| Identification | Back Directory | [Name]
Chaetominine | [CAS]
918659-56-0 | [Synonyms]
CS-493
NSC746369
NSC-746369
NSC 746369
Chaetominine
(-)-CHAETOMININE
(–)-Chaetominine
Chaetominine
(-)-Chaetominine
(2S,2a1S,4R,5AS)-5a-hydroxy-2-methyl-4-(4-oxoquinazolin-3(4H)-yl)-2a1,4,5,5a-tetrahydro-1H-2a
(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
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)- | [EINECS(EC#)]
604-604-1 | [Molecular Formula]
C22H18N4O4 | [MDL Number]
MFCD22380597 | [MOL File]
918659-56-0.mol | [Molecular Weight]
402.4 |
| Hazard Information | Back Directory | [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. | [References]
[1] RUI H. JIAO. Chaetominine, a Cytotoxic Alkaloid Produced by Endophytic Chaetomium sp. IFB-E015[J]. Organic Letters, 2006, 8 25: 5709-5712. DOI: 10.1021/ol062257t
[2] JINGYUN YAO. Assessment of the Cytotoxic and Apoptotic Effects of Chaetominine in a Human Leukemia Cell Line[J]. Biomolecules & Therapeutics, 2016, 24 1: 147-155. DOI: 10.4062/biomolther.2015.093
[3] JINGYUN YAO Yanhua L Xing Wei. Chaetominine reduces MRP1-mediated drug resistance via inhibiting PI3K/Akt/Nrf2 signaling pathway in K562/Adr human leukemia cells[J]. Biochemical and biophysical research communications, 2016, 473 4: Pages 867-873. DOI: 10.1016/j.bbrc.2016.03.141 |
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Cckinase, Inc.
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+1 (732)236-3202 |
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www.cckinase.com |
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