D,L-Buthionine-(S,R)-sulfoximine - 10mM in Water , CAS No.5072-26-4

CAS: 5072-26-4 Cat. No.: D424366 Molecular Weight: 222.31 EC Number: 628-045-7

GRADE & PURITY 10mM in Water

Synonyms

NCGC00093696-01 | DTXSID6044434 | LW4108Q0BV | B 2640 | BCP27775 | 2-Amino-4-(butylsulfonimidoyl)butanoicacid | NCGC00015148-04 | BSO | D,L-Buthionine-(S,R)-sulfoximine (Butionine sulfoximine) | EU-0100231 | LP00231 | NCGC00015148-05 | CHEBI:28714 | MFCD0

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

DL-buthionine-SR-sulfoximine (BSO) is an amino acid analogue, which acts as an inhibitor of γ-glutamylcysteine synthetase. BSO increases the sensitivity of Trypanosoma cruzi to antiparasitic drugs, such as nifurtimox or benznidazole.

Specifications

Synonyms

NCGC00093696-01 | DTXSID6044434 | LW4108Q0BV | B 2640 | BCP27775 | 2-Amino-4-(butylsulfonimidoyl)butanoicacid | NCGC00015148-04 | BSO | D, L-Buthionine-(S, R)-sulfoximine (Butionine sulfoximine) | EU-0100231 | LP00231 | NCGC00015148-05 | CHEBI:28714 | MFCD0

Specifications & Purity

10mM in Water

Biochemical and Physiological Mechanisms

Water soluble, potent, selective inhibitor of gamma-glutamyl cysteine synthase. Depletes cellular glutathione.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ACTIVATOR

Names and Identifiers

• Canonical Smiles: CCCCS(=N)(=O)CCC(C(=O)O)N
• IUPAC Name: 2-amino-4-(butylsulfonimidoyl)butanoic acid
• InChIKey: KJQFBVYMGADDTQ-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: CCCCS(=N)(=O)CCC(C(=O)O)N
• Molecular Weight: 222.31
• Reaxy-Rn: 2367136
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2367136&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Alpha amino acids
• Alternative Parents: Thia fatty acids Carbo-azosulfones Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-amino acid - Thia fatty acid - Fatty acyl - Fatty acid - Carbo-azosulfone - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Primary aliphatic amine - Organic oxygen compound - Carbonyl group - Amine - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
• External Descriptors: non-proteinogenic alpha-amino acid - sulfoximide - homocysteines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 222.310 g/mol
• XLogP3: -0.600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 222.104 Da
• Monoisotopic Mass: 222.104 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 284.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Weikai Chen, Chenxi Zhang, Dagui Chen, Yinghua Li, Shunli Wu, Can Xu, Li Su, Qin Zhang.  (2022)  Tumor redox microenvironment modulating composite hydrogels for enhanced sonodynamic therapy of colorectal cancer.  Journal of Materials Chemistry B,  10  (12): (1960-1968).  [PMID:35195150] [10.1039/D2TB00170E]

2. Hui Wang, Weitao Yang, Kexin Bian, Weiwei Zeng, Xiao Jin, Ruizhuo Ouyang, Yan Xu, Chenyu Dai, Shuang Zhou, Bingbo Zhang.  (2021)  Oxygen-Deficient BiOCl Combined with L-Buthionine-Sulfoximine Synergistically Suppresses Tumor Growth through Enhanced Singlet Oxygen Generation under Ultrasound Irradiation.  Small,  18  (9): (2104550).  [PMID:34910856] [10.1002/smll.202104550]

3. Feng Zhu, Qi-Ping Zhang, Yan-Ping Che, Peng-Xiang Zhu, Qin-Qin Zhang, Zhao-Lin Ji.  (2021)  Glutathione contributes to resistance responses to TMV through a differential modulation of salicylic acid and reactive oxygen species.  MOLECULAR PLANT PATHOLOGY,  22  (12): (1668-1687).  [PMID:34553471] [10.1111/mpp.13138]

4. Danqi Li, Jingli Ren, Jun Li, Yamin Zhang, Yuchen Lou, Jinjin Zhu, Pei Liu, Yu Chen, Zhen Yu, Liang Zhao, Lianbin Zhang, Xiang Chen, Jintao Zhu, Juan Tao.  (2021)  Ferroptosis-apoptosis combined anti-melanoma immunotherapy with a NIR-responsive upconverting mSiO2 photodynamic platform.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2021.129557]

5. Jiaojiao Chen, Ming Wu, Hanitrarimalala Veroniaina, Subhankar Mukhopadhyay, Juequan Li, Ziheng Wu, Zhenghong Wu, Xiaole Qi.  (2019)  Poly(N-isopropylacrylamide) derived nanogels demonstrated thermosensitive self-assembly and GSH-triggered drug release for efficient tumor Therapy.  Polymer Chemistry,  10  (29): (4031-4041).  [PMID:] [10.1039/C9PY00537D]

