Securinine
Modify Date: 2024-01-02 11:34:32
Securinine structure
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Common Name | Securinine | ||
|---|---|---|---|---|
| CAS Number | 5610-40-2 | Molecular Weight | 217.264 | |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 459.0±45.0 °C at 760 mmHg | |
| Molecular Formula | C13H15NO2 | Melting Point | 140-142ºC | |
| MSDS | Chinese USA | Flash Point | 197.0±19.6 °C | |
| Symbol |
GHS07 |
Signal Word | Warning | |
Use of Securinine(-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist. |
| Name | Securinine |
|---|---|
| Synonym | More Synonyms |
| Description | (-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist. |
|---|---|
| Related Catalog | |
| Target |
GABAA receptor[1] |
| In Vitro | (-)-Securinine is a major plant-derived alkaloid and also a GABAA receptor antagonist. (-)-Securinine is significantly potent on HeLa cells growth inhibition with IC50 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[1]. |
| In Vivo | 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[2]. |
| Kinase Assay | The cells are seeded in 12-well plates (1×105/well) and treated with (-)-Securinine at concentrations of 1.0 to 50.0 μg/mL. The control cells are exposed to DMSO at a concentration of 0.5% (v/v). After 6 h and 24 h of exposure, the activity of caspase-9 is measured by Caspase-Glo 9 Assay Kit and Glomax Multi+ Detection System, according to the manufacturer’s instruction. The activity of caspase-3/7 is assessed after 24 h of exposure the cells to (-)-Securinine. Then the cells are harvested and prepared using Muse Caspase-3/7 Assay Kit according with the manufacturer’s protocol. The stained cells are analyzed by Muse Cell Analyzer. The experiments are performed at least in three independent repeats[1]. |
| Cell Assay | The viability of the cells is determined by MTT assay. HeLa cells are seeded in 96-well plates at a density of 5×103 cells/well and treated for 24 h with (-)-Securinine in the concentration range of 1.0 to 20.0 μg/mL. The maximal concentrations of the solvents used in all the MTT experiments are 5.0% (v/v) and 1.0% (v/v) for methanol and DMSO, respectively. The absorption of the obtained formazan solution is measured with a plate reader. The viability results are presented as IC50 mean values of at least three independent experiments[1]. |
| Animal Admin | 6 week old female nude mice are used and injected bilaterally s.c. with 10×106 HL-60 cells. (-)-Securinine treatment is started 10 days after tumor cell injection. Palpable tumors are present for the established tumor model prior to initiating drug treatment. 15 mg/kg of (-)-Securinine or vehicle (30 µL of DMSO and 70 µL of water) are injected i.p. 2 or 3 times a day for 5 days followed by once a day for two days. This injection schedule is repeated for two additional weeks[2]. |
| References |
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 459.0±45.0 °C at 760 mmHg |
| Melting Point | 140-142ºC |
| Molecular Formula | C13H15NO2 |
| Molecular Weight | 217.264 |
| Flash Point | 197.0±19.6 °C |
| Exact Mass | 217.110275 |
| PSA | 29.54000 |
| LogP | 0.60 |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.633 |
| Storage condition | 2-8C |
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
|
| Symbol |
GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302 |
| Hazard Codes | T: Toxic; |
| Risk Phrases | R23/24/25 |
| Safety Phrases | 36/37/39-45 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | VS4115000 |
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Proteomic and systems biology analysis of monocytes exposed to securinine, a GABA(A) receptor antagonist and immune adjuvant.
PLoS ONE 7(9) , e41278, (2012) Securinine, a GABA(A) receptor antagonist, has been reported to enhance monocyte cell killing of Coxiella burnetii without obvious adverse effects in vivo. We employed multiplex 2D gel electrophoresis... |
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Securinine, a myeloid differentiation agent with therapeutic potential for AML.
PLoS ONE 6(6) , e21203, (2011) As the defining feature of Acute Myeloid Leukemia (AML) is a maturation arrest, a highly desirable therapeutic strategy is to induce leukemic cell maturation. This therapeutic strategy has the potenti... |
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L-securinine induced the human colon cancer SW480 cell autophagy and its molecular mechanism.
Fitoterapia 82(8) , 1258-64, (2011) To investigate the anti-tumor effects of L-securinine inducing colon cancer SW480 cell autophagy and explore its potential molecular mechanism.MTT method was used to detect the antitumor effect of SW4... |
| 1,2,3,4,10,10a-Hexahydro-10-hydroxy |
| securinine |
| securinin |
| Securinan-11-one (9CI) |
| (1S,2R,8S)-14-Oxa-7-azatetracyclo[6.6.1.0.0]pentadeca-9,11-dien-13-one |
| 8H-6,11b-Methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, 9,10,11,11a-tetrahydro-, (6S,11aR,11bS)- |
| Securan one |
| (6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro(2,3-c)pyrido(1,2-a)azepin-2(6H)-one |
| (6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]-pyrido[1,2-a]azepin-2(6H)-one |
| SECURAN-11-ONE |
| Securinan-11-one |
| Securinan-11-on |
| (-)-Securinine |
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