131740-09-5 Usage
Description
Flavopiridol is an orally bioavailable inhibitor of cyclin dependent kinases (IC50s = ~100, ~100, ~100, and 300 nM for Cdk1, Cdk2, Cdk4, and Cdk7, respectively). It also inhibits TEFb, a complex composed of Cdk9 and cyclin T1, with a Ki value of 3 nM. Flavopiridol inhibits transcription of a CMV promoter in HeLa nuclear extract (IC50 = 34 nM), Tat-stimulated transcription of an HIV-1 promotor (IC50 = 7 nM), and HIV-1 replication in HEK239T cells (IC50 = <10 nM). In vivo, flavopiridol (5 mg/kg, i.p.) induces apoptosis and cyclin D1 depletion and delays tumor growth in an HN-12 head and neck carcinoma mouse xenograft model. It also suppresses synovial hyperplasia and joint destruction in a mouse model of collagen-induced arthritis.
Chemical Properties
Yellow Powder
Uses
Different sources of media describe the Uses of 131740-09-5 differently. You can refer to the following data:
1. An inhibitor of cyclin-dependent kinases; the (-)-cis form induces apoptosis in certain tumor cells
2. An inhibitor of cyclin-dependent kinases; the (-)-cis form induces apoptosis in certain tumor cells.
3. 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 fibroblastsas an RNA polymerase inhibitor to study its effects on hepatic cellsas RNA transcription inhibitor to study its effects on euchromatin coarsening in zebrafish embryo
Definition
ChEBI: A hydrochloride salt resulting from the formal reaction of equimolar amounts of alvocidib and hydrogen chloride. A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic p
aque formation.
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).
References
1) Kaur?et al. (1992),?Growth inhibition with reversible cell cycle arrest of carcinoma cells by flavone L86-8275;? J. Natl. Cancer Inst.,?84?1736
2) Cartee?et al. (2002),?Synergistic induction of apoptosis in human myeloid leukemia cells by phorbol 12-myristate 13-acetate and flavopiridol proceeds via activation of both the intrinsic and tumor necrosis factor-mediated extrinsic cell death pathways;? Mol. Pharmacol.,?61?1313
3) Ambrosini?et al. (2008),?The cyclin-dependent kinase inhibitor flavopiridol potentiates the effects of topoisomerase I poisons by suppressing Rad51 expression in a p53-dependent manner;? Cancer Res.?68?2312
4) Schang?et al. (2004),?Effects of pharmacological cyclin-dependent kinase inhibitors on viral transcription and replication;? Biochim. Biophys. Acta,?1697?197
Check Digit Verification of cas no
The CAS Registry Mumber 131740-09-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,1,7,4 and 0 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 131740-09:
(8*1)+(7*3)+(6*1)+(5*7)+(4*4)+(3*0)+(2*0)+(1*9)=95
95 % 10 = 5
So 131740-09-5 is a valid CAS Registry Number.
InChI:InChI=1/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
131740-09-5Relevant articles and documents
Application of modified flavone closure for the preparation of racemic L86-8275
Tabaka, A. Christine,Murthi, Krishna K.,Pal, Kollol,Teleha, Christopher A.
, p. 256 - 259 (1999)
The laboratory preparation of racemic L86-8275 (1a) and the salt (1b) is described in 7% overall yield. Our method eliminated a number of chromatography steps from the patent procedure and improved the flavone-forming reaction by employing a stepwise mechanism. Solvent-free conditions for the demethylation step are also described.
