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SML0310

Sigma-Aldrich

Tryptanthrin

≥98% (HPLC)

Synonym(s):

Couroupitine A, Indolo(2,1-b)quinazoline-6,12-dione, NSC 349447, Tryptanthrine

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About This Item

Empirical Formula (Hill Notation):
C15H8N2O2
CAS Number:
13220-57-0
Molecular Weight:
248.24
MDL number:
MFCD00012073
UNSPSC Code:
12352200
PubChem Substance ID:
329825315
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

faintly yellow to dark yellow

solubility

DMSO: 2 mg/mL (warmed)

storage temp.

2-8°C

SMILES string

O=C1C2=NC3=CC=CC=C3C(N2C4=C1C=CC=C4)=O

InChI

1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H

InChI key

VQQVWGVXDIPORV-UHFFFAOYSA-N

Biochem/physiol Actions

Tryptanthrin is a plant alkaloid with anti-inflammatory and anti cancer activities.
Tryptanthrin is a plant alkaloid with anti-inflammatory and anti cancer activities. Tryptanthrin blocks leukotriene production in neutrophils and in whole blood assays, and in an in vivo rat pleurisy model. The compound also inhibits P-glycoprotein, and sensitizes resistant cancer cell lines to killing by cytotoxic agents.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000211072
0000211072
0000188356
0000153607
0000153606

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Hui-Man Cheng et al.
BMC complementary and alternative medicine, 17(1), 439-439 (2017-09-04)
Indigo naturalis is a Traditional Chinese Medicine (TCM) ingredient long-recognized as a therapy for several inflammatory conditions, including psoriasis. However, its mechanism is unknown due to lack of knowledge about the responsible chemical entity. We took a different approach to
Tobias Mohn et al.
Planta medica, 73(2), 151-156 (2007-01-20)
An HPLC method has been developed and validated for the quantification of the pharmacologically active principles tryptanthrin (1), 1,3-dihydro-3-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-2 H-indol-2-one (indolinone) (3), indirubin (4), alpha-linolenic acid (2), and indigo (5), an isomer of indirubin, in extracts from the traditional anti-inflammatory
Sung-Tsai Yu et al.
Biochemical and biophysical research communications, 358(1), 79-84 (2007-05-08)
Development of agents to overcome multidrug resistance (MDR) is important in cancer chemotherapy. Up to date, few chemicals have been reported to down-regulate MDR1 gene expression. We evaluated the effect of tryptanthrin on P-glycoprotein (P-gp)-mediated MDR in a breast cancer
Sung-tsai Yu et al.
Acta pharmacologica Sinica, 31(2), 259-264 (2010-02-09)
To evaluate the effects and elucidate the mechanisms of a series of indoloquinazolines as novel anticancer agents. Condensation of the substituted isatoic anhydride with the substituted isatin was performed to prepare compounds 1-4, followed by adding malononitrile to prepare compounds
C Pergola et al.
British journal of pharmacology, 165(3), 765-776 (2011-07-30)
Leukotrienes (LTs) are pro-inflammatory mediators produced by 5-lipoxygenase (5-LO). Currently available 5-LO inhibitors either lack efficacy or are toxic and novel approaches are required to establish a successful anti-LT therapy. Here we provide a detailed evaluation of the effectiveness of
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