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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. 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

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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Li-Ping Bai et al.
Bioorganic & medicinal chemistry, 14(16), 5439-5445 (2006-05-30)
A comparative study on the intercalating binding of sanguinarine, chelerythrine, and nitidine with CT DNA, poly(dG-dC).poly(dG-dC), poly(dA-dT).poly(dA-dT), and seven sequence-designed double-stranded oligodeoxynucleotides has been performed using fluorometric and spectrophotometric techniques, aiming at providing insights into their sequence selectivity for DNA-binding.
Huagang Liu et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 34(11), 1406-1409 (2009-09-24)
A high performance liquid chromatography (HPLC) method was developed to determine the concentration of nitidine chloride in plasma and successfully applied to study pharmacokinetics after i.v. administration in rabbits. Twelve rabbits, randomized into 2 groups , were given i.v. at
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
Ziqiang Wang et al.
Journal of ethnopharmacology, 144(1), 145-150 (2012-09-14)
Zanthoxylum nitidium (Roxb.) DC. has long been used as a traditional herbal medicine for inflammatory diseases such as rheumatic arthritis and peridentitis. However, the anti-inflammatory mechanism of Nitidine chloride has not been fully elucidated. To determine the anti-inflammatory effects and
Hironori Iwasaki et al.
Cancer chemotherapy and pharmacology, 66(5), 953-959 (2010-03-20)
Nitidine (NTD) cytotoxicity is highly specific for A549 human lung adenocarcinoma cells. We hypothesized that this cytotoxicity involved the accumulation of NTD in intracellular organelles. However, there have been no reports of NTD transporting factors. In this study, we screened
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