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54274

Sigma-Aldrich

Chelidonine

≥97.0% (HPLC)

Synonym(s):

Stylophorin

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About This Item

Empirical Formula (Hill Notation):
C20H19NO5
CAS Number:
476-32-4
Molecular Weight:
353.37
EC Number:
207-504-1
MDL number:
MFCD00069660
UNSPSC Code:
12352202
PubChem Substance ID:
329758025
NACRES:
NA.77

assay

≥97.0% (HPLC)

form

solid

impurities

~5% water

storage temp.

2-8°C

SMILES string

[H][C@]12[C@@H](O)Cc3cc4OCOc4cc3[C@@]1([H])N(C)Cc5c6OCOc6ccc25

InChI

1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1

InChI key

GHKISGDRQRSCII-ZOCIIQOWSA-N

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Biochem/physiol Actions

Inhibits tubulin polymerisation (IC50=24 μM), thereby disrupting microtubule structure in cells and inducing a G2/M mitotic arrest.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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Maria Emilia Isolani et al.
European journal of pharmacology, 686(1-3), 1-7 (2012-04-17)
The presence of adult pluripotent stem cells and the amazing regenerative capabilities make planarian flatworms an extraordinary experimental model to assess in vivo the effects of substances of both natural and synthetic origin on stem cell dynamics. This study focuses
Sakineh Kazemi Noureini et al.
World journal of gastroenterology, 15(29), 3603-3610 (2009-08-05)
To investigate the potential effects of chelidonine, the main alkaloid of Chelidonium majus, on telomerase activity and its regulation in HepG2 cells. Cytotoxicity of chelidonine for HepG2 cells was determined by neutral red assay. A modified polymerase chain reaction (PCR)-based
Stepwise gradient in thin-layer chromatography of Chelidonium alkaloids.
G Matysik et al.
Journal of chromatography, 518(1), 273-276 (1990-09-28)
Vitaliy Kaminskyy et al.
Toxicology letters, 177(3), 168-181 (2008-03-08)
Sanguinarine, chelerythrine and chelidonine possess prominent apoptotic effects towards cancer cells. In this study, we found that sanguinarine and chelerythrine induce apoptosis in human CEM T-leukemia cells, and that is accompanied by an early increase in cytosolic cytochrome c that
Matthew J Fleming et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(7), 2112-2124 (2008-01-18)
New enantioselective syntheses of the B/C hexahydrobenzo[c]phenanthridine alkaloids (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine, and (+)-norchelidonine are described. Our rapid and convergent route to this class of natural products involved the development and application of a Pd II-catalyzed asymmetric ring-opening reaction of
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