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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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$217.00
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100 MG
$217.00
500 MG
$734.00

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

$217.00

Available to ship onApril 08, 2025Details

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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.[1]

Application

Seleno-L-methionine has been used:
  • in toxicity studies in Japanese Medaka embryos[2]
  • to study its effects on selenium status indicators in pregnant long-tailed macaques (Macaca Fascicularis)[3]
  • to label proteins for single wavelength anomalous dispersion (SAD) phasing[4]

Seleno-L-methionine has been used:
  • as a nonchemical stressor to treat Japanese Medaka fish embryos[2]
  • to label proteins for Single wavelength Anomalous Dispersion (SAD) phasing[5]
  • to study the distribution and inhibition effects of seleno-L-methionine on 4T1 mouse mammary carcinoma[6]

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).[7] It can cause ecotoxicity as it is absorbed by fish through diet.[8]
Seleno-L-methionine displays antioxidant activity[9] and has been shown to increase the activity of glutathione peroxidase in endothelial cells.[10] 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.[11][12] 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.[13]

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Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

250.3 - 346.3 °F

flash_point_c

121.3 - 174.6 °C

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Certificates of Analysis (COA)

Lot/Batch Number
0000365046
0000365045
0000365046
0000365045
0000291122

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Distribution and inhibition effect of Seleno-L-Methionine on 4T1 mouse mammary carcinoma.
Song H
International Journal of Physiology, Pathophysiology and Pharmacology, 7(2), 76-86 (2015)
Application of linker technique to trap transiently interacting protein complexes for structural studies.
Reddy Chichili VP
Journal of biomechanics, 3(1), e34-e34 (2016)
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
Seleno-L-methionine is the predominant organic form of selenium in Cupriavidus metallidurans CH34 exposed to selenite or selenate
Avoscan L, et al.
Applied and Environmental Microbiology, 72(9), 6414-6416 (2006)
H Sies et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 53(3-4), 228-232 (1998-06-10)
Cellular defense against excessive peroxynitrite generation is required 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. We recently demonstrated a role of selenium-containing enzymes catalyzing
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Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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