L-Buthionine-(S,R)-sulfoximine (L-Butionine sulfoximine)
(Synonyms: 丁硫氨酸-亚砜亚胺,L-BSO) 目录号 : GC33098
L-Buthionine-(S,R)-sulfoximine (L-Butionine sulfoximine)是一种谷胱甘肽合成抑制剂。
Cas No.:83730-53-4
Sample solution is provided at 25 µL, 10mM.
L-Buthionine-(S,R)-sulfoximine (L-Butionine sulfoximine) is a glutathione synthesis inhibitor [1]. L-Buthionine-(S,R)-sulfoximine specifically inhibits the activity of γ-glutamylcysteine synthetase, thereby significantly reducing intracellular glutathione (GSH) levels [2-3]. L-Buthionine-(S,R)-sulfoximine is often used in cancer research [4].
In fibroblasts, treatment with L-Buthionine-(S,R)-sulfoximine (200-500μM; 48h) showed dose-dependent enhancement of cell death within 48 hours [5]. In SCLC cells, the GSH content in the cells decreased by 57% after treatment with L-Buthionine-(S,R)-sulfoximine (500μM; 30h) [6]. In retinal ganglion cells (RGCs), L-Buthionine-(S,R)-sulfoximine (0.75mM; 24h, 48h) administration resulted in oxidative stress caused by glutathione depletion, and RGC survival rate was significantly decreased [7].
In B6C3F1 mice, after treatment with L-Buthionine-(S,R)-sulfoximine (0, 252mg/kg, 536.995mg/kg, 1502mg/kg; po; 14d), the GSH levels in mice were significantly reduced in a dose-dependent manner [8]. In HT1080 cells subcutaneous tumor mouse model, treatment with L-Buthionine-(S,R)-sulfoximine (600mg/kg; iv; 48h) produced a 60% reduction of GSH plasma levels and greater than 95% reduction in GSH tumor levels in both parental and multidrug-resistant tumors [9].
References:
[1]. Fruehauf J P, Zonis S, AL‐BASSAM M, et al. Selective and Synergistic Activity of L‐S, R‐Buthionine Sulfoximine on Malignant Melanoma Is Accompanied by Decreased Expression of Glutathione‐S‐Transferase[J]. Pigment cell research, 1997, 10(4): 236-249.
[2]. Reliene R, Schiestl R H. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice[J]. Carcinogenesis, 2006, 27(2): 240-244.
[3]. Nishizawa S, Araki H, Ishikawa Y, et al. Low tumor glutathione level as a sensitivity marker for glutamate‑cysteine ligase inhibitors[J]. Oncology Letters, 2018, 15(6): 8735-8743.
[4]. Seo Y J, Lee J W, Lee E H, et al. Role of glutathione in the adaptive tolerance to H2O2[J]. Free radical biology and medicine, 2004, 37(8): 1272-1281.
[5]. Miyauchi A, Kouga T, Jimbo E F, et al. Apomorphine rescues reactive oxygen species-induced apoptosis of fibroblasts with mitochondrial disease[J]. Mitochondrion, 2019, 49: 111-120.
[6]. Lee C S. Effect of Depletion and Oxidation of Cellular GSH on Cytotoxicity of Mitomycin Small Cell Lung Cancer Cells[J]. Biomolecules & Therapeutics, 2004, 12(2): 92-100.
[7]. del Valle Bessone C, Fajreldines H D, de Barboza G E D, et al. Protective role of melatonin on retinal ganglionar cell: In vitro an in vivo evidences[J]. Life Sciences, 2019, 218: 233-240.
[8]. Watanabe T, Sagisaka H, Arakawa S, et al. A novel model of continuous depletion of glutathione in mice treated with L-buthionine (S, R)-sulfoximine[J]. The Journal of toxicological sciences, 2003, 28(5): 455-469.
[9]. Vanhoefer U, Cao S, Minderman H, et al. d, l-buthionine-(S, R)-sulfoximine potentiates in vivo the therapeutic efficacy of doxorubicin against multidrug resistance protein-expressing tumors[J]. Clinical cancer research: an official journal of the American Association for Cancer Research, 1996, 2(12): 1961-1968.
