-sulfoximine hydrochloride (L-Buthionine sulfoximine hydrochloride; L-BSO hydrochloride) Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C8H19CLN2O3S |
| Related CAS # | DL-Buthionine-(S,R)-sulfoximine;5072-26-4;L-Buthionine-(S,R)-sulfoximine;83730-53-4;DL-Buthionine-(S,R)-sulfoximine hydrochloride |
| Appearance | Typically exists as solid at room temperature |
| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In ZAZ and M14 melanoma cell lines, 48 hours of treatment with L-Buthionine-(S,R)-suLfoximine (BSO: 50 μM) led to a 95% reduction in GSH levels and a 60% reduction in GST enzyme activity. In both cell lines, there was a considerable decrease in the amounts of GST-π protein and mRNA [1]. By irreversibly blocking g-glutamylcysteine synthase, which synthesizes glutathione Essential enzyme for glycopeptide (GSH), L-buthionine-(S,R)-suLfoximine (BSO) produces cellular oxidative stress[2]. In cancer cells, L-Buthionine-(S,R)-suLfoximine (BSO) causes ferroptosis [3]. |
| ln Vivo | BSO increases the frequency of DNA deletions in developing mice. BSO treatment decreased GSH levels in mouse fetuses by 55% and 70% at 2 mM and 20 mM BSO dosages, respectively, in comparison to untreated mice. In line with BSO's ability to inhibit the g-GCS enzyme, which is necessary for GSH synthesis, co-treatment with 2 mM BSO and 20 mM NAC reduced GSH to a level comparable to that of 2 mM BSO. Following BSO therapy, cysteine levels fall, similar to GSH [2]. |
| Animal Protocol |
Animal/Disease Models: C57BL/6J pun/pun mice[2]. Doses: 2mM L-Buthionine-(S,R)-sulfoximine (BSO), 20mM BSO, 2mMBSO and 20mM NAC, 20mM NAC or unsupplemented water for 18 days from 0.5 to 18.5 dpc The pH of supplemented water is as follows: 6.88, 20mM BSO; 3.37, 2mMBSO; 2.65, 2mMBSO plus 20mM NAC; and 2.58, 20mM NAC. The pH of regular water used in our facility is ~4. Route of Administration: Drinking water. Experimental Results: The average number of eye-spots (mean±SEM) is 5.36±0.29 (n=46), 7.79±0.45 (n=34) and 8.78± 0.61 (n=32) in untreated controls, 2 mM L-Buthionine-(S,R)-sulfoximine (BSO) and 20 mM BSO treated mice, respectively. The 2 mM BSO treatment results in ~30% more eye-spots, and the 20 mM treatment results in 40% more eye-spots compared with untreated mice. |
| References |
[1]. Selective and synergistic activity of L-S,R-buthionine sulfoximine on malignant melanoma is accompanied by decreased expression of glutathione-S-transferase. Pigment Cell Res. 1997 Aug;10(4):236-49. [2]. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis. 2006 Feb;27(2):240-4. [3]. Low tumor glutathione level as a sensitivity marker for glutamate-cysteine ligase inhibitors. Oncol Lett. 2018 Jun;15(6):8735-8743. |
Solubility Data
| Solubility (In Vitro) |
DMSO :~250 mg/mL (~966.11 mM) H2O :~70 mg/mL (~270.51 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.04 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (8.04 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (8.04 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |