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SML2805

Sigma-Aldrich

Narciclasine

≥98% (HPLC)

Synonym(s):

Narciclasine, (2S-(2-alpha,3-beta,4-beta,4a-beta))-3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one, 3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one, BRN 1087400, Lycoricidin-A, Lycoricidinol, NSC 266535

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About This Item

Empirical Formula (Hill Notation):
C14H13NO7
CAS Number:
29477-83-6
Molecular Weight:
307.26
MDL number:
MFCD01729949
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D 167 to 187° in DMSO

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O[C@H]1C=C2[C@@H](NC(=O)c3c(O)c4OCOc4cc23)[C@H](O)[C@@H]1O

InChI

1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1

InChI key

LZAZURSABQIKGB-AEKGRLRDSA-N

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Biochem/physiol Actions

Narciclasine is a Rho/Rho kinase/LIM kinase/cofilin signaling pathway activator. Also narciclasine is an actin stress fiber formation inducer; a plant growth modulator.
Recent report in Blood Identified cinobufagin, anisomycin and narciclasine as novel expression-mimickers (Ems) that exert in vitro as well as in vivo anti-AML efficacy against AML expressing mtRUNX1. Recent report identifies cinobufagin, anisomycin and narciclasine as novel expression-mimickers (Ems) that exert in vitro as well as in vivo anti-AML efficacy against AML expressing mtRUNX1.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anna Stark et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 33(8), 8771-8781 (2019-04-25)
The alkaloid narciclasine has been characterized extensively as an anticancer compound. Accumulating evidence suggests that narciclasine has anti-inflammatory potential; however, the underlying mechanism remains poorly understood. We hypothesized that narciclasine affects the activation of endothelial cells (ECs), a hallmark of
Christopher P Mill et al.
Blood, 134(1), 59-73 (2019-04-27)
RUNX1 transcription factor regulates normal and malignant hematopoiesis. Somatic or germline mutant RUNX1 (mtRUNX1) is associated with poorer outcome in acute myeloid leukemia (AML). Knockdown or inhibition of RUNX1 induced more apoptosis of AML expressing mtRUNX1 versus wild-type RUNX1 and
Florence Lefranc et al.
Molecular cancer therapeutics, 8(7), 1739-1750 (2009-06-18)
Cell motility and resistance to apoptosis characterize glioblastoma multiforme growth and malignancy. Narciclasine, a plant growth modulator, could represent a powerful new weapon targeting the Achilles' heel of glioblastoma multiforme and may offer the potential to better combat these devastating

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