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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)
Número MDL:
MFCD26792554
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24724481
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

condiciones de almacenamiento

desiccated

color

white to light brown

solubilidad

H2O: ~2 mg/mL
DMSO: >5 mg/mL

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

LGMSNQNWOCSPIK-LWHGMNCYSA-N

Información sobre el gen

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

Aplicación

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

Acciones bioquímicas o fisiológicas

Flavopiridol hydrochloride is a potent CDK (cyclin-dependent kinase), and a CDC25 phosphatase family inhibitor.
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).

Características y beneficios

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

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
116M4755V
035M4737V
042M4718V
100M4723
019K46111

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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
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
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
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
Nazia Abbasi et al.
Life science alliance, 3(10) (2020-08-21)
Tumorigenesis in different segments of the intestinal tract involves tissue-specific oncogenic drivers. In the colon, complement component 3 (C3) activation is a major contributor to inflammation and malignancies. By contrast, tumorigenesis in the small intestine involves fatty acid-binding protein 1
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