SML0055

Sigma-Aldrich

Securinine

≥98% (HPLC)

Empirical Formula (Hill Notation):
C13H15NO2
CAS Number:
Molecular Weight:
217.26
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -980 to -1015 (C=1, MeOH)

color

yellow

solubility

DMSO: ≥25 mg/mL

storage temp.

2-8°C

SMILES string

O=C1O[C@@]23C[C@@H](C=CC2=C1)N4CCCC[C@H]34

InChI

1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1

InChI key

SWZMSZQQJRKFBP-WZRBSPASSA-N

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Application

Securinine was used as a standard in the synthesis of the members of Securinega alkaloid family.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

Securinine is an alkaloid widely in traditional folk medicine. Long known as a GABAA antagonist, securinine was recently found to up-regulate p53 protein and to modulate the related family member p73 protein in a p53-dependent fashion, inducing p73 in the HCT116 p53(-) cells and down-regulating it in the p53(+) cells. Induction of proapoptotic protein p73 only in p53 cells could be used to target cancer cells preferentially. Securinine has been found to induce p53-independent, p73-dependent apoptosis in RKO colon cancer cells.

Features and Benefits

This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Jung-Hsuan Chen et al.
Organic letters, 14(17), 4531-4533 (2012-08-24)
Total syntheses of (±)-securinine and (±)-allosecurinine that employ a tandem rhodium carbenoid-initiated Claisen/α-ketol rearrangement sequence as a key step are described.
Wei Yuan et al.
Natural product research, 21(3), 234-242 (2007-03-17)
Investigations on callus cultures of Securinega suffruticosa indicated that the cell line of S. suffruticosa callus was able to accumulate four known Securinega alkaloids with dextro rotation but not levo rotation as reported before: virosecurinine (1), viroallosecurinine (2), 14,15-dihydrovirosecurinine (3)...
D Raj et al.
Fitoterapia, 79(6), 419-427 (2008-06-07)
This review gives an account of the current knowledge on the chemical constituents, biological activity and pharmacological properties of Securinega suffruticosa. A wide range of chemical compounds have been isolated, mainly alkaloids, flavonoids, tannins and lipids. From the pharmacological point...
Kalpana Gupta et al.
PloS one, 6(6), e21203-e21203 (2011-07-07)
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 potential of avoiding the significant side effects that occur with the...
Matt Shipman et al.
PloS one, 7(9), e41278-e41278 (2012-10-03)
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 using Zdyes, a new generation of covalently linked fluorescent differential protein detection...
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