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MedKoo Cat#: 596509 | Name: Selenocystine, L-
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

L-Selenocystine is used as a building block in biologically active selenol compounds. L-Selenocystine is a redox-active selenium compound that has both anti- and pro-oxidant actions. It is different than selenocysteine, a rare amino acid.

Chemical Structure

Selenocystine, L-
CAS#29621-88-3

Theoretical Analysis

MedKoo Cat#: 596509

Name: Selenocystine, L-

CAS#: 29621-88-3

Chemical Formula: C6H12N2O4Se2

Exact Mass: 335.9128

Molecular Weight: 334.09

Elemental Analysis: C, 21.57; H, 3.62; N, 8.39; O, 19.16; Se, 47.27

Price and Availability

Size Price Availability Quantity
250mg USD 310.00
1g USD 500.00
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Related CAS #
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Synonym
Selenocystine, L-; L-Selenocystine; Seleno-L-cystine
IUPAC/Chemical Name
(2R,2'R)-3,3'-diselanediylbis(2-aminopropanoic acid)
InChi Key
JULROCUWKLNBSN-IMJSIDKUSA-N
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
SMILES Code
N[C@@H](C[Se][Se]C[C@@H](C(O)=O)N)C(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
L-Selenocystine can be reduced by low molecular thiols and disulfide reductases to selenocysteine. 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.
In vitro activity:
In this study, L-selenocystine blocked Nrf2 and autophagy, which in turn induced selective death in Nrf2-addicted colorectal cancer cells through the p62-Keap-1-Nrf2 axis. L-selenocystine also activated the Nrf2 and autophagy pathway in non-Nrf2-addicted mesenchymal stem cells. Reference: Cell Death Dis. 2022 Dec 20;13(12):1060. https://pubmed.ncbi.nlm.nih.gov/36539411/
In vivo activity:
To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 334.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Hsu WL, Wang CM, Yao CL, Chen SC, Nien CY, Sun YH, Tseng TY, Luo YH. Blockage of Nrf2 and autophagy by L-selenocystine induces selective death in Nrf2-addicted colorectal cancer cells through p62-Keap-1-Nrf2 axis. Cell Death Dis. 2022 Dec 20;13(12):1060. doi: 10.1038/s41419-022-05512-2. PMID: 36539411; PMCID: PMC9768144. 2. Wallenberg M, Misra S, Wasik AM, Marzano C, Björnstedt M, Gandin V, Fernandes AP. Selenium induces a multi-targeted cell death process in addition to ROS formation. J Cell Mol Med. 2014 Apr;18(4):671-84. doi: 10.1111/jcmm.12214. Epub 2014 Jan 8. PMID: 24400844; PMCID: PMC4000118.
In vitro protocol:
1. Hsu WL, Wang CM, Yao CL, Chen SC, Nien CY, Sun YH, Tseng TY, Luo YH. Blockage of Nrf2 and autophagy by L-selenocystine induces selective death in Nrf2-addicted colorectal cancer cells through p62-Keap-1-Nrf2 axis. Cell Death Dis. 2022 Dec 20;13(12):1060. doi: 10.1038/s41419-022-05512-2. PMID: 36539411; PMCID: PMC9768144. 2. Wallenberg M, Misra S, Wasik AM, Marzano C, Björnstedt M, Gandin V, Fernandes AP. Selenium induces a multi-targeted cell death process in addition to ROS formation. J Cell Mol Med. 2014 Apr;18(4):671-84. doi: 10.1111/jcmm.12214. Epub 2014 Jan 8. PMID: 24400844; PMCID: PMC4000118.
