Name | Securinine |
Synonyms | securinin SECURININE Securinine (-)-securinin (-)-SECURININE SECURAN-11-ONE SECURININE(RG) Securinan-11-on securinan-11-one |
CAS | 5610-40-2 |
EINECS | 694-738-6 |
Molecular Formula | C13H15NO2 |
Molar Mass | 217.26 |
Density | 1.30±0.1 g/cm3 (20 ºC 760 Torr) |
Melting Point | 140-1420C |
Boling Point | 357.82°C (rough estimate) |
Specific Rotation(α) | D20 -1042° (c = 1 in alc) |
Solubility | Easily soluble in ethanol, chloroform, difficult to easy ether, petroleum ether, cold water. |
Appearance | Yellow crystalline powder |
Color | yellow |
pKa | 8.29±0.20(Predicted) |
Storage Condition | Sealed in dry,2-8°C |
Refractive Index | 1.5300 (estimate) |
MDL | MFCD00078775 |
Physical and Chemical Properties | Yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from the Euphorbiaceae plant leaf bottom beads tender leaves or roots, leaf beads. |
In vitro study | (-)-Securinine is a major plant-derived alkaloid and also a GABA A receptor antagonist. (-)-Securinine is significantly potent on HeLa cells growth inhibition with IC 50 values of 7.02±0.52 μg/mL (32.3 μM). (-)-Securinine induces apoptosis in a dose-dependent manner in the tested cells, increases the percentage of ROS positive cells and depolarized cells as well as stimulates the activity of ERK1/2, caspase-9 and -3/7. (-)-Securinine also induces cell cycle arrest in S phase. Real-time PCR analysis shows high expression of tumor necrosis factor receptor superfamily (TNFRSF) genes in the cells stimulated with (-)-Securinine. |
In vivo study | In this tumor model, tumor growth is significantly impaired with (-)-Securinine treatment indicating that (-)-Securinine has potential as an Acute Myeloid Leukemia (AML) therapeutic. (-)-Securinine treated mice (n=5 mice, bilateral tumors), exhibit an average of more than 75% smaller tumors than vehicle treated mice at the end of the study period. |
Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R22 - Harmful if swallowed |
Safety Description | S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
WGK Germany | 3 |
RTECS | VS4115000 |
Reference Show more | 1. [IF=6.514] Wen Hou et al."Novel virosecurinine bivalent mimetics as potent reversal agents against P-glycoprotein-mediated multidrug resistance."Eur J Med Chem. 2019 Dec;183:111726 |
biological activity | (-)-securine is a plant-derived alkaloid and a GABAA receptor antagonist. |
Target | Value |
Use | CNS stimulant. antibacterial activity; Excitatory effect on central nervous system; Antitumor effect |