CAS Number83730-53-4
SynonymsL-BUTHIONINESULPHOXIMINE; L-BUTHIONINE-S,R-SULPHOXIMINE; L-BUTHIONINE-SULFOXIMINE; L-BUTHIONINE-[S,R]-SULFOXIME; MFCD00067000; (2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic acid; dl-S-(n-butyl)-homocystein-DR-sulfoximine; buthionine-<S,R>-sulfoximine; L-Buthionine (S,R)-sulfoximine; D-Buthionine Sulfoximine; D,L-buthionine-(S,R)-sulfoximine; Buthionine sulfoximine; L-BUTHIONINE (R,S)-SULFOXIMINE; L-BSO; DL-buthionine-(S,-R)-sulphoximine
Molecular FormulaC8H18N2O3S
Molecular Weight222.31
Purity≥97 (TLC)%
Density1.3±0.1 g/cm3
Boiling Point382.3±52.0 °C at 760 mmHg
Melting Point224-226 °C
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 83730-53-4 |
| Catalog No. | 2A-2177187 |
| Chinese Name | 丁硫氨酸-亚砜亚胺 |
| Synonyms | L-BUTHIONINESULPHOXIMINE; L-BUTHIONINE-S,R-SULPHOXIMINE; L-BUTHIONINE-SULFOXIMINE; L-BUTHIONINE-[S,R]-SULFOXIME; MFCD00067000; (2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic acid; dl-S-(n-butyl)-homocystein-DR-sulfoximine; buthionine-<S,R>-sulfoximine; L-Buthionine (S,R)-sulfoximine; D-Buthionine Sulfoximine; D,L-buthionine-(S,R)-sulfoximine; Buthionine sulfoximine; L-BUTHIONINE (R,S)-SULFOXIMINE; L-BSO; DL-buthionine-(S,-R)-sulphoximine |
| Molecular Formula | C8H18N2O3S |
| Molecular Weight | 222.31 |
| Purity | ≥97 (TLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 382.3±52.0 °C at 760 mmHg |
| Melting Point | 224-226 °C |
| Appearance | powder |
| Storage Condition | Refrigerated, airtight, dry place at 2-8°C |
| Application | L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast-acting, irreversible inhibitor of G-glutamylcysteine synthetase (γ-glutamylcysteine synthetase), which can reduce intracellular glu |
| HTC | 2925290090 |
| PubChem ID | 24278263 |
| MDL Number | MFCD00067000 |
| SMILES | CCCCS(=N)(=O)CC[C@H](N)C(O)=O |
| InChI | 1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)/t7-,14?/m0/s1 |
| InChI Key | KJQFBVYMGADDTQ-CVSPRKDYSA-N |
| Beilstein/REAXYS | 2367136 |
| NACRES Code | NA.77 |
| UNSPSC | 12352202 |
| Hazard Symbols | transportation |
| MSDS | msds/177753_1_83730_53_4.pdf |
| Bioactivity | L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase and depletes cellular glutathione levels. The IC50 value of L-Buthionine-(S,R)-sulfoximine on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer Target γ-glutamylcysteine synthetase[1]. In Vitro L-Buthionine-(S,R)-sulfoximine (BSO: 50 μM) treatment for 48 hr results in a 95% decrease in ZAZ and M14 melanoma cell line GSH levels, and a 60% decrease in GST enzyme activity. GST-π protein and mRNA levels are significantly reduced in both cell lines[1]. L-Buthionine-(S,R)-sulfoximine (BSO) induces oxidative stress in a cell by irreversibly inhibiting g-glutamylcysteine synthetase, an essential enzyme for the synthesis of glutathione (GSH)[2]. In Vivo 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. It is showed that BSO causes an elevated frequency of DNA deletions during mouse development. BSO treatment reduced GSH concentration in mouse fetuses by 55% and 70% at 2 mM and 20 mM BSO doses, respectively, compared to untreated mice. Co-treatment with 2 mM BSO and 20 mM NAC depleted GSH to a similar extent as 2 mM BSO, consistent with the function of BSO to inhibit the g-GCS enzyme indispensable for GSH synthesis. Like GSH, cysteine levels dropped following BSO treatment[2]. Animal Admin Mice[2] C57BL/6J pun/pun mice are used in the study. Pregnancy is timed by checking for vaginal plugs. Noon of the day of discovery is counted as 0.5 days post coitum (d.p.c.). Similarly, the time of birth of a litter is timed with the noon of discovery counted as 0.5 days post-partum (d.p.p.). Pregnant dams are given free access to drinking water supplemented by either 2 mM L-Buthionine-(S,R)-sulfoximine (BSO), 20 mM BSO, 2 mM BSO and 20 mM NAC, 20 mM NAC or unsupplemented water for 18 days from 0.5 to 18.5 d.p.c. The pH of supplemented water is as follows: 6.88, 20 mM BSO; 3.37, 2 mM BSO; 2.65, 2 mM BSO plus 20 mM NAC; and 2.58, 20 mM NAC. The pH of regular water used in our facility is ~4. To determine the DNA deletion frequency, 20-day-old offspring (23 mice in the control group and 16-17 mice per exposure group) are sacrificed to visualize eye-spots (DNA deletions) in their RPE[2]. References [1]. Fruehauf JP, et al. 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]. Reliene R, et al. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis. 2006 Feb;27(2):240-4. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 382.3±52.0 °C at 760 mmHg Melting Point 224-228ºC (dec.) Molecular Formula C8H18N2O3S Molecular Weight 222.305 Flash Point 185.0±30.7 °C Exact Mass 222.103806 PSA 112.62000 LogP 0.22 Vapour Pressure 0.0±1.9 mmHg at 25°C Index of Refraction 1.538 InChIKey KJQFBVYMGADDTQ-CVSPRKDYSA-N SMILES CCCCS(=N)(=O)CCC(N)C(=O)O Storage condition 2~8°C |
| Use of | L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase and depletes cellular glutathione levels. The IC50 value of L-Buthionine-(S,R)-sulfoximine on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively. Properties Articles13 Name l-buthionine-(s,r)-sulfoximine Synonym More Synonyms L-Buthionine (S,R)-sulfoximine Biological Activity Description L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase and depletes cellular glutathione levels. The IC50 value of L-Buthionine-(S,R)-sulfoximine on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer γ-glutamylcysteine synthetase[1]. References [1]. Fruehauf JP, et al. 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]. Reliene R, et al. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis. 2006 Feb;27(2):240-4. Chemical & Physical Properties Molecular Formula C8H18N2O3S Exact Mass 222.103806 PSA 112.62000 Index of Refraction 1.538 InChIKey KJQFBVYMGADDTQ-CVSPRKDYSA-N SMILES CCCCS(=N)(=O)CCC(N)C(=O)O |
| Tax Rebate | 9.0% |
| Supervision | none |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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