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SML2805

Narciclasine

Name: Narciclasine
Brand: SIGMA

≥98% (HPLC), Rho/Rho kinase/LIM kinase/cofilin signaling pathway activator, powder

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

NACRES:

NA.77

UNSPSC Code:

12352200

MDL number:

MFCD01729949

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Narciclasine, ≥98% (HPLC)

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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Related Categories

Bioactive Small Molecules

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

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

Regulatory Information

涉药品监管产品

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Narciclasine exerts anti-inflammatory actions by blocking leukocyte-endothelial cell interactions and down-regulation of the endothelial TNF receptor 1.

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

Narciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells.

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

RUNX1-targeted therapy for AML expressing somatic or germline mutation in RUNX1.

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

Global Trade Item Number

SKU	GTIN
SML2805-5MG	04061841844969
SML2805-1MG	04061841844952

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