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SML0055

Sigma-Aldrich

Securinine

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C13H15NO2
CAS Number:
5610-40-2
Molecular Weight:
217.26
MDL number:
MFCD00078775
UNSPSC Code:
12352200
PubChem Substance ID:
329825122

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.

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

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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.
S Liras et al.
Organic letters, 3(5), 703-706 (2001-03-22)
[structure: see text]. The concise total synthesis of securinine in nine steps from readily available starting materials is described. Key steps of the synthesis include an addition of a silyloxyfuran to an in situ generated iminium ion and a novel
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
Gisela G Bardají et al.
The Journal of organic chemistry, 73(19), 7657-7662 (2008-09-11)
A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has
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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