A diselenide-bridged amino acid
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L-Selenocystine

Item No. 17793

Technical Information
Formal Name
3,3'-diselenobis-L-alanine
CAS Number
29621-88-3
Synonyms
  • Seleno-L-cystine
Molecular Formula
C6H12N2O4Se2
Formula Weight
Purity
≥90%
A crystalline solid
SMILES
OC([C@@H](N)C[Se][Se]C[C@H](N)C(O)=O)=O
InChi Code
InChI=1S/C6H12N2O4Se2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
InChi Key
JULROCUWKLNBSN-IMJSIDKUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    L-Selenocystine is a diselenide-bridged amino acid that may be confused with selenocysteine (Sec), which is a rare amino acid featuring a single selenium atom. L-Selenocystine is a redox-active selenium compound that has both anti- and pro-oxidant actions.1,2 This compound can be reduced by low molecular thiols and disulfide reductases to Sec. It is reduced to Sec by mammalian thioredoxin reductase (apparent Km = 6.0 µM), and this property can be used to assay thioredoxin reductase activity.2,3 L-Selenocystine induces an unfolded protein response, ER stress, and large cytoplasmic vacuolization in HeLa cells and has cytostatic effects in a range of cancer cell types.2,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Spallholz, J.E. On the nature of selenium toxicity and carcinostatic activity. Free Radic. Biol. Med. 17(1), 45-64 (1994).

    2. Misra, S., Boylan, M., Selvam, A., et alRedox-active selenium compounds—from toxicity and cell death to cancer treatment. Nutrients 7(5), 3536-3556 (2015).

    3. Cunniff, B., Snider, G.W., Fredette, N., et alA direct and continuous assay for the determination of thioredoxin reductase activity in cell lysates. Anal. Biochem. 443(1), 34-40 (2013).

    4. Wallenberg, M., Misra, S., Wasik, A.M., et alSelenium induces a multi-targeted cell death process in addition to ROS formation. J. Cell. Mol. Med. 18(4), 671-684 (2014).