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{{Chembox
Methylselenocysteine (CAS# 26046-90-2),
| ImageFile = Methylselenocysteine.svg
also known as Se-methylseleno-L-cysteine;
| ImageAlt =
Selenium-methylselenocysteine
| SystematicName = 3-(Methylselanyl)-<small>L</small>-alanine
or Se-(Methyl)selenocysteine,
| OtherNames = ''Se''-methylseleno-<small>L</small>-cysteine; <small>L</small>-Methylselenocysteine; ''Se''-Methylselenocysteine
is best known as "an inhibitor of DMBA-induced mammary tumors"
|Section1={{Chembox Identifiers
<ref>
| CASNo = 26046-90-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = TWK220499Z
| ChEBI=27812
| KEGG=C05689
| StdInChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
| StdInChIKey = XDSSPSLGNGIIHP-VKHMYHEASA-N
| PubChem = 147004
| ChemSpiderID = 129633
| SMILES = C[Se]C[C@@H](C(=O)O)N
| InChI = 1/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
| InChIKey = XDSSPSLGNGIIHP-VKHMYHEABS

}}
|Section2={{Chembox Properties
| C=4 | H=9 | N=1 | O=2 | Se=1
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Methylselenocysteine''', also known as '''''Se''-methylselenocysteine''', is an [[structural analog|analog]] of [[methylcysteine|''S''-methylcysteine]] in which the sulfur atom is replaced with a selenium atom. It is an inhibitor of [[7,12-Dimethylbenz(a)anthracene|DMBA]]-induced mammary tumors<ref>
{{cite web
{{cite web
|url=http://www.scbt.com/datasheet-394409.html
| url=http://www.scbt.com/datasheet-394409.html
|title=product data sheet CAS# 26046-90-2
| title=product data sheet CAS# 26046-90-2
|author=Santa Cruz Biotechnology Inc.
| publisher=Santa Cruz Biotechnology Inc.
|accessdate=2015-02-01}}
| access-date=2015-02-01}}
</ref> and a "[[chemopreventive agent]] that blocks [[cell cycle]] progression and proliferation of premalignant mammary lesions and induces [[apoptosis]] of cancer cell lines in culture."<ref>
</ref>
and a "chemopreventive agent that blocks
cell cycle progression and proliferation
of premalignant mammary lesions
and induces apoptosis of cancer cell lines in culture."
<ref>
{{cite web
{{cite web
|url=http://www.sigmaaldrich.com/catalog/product/sigma/m6680?lang=en&region=US
| url=http://www.sigmaaldrich.com/catalog/product/sigma/m6680?lang=en&region=US
|title=product data sheet CAS# 26046-90-2
| title=product data sheet CAS# 26046-90-2
|author=Sigma-Aldrich,
| publisher=Sigma-Aldrich
|accessdate=2015-02-01}}
| access-date=2015-02-01}}
</ref>
</ref>


[[Apoptosis]] has been proposed as the most plausible mechanism for the chemopreventive activities of selenocompounds. ''Se''-Methylselenocysteine was more efficient at inducing apoptosis than [[sodium selenite|selenite]], but was less toxic. The "selenite-induced cell death could be derived from [[necrosis]] rather than apoptosis, since selenite did not significantly induce several apoptotic phenomena, including the activation of [[caspase-3]]."<ref>
"Apoptosis, a programmed process of cell suicide,
{{cite journal
has been proposed as the most plausible mechanism
| title=''Se''-Methylselenocysteine induces apoptosis through caspase activation in HL-60 cells|journal=Carcinogenesis |date=2001 |volume=22 |issue=4 | pages=559–65|author1=Kim Taeho |author2=Jung Uhee |author3=Cho Dae-yeon |author4=Chung An-sik | doi=10.1093/carcin/22.4.559| pmid=11285189|doi-access=free }}
for the chemopreventive activities of selenocompounds."
"Se-Methylselenocysteine was more efficient at inducing apoptosis
than selenite, but was less toxic."
The "selenite-induced cell death could be derived from
necrosis rather than apoptosis,
since selenite did not significantly induce
several apoptotic phenomena,
including the activation of caspase-3."
<ref>
{{cite web
|url=http://carcin.oxfordjournals.org/content/22/4/559.full
|title="Se-Methylselenocysteine induces apoptosis through caspase activation in HL-60 cells"Carcinogenesis (2001) 22 (4): 559-565.
|author=Taeho Kim, Uhee Jung, Dae-Yeon Cho and An-Sik Chung
|accessdate=2015-02-01}}
</ref>
</ref>


