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SML0610

Sigma-Aldrich

Nitidine chloride

≥97% (HPLC)

Synonym(s):

2,3-Dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium chloride, NSC 146397

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About This Item

Empirical Formula (Hill Notation):
C21H18NO4 · Cl
CAS Number:
13063-04-2
Molecular Weight:
383.82
MDL number:
MFCD01659688
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 1 mg/mL, clear (warmed)

shipped in

wet ice

storage temp.

−20°C

SMILES string

C[N+]1=CC2=CC(OC)=C(OC)C=C2C3=CC=C4C=C5C(OCO5)=CC4=C31.[Cl-]

InChI

1S/C21H18NO4.ClH/c1-22-10-13-7-17(23-2)18(24-3)8-15(13)14-5-4-12-6-19-20(26-11-25-19)9-16(12)21(14)22;/h4-10H,11H2,1-3H3;1H/q+1;/p-1

InChI key

QLDAACVSUMUMOR-UHFFFAOYSA-M

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Biochem/physiol Actions

Nitidine chloride is a natural product with anti-cancer activity.
Nitidine chloride is a natural product with anti-cancer activity. Its mechanism of action likely involves several pathways. Nitidine chloride has been found to inhibit topoisomerase I and topoisomerase II, induce cell apoptosis by activation of the caspase-dependent pathway, suppress c-Src/FAK associated signaling pathways and suppress Janus kinase 2/STAT3 signaling and the expression of STAT3-dependent target genes, including cyclin D1, Bcl-xL, and VEGF. Nitidine chloride has also been found to have anti-malaria activity.

Features and Benefits

This compound is featured on the Caspases, Fak and JAKs pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P301 + P310 + P330

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
057M4717V
033M4709V

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Min Kang et al.
Journal of B.U.ON. : official journal of the Balkan Union of Oncology, 19(1), 130-136 (2014-03-25)
This study was conducted to investigate the effect of nitidine chloride (NC) on the proliferation and apoptosis of nasopharyngeal carcinoma cell line CNE1, CNE2, TWO3, and C666-1, and to explore its antitumor mechanism. NC was dissolved in IMDM medium and
Mathieu Blanchot et al.
Organic letters, 13(6), 1486-1489 (2011-02-26)
The use of aryl triflates as reaction partners in a palladium-catalyzed domino direct arylation/N-arylation provides a great advantage due to the availability of starting materials. Furthermore, it allows expedient access to biologically interesting benzo[c]phenanthridine alkaloids.
Zhiqing Fang et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 60, 246-251 (2013-08-06)
Nitidine Chloride (NC) has been shown to have anti-cancer effects on various tumors. However, whether NC could exert anti-metastasis activity in renal cancer cells and the underlying mechanisms have not been elucidated. In this work, our data demonstrated the anti-metastasis
Can Xiao et al.
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 34(4), 551-553 (2011-08-04)
To study the alkaloids from the stems of Zanthoxylum dissitum. Added ammonia to the 0.5% HCl extract solution of the plants until the pH was 11 to collect the total alkaloids. Using the chromatography of alumina and silica gel to
S Zhang et al.
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 24(9), 649-650 (2002-01-22)
To determine the nitidine in different parts of Zanthoxylum nitidum (Roxb.) DC. HPLC method was used. The column was HYPERSIL BDS C18. The mobile phase was 0.02 mol/L monobasic potassium phosphate: acetonitrile (66:34). The detective wavelength was 328 nm. The
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