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Merck
CN

SML0610

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
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD01659688

Key Documents

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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

SMILES string

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

InChI key

QLDAACVSUMUMOR-UHFFFAOYSA-M

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 1 mg/mL, clear (warmed)

shipped in

wet ice

storage temp.

−20°C

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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

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
057M4717V
033M4709V

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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
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
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
Qiang Xu et al.
Nan fang yi ke da xue xue bao = Journal of Southern Medical University, 31(2), 361-364 (2011-03-01)
To investigate the apoptosis-inducing effect of nitidine chloride in human osteosarcoma MG-63 cells and explore its mechanism. The effect of nitidine chloride on the proliferation of MG-63 cells was detected by colorimetric MTT assay, and the morphological changes of cells
Taro Enomoto et al.
The Journal of organic chemistry, 74(23), 9158-9164 (2009-11-17)
As a convenient and direct synthesis of 1,2-dihydroisoquinolines, the gold(I)-catalyzed intramolecular hydroamination of (2-alkynyl)benzyl carbamates has been developed. The reaction with cationic gold(I) complex [AuCl(PPh(3))/AgNTf(2)] proceeded at room temperature, giving the desired 6-endo adducts. The addition of alcohol efficiently promoted
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Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

Focal Adhesion Kinase (FAK) Overview

The focal adhesion kinase (FAK) is a cytoplasmic protein tyrosine kinase. FAK has been implicated as a downstream signaling molecule that functions in the control of several integrin-regulated biological processes.

Src Family Kinases Overview

Src is the original member of a group of non-receptor protein-tyrosine kinases termed the Src family kinases (SFKs). Learn about the SFKs that, in humans, consist of eight members, a small group of atypical members, and two related kinases.

半胱天冬酶抑制剂和活化剂

据报道可激活细胞半胱天冬酶的试剂包括化疗药物、TNF 受体激动剂和其他酶。细胞凋亡抑制剂是第一个确定的内源性半胱天冬酶抑制剂。

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