In vivo protocol:
To be determined
1: Uehara W, Yoshida S, Emaya Y, Fuchigami T, Haratake M, Nakayama M. Selenoprotein L-inspired nano-vesicular peroxidase mimics based on amphiphilic diselenides. Colloids Surf B Biointerfaces. 2018 Feb 1;162:172-178. doi: 10.1016/j.colsurfb.2017.11.063. Epub 2017 Nov 26. PubMed PMID: 29190468. 2: Puy-Llovera J, Pérez-Ràfols C, Serrano N, Díaz-Cruz JM, Ariño C, Esteban M. Selenocystine modified screen-printed electrode as an alternative sensor for the voltammetric determination of metal ions. Talanta. 2017 Dec 1;175:501-506. doi: 10.1016/j.talanta.2017.07.089. Epub 2017 Jul 29. PubMed PMID: 28842024. 3: Yang Z, Lu L, Kiely CJ, Berger BW, McIntosh S. Single Enzyme Direct Biomineralization of CdSe and CdSe-CdS Core-Shell Quantum Dots. ACS Appl Mater Interfaces. 2017 Apr 19;9(15):13430-13439. doi: 10.1021/acsami.7b00133. Epub 2017 Apr 5. PubMed PMID: 28358193. 4: Ono K, Jung M, Zhang T, Tsutsuki H, Sezaki H, Ihara H, Wei FY, Tomizawa K, Akaike T, Sawa T. Synthesis of l-cysteine derivatives containing stable sulfur isotopes and application of this synthesis to reactive sulfur metabolome. Free Radic Biol Med. 2017 May;106:69-79. doi: 10.1016/j.freeradbiomed.2017.02.023. Epub 2017 Feb 9. PubMed PMID: 28189853. 5: Fan Y, Pan X, Wang K, Wu S, Han H, Yang P, Luo R, Wang H, Huang N, Tan W, Weng Y. Influence of chirality on catalytic generation of nitric oxide and platelet behavior on selenocystine immobilized TiO2 films. Colloids Surf B Biointerfaces. 2016 Sep 1;145:122-129. doi: 10.1016/j.colsurfb.2016.04.043. Epub 2016 Apr 26. PubMed PMID: 27153116; PubMed Central PMCID: PMC4947556. 6: Humann-Ziehank E, Ganter M, Michalke B. Selenium speciation in paired serum and cerebrospinal fluid samples of sheep. J Trace Elem Med Biol. 2016 Jan;33:14-20. doi: 10.1016/j.jtemb.2015.07.010. Epub 2015 Aug 1. PubMed PMID: 26653738. 7: Struppe J, Zhang Y, Rozovsky S. (77)Se chemical shift tensor of L-selenocystine: experimental NMR measurements and quantum chemical investigations of structural effects. J Phys Chem B. 2015 Mar 5;119(9):3643-50. doi: 10.1021/jp510857s. Epub 2015 Feb 18. PubMed PMID: 25654666; PubMed Central PMCID: PMC4581879. 8: Deutch CE, Spahija I, Wagner CE. Susceptibility of Escherichia coli to the toxic L-proline analogue L-selenaproline is dependent on two L-cystine transport systems. J Appl Microbiol. 2014 Nov;117(5):1487-99. doi: 10.1111/jam.12623. Epub 2014 Sep 13. PubMed PMID: 25139244. 9: Hladun KR, Kaftanoglu O, Parker DR, Tran KD, Trumble JT. Effects of selenium on development, survival, and accumulation in the honeybee (Apis mellifera L.). Environ Toxicol Chem. 2013 Nov;32(11):2584-92. doi: 10.1002/etc.2357. Epub 2013 Oct 3. PubMed PMID: 24115124. 10: Zembrzuska J, Matusiewicz H, Polkowska-Motrenko H, Chajduk E. Simultaneous quantitation and identification of organic and inorganic selenium in diet supplements by liquid chromatography with tandem mass spectrometry. Food Chem. 2014 Jan 1;142:178-87. doi: 10.1016/j.foodchem.2013.05.004. Epub 2013 May 16. PubMed PMID: 24001829. 