In the Nutritional Prevention of Cancer Trial, [[selenized yeast]] resulted in "a reduction in the incidence of prostate cancer and in total cancer incidence"; subsequent anticancer studies using selenomethionine did not show any benefit against cancer; but, selenized yeast contains both selenomethionine and methylselenocysteine.<ref>
In the Nutritional Prevention of Cancer Trial,
{{cite journal
selenized yeast resulted in "a reduction in
| title=Selenium Metabolism in Cancer Cells: The Combined Application of XAS and XFM Techniques to the Problem of Selenium Speciation in Biological Systems|journal=Nutrients |date=2013 |volume=5 |issue=5 | pages=1734–56|author1=Claire M. Weekley |author2=Jade B. Aitken |author3=Lydia Finney |author4=Stefan Vogt |author5=Paul K. Witting |author6=Hugh H. Harris | doi=10.3390/nu5051734| pmid=23698165| pmc=3708347|doi-access=free }}
the incidence of prostate cancer
and in total cancer incidence";
subsequent anti-cancer studies using Selenomethionine
did not show any benefit against cancer;
but, selenized yeast contains both
Selenomethionine and methylselenocysteine.
<ref>
{{cite web
|url=http://www.mdpi.com/2072-6643/5/5/1734/htm
|title="Selenium Metabolism in Cancer Cells: The Combined Application of XAS and XFM Techniques to the Problem of Selenium Speciation in Biological Systems"Nutrients 2013, 5(5), 1734-1756;
|author=Claire M. Weekley, Jade B. Aitken, Lydia Finney, Stefan Vogt, Paul K. Witting, Hugh H. Harris
|accessdate=2015-02-01}}
</ref>
</ref>


Methylselenocysteine is found in selenized yeast, and many vegetables: "As much as 80% of the total selenium" found in
The European Food Safety Authority (EFSA)
''[[Allium]]'' species ([[onion]], [[leek]], [[garlic]], [[ramps]]) ''[[Brassica]]'' species ([[broccoli]], [[radish]], [[Brussels sprouts]], [[cabbage]]), and [[milk vetch]] (''[[Astragalus (plant)|Astragalus]]'' species, [[Fabaceae]]) "is present as ''Se''-methylselenocysteine." The bioavailability of selenium from ''Se''-methylselenocysteine, "is likely to be similar to that from other organic selenium compounds." Specifically, "It is converted via the action of [[beta-lyase|β-lyase]], to [[methylselenol]] and then to [[hydrogen selenide]], which is also the key metabolite derived from" all other common forms of selenium. But EFSA concluded that "given the absence of human studies on ''Se''-methylselenocysteine, the relatively sparse database on the [[bioavailability]] of selenium from this source and the limited data on the safety of this source compared with other selenium compounds, the Upper Limit for selenium defined by the [[Scientific Committee on Food]] cannot be used for judging its safety."<ref>
states that Se-methylselenocysteine
{{cite journal|url=https://www.efsa.europa.eu/en/efsajournal/pub/1067 |title=''Se''-methyl-L-selenocysteine added as a source of selenium for nutritional purposes to food supplements:Scientific Opinion of the Panel on Food Additives and Nutrient Sources added to Food (Question No: EFSA-Q-2005-170, EFSA-Q-2006-306, EFSA-Q-2006-308) |journal=The EFSA Journal |date=2009 |volume=1067 |pages=1–23 |author1=F. Aguilar |author2=U.R. Charrondiere |author3=B. Dusemund |author4=P. Galtier |author5=J. Gilbert |author6=D.M. Gott |author7=S. Grilli |author8=R. Guertler |author9=G.E.N. Kass |author10=J. Koenig |author11=C. Lambré |author12=J-C. Larsen |author13=J-C. Leblanc |author14=A. Mortensen |author15=D. Parent-Massin |author16=I. Pratt |author17=I.M.C.M. Rietjens |author18=I. Stankovic |author19=P. Tobback |author20=T. Verguieva |author21=R. Woutersen. |access-date=2015-02-01 }}
(CAS# 26046-90-2) is a monomethylated selenoamino acid
in which selenium replaces the sulphur of the S-methylcysteine molecule;
it is found in selenized yeast, and many vegetables:
"As much as 80% of the total selenium" found in
Alliums (onion, leek, garlic, ramps)
Brassicas (broccoli, radish, Brussels sprouts, cabbage),
and milk vetch(Astragalus spp, Fabaceae)
"is present as Se-methylselenocysteine."
The EFSA Panel concludes that the bioavailability
of Selenium from Semethylselenocysteine,
"is likely to be similar to that from
other organic selenium compounds."
Specifically, "It is converted via the action of β-lyase,
to methylselenol and then to hydrogen selenide,
which is also the key metabolite derived from"
all other common forms of selenium.
But EFSA concluded that "given the absence of
human studies on Se-methylselenocysteine,
the relatively sparse database on the
bioavailability of selenium from this source
and the limited data on the safety of this source
compared with other selenium compounds,
the Upper Limit for selenium defined by
the Scientific Committee on Food
cannot be used for judging its safety."<ref>
{{cite web
|url=http://www.efsa.europa.eu/en/scdocs/doc/ans_ej1067_Se_methyl_L_selenocysteine_op_en.pdf?ssbinary=true
|title="Se-methyl-L-selenocysteine added as a source of selenium for nutritional purposes to food supplements:Scientific Opinion of the Panel on Food Additives and Nutrient Sources added to Food(Question No: EFSA-Q-2005-170, EFSA-Q-2006-306, EFSA-Q-2006-308)"The EFSA Journal (2009) 1067, 1-23
|author=F. Aguilar, U.R. Charrondiere, B. Dusemund, P. Galtier, J. Gilbert, D.M. Gott, S. Grilli, R. Guertler, G.E.N. Kass, J. Koenig, C. Lambré, J-C. Larsen, J-C. Leblanc, A. Mortensen, D. Parent-Massin, I. Pratt, I.M.C.M. Rietjens, I. Stankovic, P. Tobback, T. Verguieva, R. Woutersen.
|accessdate=2015-02-01}}
</ref>
</ref>

