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L-Se-Methylselenocysteine(L-SeMC)

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L-Se-Methylselenocysteine(L-SeMC) is an L-alpha-amino acid compound having methylselanylmethyl as the side-chain. It has a role as an antineoplastic agent. It is a Se-methylselenocysteine, a non-proteinogenic L-alpha-amino acid and a L-selenocysteine derivative. It is a conjugate base of a Se-methyl-L-selenocysteinium. It is a conjugate acid of a Se-methyl-L-selenocysteinate. It is an enantiomer of a Se-methyl-D-selenocysteine. It is a tautomer of a Se-methyl-L-selenocysteine zwitterion.

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Product Description

L-Se-Methylselenocysteine(L-SeMC) Basic Characteristics

Product Name L-Se-Methylselenocysteine(L-SeMC)
CAS number 26046-90-2
Synonyms SEMC;

L-semc;

Se-(Methyl)seleno-L-cysteine;

3-(Methylseleno)-L-alanine;

Methylselenocysteine;

Seleno-amino acid;

(R)-2-Amino-3-(methylseleno)propionic acid.

Molecular Formula C4H9NO2Se
Formula weight 182.08
Melting point 177 °C
Boiling point 314.1±37.0 °C
Appearance White to slightly yellow
Solubility Soluble in water (5 mg/mL)
SMILES Code C[Se]CC(C(=O)O)N
InChi Key XDSSPSLGNGIIHP-VKHMYHEASA-N
InChi Code 1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
Storage Condition Keep in dark place,Inert atmosphere,2-8°C

 

L-Se-Methylselenocysteine(L-SeMC) is an L-alpha-amino acid compound having methylselanylmethyl as the side-chain. It has a role as an antineoplastic agent. It is a Se-methylselenocysteine, a non-proteinogenic L-alpha-amino acid and a L-selenocysteine derivative. It is a conjugate base of a Se-methyl-L-selenocysteinium. It is a conjugate acid of a Se-methyl-L-selenocysteinate. It is an enantiomer of a Se-methyl-D-selenocysteine. It is a tautomer of a Se-methyl-L-selenocysteine zwitterion.

Methylselenocysteine is a naturally occurring organoselenium compound found in many plants, including garlic, onions, and broccoli, with potential antioxidant and chemopreventive activities. However, L-Se-Methylselenocysteine(L-SeMC) is an amino acid analogue of cysteine in which a methylselenium moiety replaces the sulphur atom of cysteine. This agent acts as an antioxidant when incorporated into glutathione peroxidase and has been shown to exhibit potent chemopreventive activity in animal models.

 

Reference

[1] Cao S, Durrani FA, Tóth K, et al. Se-methylselenocysteine offers selective protection against toxicity and potentiates the antitumour activity of anticancer drugs in preclinical animal models. Br J Cancer. 2014 Apr 2;110(7):1733-43. PMID: 24619073.

[2] Shin HS, Yang WJ, Choi EM. The preventive effect of Se-methylselenocysteine on γ-radiation-induced oxidative stress in rat lungs. J Trace Elem Med Biol. 2013 Apr;27(2):154-9. PMID: 23176811.

[3] Cell Prolif. 2021 May;54(5):e13038. doi: 10.1111 r.13038. Epub 2021 Apr 1. PMID: 33793020

[4] Biochem Pharmacol. 2004 Feb 1;67(3):547-54. doi: 10.1016/j.bcp.2003.09.004. PMID: 15037206

[5] J Food Sci. 2021 Dec;86(12):5424-5438. doi: 10.1111/1750-3841.15970. Epub 2021 Nov 18. PMID: 34796490

[6] Zhang J, Wang L, Anderson LB, et al. Proteomic profiling of potential molecular targets of methyl-selenium compounds in the transgenic adenocarcinoma of mouse prostate model. Cancer Prev Res (Phila). 2010 Aug;3(8):994-1006. PMID: 20647336.

 

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