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S3132

Sigma-Aldrich

Seleno-L-methionine

≥98% (TLC), powder, IgE expression inhibitor

Synonym(s):

(S)-2-Amino-4-(methylseleno)butyric acid

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About This Item

Linear Formula:
CH3SeCH2CH2CH(NH2)CO2H
CAS Number:
3211-76-5
Molecular Weight:
196.11
MDL number:
MFCD00037210
UNSPSC Code:
12352209
PubChem Substance ID:
24899544
NACRES:
NA.32

product name

Seleno-L-methionine, ≥98% (TLC), powder

Assay

≥98% (TLC)

form

powder

color

white to off-white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

C[Se]CC[C@H](N)C(O)=O

InChI

1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

InChI key

RJFAYQIBOAGBLC-BYPYZUCNSA-N

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General description

Seleno-L-Methionine (SeMet), an organic form of selenium is found in Cupriavidus metallidurans.

Application

Seleno-L-methionine has been used:
  • in toxicity studies in Japanese Medaka embryos
  • to study its effects on selenium status indicators in pregnant long-tailed macaques (Macaca Fascicularis)
  • to label proteins for single wavelength anomalous dispersion (SAD) phasing

Seleno-L-methionine has been used:
  • as a nonchemical stressor to treat Japanese Medaka fish embryos
  • to label proteins for Single wavelength Anomalous Dispersion (SAD) phasing
  • to study the distribution and inhibition effects of seleno-L-methionine on 4T1 mouse mammary carcinoma

Biochem/physiol Actions

Seleno-L-Methionine (SeMet) is capable of repressing atopic dermatitis (AD)-like skin lesions. It can also prevent the expression of total immunoglobulin E (IgE) and interleukin 4 (IL-4). It can cause ecotoxicity as it is absorbed by fish through diet.
Seleno-L-methionine displays antioxidant activity and has been shown to increase the activity of glutathione peroxidase in endothelial cells. Glutathione peroxidase protects cells from oxidative damage, such as DNA strand breaks, mutations and interference with protein tyrosine-based signaling and other protein functions due to formation of 3-nitrotyrosine, caused by excessive peroxynitrite. Seleno-L-methionine administration to cancer cell lines (MCF-7/S breast carcinoma, DU-145 prostate cancer cells and UACC-375 melanoma) results in apoptotic cell death and aberrant mitosis. These human tumor cell lines exhibited dose-dependent growth inhibition by selenomethionine in the micromolar range (45 to 130μM), while growth inhibition of normal fibroblasts required 1mM selenomethionine.

Signal Word

Danger

Hazard Statements

H301 + H331,H373,H410

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

250.3 - 346.3 °F

Flash Point(C)

121.3 - 174.6 °C

Certificates of Analysis (COA)

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L Jornot et al.
The Biochemical journal, 306 ( Pt 2), 581-587 (1995-03-01)
We have studied the effect of selenomethionine (SeMet) and hyperoxia on the expression of glutathione peroxidase (GP) in human umbilical vein endothelial cells. Incubation of HUVEC with 1 x 10(-6) M SeMet for 24 h and 48 h caused a
Mechanisms of selenomethionine developmental toxicity and the impacts of combined hypersaline conditions on Japanese medaka (Oryzias latipes).
Kupsco A and Schlenk D
Environmental Science & Technology, 48(12), 7062-7068 (2014)
G Feroci et al.
Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS), 12(2), 96-100 (1998-10-07)
Four selenium derivatives (sodium selenate, sodium selenite, selenourea and selenomethionine) and the sulphur analogues (sodium sulfate, sodium sulfite, thiourea and methionine), together with urea, were examined by means of polarography to study their reactivity towards superoxide ion O2. In order
H Sies et al.
The Journal of biological chemistry, 272(44), 27812-27817 (1997-11-05)
There is a requirement for cellular defense against excessive peroxynitrite generation to protect against DNA strand breaks and mutations and against interference with protein tyrosine-based signaling and other protein functions due to formation of 3-nitrotyrosine. Here, we demonstrate a role
C Redman et al.
Cancer letters, 125(1-2), 103-110 (1998-05-05)
Selenium supplementation has been shown for many years to work as an anticarcinogenic agent both in epidemiology and in in vitro studies. Selenium supplementation has recently been shown to decrease total cancer incidence. However, the mechanism of action of selenium
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