CAS 146426-40-6|Flavopiridol
Introduction：Basic information about CAS 146426-40-6|Flavopiridol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | / |
| MSDS | / | Flash Point | 318.8±31.5 °C |
Names
| Name | Flavopiridol |
|---|---|
| Synonym | More Synonyms |
Flavopiridol BiologicalActivity
| 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 | Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>CDKResearch Areas >>Cancer |
| 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 |
| InChIKey | BIIVYFLTOXDAOV-YVEFUNNKSA-N |
| SMILES | CN1CCC(c2c(O)cc(O)c3c(=O)cc(-c4ccccc4Cl)oc23)C(O)C1 |
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 |
