S3132

Seleno-L-methionine

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

• Synonym(s): (S)-2-Amino-4-(methylseleno)butyric acid
• 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

Properties

• Product Name: Seleno-L-methionine, ≥98% (TLC), powder
• 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

Description

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]

Safety Information

• Pictograms: GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H301 + H331,H373,H410
• Precautionary Statements: P260 - P264 - P273 - P301 + P310 - P304 + P340 + P311 - P314
• 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