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SML0310

Sigma-Aldrich

Tryptanthrin

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C15H8N2O2
Numéro CAS:
13220-57-0
Poids moléculaire :
248.24
Numéro MDL:
MFCD00012073
Code UNSPSC :
12352200
ID de substance PubChem :
329825315
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Couleur

faintly yellow to dark yellow

Solubilité

DMSO: 2 mg/mL (warmed)

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

VQQVWGVXDIPORV-UHFFFAOYSA-N

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Conseils de prudence

P301 + P312 + P330

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Man Hagiyama et al.
Experimental and therapeutic medicine, 23(4), 274-274 (2022-03-08)
Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) uses its S1 spike protein to bind to angiotensin-converting enzyme 2 (ACE2) on human cells in the first step of cell entry. Tryptanthrin, extracted from leaves of the indigo plant, Polygonum tinctorium, using
C Vlachos et al.
The British journal of dermatology, 167(3), 496-505 (2012-04-27)
The aryl hydrocarbon receptor (AhR) is a nuclear receptor and transcriptional regulator with pleiotropic effects. The production of potent AhR ligands by Malassezia yeasts, such as indirubin, indolo[3,2-b]carbazole (ICZ), tryptanthrin and malassezin, has been associated with the pathogenesis of seborrhoeic
Jae-Min Hwang et al.
Journal of natural products, 76(3), 354-367 (2013-01-31)
The natural product tryptanthrin (1a) represents a potential lead for new tuberculosis (TB) drugs since tryptanthrin and its synthetic analogues possess potent in vitro activity against Mycobacterium tuberculosis (Mtb). However, in spite of their in vitro activity, none of these
Bing-Chung Liau et al.
Journal of pharmaceutical and biomedical analysis, 43(1), 346-351 (2006-08-04)
A rapid, selective, and sensitive LC-APCI-MS method is developed in this study for detecting and analyzing tryptanthrin, indigo, and indirubin in daqingye and banlangen, which are, respectively, the leaves and roots of Isatis indigotica and Strobilanthes cusia in traditional Chinese
Pooja P Bandekar et al.
Journal of medicinal chemistry, 53(9), 3558-3565 (2010-04-09)
Tryptanthrins have potential therapeutic activity against a wide variety of pathogenic organisms, although little is known about their mechanism. Activity against Escherichia coli, however, has not been examined. The effects of tryptanthrin (indolo[2,1-b]quinazolin-6,12-dione) and nine derivatives on growth, survival, and
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