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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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X Wang et al.
Biochemistry, 37(8), 2691-2700 (1998-03-28)
The ability of DNA topoisomerase I to mediate the formation of structurally modified DNA duplexes was studied utilizing suicide substrates containing high-efficiency cleavage sites and acceptor oligonucleotides in which the 5'-terminal nucleotides were varied. When the substrates were nicked duplexes
Jie Feng et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 887-888, 43-47 (2012-02-11)
A new liquid chromatography-electrospray ionization-mass/mass spectrometry (LC-ESI-MS/MS) assay method has been developed and validated for the quantification of nitidine chloride (NC), an anti-cancer bioactive substance of Zanthoxylum nitidum (Roxb.) DC. plants, in rat plasma using carbamazepine as an internal standard
M Del Poeta et al.
Antimicrobial agents and chemotherapy, 43(12), 2862-2868 (1999-12-03)
The activities of a series of camptothecin and nitidine derivatives that might interact with topoisomerase I were compared against yeast and cancer cell lines. Our findings reveal that structural modifications to camptothecin derivatives have profound effects on the topoisomerase I-drug
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.
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