibitor of CDKs, inhibiting CDK1, CDK2, CDK4 with IC50s of 30, 170, 100 nM, respectively.

 Names

Name Flavopiridol
Synonym More Synonyms

 Flavopiridol Biological Activity

Description Flavopiridol is a broad spectrum and competitive inhibitor of CDKs, inhibiting CDK1, CDK2, CDK4 with IC50s of 30, 170, 100 nM, respectively.
Related Catalog
Target

CDK1/Cyc B1:30 nM (IC50)

CDK2/Cyc E:170 nM (IC50)

CDK4/Cyc D1:100 nM (IC50)

MAP:19000 nM (IC50)

PKC:14000 nM (IC50)

EGFR:22000 nM (IC50)

In Vitro Flavopiridol (2 μM) robustly induces a distinct pattern of ER stress in CLL cells that contributes to cell death through IRE1-mediated activation of ASK1 and possibly downstream caspases[1]. Flavopiridol results in potent upregulation of a number of PRGs in treatments lasting 4-24 h. Flavopiridol has and immediate and long-term effect on the expression of several PRGs. In serum starved cells re-stimulated with serum, flavopiridol also inhibits the expression of these genes, but subsequently, JUNB, GADD45B and EGR1 are upregulated in the presence of flavopiridol[2].
Kinase Assay Briefly, lysates containing approximately 3×106 cells are incubated with 50 μM LEVD-AFC (caspase 4 substrate) or LETD-AFC (caspase 8 substrate) containing 10 mM dithiothretiol (DTT). caspase 4 activity is measured one hour after addition of substrate and caspase 8 activity is measured 30 minutes after addition of substrate. Release of free AFC is measured with a Beckman-Coulter DTX 880 multimode detector.
Cell Assay The cells treated with flavopiridol are washed after 4 hours with PBS and resuspended in regular growth medium (RPMI 1640) supplemented with 10% human serum and antibiotics for the remainder of the incubation time. In the case of flavopiridol/chloroquine samples, chloroquine is re-added in the fresh media after flavopiridol is washed at 4 hours. For all the other conditions, cells are incubated with the respective drugs for 24 hours continuously.
References

[1]. Mahoney E, et al. ER stress and autophagy: new discoveries in the mechanism of action and drug resistance of the cyclin-dependent kinase inhibitor flavopiridol.Blood. 2012 Aug 9;120(6):1262-1273.

[2]. Keskin H, et al. Complex effects of flavopiridol on the expression of primary response genes. Cell Div. 2012 Mar 29;7:11.

[3]. Kim KS, et al.Thio- and oxoflavopiridols, cyclin-dependent kinase 1-selective inhibitors: synthesis and biological effects. J Med Chem. 2000 Nov 2;43(22):4126-34.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 603.6±55.0 °C at 760 mmHg
Molecular Formula C21H20ClNO5
Molecular Weight 401.840
Flash Point 318.8±31.5 °C
Exact Mass 401.102997
PSA 94.14000
LogP 1.92
Vapour Pressure 0.0±1.8 mmHg at 25°C
Index of Refraction 1.673

 Safety Information

Hazard Codes Xi

 Synonyms

Flavopiridol
MFCD00894265
4H-1-Benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-
(−)-cis-2-(2-chlorophenyl)-5,7-dihydroxy-8-[4R-(3S-hydroxy-1-methyl)-piperidinyl]-4H-1-benzopyran-4-one
Flavopirodol
2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-chromen-4-one
Alvocidib,Free Base
(-)-2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4H-1-benzopyran-4-one
Alvocidib
Flavopiridol HCl
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