| Identification | Back Directory | [Name]
Luotonine A | [CAS]
205989-12-4 | [Synonyms]
Luotonine A
LUMDXNLBIYLTER-UHFFFAOYSA-N
Quino[2',3':3,4]pyrrolo[2,1-b]quinazolin-11(13H)-one | [Molecular Formula]
C18H11N3O | [MDL Number]
MFCD16876401 | [MOL File]
205989-12-4.mol | [Molecular Weight]
285.3 |
| Chemical Properties | Back Directory | [Melting point ]
283-285 °C | [Boiling point ]
530.9±60.0 °C(Predicted) | [density ]
1.44±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
≤3mg/ml in DMSO;3mg/ml in dimethyl formamide | [form ]
crystalline solid | [pka]
1.61±0.20(Predicted) |
| Hazard Information | Back Directory | [Description]
Luotonin A is an alkaloid originally isolated from a plant used in traditional Chinese medicine. It inhibits the growth of mouse leukemia P388 cells (IC50 = 1.8 μg/ml). Luotonin A is structurally similar to the alkaloid camptothecin and, like camptothecin, it binds to and stabilizes the topoisomerase I-DNA binary complex, leading to DNA breakage and cell death (IC50 = 5.07-12.6 μM). Also like camptothecin, luotonin A forms non-covalent complexes with double-stranded DNA in the minor groove and this association can be followed by native fluorescence associated with the aromatic and heterocyclic ring structure. Luotonin A also selectively inhibits the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2 (IC50 = ~6 μM for each) in human liver microsomes. | [Uses]
Luotonine A is a pyrroloquinoline alkaloid, a topoisomerase I inhibitor and a potent CYP1A inhibitor. | [Definition]
ChEBI: Luotonin A is a member of quinazolines. | [in vitro]
luotonin a was isolated as a pyrroloquinazolinoquinoline alkaloid from the chinese medicinal plant peganum nigellastrum. luotonin a could stabilize the human dna topoisomerase i-dna covalent binary complex and mediate topoisomerase i-dependent cytotoxicity in intact cells. similar to camptothecin, luotonin a was able to effect concentration-dependent stabilization of the enzyme-dna binary complex. however, neither camptothecin nor luotonin a had any measurable effect on dna in the absence of topoisomerase i. in addition, luotonin a was evaluated in a strain of saccharomyces cerevisiae lacking yeast topoisomerase i, but having a plasmid having the human topoisomerase i gene under the control of a galactose promoter. results showed that luotonin a at 1 μm concentration could produce 36% inhibition of growth in the presence of galactose. moreover, in replicate experiments, lutonin a exhibited ic50 values from 5.7 to 12.6 μm in the presence of galactose, while the comparable values for camptothecin were from 0.74 to 0.86 μm [1]. | [IC 50]
1.8 μg/ml for p-388 cell line | [References]
[1] cagir, a. ,jones, s.h.,gao, r., et al. luotonin a. a naturally occurring human dna topoisomerase i poison. journal of the american chemical society 125(45), 13628-13629 (2003). |
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Energy Chemical
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