ChemicalBook--->CAS DataBase List--->112953-11-4

112953-11-4

112953-11-4 Structure

112953-11-4 Structure
IdentificationBack Directory
[Name]

UCN-01
[CAS]

112953-11-4
[Synonyms]

UCN-01
UNC 01
KW-2401
KRX-0601
NSC 638850
KRX-0601,UCN-01
7-hydroxystaurosporine
(5S,6R,7R,9R,16R)-16-Hydroxy-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-17-oxa
(9S)-2,3,10,11,12,13-Hexahydro-3α-hydroxy-10α-methoxy-9-methyl-11α-methylamino-9β,13β-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one
9,13-Epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lM]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-3-hydroxy-10-Methoxy-9-Methyl-11-(MethylaMino)-, (3R,9S,10R,11R,13R)-
(5S,6R,7R,9R,16R)-16-Hydroxy-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-14(5H)-one
[Molecular Formula]

C28H26N4O4
[MDL Number]

MFCD26960886
[MOL File]

112953-11-4.mol
[Molecular Weight]

482.53
Chemical PropertiesBack Directory
[Boiling point ]

705.7±60.0 °C(Predicted)
[density ]

1.63±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO: >5mg/mL
[form ]

Tan solid
[pka]

12.25±0.70(Predicted)
[color ]

light yellow
[optical activity]

[α]20/D 130 to 160°, c = 0.2 in DMSO
Safety DataBack Directory
[WGK Germany ]

3
[RTECS ]

KC6600010
[Toxicity]

mouse,LD50,intraperitoneal,25mg/kg (25mg/kg),Journal of Antibiotics. Vol. 42, Pg. 571, 1989.
Hazard InformationBack Directory
[Description]

UCN-01 is a synthetic derivative of staurosporine with antiproliferative activity against several in vitro and in vivo cancer models. It inhibits a variety of kinases, including Akt, protein kinase C (IC50 = 30 nM), PDK1 (IC50 = 6 nM) and cyclin-dependent kinases (IC50s = 300-600 nM for Cdk1 and Cdk2). UCN-01 arrests tumor cells in the G1/S phase of the cell cycle and prevents nucleotide excision repair by inhibiting the G2 checkpoint kinase Chk1 (IC50 = 7 nM), leading to apoptosis.
[Uses]

UCN 01 is a protein kinase C inhibitor which overrides ZEB1-induced chemoresistance in hepatocellular cancer in human. A cell-permeable Staurosporine derived anticancer agent that inhibits several protein kinases.
[Uses]

UCN-01 is an indolocarbazole isolated from a high staurosporine-producing Streptomyces culture. UCN-01 inhibits protein kinase C (PKC) and cyclin-dependant kinase 2 (CDK2), resulting in accumulation of cells in the G1 phase and induction of apoptosis. UCN-01 also enhances the cytotoxicity of other anti-cancer drugs, such as DNA-damaging agents and anti-metabolite drugs, through putative abrogation of G2 and/or S phase accumulation induced by the latter agents.
[General Description]

A cell-permeable Staurosporine (Cat. No. 569397) derived anticancer agent that reversibly and ATP-competitively inhibits several protein kinases (IC50 = 29 nM, 34 nM, 30 nM, 590 nM and 530 nM for PKCα, PKCβ, PKCγ, PKCδ and PKCε; IC50 = 7 nM, 27 nM, 50 nM, 50 nM, 150 nM and 1.04 M for Chk1, Cdc25C-associated protein kinase 1, Cdk1, PAK4, Cdk5/p25 and Chk2; IC50 = 33 nM, 50 nM, 95 nM, 500 nM, 500 nM and 1.0 M for PDK1, lck, MAPKAP kinase-2, Akt, GSK-3β and PKA, respectively). At higher concentrations (>15 M), affects the activities of Src, PIM-1, CKII, DNA-PK, ErK1, ILK-1 and MAPKK1). Reported to suppress thymidylate synthase expression, induce apoptosis with caspase activation, and sensitize tumor cells to a range of DNA-damaging agents.
[Biochem/physiol Actions]

Cell permeable: yes
[storage]

Store at -20°C
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