| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
|
||
| 100mg |
|
||
| 250mg |
|
||
| Other Sizes |
| Targets |
The biological effects of L-Selenocystine are primarily mediated through its redox activity and modulation of multiple signaling pathways. This compound can be reduced by mammalian thioredoxin reductase (TrxR) with an apparent Km value of 6.0 µM, a property that can be utilized to assay TrxR activity . L-Selenocystine promotes the phosphorylation of JNK, p38 MAPK, ERK, and Akt in cells, induces caspase activation, PARP cleavage, and DNA fragmentation, ultimately leading to apoptosis . Furthermore, this compound inhibits Nrf2 activation and nuclear translocation of its downstream proteins, inducing unfolded protein response and endoplasmic reticulum stress .
|
|---|---|
| ln Vitro |
In vitro studies demonstrate that L-Selenocystine exhibits significant antiproliferative effects against various cancer cell lines. In HepG2 and L02 cells, IC₅₀ values after 24-hour treatment are 71.880 μM and 5.444 μM, respectively . In MCF-7 breast cancer cells, this compound increases hydrogen peroxide production starting from relatively low concentrations (100 nM) and significantly elevates ROS levels at higher concentrations, while decreasing UCP2 and MnSOD protein expression . Treatment with 50 μM L-Selenocystine for 24 hours significantly inhibits Nrf2 activation and nuclear translocation of downstream proteins in WiDr cells, inducing autophagy . Co-treatment of 10 μM L-Selenocystine with 400 μM 5-fluorouracil for 24 hours triggers mitochondria-mediated apoptosis in A375 cells, inducing mitochondrial dysfunction and enhancing DNA damage .
|
| ln Vivo |
L-Selenocystine demonstrates anticancer potential in various animal models. The compound is well tolerated in mice and rats but exhibits a narrow safety window between no observed effects and toxicity . Limited pharmacokinetic studies indicate that L-Selenocystine has a rather long half-life and biphasic elimination kinetics . In mice and rats, the compound is effectively absorbed and distributed to various tissues. Preclinical studies have evaluated its potential as an anticancer agent, with reported cytotoxic effects including DNA damage, S-phase arrest, P53 activation, alteration of MAPK and PI3K-AKT signaling pathways, loss of mitochondrial membrane potential, and release of cytochrome C . However, findings from published studies suggest limited antineoplastic effects of selenocystine in various animal models of cancer .
|
| Enzyme Assay |
Cell-free assays for L-Selenocystine primarily focus on its interaction with thioredoxin reductase (TrxR). A typical protocol includes: 1) Prepare a reaction system containing purified TrxR (with 100 mM potassium phosphate buffer pH 7.0, 2 mM EDTA); 2) Dissolve L-Selenocystine in appropriate buffer to prepare various concentrations (0-20 μM); 3) Add NADPH (final concentration 200 μM) and L-Selenocystine to the reaction system; 4) Incubate at 37°C for a certain period; 5) Monitor TrxR activity by measuring the decrease in NADPH absorbance at 340 nm; 6) Calculate the apparent Km value (reference value: 6.0 μM). This method, based on the property of L-Selenocystine as a TrxR substrate, is widely used for TrxR activity determination .
|
| Cell Assay |
The in vitro cell assay protocol for L-Selenocystine is as follows: 1) Seed target cells (such as MCF-7, HepG2, HeLa, A375, or WiDr cells) in culture plates and culture to appropriate density (typically 70-80% confluence) at 37°C with 5% CO₂; 2) Treat cells with various concentrations of L-Selenocystine (typically ranging from 0.1-100 μM) for 24-72 hours; 3) Assess cell viability using MTT or CCK-8 assays to calculate IC₅₀ values; 4) Measure intracellular reactive oxygen species levels using DCFH-DA fluorescent probe; 5) Detect expression changes of relevant proteins by Western blot, including phosphorylated JNK, p38 MAPK, ERK, Akt, Nrf2, as well as caspase-3, PARP, UCP2, and MnSOD; 6) Assess apoptosis rate using flow cytometry (Annexin V/PI double staining) or detect DNA damage using TUNEL staining.
|
| Animal Protocol |
The in vivo animal assay protocol for L-Selenocystine is as follows: 1) Use 6-8 week old female or male mice or rats; 2) Establish tumor models (such as xenograft or chemically induced models); 3) Randomize animals into vehicle control, low-dose, and high-dose groups (8-12 animals per group), with L-Selenocystine doses typically ranging from 1-10 mg/kg; 4) Administration routes: intraperitoneal or intravenous injection, once daily or every other day for 2-4 weeks; 5) Observe general animal condition daily and measure tumor volume (length × width²/2) and body weight 2-3 times per week; 6) Euthanize animals at study termination and collect blood and major organs (liver, kidney, spleen, tumor) for histopathological examination; 7) Measure biochemical parameters, selenium content, and oxidative stress markers in blood .
