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Chaetominine

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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
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Chaetominine Chemical Properties

Melting point:
164℃
Density 
1.63
storage temp. 
Store at -20°C
solubility 
Soluble in DMSO
form 
A solid
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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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