S-D-Lactoylglutathione
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S-D-Lactoylglutathione (S-Lactylglutathione; (R)-S-Lactoylglutathione) is a multifunctional metabolic intermediate of the glyoxalase system. S-D-Lactoylglutathione activates K+ efflux in bacteria by displacing inhibitory glutathione from KefGB channels, thereby acidifying the cytoplasm. In eukaryotic cells, S-D-Lactoylglutathione mediates S-glutathionylation as a substrate of glyoxalase 2. S-D-Lactoylglutathione serves as a sensitive metabolic biomarker for neodymium nitrate neurotoxicity; when used in combination with MSCs-exo, it upregulates glutathione levels, downregulates lactate dehydrogenase and Glo2 levels, and inhibits cellular inflammatory responses and pyroptosis. S-D-Lactoylglutathione can be used in research related to prostate cancer, breast cancer, non-small cell lung cancer, sepsis-associated encephalopathy, and neurotoxicity.
For research use only. We do not sell to patients.
- Purity: 98.88%
- CAS No.: 41656-56-8
- Formula: C13H21N3O8S
- Molecular Weight:379.39
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Storage:
Sealed storage, away from moisture.
Powder -80°C, 2 years , -20°C, 1 year* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
All Endogenous Metabolite Isoforms
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Biological Activity
S-D-Lactoylglutathione (50-200 μM; 45 min) significantly enhances anti-IgE-induced histamine release from leukocytes of normal non-atopic human donors[1].
S-D-Lactoylglutathione (200 μM; 5 min preincubation, followed by 45 min co-incubation with anti-IgE) reverses the inhibitory effect of glyoxalase I inhibitors on IgE-induced histamine release from human leukocytes, restoring histamine release to levels comparable to or higher than those of the control group[1].
S-D-Lactoylglutathione (1 mM) serves as a substrate for GlxII; the GlxII activity of ΔgloB *E. coli* MJF595 is approximately 6% of that of the parental strain, while the GlxII activity of MJF274 pGlxII is about 25-fold higher than that of the parental strain[2].
Accumulation of S-D-Lactoylglutathione in ΔgloB *E. coli* MJF595 leads to excessive activation of K+ efflux, whereas reduced levels of S-lactoylglutathione in MJF274 pGlxII prevent the activation of K+ efflux following exposure to MG[2].
In the presence of Glo2, S-D-lactoylglutathione specifically mediates S-glutathionylation of actin at the cysteine 374 (Cys374) site, thereby inhibiting actin polymerization and reducing the hydrolase activity of Glo2[3].
In the presence of Glo2, S-D-lactoylglutathione specifically induces S-glutathionylation of malate dehydrogenase, promotes its tetramer formation and enhances its enzymatic activity, while reducing the hydrolase activity of Glo2[3].
S-D-lactoylglutathione (1 mM) induces non-enzymatic lysine lactylation modification of cellular proteins, which mainly acts on glycolytic enzymes and inhibits their activity[3].
S-D-lactoylglutathione enhances GTP-dependent polymerization of porcine brain tubulin in a cell-free system[3].
S-D-Lactoylglutathione accumulates in large quantities in ΔgloB *E. coli* MJF595 upon exposure to MG, whereas overexpression of GlxII prevents the accumulation of S-lactoylglutathione, and overexpression of GlxI increases the level of S-lactoylglutathione compared with the parental strain[2].
S-D-Lactoylglutathione is one of the most sensitive differential metabolites in BV2 microglia (with the lowest BMDL value among the detected metabolites). Its level decreases in a concentration-dependent manner after neodymium nitrate exposure, and correlates with oxidative stress, mitochondrial dysfunction, and impaired cell viability[5].
S-D-Lactoylglutathione is undetectable in untreated LNCaP prostate cancer cells, but when the cells are treated with 10 μM SKi for 24 h, its accumulation reaches a peak level of 5790 relative to the control group[6].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Male 6- to 8-week-old C57BL/6J mice were subjected to cecal ligation and puncture to establish a sepsis-associated encephalopathy model, followed by tail vein injection of 200 μg MSCs-exo on day 8 post-surgery and intraperitoneal administration of 25 mg/kg imipenem/cilastatin once daily for 5 consecutive days[4]
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Dosage:This compound is an endogenous metabolite
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Administration:This compound is an endogenous metabolite
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Result:In a mouse model of sepsis-associated encephalopathy, the level of S-D-Lactoylglutathione in the hippocampal tissue was significantly upregulated following treatment with MSCs-exo-mediated miR-140-3p delivery. This finding suggested that this molecule played an important role in the mechanism underlying the improvement of cognitive dysfunction in sepsis-associated encephalopathy.
Chemical Information
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CAS No. 41656-56-8
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Appearance Solid
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Molecular Weight 379.39
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Formula C13H21N3O8S
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Color White to off-white
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Synonyms
S-Lactylglutathione; (R)-S-Lactoylglutathione
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Sealed storage, away from moisture
Powder -80°C 2 years -20°C 1 year * In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
Solvent & Solubility
H2O : 50 mg/mL (131.79 mM; Need ultrasonic)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (279 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[2]. Ozyamak E, et al. The critical role of S-lactoylglutathione formation during methylglyoxal detoxification in Escherichia coli. Molecular microbiology. 2010 Dec;78(6):1577-90. [Content Brief]
[3]. Scirè A, et al. Glyoxalase 2: Towards a Broader View of the Second Player of the Glyoxalase System. Antioxidants (Basel, Switzerland). 2022 Oct 28;11(11):2131. [Content Brief]
[4]. Ma Y, et al. MSC-derived exosomal miR-140-3p improves cognitive dysfunction in sepsis-associated encephalopathy by HMGB1 and S-lactoylglutathione metabolism. Commun Biol. 2024 May 11;7(1):562. [Content Brief]
[5]. Wang J, et al. Redox imbalance and glutathione metabolism disruption drive neodymium - induced neurotoxicity in microglia. Toxicology. 2026 Jun;523:154444. [Content Brief]
[6]. Watson DG, et al. The roles of sphingosine kinases 1 and 2 in regulating the Warburg effect in prostate cancer cells. Cellular signalling. 2013 Apr;25(4):1011-7. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| H2O | 1 mM | 2.6358 mL | 13.1791 mL | 26.3581 mL | 65.8953 mL |
| 5 mM | 0.5272 mL | 2.6358 mL | 5.2716 mL | 13.1791 mL | |
| 10 mM | 0.2636 mL | 1.3179 mL | 2.6358 mL | 6.5895 mL | |
| 15 mM | 0.1757 mL | 0.8786 mL | 1.7572 mL | 4.3930 mL | |
| 20 mM | 0.1318 mL | 0.6590 mL | 1.3179 mL | 3.2948 mL | |
| 25 mM | 0.1054 mL | 0.5272 mL | 1.0543 mL | 2.6358 mL | |
| 30 mM | 0.0879 mL | 0.4393 mL | 0.8786 mL | 2.1965 mL | |
| 40 mM | 0.0659 mL | 0.3295 mL | 0.6590 mL | 1.6474 mL | |
| 50 mM | 0.0527 mL | 0.2636 mL | 0.5272 mL | 1.3179 mL | |
| 60 mM | 0.0439 mL | 0.2197 mL | 0.4393 mL | 1.0983 mL | |
| 80 mM | 0.0329 mL | 0.1647 mL | 0.3295 mL | 0.8237 mL | |
| 100 mM | 0.0264 mL | 0.1318 mL | 0.2636 mL | 0.6590 mL |
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
S-D-Lactoylglutathione Related Classifications
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