112953-11-4

Basic information

• Product Name: UCN-01
• Synonyms: UCN-01;7-hydroxystaurosporine;KW-2401;(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)-;KRX-0601;NSC 638850;UNC 01
• CAS NO: 112953-11-4
• Molecular Formula: C28H26N4O4
• Molecular Weight: 482.53044
• Mol File: 112953-11-4.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 705.7°Cat760mmHg
• Flash Point: 380.6°C
• Appearance: light yellow/
• Density: 1.63g/cm³
• Vapor Pressure: 6.64E-21mmHg at 25°C
• Refractive Index: 1.827
• Storage Temp.: 2-8°C
• Solubility: DMSO: >5mg/mL
• PKA: 12.25±0.70(Predicted)
• CAS DataBase Reference: UCN-01(CAS DataBase Reference)
• NIST Chemistry Reference: UCN-01(112953-11-4)
• EPA Substance Registry System: UCN-01(112953-11-4)

Safety Data

• WGK Germany: 3
• RTECS: KC6600010
• Hazardous Substances Data: 112953-11-4(Hazardous Substances Data)

Usage

Description

UCN-01 is a synthetic derivative of staurosporine, an indolocarbazole isolated from a high staurosporine-producing Streptomyces culture. It is a cell-permeable anticancer agent that reversibly and ATP-competitively inhibits several protein kinases, including Akt, protein kinase C, PDK1, and cyclin-dependent kinases. UCN-01 possesses antiproliferative activity against various in vitro and in vivo cancer models, arresting tumor cells in the G1/S phase of the cell cycle and preventing nucleotide excision repair by inhibiting the G2 checkpoint kinase Chk1.

Uses

Used in Anticancer Applications:
UCN-01 is used as an anticancer agent for its ability to inhibit protein kinase C (PKC) and cyclin-dependent kinase 2 (CDK2), resulting in the accumulation of cells in the G1 phase and induction of apoptosis. It also enhances the cytotoxicity of other anti-cancer drugs, such as DNA-damaging agents and anti-metabolite drugs, through the putative abrogation of G2 and/or S phase accumulation induced by these agents.
Used in Overcoming Chemoresistance:
UCN-01 is used as a protein kinase C inhibitor to override ZEB1-induced chemoresistance in hepatocellular cancer in humans, making it a promising agent for improving the effectiveness of chemotherapy in resistant cases.
Used in Enhancing Apoptosis and Sensitizing Tumor Cells:
UCN-01 is used to suppress thymidylate synthase expression, induce apoptosis with caspase activation, and sensitize tumor cells to a range of DNA-damaging agents, thereby increasing the effectiveness of cancer treatment.

Biochem/physiol Actions

Cell permeable: yes

InChI:InChI=1/C28H26N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,27,29,34H,12H2,1-3H3,(H,30,33)/t15-,18+,25-,27-,28+/m1/s1

Related news

Controlled release of a protein kinase inhibitor UCN-01 (cas 112953-11-4) from liposomes influenced by the particle size08/04/2019

A protein kinase inhibitor UCN-01 binds with high affinity to human α1-acid glycoprotein (hAGP) which may compromise the drugs therapeutic effectiveness. Liposomal formulations of UCN-01 have been evaluated as a means of reducing the impact of binding to hAGP. However, in an initial study, UCN-...detailed

UCN-01 (cas 112953-11-4) in combination with topotecan in patients with advanced recurrent ovarian cancer: A study of the Princess Margaret Hospital Phase II consortium08/03/2019

Background and objectiveUCN-01 is a staurosporine analogue shown to abrogate the G2 checkpoint through inhibition of cyclin-dependent kinases. Preclinical evidence suggests synergy between UCN-01 and cytotoxic chemotherapy. Topotecan is an active agent in ovarian cancer. This phase II study was ...detailed

Development of a simplified, sensitive high-performance liquid chromatographic method using fluorescence detection to determine the concentration of UCN-01 (cas 112953-11-4) in human plasma07/31/2019

UCN-01 is a naturally derived anticancer agent isolated in the culture broth of actinomyces streptomyces. We have developed a sensitive high-performance liquid chromatographic method for the determination of UCN-01 in human plasma. UCN-01 was isolated from human plasma after intravenous administ...detailed

MK-8776, a novel Chk1 inhibitor, exhibits an improved radiosensitizing effect compared to UCN-01 (cas 112953-11-4) by exacerbating radiation-induced aberrant mitosis07/30/2019

Checkpoint kinase 1 (Chk1) is an evolutionarily conserved serine/threonine kinase that plays an important role in G2/M checkpoint signaling. Here, we evaluate the radiosensitizing effects of a novel selective Chk1 inhibitor MK-8776, comparing its efficacy with a first-generation Chk1 inhibitor U...detailed

The combination of UCN-01 (cas 112953-11-4) and ATRA triggers differentiation in ATRA resistant acute promyelocytic leukemia cell lines via RAF-1 independent activation of MEK/ERK07/27/2019

With the introduction of arsenic trioxide and all-trans retinoic acid, the prognosis of acute promyelocytic leukemia has greatly improved. However, all-trans retinoic acid resistance is still unresolved in acute promyelocytic leukemia relapsed patients. In this study, the clinical achievable con...detailed