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S3132

Sigma-Aldrich

Seleno-L-methionine

≥98% (TLC), powder

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

Quality Level

200

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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A protocol to retain weakly interacting protein complexes for structural studies using an appropriate linker
Chichili VPR, et al.
Protocol Exchange (2013)
Effects of excess selenomethionine on selenium status indicators in pregnant long-tailed macaques (Macaca fascicularis)
Hawkes WC, et al.
Biological trace element research, 35(3), 281-297 (1992)
Arka Chakraborty et al.
Nucleic acids research, 45(2), 951-967 (2016-12-03)
The mitochondrial genome (mtDNA) is assembled into nucleo-protein structures termed nucleoids and maintained differently compared to nuclear DNA, the involved molecular basis remaining poorly understood. In yeast (Saccharomyces cerevisiae), mtDNA is a ∼80 kbp linear molecule and Abf2p, a double
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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