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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

Signal Word

Danger

Hazard Statements

H301 + H331

Hazard Classifications

Acute Tox. 3 Inhalation - 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

Personal Protective Equipment

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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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
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
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
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
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