GSeSeG
GSeSeG (Glutaselenone diselenide) is the oxidized diselenide form of selenoglutathione (GSeH), a selenium analog of glutathione in which selenocysteine replaces cysteine. GSeSeG serves as a substrate for Glutathione Reductase (GR) with a Km of 54 μM. GSeSeG is reduced by the GR/NADPH system to generate GSeH. GSeSeG also promotes the oxidative folding of disulfide-containing proteins and the rearrangement of incorrect disulfide bonds. GSeSeG is used in studies of redox regulation, oxidative/glycation stress, and protein folding.
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- CAS No.: 2487-09-4
- Formula: C20H32N6O12Se2
- Molecular Weight:706.42
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
Biological Activity
Description
In Vitro
GSeSeG (Glutaselenone diselenide) (3 or 8 μM; pH 7.0) has a formal reduction potential of -407 mV in a cell-free redox equilibrium system, which is 151 mV lower than that of GSSG, and reaches equilibrium with DTT more rapidly than GSSG[2].
GSeSeG (150 μM; 0.5-240 min) eliminates the initial lag phase in BPTI oxidative folding and completes folding within 4 h, whereas the GSSG group completes approximately two-thirds[2].
GSeSeG (150 μM; 2-240 min) yields 90% native BPTI after 4 h of BPTI oxidative folding, which is higher than the 67% obtained with GSSG[2].
GSeSeG (10-200 μM; NADPH 100 μM; 25 °C; pH 7.0) is reduced as a GR substrate with a Km of 54 μM and a kcat of 69 s-1[2].
GSeSeG (0.5 mM; GR 10 U/mL; NADPH 1.5 mM; 10 min) generates GSeH (1 mM) in situ, and the resulting GSeH (30 min) reduces more than 80% of 0.1 mM H2O2, exhibiting GPx-like antioxidant activity[3].
GSeH generated in situ from GSeSeG (0.5 mM; 0.5-48 h) reacts with 0.5 mM methylglyoxal, consuming approximately 50% of MG within 30 min and reducing residual MG to about 35% at 48 h, demonstrating GLO1-like antiglycative stress activity[3].
GSeSeG (0.05-0.5 mM; GSH 2 mM; CDNB 1 mM; 10 min) exhibits GST-like activity and retains significant activity even at the lowest tested concentration of 0.05 mM[3].
GSeSeG (0.3 mM; GSH 2 mM; CDNB 1 mM; 60 min) forms GS-DNB and GSe-DNB in the reaction system; the results support that GSH can generate GSeH from GSeSeG via a non-enzymatic pathway, and GSeH subsequently reacts directly with CDNB[3].
GSeSeG (3 μM; overnight pretreatment; MG 4 mM; overnight) increases the average cell viability of HeLa cells after MG stress from 38% to 56%[3].
GSeSeG (25, 50 μM; overnight pretreatment; H2O2 0 or 1 mM; overnight) alone does not reduce cell viability in HeLa cells and, under H2O2 stress, increases cell viability from 41% in the control group to 83% and 88%[3].
GSeSeG (0-25 μM; overnight pretreatment; H2O2 1.2 mM; overnight) increases the tolerance of HeLa cells to oxidative stress, with 0.5 μM increasing cell viability from 21% to 57%[3].
GSeSeG (3 μM; overnight pretreatment; MG 4 mM overnight; H2O2 1.2 mM overnight) increases cell viability under combined stress from 26% to 38% in HeLa cells, and its cytoprotective effect lasts for at least 2 days[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
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Cell Line:HeLa cells
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Concentration:25, 50 μM
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Incubation Time:Overnight pretreatment; H2O2 0 or 1 mM overnight
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Result:Maintained approximately 100% viability without H2O2 and increased H2O2-stressed viability from 41% to 83% and 88%, respectively.
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Cell Line:HeLa cells
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Concentration:0, 0.5, 1, 2, 5, 25 μM
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Incubation Time:Overnight pretreatment; 1.2 mM H2O2 overnight
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Result:Increased resistance to oxidative stress; 0.5 μM increased viability from 21% to 57%.
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Cell Line:HeLa cells
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Concentration:3 μM
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Incubation Time:Overnight pretreatment; 4 mM MG overnight
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Result:Increased mean viability under MG stress from 38% to 56%.
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Cell Line:HeLa cells
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Concentration:3 μM
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Incubation Time:Overnight pretreatment; 4 mM MG overnight; 1.2 mM H2O2 overnight
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Result:Increased viability from 26% to 38%; the protective effect persisted for at least 2 days.
Chemical Information
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CAS No. 2487-09-4
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Molecular Weight 706.42
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Formula C20H32N6O12Se2
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SMILES
OC([C@@H](N)CCC(N[C@@H](C[Se][Se]C[C@@H](C(NCC(O)=O)=O)NC(CC[C@H](N)C(O)=O)=O)C(NCC(O)=O)=O)=O)=O
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Synonyms
Glutaselenone diselenide
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Protocols
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ROS/oxidative-stress fluorescent staining
ROS/oxidative-stress fluorescent staining uses cell-permeant fluorogenic probes that become fluorescent after oxidation inside cells or tissues; commonly used examples include DCFH-DA/DCFDA for broad cellular oxidant detection, DHE for superoxide-related signal detection, MitoSOX for mitochondrial superoxide-related signal detection, and CellROX probes for oxidative-stress-associated fluorescence readouts. The assay detects probe oxidation rather than a single ROS species unless the probe and analysis method have been chemically validated for that species. DCFH-DA enters cells, is deacetylated by intracellular esterases to DCFH, and produces fluorescent DCF after oxidation, so the readout is used as an operational measure of total cellular oxidative stress rather than a species-specific ROS measurement. DHE and MitoSOX can report superoxide-related oxidation, but red fluorescence alone can include non-specific ethidium-like oxidation products; HPLC or optimized spectral approaches are
Purity & Documentation
References
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)