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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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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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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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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
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
Sakineh Kazemi Noureini et al.
PloS one, 13(10), e0204901-e0204901 (2018-10-04)
Telomeres, the specialized dynamic structures at chromosome ends, regularly shrink with every replication. Thus, they function as an internal molecular clock counting down the number of cell divisions. However, most cancer cells escape this limitation by activating telomerase, which can
E Jagiełło-Wójtowicz et al.
Polish journal of pharmacology and pharmacy, 41(2), 125-131 (1989-03-01)
Our studies showed that the chelidonine administered intraperitoneally (ip) exerted an inhibitory effect on the central nervous system of the rodents. It was shown that chelidonine depressed the spontaneous and explorative motor activities, decreased body temperature, potentiated the action of
Avijit Paul et al.
Toxicology letters, 222(1), 10-22 (2013-07-16)
Poor oral bioavailability of chelidonine, a bio-active ingredient of Chelidonium majus, showing anti-cancer potentials against cancer cells with multidrug resistance, makes its optimal use rather limited. To address this problem, we encapsulated chelidonine in biodegradable poly(lactide-co-glycolide) (PLGA) polymers and evaluated
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