Xylopine

Modify Date: 2024-01-08 12:00:07

Xylopine Structure
Xylopine structure
Common Name Xylopine
CAS Number 517-71-5 Molecular Weight 295.33200
Density 1.289g/cm3 Boiling Point 483.4ºC at 760mmHg
Molecular Formula C18H17NO3 Melting Point N/A
MSDS N/A Flash Point 193.7ºC

 Use of Xylopine


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].

 Names

Name Xylopine
Synonym More Synonyms

 Xylopine 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
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

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Xylopine Structure

Xylopine

CAS#:517-71-5

Literature: Lu, Sheng-Teh; Wu, Yang-Chang; Leou, Shiow-Piaw Phytochemistry (Elsevier), 1985 , vol. 24, # 8 p. 1829 - 1834

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Xylopine Structure

Xylopine

CAS#:517-71-5

Literature: Lu, Sheng-Teh; Wu, Yang-Chang; Leou, Shiow-Piaw Phytochemistry (Elsevier), 1985 , vol. 24, # 8 p. 1829 - 1834

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Xylopine Structure

Xylopine

CAS#:517-71-5

Literature: Manske Canadian Journal of Research, Section B: Chemical Sciences, 1938 , vol. 16, p. 85 Chem. Zentralbl., 1938 , vol. 109, # II p. 324

 Synonyms

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
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