==References==
==References==
{{Reflist}}
{{Reflist}}


[[Category:Amino acid derivatives]]
[[Category:Amino acid derivatives]]
[[Category:Organoselenium compounds]]
[[Category:Selenium(−II) compounds]]
[[Category:Selenoethers]]

Latest revision as of 12:13, 7 November 2023

Methylselenocysteine
Names
Systematic IUPAC name
3-(Methylselanyl)-L-alanine
Other names
Se-methylseleno-L-cysteine; L-Methylselenocysteine; Se-Methylselenocysteine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.209.682 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
    Key: XDSSPSLGNGIIHP-VKHMYHEASA-N
  • InChI=1/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
    Key: XDSSPSLGNGIIHP-VKHMYHEABS
  • C[Se]C[C@@H](C(=O)O)N
Properties
C4H9NO2Se
Molar mass 182.092 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylselenocysteine, also known as Se-methylselenocysteine, is an analog of S-methylcysteine in which the sulfur atom is replaced with a selenium atom. It is an inhibitor of DMBA-induced mammary tumors[1] and a "chemopreventive agent that blocks cell cycle progression and proliferation of premalignant mammary lesions and induces apoptosis of cancer cell lines in culture."[2]

Apoptosis has been proposed as the most plausible mechanism for the chemopreventive activities of selenocompounds. Se-Methylselenocysteine was more efficient at inducing apoptosis than selenite, but was less toxic. The "selenite-induced cell death could be derived from necrosis rather than apoptosis, since selenite did not significantly induce several apoptotic phenomena, including the activation of caspase-3."[3]

In the Nutritional Prevention of Cancer Trial, selenized yeast resulted in "a reduction in the incidence of prostate cancer and in total cancer incidence"; subsequent anticancer studies using selenomethionine did not show any benefit against cancer; but, selenized yeast contains both selenomethionine and methylselenocysteine.[4]

Methylselenocysteine is found in selenized yeast, and many vegetables: "As much as 80% of the total selenium" found in Allium species (onion, leek, garlic, ramps) Brassica species (broccoli, radish, Brussels sprouts, cabbage), and milk vetch (Astragalus species, Fabaceae) "is present as Se-methylselenocysteine." The bioavailability of selenium from Se-methylselenocysteine, "is likely to be similar to that from other organic selenium compounds." Specifically, "It is converted via the action of β-lyase, to methylselenol and then to hydrogen selenide, which is also the key metabolite derived from" all other common forms of selenium. But EFSA concluded that "given the absence of human studies on Se-methylselenocysteine, the relatively sparse database on the bioavailability of selenium from this source and the limited data on the safety of this source compared with other selenium compounds, the Upper Limit for selenium defined by the Scientific Committee on Food cannot be used for judging its safety."[5]

References

[edit]
  1. ^ "product data sheet CAS# 26046-90-2". Santa Cruz Biotechnology Inc. Retrieved 2015-02-01.
  2. ^ "product data sheet CAS# 26046-90-2". Sigma-Aldrich. Retrieved 2015-02-01.
  3. ^ Kim Taeho; Jung Uhee; Cho Dae-yeon; Chung An-sik (2001). "Se-Methylselenocysteine induces apoptosis through caspase activation in HL-60 cells". Carcinogenesis. 22 (4): 559–65. doi:10.1093/carcin/22.4.559. PMID 11285189.
  4. ^ Claire M. Weekley; Jade B. Aitken; Lydia Finney; Stefan Vogt; Paul K. Witting; Hugh H. Harris (2013). "Selenium Metabolism in Cancer Cells: The Combined Application of XAS and XFM Techniques to the Problem of Selenium Speciation in Biological Systems". Nutrients. 5 (5): 1734–56. doi:10.3390/nu5051734. PMC 3708347. PMID 23698165.
  5. ^ F. Aguilar; U.R. Charrondiere; B. Dusemund; P. Galtier; J. Gilbert; D.M. Gott; S. Grilli; R. Guertler; G.E.N. Kass; J. Koenig; C. Lambré; J-C. Larsen; J-C. Leblanc; A. Mortensen; D. Parent-Massin; I. Pratt; I.M.C.M. Rietjens; I. Stankovic; P. Tobback; T. Verguieva; R. Woutersen. (2009). "Se-methyl-L-selenocysteine added as a source of selenium for nutritional purposes to food supplements:Scientific Opinion of the Panel on Food Additives and Nutrient Sources added to Food (Question No: EFSA-Q-2005-170, EFSA-Q-2006-306, EFSA-Q-2006-308)". The EFSA Journal. 1067: 1–23. Retrieved 2015-02-01.
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