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F3055

Sigma-Aldrich

Flavopiridol hydrochloride

≥98% (HPLC), powder

Sinónimos:

(−)-2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methyl-4-piperidinyl]-4h-1-benzopyran-4-one hydrochloride, L-86-8276, NSC-649890

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About This Item

Fórmula empírica (notación de Hill):
C21H20ClNO5 ·HCl · xH2O
Número de CAS:
131740-09-5
Peso molecular:
438.30 (anhydrous basis)
MDL number:
MFCD26792554
UNSPSC Code:
12352200
PubChem Substance ID:
24724481
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to light brown

solubility

H2O: ~2 mg/mL
DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

OC1=C(C(C=C(C2=C(Cl)C=CC=C2)O3)=O)C3=C([C@H]4CCN(C)C[C@H]4O)C(O)=C1.Cl

InChI

1S/C21H20ClNO5.ClH/c1-23-7-6-12(17(27)10-23)19-14(24)8-15(25)20-16(26)9-18(28-21(19)20)11-4-2-3-5-13(11)22;/h2-5,8-9,12,17,24-25,27H,6-7,10H2,1H3;1H/t12-,17+;/m0./s1

InChI key

LGMSNQNWOCSPIK-LWHGMNCYSA-N

Gene Information

human ... CDK1(983) , CDK2(1017) , CDK4(1019) , CDK6(1021) , CDK7(1022) , CDK9(1025)

Application

Flavopiridol hydrochloride hydrate has been used:
  • as a cyclin-dependent kinase 9 (CDK9) inhibitor to study its effects on histone H3 methylation at lysine 36 (H3K36) and deactivation of transcription in porcine fetal fibroblasts
  • as an RNA polymerase inhibitor to study its effects on hepatic cells
  • as RNA transcription inhibitor to study its effects on euchromatin coarsening in zebrafish embryo

Biochem/physiol Actions

Flavopiridol is a semi-synthetic flavone obtained from Dysoxylum binectariferum that acts as an anti-tumor agent against several cancers. It also shows anti-cancer properties due to which it has been studied in the treatment of acute myeloid leukemia (AML).
Flavopiridol hydrochloride is a potent CDK (cyclin-dependent kinase), and a CDC25 phosphatase family inhibitor.

Features and Benefits

This compound is featured on the CDKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Saowaluk Saisomboon et al.
Heliyon, 5(5), e01675-e01675 (2019-06-14)
Flavopiridol, a pan-cyclin-dependent kinase (CDK) inhibitor, was recently identified as an effective antitumor agent for several cancers. We investigated the antitumor effect of flavopiridol on cholangiocarcinoma (CCA), in vitro and in vivo. A methylthiotetrazole assay revealed that the proliferation of
Elisa Barbieri et al.
Cell reports, 33(6), 108373-108373 (2020-11-12)
Genome-wide profiling of nascent RNA has become a fundamental tool to study transcription regulation. Unlike steady-state RNA-sequencing (RNA-seq), nascent RNA profiling mirrors real-time activity of RNA polymerases and provides an accurate readout of transcriptome-wide variations. Some species of nuclear RNAs
Uma Raju et al.
Cancer research, 63(12), 3263-3267 (2003-06-18)
Flavopiridol, a cyclin-dependent kinase (cdk) inhibitor, can cause cell cycle arrest, induce apoptosis in cancer cells, and inhibit tumor cell growth in vivo. The present study investigated the in vitro radiosensitizing effect of flavopiridol and the underlying molecular mechanisms in
Stefano de Pretis et al.
Genome research, 27(10), 1658-1664 (2017-09-15)
Overexpression of the MYC transcription factor causes its widespread interaction with regulatory elements in the genome but leads to the up- and down-regulation of discrete sets of genes. The molecular determinants of these selective transcriptional responses remain elusive. Here, we
Anne Pumfery et al.
Current pharmaceutical design, 12(16), 1949-1961 (2006-06-22)
Cyclin-dependent kinases (CDKs) are key regulators of the cell cycle and RNA polymerase II transcription. Several pharmacological CDK inhibitors (PCIs) are currently in clinical trials as potential cancer therapeutics since CDK hyperactivation is detected in the majority of neoplasias. Within
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