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M6680

Sigma-Aldrich

Se-(Methyl)selenocysteine hydrochloride

≥95% (TLC)

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About This Item

Empirical Formula (Hill Notation):
C4H9NO2Se · HCl
CAS Number:
863394-07-4
Molecular Weight:
218.54
MDL number:
MFCD03412450
UNSPSC Code:
12352209
PubChem Substance ID:
24278564
NACRES:
NA.32

Assay

≥95% (TLC)

storage temp.

−20°C

SMILES string

Cl.C[Se]C[C@H](N)C(O)=O

InChI

1S/C4H9NO2Se.ClH/c1-8-2-3(5)4(6)7;/h3H,2,5H2,1H3,(H,6,7);1H/t3-;/m0./s1

InChI key

JMPVTFHGWJDSDV-DFWYDOINSA-N

General description

Selenium (Se)-(Methyl) selenocysteine (MeSeCys) is a methylated product of selenocysteine, this reaction is catalyzed by selenocysteine methyltransferase (SMT) in Astragalus bisulcatus.

Application

Se-(Methyl) selenocysteine hydrochloride has been used as a standard in fluorescence-XANES (X-ray absorption near-edge spectroscopy) imaging.

Biochem/physiol Actions

Selenium (Se)-(Methyl) selenocysteine functions as a potent chemotherapeutic agent for human breast cancer. Enhanced production of methlylselenol from L-Se-methylselenocysteine in vivo alters redox status of cells and oxidatively triggers cellular apoptosis. It is implicated in inhibition of mammary tumor formation in rats.
Se-(Methyl)selenocysteine is a chemopreventive agent that blocks cell cycle progression and proliferation of premalignant mammary lesions and induces apoptosis of cancer cell lines in culture.

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)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Production of Se-methylselenocysteine in transgenic plants expressing selenocysteine methyltransferase.
Ellis DR
BMC plant biology, 4:1 (2004)
In situ speciation and distribution of toxic selenium in hydrated roots of cowpea.
Wang P
Plant Physiology, 163(1), 407-418 (2013)
Se-methylselenocysteine: a new compound for chemoprevention of breast cancer.
Medina D
Nutrition and Cancer, 40(1), 12-17 (2001)
Junkun Ma et al.
Biological trace element research, 191(1), 159-166 (2018-12-14)
Mastitis is one of the most important diseases affecting the dairy industry in the world, and it also poses a great threat to human food safety. In this study, we explored whether selenium can inhibit the activation of the NALP3
Dimethyldiselenide and methylseleninic acid generate superoxide in an in vitro chemiluminescence assay in the presence of glutathione: implications for the anticarcinogenic activity of L-selenomethionine and L-Se-methylselenocysteine.
Spallholz JE
Nutrition and Cancer, 40(1), 34-41 (2001)
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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.

Chromatograms

application for HPLC

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