11: Franz ED, Wiramanaden CI, Gallego-Gallegos M, Tse JJ, Phibbs J, Janz DM, Pickering IJ, Liber K. An in situ assessment of selenium bioaccumulation from water-, sediment-, and dietary-exposure pathways using caged Chironomus dilutus larvae. Environ Toxicol Chem. 2013 Dec;32(12):2836-48. doi: 10.1002/etc.2382. PubMed PMID: 23996699. 12: Freeman JL, Marcus MA, Fakra SC, Devonshire J, McGrath SP, Quinn CF, Pilon-Smits EA. Selenium hyperaccumulator plants Stanleya pinnata and Astragalus bisulcatus are colonized by Se-resistant, Se-excluding wasp and beetle seed herbivores. PLoS One. 2012;7(12):e50516. doi: 10.1371/journal.pone.0050516. Epub 2012 Dec 3. PubMed PMID: 23226523; PubMed Central PMCID: PMC3513300. 13: Suzuki T, Sturgeon RE, Zheng C, Hioki A, Nakazato T, Tao H. Influence of speciation on the response from selenium to UV-photochemical vapor generation. Anal Sci. 2012;28(8):807-11. PubMed PMID: 22878637. 14: Tabei Y, Era M, Ogawa A, Ninomiya J, Kawano T, Morita H. Selenium cannot substitute for sulfur in cell density-independent bioluminescence in Vibrio fischeri. J Basic Microbiol. 2013 Feb;53(2):175-80. doi: 10.1002/jobm.201100578. Epub 2012 Jun 26. PubMed PMID: 22733648. 15: Huang SS, Strathe AB, Wang WF, Deng DF, Fadel JG, Hung SS. Selenocompounds in juvenile white sturgeon: evaluating blood, tissue, and urine selenium concentrations after a single oral dose. Aquat Toxicol. 2012 Mar;109:158-65. doi: 10.1016/j.aquatox.2011.12.009. Epub 2011 Dec 16. PubMed PMID: 22226619. 16: Huang SS, Strathe AB, Hung SS, Boston RC, Fadel JG. Selenocompounds in juvenile white sturgeon: estimating absorption, disposition, and elimination of selenium using Bayesian hierarchical modeling. Aquat Toxicol. 2012 Mar;109:150-7. doi: 10.1016/j.aquatox.2011.11.005. Epub 2011 Nov 22. PubMed PMID: 22172476. 17: Bulut H, Moniot S, Licht A, Scheffel F, Gathmann S, Saenger W, Schneider E. Crystal structures of two solute receptors for L-cystine and L-cysteine, respectively, of the human pathogen Neisseria gonorrhoeae. J Mol Biol. 2012 Jan 20;415(3):560-72. doi: 10.1016/j.jmb.2011.11.030. Epub 2011 Nov 23. PubMed PMID: 22138345. 18: Franz ED, Wiramanaden CI, Janz DM, Pickering IJ, Liber K. Selenium bioaccumulation and speciation in Chironomus dilutus exposed to water-borne selenate, selenite, or seleno-DL-methionine. Environ Toxicol Chem. 2011 Oct;30(10):2292-9. doi: 10.1002/etc.624. Epub 2011 Aug 12. PubMed PMID: 21766323. 19: Mechora S, Cuderman P, Stibilj V, Germ M. Distribution of Se and its species in Myriophyllum spicatum and Ceratophyllum demersum growing in water containing Se (VI). Chemosphere. 2011 Sep;84(11):1636-41. doi: 10.1016/j.chemosphere.2011.05.024. Epub 2011 Jun 23. PubMed PMID: 21703659. 20: Wang B, Xie L, Lin Y, Yan Z, Wang L. [Determination of selenium species in food by high performance liquid chromatography with inductively coupled plasma mass spectrometry]. Se Pu. 2011 Mar;29(3):223-7. Chinese. PubMed PMID: 21657051.

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ST-1892

ST-1892