L-Buthionine-(S,R)-sulfoximine (L-Butionine sulfoximine)是一种谷胱甘肽合成抑制剂 [1]。L-Buthionine-(S,R)-sulfoximine特异性抑制γ-谷氨酰半胱氨酸合成酶的活性,从而显著降低细胞内谷胱甘肽(GSH)水平 [2-3]。L-Buthionine-(S,R)-sulfoximine常用于癌症研究 [4]。
在成纤维细胞中,用L-Buthionine-(S,R)-sulfoximine(200-500μM;48h)处理后,48小时内细胞死亡呈剂量依赖性增加 [5]。在小细胞肺癌(SCLC)细胞中,用L-Buthionine-(S,R)-sulfoximine(500μM;30h)处理后,细胞内GSH含量下降了57% [6]。在视网膜神经节细胞(RGC)中,用L-Buthionine-(S,R)-sulfoximine(0.75mM;24h,48h)处理后,由于谷胱甘肽耗竭导致氧化应激,RGC存活率显著降低 [7]。
在B6C3F1小鼠中,用L-Buthionine-(S,R)-sulfoximine(0,252mg/kg、536.995mg/kg,1502mg/kg;po;14d)治疗后,小鼠体内的GSH水平显著降低,且呈剂量依赖性 [8]。在HT1080细胞皮下肿瘤小鼠模型中,用L-Buthionine-(S,R)-sulfoximine(600mg/kg;iv;48h)治疗后,小鼠血浆GSH水平降低了60%,亲本肿瘤和耐多药肿瘤中的GSH肿瘤水平降低了95%以上 [9]。
Cell experiment [1]: | |
Cell lines | Fibroblasts |
Preparation Method | Fibroblasts were cultured in 1.0g/L low-glucose DMEM with 10% FBS at 37℃ in 5% CO2 until they reached semi-confluence. Fibroblasts were then seeded at 5000 cells per well in a 96-well plate. After 24h of incubation, we divided the cells into three groups: L-Buthionine-(S,R)-sulfoximine-untreated group, L-Buthionine-(S,R)-sulfoximine-treated group, and L-Buthionine-(S,R)-sulfoximine co-treated with each chemical group. Each chemical was applied at a final concentration of 1μM. After 48h of incubation, we checked the cell survival rate using Cell Count Reagent SF and compared the findings to those of the L-Buthionine-(S,R)-sulfoximine-untreated group and L-Buthionine-(S,R)-sulfoximine-treated group to evaluate cell protective effect of each chemical. The concentration of L-Buthionine-(S,R)-sulfoximine was regulated to within 200-500μM in order to obtain a survival rate of patient fibroblasts of 10%–20%. |
Reaction Conditions | 200-500μM; 48h |
Applications | In fibroblasts, treatment with L-Buthionine-(S,R)-sulfoximine showed dose-dependent enhancement of cell death within 48 hours. |
Animal experiment [2]: | |
Animal models | B6C3F1 mice |
Preparation Method | To investigate the effect of L-Buthionine-(S,R)-sulfoximine on toxicity and the levels of GSH and various drug-metabolizing enzymes, mice were treated with L-Buthionine-(S,R)-sulfoximine via drinking water for 14 days at dose levels of 0,5,10,20 or 30mM. In this study, actual dose levels were calculated from the amount of water drunk and were 0, 252, 536.995 and 1502mg/kg/day on average, respectively. Each group was composed of four animals. On the day of autopsy, mice were euthanized and autopsied at 9:00. |
Dosage form | 0, 252mg/kg, 536.995mg/kg, 1502mg/kg; po; 14d |
Applications | After treatment with L-Buthionine-(S,R)-sulfoximine, the GSH levels in mice were significantly reduced in a dose-dependent manner. |
References: |
Cas No. | 83730-53-4 | SDF | |
别名 | 丁硫氨酸-亚砜亚胺,L-BSO | ||
Canonical SMILES | N[C@H](C(O)=O)CCS(CCCC)(=O)=N | ||
分子式 | C8H18N2O3S | 分子量 | 222.31 |
溶解度 | Water : 41.67 mg/mL (187.44 mM) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
1 mM | 4.4982 mL | 22.4911 mL | 44.9822 mL |
5 mM | 0.8996 mL | 4.4982 mL | 8.9964 mL |
10 mM | 0.4498 mL | 2.2491 mL | 4.4982 mL |
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