TRYPTANTHRIN
- Product Name
- TRYPTANTHRIN
- CAS No.
- 13220-57-0
- Chemical Name
- TRYPTANTHRIN
- Synonyms
- Couroupitine A;INDOLO[2,1-B]QUINAZOLINE-6,12-DIONE;NSC 349447;TRYPTANTHRIN;Trypanthrine;tryptanthrine;TRYPTANTHRIN-D4;Color amine ketone;6,12-Dihydroindolo[2,1-b]quinazoline-6,12-dione;CouroupitineAIndolo(2,1-b)quinazoline-6,12-dioneTryptanthrine
- CBNumber
- CB4477493
- Molecular Formula
- C15H8N2O2
- Formula Weight
- 248.24
- MOL File
- 13220-57-0.mol
TRYPTANTHRIN Property
- Melting point:
- 258 °C(Solv: ethanol (64-17-5))
- Boiling point:
- 469.3±28.0 °C(Predicted)
- Density
- 1.45±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- DMSO: soluble2mg/mL (warmed)
- pka
- -3.06±0.20(Predicted)
- form
- powder
- color
- faint yellow to dark yellow
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- InChIKey
- VQQVWGVXDIPORV-UHFFFAOYSA-N
Safety
- WGK Germany
- 3
- HS Code
- 29339900
N-Bromosuccinimide Price
- Product number
- SML0310
- Product name
- Tryptanthrin
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $78.1
- Updated
- 2024/03/01
- Product number
- SML0310
- Product name
- Tryptanthrin
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $252
- Updated
- 2024/03/01
- Product number
- 17913
- Product name
- Tryptanthrin
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 17913
- Product name
- Tryptanthrin
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $63
- Updated
- 2024/03/01
- Product number
- PHL83458
- Product name
- Tryptanthrine
- Purity
- phyproof Reference Substance
- Packaging
- 10mg
- Price
- $430
- Updated
- 2024/03/01
TRYPTANTHRIN Chemical Properties,Usage,Production
Description
The matured fruit of Couroupita guianensis yields two highly unsaturated alkaloids. Couroupitine A is obtained in the form of yellow needles when crystallized from MeOH-CHCI3. It gives an ultraivolet spectrum with absorption maxima at 225 and 251 nm and an inflexion at 315 nm in EtOH.
Uses
Tryptanthrin is natural alkaloid, and a potent inhibitor of cyclooxygenase COX-2 and 5-lipoxygenase acting as an anti-inflammatory agent.
Definition
ChEBI: Tryptanthrine is an organonitrogen heterocyclic compound, an organic heterotetracyclic compound and an alkaloid antibiotic.
General Description
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Biochem/physiol Actions
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.
in vitro
in human hepatocyte-derived hepg2 cells, tryptanthrin inhibited the reactive oxygen species formation, mitochondrial dysfunction, and cell death triggered by tert-butyl hydroperoxide (tbhp). furthermore, tryptanthrin reversed the reduction of glutathione (gsh) induced by tbhp. specifically, nuclear translocation, transactivation of nuclear factor erythroid 2-related factor 2 (nrf2), and phosphorylation of extracellular signal-regulated kinase (erk) were evoked by the treatment of tryptanthrin. additionally, the expression of the heme oxygenase 1 and glutamate was upregulated by tryptanthrin [1].
in vivo
balb/c (h-2d) mice, intraperitoneally (i.p.) inoculated with leukemia wehi-3b jcs cells, were injected i.p with tryptanthrin at doses of 0.04 mg/kg, 0.08 mg/kg and 0.16 mg/kg body weight for 5 consecutive days. tryptanthrin inhibited the growth of wehi-3b jcs cells in balb/c mice, and at the dosages of 0.08 mg/kg and 0.16 mg/kg, significant inhibition was seen. moreover, tryptanthrin, in a dose-dependent fashion, triggered cell cycle arrest of the wehi-3b jcs cells at g0/g1 phase [2].
References
Sen, Mahato, Dutta, Tetrahedron Lett., 609 (1974)
TRYPTANTHRIN Preparation Products And Raw materials
Raw materials
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