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Xylopine

Names

[ CAS No. ]:
517-71-5

[ Name ]:
Xylopine

[Synonym ]:
6Abeta-noraporphine,9-methoxy-1,2-(methylenedioxy)
(7aR)-6,7,7a,8-Tetrahydro-10-methoxy-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline

Biological Activity

[Description]:

Xylopine is an aporphine alkaloid with cytotoxic activity on cancer cells. Xylopine induces oxidative stress, causes G2/M cell cycle arrest and apoptosis in cancer cells[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer

[In Vitro]

Xylopine (3.5 μM-14 μM; 24-48 hours) displays potent cytotoxicity in a time- and does-depenpent manner[1]. Xylopine (72 h) has cytotoxic activity, with IC50 values ranging from 6.4 to 26.6 μM in eight different cancer cell lines (MCF7, HCT116, HepG2, SCC-9, HSC-3, HL-60, K-562, and B16-F10)[1]. Xylopine (3.5 μM-14 μM; 24-48 hours) causes cell cycle block at the phase G2/M, which is followed by internucleosomal DNA fragmentation[1]. Xylopine (3.5 μM-14 μM; 24-48 hours) significantly increases the early and late apoptosis, induces mitochondrial depolarization, and increases caspase-3 activation[1]. Xylopine also causes an increase in the production of reactive oxygen/nitrogen species (ROS/RNS), including hydrogen peroxide and nitric oxide, but not superoxide anion, and reduces glutathione levels are decreased in Xylopine-treated HCT116 cells[1].HCT116 cells[1]3.5 μM, 7 μM, and 14 μM 24 hours, 48 hoursInduced G2/M phase arrest.HCT116 cells[1]3.5 μM, 7 μM, and 14 μM 24 hours, 48 hoursSignificantly increased the early and late apoptosis. Cell Viability Assay[1] Cell Line: HCT116 cells Concentration: 3.5 μM, 7 μM, and 14 μM Incubation Time: 24 hours, 48 hours Result: Displayed potent cytotoxicity in HCT116 cells. Cell Cycle Analysis[1] Cell Line: HCT116 cells Concentration: 3.5 μM, 7 μM, and 14 μM Incubation Time: 24 hours, 48 hours Result: Induced G2/M phase arrest. Apoptosis Analysis[1] Cell Line: HCT116 cells Concentration: 3.5 μM, 7 μM, and 14 μM Incubation Time: 24 hours, 48 hours Result: Significantly increased the early and late apoptosis.

[References]

[1]. Luciano de Souza Santos, et al. Xylopine Induces Oxidative Stress and Causes G 2/M Phase Arrest, Triggering Caspase-Mediated Apoptosis by p53-Independent Pathway in HCT116 Cells. Oxid Med Cell Longev. 2017;2017:7126872.

Chemical & Physical Properties

[ Density]:
1.289g/cm3

[ Boiling Point ]:
483.4ºC at 760mmHg

[ Molecular Formula ]:
C18H17NO3

[ Molecular Weight ]:
295.33200

[ Flash Point ]:
193.7ºC

[ Exact Mass ]:
295.12100

[ PSA ]:
39.72000

[ LogP ]:
3.16260

[ Index of Refraction ]:
1.635

Synthetic Route

Precursor & DownStream


Related Compounds

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