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Merck

54274

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
NACRES:
NA.77
PubChem Substance ID:
329758025
UNSPSC Code:
12352202
EC Number:
207-504-1
MDL number:
MFCD00069660
Assay:
≥97.0% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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Product Name

Chelidonine, ≥97.0% (HPLC)

InChI key

GHKISGDRQRSCII-ZOCIIQOWSA-N

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

SMILES string

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

assay

≥97.0% (HPLC)

form

solid

impurities

~5% water

storage temp.

2-8°C

Quality Level

100

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Related Categories

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD7509
BCBZ6536
BCBF0551V
BCBV3780
BCBQ5285V

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Alex Philchenkov et al.
Toxicology in vitro : an international journal published in association with BIBRA, 22(2), 287-295 (2007-11-21)
Apoptogenic and DNA damaging effects of chelidonine (CHE) and sanguinarine (SAN), two structurally related benzophenanthridine alkaloids isolated from Chelidonium majus L. (Papaveraceae), were compared. Both alkaloids induced apoptosis in human acute T-lymphoblastic leukaemia MT-4 cells. Apoptosis induction by CHE and
Mahmoud Zaki El-Readi et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 20(3-4), 282-294 (2012-12-15)
Cancer cells often develop multidrug resistance (MDR) which is a multidimensional problem involving several mechanisms and targets. This study demonstrates that chelidonine and an alkaloid extract from Chelidonium majus, which contains protoberberine and benzo[c]phenanthridine alkaloids, has the ability to overcome
G Grynkiewicz et al.
European journal of medicinal chemistry, 36(11-12), 951-960 (2002-01-05)
A group of 11 derivatives of chelidonine was obtained by acylations and/or alkylations of the secondary hydroxyl group with the aim of testing their biological activity. This paper focuses on the new derivatives influence on CNS in mice. The highest
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
S S Lee et al.
Phytotherapy research : PTR, 15(2), 167-169 (2001-03-27)
The effects of benzophenanthridine alkaloids, such as sanguinarine and chelidonine, on monoamine -oxidase (MAO) activity in mouse brain were investigated. Sanguinarine showed an inhibitory effect on MAO activity in a concentration dependent manner (53.4% inhibition at 25 microM). However, chelidonine
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