Chaetominine
Chaetominine Basic information
- Product Name:
- Chaetominine
- Synonyms:
-
- Chaetominine
- (2S,4R,5aS,9cS)-4,5,5a,9c-Tetrahydro-5a-hydroxy-2-methyl-4-(4-oxo-3(4H)-quinazolinyl)-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione
- Chaetominine (-)-Chaetominine
- (2S,2a1S,4R,5AS)-5a-hydroxy-2-methyl-4-(4-oxoquinazolin-3(4H)-yl)-2a1,4,5,5a-tetrahydro-1H-2a
- (-)-CHAETOMININE
- CS-493
- 3H-2a,9b-Diazacyclopenta[jk]fluorene-1,3(2H)-dione, 4,5,5a,9c-tetrahydro-5a-hydroxy-2-methyl-4-(4-oxo-3(4H)-quinazolinyl)-, (2S,4R,5aS,9cS)-
- (–)-Chaetominine
- CAS:
- 918659-56-0
- MF:
- C22H18N4O4
- MW:
- 402.4
- EINECS:
- 604-604-1
- Mol File:
- 918659-56-0.mol
Chaetominine Chemical Properties
- Melting point:
- 164℃
- Density
- 1.63
- storage temp.
- Store at -20°C
- solubility
- Soluble in DMSO
- form
- A solid
Chaetominine Usage And Synthesis
Description
(–)-Chaetominine is a cytotoxic alkaloid originally isolated from Chaetomium sp. IFB-E015. It inhibits the growth of K562 leukemia and SW1116 colon cancer cells (IC50s = 20 and 28 nM, respectively). (–)-Chaetominine induces apoptosis of K562 cells via upregulation of the Bax/Bcl-2 ratio, decreasing mitochondrial membrane potential, inducing mitochondrial cytochrome C release, and activation of caspase-3 and caspase-9. It also decreases doxorubicin efflux mediated by multidrug resistance-associated protein 1 (MRP1) and restores sensitivity to doxorubicin in resistant K562 cells.
Definition
ChEBI: Chaetominine is an organic heterotetracyclic compound that consists of 4,5,5a,9c-tetrahydro-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione substituted by a hydroxy group at position 5, a methyl group at position 2 and a 4-oxoquinazolin-3(4H)-yl group at position 4 (the 2S,4R,5aS,9cS stereoisomer). It is a cytotoxic alkaloid isolated from the endophytic fungus Chaetomium. It has a role as a metabolite. It is an organic heterotetracyclic compound, a member of quinazolines, a lactam and an indole alkaloid.
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