Narciclasine

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Cat.No. 3715 - Narciclasine | C14H13NO7 | CAS No. 29477-83-6
Description: Antiproliferative agent; slows cell cycle progression
Chemical Name: (2S,3R,4S,4aR)-3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature

Biological Activity

Exhibits antiproliferative and pro-apoptotic effects in carcinoma cells and displays cytotoxic activity against a panel of 60 cancer cell lines (mean IC50 = 47 nM). Activity decreases rate of cell division and increases mitosis duration in vitro. Also modulates the Rho/ROCK/LIM kinase/cofilin pathway; stimulates RhoA activation and induces actin polymerization.

Technical Data

M. Wt 307.26
Formula C14H13NO7
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 29477-83-6
PubChem ID 72376
InChI Key LZAZURSABQIKGB-AEKGRLRDSA-N
Smiles OC1=C(C(N[C@]4([H])C3=C[C@H](O)[C@@H](O)[C@H]4O)=O)C3=CC2=C1OCO2

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.73 100

Preparing Stock Solutions

The following data is based on the product molecular weight 307.26. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.25 mL 16.27 mL 32.55 mL
5 mM 0.65 mL 3.25 mL 6.51 mL
10 mM 0.33 mL 1.63 mL 3.25 mL
50 mM 0.07 mL 0.33 mL 0.65 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Dumont et al (2007) The Amaryllidaceae isocarbostyril narciclasine induces apoptosis by activation of the death receptor and/or mitochondrial pathways in cancer cells but not in normal fibroblasts. Neoplasia 9 766 PMID: 17898872

Ingrassia et al (2009) Structure-activity relationship analysis of novel derivatives of narciclasine (an Amaryllidaceae isocarbostyril derivative) as potential anticancer agents. J.Med.Chem. 52 1100 PMID: 19199649

Lefranc et al (2009) Narciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells. Mol.Cancer Ther. 8 1739 PMID: 19531573


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Keywords: Narciclasine small g proteins rhoA rho kinases ROCK signaling signalling modulators anticancer antiproliferative agents cell cycle inhibitors inhibits actin Cell Cycle Inhibitors

Citations for Narciclasine

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Cell Cycle & DNA Damage Repair

Cell Cycle & DNA Damage Repair Poster

In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.

Pathways for Narciclasine

Protocols

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