Xylopine

• CAT Number: I044782
• CAS Number: 517-71-5
• Molecular Formula: C18H17NO3
• Molecular Weight: 295.33
• Purity: ≥95%
• Synonyms: (12R)-16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14(19),15,17-hexaene
• InChI: InChI=1S/C18H17NO3/c1-20-12-2-3-13-11(6-12)7-14-16-10(4-5-19-14)8-15-18(17(13)16)22-9-21-15/h2-3,6,8,14,19H,4-5,7,9H2,1H3/t14-/m1/s1
• InChIKey: RFWCCZDSXIZJMF-CQSZACIVSA-N
• SMILES: COC1=CC2=C(C=C1)C3=C4C(C2)NCCC4=CC5=C3OCO5

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].
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 hours
Induced G2/M phase arrest.
HCT116 cells[1]
3.5 μM, 7 μM, and 14 μM
24 hours, 48 hours
Significantly increased the early and late apoptosis.

Reference

[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.
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