|
| ADME/Pharmacokinetics |
Pharmacokinetic studies of L-Selenocystine indicate that this compound has a rather long half-life and exhibits biphasic elimination kinetics . In mice and rats, L-Selenocystine is absorbed and distributed to various tissues. Due to the unique metabolic pathways of selenium in vivo, L-Selenocystine can be reduced to more reactive selenol forms or converted to other selenoamino acids such as selenomethionine . The typical dose range for in vivo studies is 1-10 mg/kg, primarily administered via intravenous or intraperitoneal injection. This compound is soluble in water , facilitating its formulation. It should be noted that the exposure level of this compound is closely associated with toxicity, with a narrow therapeutic window .
|
| Toxicity/Toxicokinetics |
207306 rat LD50 intraperitoneal 8463 ug/kg Journal of Pharmacology and Experimental Therapeutics., 108(437), 1953 [PMID:13070164]
L-Selenocystine exhibits significant toxicity and is classified as a hazardous substance. According to GHS hazard classification, the compound has a signal word of "Danger" with hazard statements including: Toxic if swallowed or inhaled (H301+H331); May cause damage to organs through prolonged or repeated exposure (H373); Very toxic to aquatic life with long-lasting effects (H410) . The compound has UN number UN3283, hazard class 6.1 (Toxic substances), and packing group III . The RTECS number is AY6032000 . L-Selenocystine has a narrow safety window in animals, between no observed effects and toxicity . This compound is for research use only and is not intended for human or veterinary use . When handling, avoid inhaling dust, use appropriate personal protective equipment, and operate in well-ventilated areas . |
| References | |
| Additional Infomation |
- L-Selenocysteine (L-SeCys, 1) is the selenium analog of L-cysteine (L-Cys, 3) and is recognized as the 21st proteinogenic amino acid with a unique translational codon (UGA). [1]
- Many selenoenzymes (e.g., glutathione peroxidases, thioredoxin reductases) have a selenocysteine residue at the active site as a catalyst for redox reactions. The functions rely on the enhanced abilities of the selenium atom to oxidize and reduce redox couples compared to sulfur. [1] - L-SeCys itself is unstable due to the high reactivity of the selenol (SeH) functional group; it is usually generated in situ by reduction of the oxidized dimer L-selenocystine ([L-SeCys]2, 7) with reducing reagents such as H3PO4, dithiothreitol (DTT), β-mercaptoethanol (ME), or NaBH4. [1] - Diselenide 7 is a primary synthetic target as an equivalent to L-SeCys. It can be converted to various selenides by reduction and subsequent treatment with organic halides. [1] - The S → Se transformation protocol described in the article involves conversion of L-cystine to L-β-iodoalanine intermediates, followed by reaction with NaHSe and air oxidation to yield diselenides (66-75% yield). The configuration at the C(α) atoms is retained during the transformation. [1] - The article provides detailed experimental procedures for the synthesis of protected selenocysteine derivatives, including N,N′-bis[((9H-fluoren-9-yl)methoxy)carbonyl]-L-selenocystine diethyl ester (16a), N,N′-bis(benzyloxycarbonyl)-L-selenocystine diethyl ester (16b), and L-selenocystine (7). Characterization data (1H NMR, 13C NMR, 77Se NMR, elemental analysis) are provided. [1] |
| Molecular Formula |
C6H12N2O4SE2
|
|---|---|
| Molecular Weight |
334.09
|
| Exact Mass |
335.912
|
| Elemental Analysis |
C, 21.57; H, 3.62; N, 8.39; O, 19.16; Se, 47.27
|
| CAS # |
29621-88-3
|
| PubChem CID |
207306
|
| Appearance |
Light yellow to brown solid powder
|
| Boiling Point |
538.3±60.0 °C at 760 mmHg
|
| Melting Point |
224.5-229.5ºC(lit.)
|
| Flash Point |
279.3±32.9 °C
|
| Vapour Pressure |
0.0±3.1 mmHg at 25°C
|
| LogP |
1.86
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
14
|
| Complexity |
192
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
C([C@@H](C(=O)O)N)[Se][Se]C[C@@H](C(=O)O)N
|
| 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
|
| Chemical Name |
(2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]diselanyl]propanoic acid
|
| Synonyms |
Selenocystine, L-; 1464-43-3; CHEBI:28553; RefChem:884832; 3,3'-diselane-1,2-diylbis(2-aminopropanoic acid); ...; 29621-88-3; L-Selenocystine
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O : ~5.88 mg/mL (~17.60 mM)
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9932 mL | 14.9660 mL | 29.9321 mL | |
| 5 mM | 0.5986 mL | 2.9932 mL | 5.9864 mL | |
| 10 mM | 0.2993 mL | 1.4966 mL | 2.9932 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
