| Identification | Back 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 Properties | Back 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 Rotation]
[α]20/D 130 to 160°, c = 0.2 in DMSO | [InChIKey]
PBCZSGKMGDDXIJ-HQCWYSJUSA-N | [SMILES]
[n]21c3c4[n](c6c(c4c7c(c3c8c2cccc8)[C@H](NC7=O)O)cccc6)[C@@H]5O[C@]1([C@@H]([C@@H](C5)NC)OC)C |
| Safety Data | Back Directory | [WGK Germany ]
3 | [RTECS ]
KC6600010 | [Storage Class]
11 - Combustible Solids | [Toxicity]
mouse,LD50,intraperitoneal,25mg/kg (25mg/kg),Journal of Antibiotics. Vol. 42, Pg. 571, 1989. |
| Hazard Information | Back 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 | [References]
[1] KAWABE T. G2 checkpoint abrogators as anticancer drugs.[J]. Molecular Cancer Therapeutics, 2004, 3 4 1: 513-519. DOI: 10.1158/1535-7163.513.3.4
[2] CHRISTIAN PEIFER DR. Dario?R. A Prof??Dr. Small-Molecule Inhibitors of PDK1[J]. ChemMedChem, 2008, 3 12: 1810-1838. DOI: 10.1002/cmdc.200800195
[3] A M SENDEROWICZ E A S. Preclinical and clinical development of cyclin-dependent kinase modulators.[J]. JNCI Journal of the National Cancer Institute, 2000, 92 5: 376-387. DOI: 10.1093/jnci/92.5.376
[4] Q WANG. UCN-01: a potent abrogator of G2 checkpoint function in cancer cells with disrupted p53.[J]. JNCI Journal of the National Cancer Institute, 1996, 88 14: 956-965. DOI: 10.1093/jnci/88.14.956
[5] TAKAHIRO YAMAUCHI William P Michael J Keating. UCN-01 (7-hydroxystaurosporine) inhibits DNA repair and increases cytotoxicity in normal lymphocytes and chronic lymphocytic leukemia lymphocytes.[J]. Molecular Cancer Therapeutics, 2002, 1 4: 287-294.
[6] MARIA M FACCHINETTI. UCN-01-induced cell cycle arrest requires the transcriptional induction of p21(waf1/cip1) by activation of mitogen-activated protein/extracellular signal-regulated kinase kinase/extracellular signal-regulated kinase pathway.[J]. Cancer research, 2004, 64 10: 3629-3637. DOI: 10.1158/0008-5472.can-03-3741 |
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BOC Sciences
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Sigma-Aldrich
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Lynnchem
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