Methylselenocysteine

Structural formula
	( R ) - Se - (methyl) selenocysteine
General
Surname	Methylselenocysteine
other names	Se - (methyl) selenocysteine; 3- (Methylselenyl) - L -alanine; (2 R ) -2-amino-3- (methylselanyl) propanoic acid;
Molecular formula	C 4 H 9 NO 2 Se; C 4 H 9 NO 2 Se HCl ( hydrochloride );
External identifiers / databases
EC number	684-218-7
ECHA InfoCard	100.209.682
PubChem	147004
ChemSpider	129633
DrugBank	DB12697
Wikidata	Q21099600
properties
Molar mass	218.54 g mol −1 ( hydrochloride )
Physical state	firmly
safety instructions
H and P phrases	H: 301-331-373-410
	P: 261-273-301 + 310-311-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methylselenocysteine is a chemical compound from the group of non-proteinogenic amino acids . It is the methylated form of L- selenocysteine at the selenium atom .

Occurrence

Methylselenocysteine occurs naturally in large quantities in garlic and onions , but also in other members of the Allium and Brassica genus and in yeasts . Up to 80% of the total selenium in vegetables such as broccoli , Brussels sprouts , cabbage , garlic, onions, leeks and tragacanth is bound in methylselenocysteine.

It is also formed in all mammals. In rats it is metabolized to methylselenol by beta- lyase . The LOAEL for adults is 300 micrograms per day.

proof

Methylselenocysteine can by high - ion exchange chromatography with mass spectrometry or by gas chromatography with atomic emission spectrometry separated and detected.

use

Methylselenocysteine has anti- tumor effects.

literature

CM Weekley, HH Harris: Which form is that? The importance of selenium speciation and metabolism in the prevention and treatment of disease. In: Chemical Society reviews. Volume 42, Number 23, December 2013, pp. 8870-8894, doi : 10.1039 / c3cs60272a , PMID 24030774 .

Individual evidence

↑ ^a ^b ^c Data sheet Se- (methyl) selenocysteine hydrochloride, ≥95% (TLC) from Sigma-Aldrich , accessed on March 29, 2018 ( PDF ).
^ I. Arnault, J. Auger: Seleno compounds in garlic and onion. In: Journal of chromatography. A. Volume 1112, number 1-2, April 2006, pp. 23-30, doi : 10.1016 / j.chroma.2006.01.036 , PMID 16480995 .
↑ ^a ^b ^c ^d EFSA : Se-methyl-L-selenocysteine added as a source of selenium for nutritional purposes to food supplements. In: EFSA Journal. 7, 2009, p. 1067, doi : 10.2903 / j.efsa.2009.1067 .
↑ A. Bhattacharya: Methylselenocysteine: a promising antiangiogenic agent for overcoming drug delivery barriers in solid malignancies for therapeutic synergy with anticancer drugs. In: Expert opinion on drug delivery. Volume 8, number 6, June 2011, pp. 749-763, doi : 10.1517 / 17425247.2011.571672 , PMID 21473705 , PMC 3111097 (free full text).
^ Y. Tsuji, N. Suzuki, K. T Suzuki, Y. Ogra: Selenium metabolism in rats with long-term ingestion of Se-methylselenocysteine using enriched stable isotopes. In: The Journal of toxicological sciences. Volume 34, Number 2, April 2009, pp. 191-200, PMID 19336976 .
↑ Howard E. Ganther, J. Robert Lawrence: Chemical transformations of selenium in living organisms. Improved forms of selenium for cancer prevention. In: Tetrahedron. 53, 1997, p. 12299, doi : 10.1016 / S0040-4020 (97) 00561-9 .
↑ CM Weekley, JB Aitken, L. Finney, S. Vogt, PK Witting, HH Harris: Selenium metabolism in cancer cells: the combined application of XAS and XFM techniques to the problem of selenium speciation in biological systems. In: Nutrients. Volume 5, number 5, May 2013, pp. 1734-1756, doi : 10.3390 / nu5051734 , PMID 23698165 , PMC 3708347 (free full text).

[Sigma-1] Data sheet Se- (methyl) selenocysteine hydrochloride, ≥95% (TLC) from Sigma-Aldrich , accessed on March 29, 2018 ( PDF ).

[2] I. Arnault, J. Auger: Seleno compounds in garlic and onion. In: Journal of chromatography. A. Volume 1112, number 1-2, April 2006, pp. 23-30, doi : 10.1016 / j.chroma.2006.01.036 , PMID 16480995 .

[EFSA-3] EFSA : Se-methyl-L-selenocysteine added as a source of selenium for nutritional purposes to food supplements. In: EFSA Journal. 7, 2009, p. 1067, doi : 10.2903 / j.efsa.2009.1067 .

[4] A. Bhattacharya: Methylselenocysteine: a promising antiangiogenic agent for overcoming drug delivery barriers in solid malignancies for therapeutic synergy with anticancer drugs. In: Expert opinion on drug delivery. Volume 8, number 6, June 2011, pp. 749-763, doi : 10.1517 / 17425247.2011.571672 , PMID 21473705 , PMC 3111097 (free full text).

[5] Y. Tsuji, N. Suzuki, K. T Suzuki, Y. Ogra: Selenium metabolism in rats with long-term ingestion of Se-methylselenocysteine using enriched stable isotopes. In: The Journal of toxicological sciences. Volume 34, Number 2, April 2009, pp. 191-200, PMID 19336976 .

[DOI10.1016/S0040-4020(97)00561-9-6] Howard E. Ganther, J. Robert Lawrence: Chemical transformations of selenium in living organisms. Improved forms of selenium for cancer prevention. In: Tetrahedron. 53, 1997, p. 12299, doi : 10.1016 / S0040-4020 (97) 00561-9 .

[7] CM Weekley, JB Aitken, L. Finney, S. Vogt, PK Witting, HH Harris: Selenium metabolism in cancer cells: the combined application of XAS and XFM techniques to the problem of selenium speciation in biological systems. In: Nutrients. Volume 5, number 5, May 2013, pp. 1734-1756, doi : 10.3390 / nu5051734 , PMID 23698165 , PMC 3708347 (free full text).