6. Gaofei Wei, Liangfeng Huang, Yali Jiang, Yifeng Shen, Zeqian Huang, Yanjuan Huang, Xiaoqi Sun, Chunshun Zhao.  (2019)  Lenvatinib-zinc phthalocyanine conjugates as potential agents for enhancing synergistic therapy of multidrug-resistant cancer by glutathione depletion.  EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:30856406] [10.1016/j.ejmech.2019.02.065]

7. Zixuan Liu, Wenjing Dong, Bingwei Yang, Lu Peng, Xiaomin Xia, Lanxiang Pu, Na Zhang, Erqun Song, Yang Song.  (2018)  Tetrachlorobenzoquinone-Induced Nrf2 Confers Neuron-like PC12 Cells Resistance to Endoplasmic Reticulum Stress via Regulating Glutathione Synthesis and Protein Thiol Homeostasis.  CHEMICAL RESEARCH IN TOXICOLOGY,      [PMID:30358983] [10.1021/acs.chemrestox.8b00209]

8. Zhao Yixiu, Zhang Xin, Luan Jing, Zhao Buchang, An Na, Sun Na, Wang Xinhui, Zhao Tao, Sun Yanhong, Fu Zidong Donna, Zhang Yan, Zhang Yan.  (2018)  Shenxian-Shengmai Oral Liquid Reduces Myocardial Oxidative Stress and Protects Myocardium from Ischemia-Reperfusion Injury.  CELLULAR PHYSIOLOGY AND BIOCHEMISTRY,  48  (6): (2503-2516).  [PMID:30121659] [10.1159/000492688]

9. Li Huan, Chen Yangjun, Chen Tingting, Han Haijie, Tong Hongxin, Jin Qiao, Ji Jian.  (2017)  Methemoglobin as a redox-responsive nanocarrier to trigger the in situ anticancer ability of artemisinin.  NPG Asia Materials,  9  (8): (e423).  [PMID:] [10.1038/am.2017.150]

10. Lei Liu, Xiao Tu, Yu-Feng Shen, Wei-Chao Chen, Bin Zhu, Gao-Xue Wang.  (2017)  The replication of spring viraemia of carp virus can be regulated by reactive oxygen species and NF-κB pathway.  FISH & SHELLFISH IMMUNOLOGY,      [PMID:28602749] [10.1016/j.fsi.2017.05.068]

11. Hongxin Tong, Yangjun Chen, Zuhong Li, Huan Li, Tingting Chen, Qiao Jin, Jian Ji.  (2016)  Glutathione Activatable Photosensitizer-Conjugated Pseudopolyrotaxane Nanocarriers for Photodynamic Theranostics.  Small,  12  (45): (6223-6232).  [PMID:27622556] [10.1002/smll.201601966]

12. Zhang Keyu, Zheng Wenli, Zheng Haihong, Wang Chunmei, Wang Mi, Li Tao, Wang Xiaoyang, Zhang Lifang, Xiao Sui, Fei Chenzhong, Xue Feiqun.  (2014)  Identification of oxidative stress and responsive genes of HepG2 cells exposed to quinocetone, and compared with its metabolites.  CELL BIOLOGY AND TOXICOLOGY,  30  (6): (313-329).  [PMID:25223261] [10.1007/s10565-014-9287-0]

13. Yanjuan Huang, Meng Xia, Congjun Xu, Zijun Lin, Meixu Chen, Xianmin Shi, Yaqing Ding, Yan Xiao, Chunshun Zhao.  (2024)  A GSH-responsive oxidative stress nanoamplifier for self-augmented chemo/chemodynamic therapy to reverse cisplatin resistance.  Acta Biomaterialia,      [PMID:39706539] [10.1016/j.actbio.2024.12.041]

14. Xiaoyan Sun, Chunli Zhang, Bo Fan, Qingyu Liu, Xiaofeng Shi, Shuxia Wang, Ting Chen, Xueting Cai, Chunping Hu, Handong Sun, Pematenzin Puno, Peng Cao.  (2025)  Cotargeting of thioredoxin 1 and glutamate-cysteine ligase in both imatinib-sensitive and imatinib-resistant CML cells.  BIOCHEMICAL PHARMACOLOGY,      [PMID:39832669] [10.1016/j.bcp.2025.116763]

15. Haibin Lu, Weifang Tong, Meixu Jiang, Huimin Liu, Chen Meng, Kai Wang, Xupeng Mu.  (2024)  Mitochondria-Targeted Multifunctional Nanoprodrugs by Inhibiting Metabolic Reprogramming for Combating Cisplatin-Resistant Lung Cancer.  ACS Nano,      [PMID:39088743] [10.1021/acsnano.4c04024]

16. Huiqun Hu, Shiyuan Hua, Feng Lu, Wenting Zhang, Zengwen Zhang, Jiarong Cui, Xiaoyue Lei, Jingyan Xia, Feng Xu, Min Zhou.  (2025)  Mucous Permeable Nanoparticle for Inducing Cuproptosis-Like Death In Broad-Spectrum Bacteria for Nebulized Treatment of Acute Pneumonia.  Advanced Science,      [PMID:39985298] [10.1002/advs.202408580]

17. Jiaojiao Chen, Shaoxia Wang, Huiyuan Zhang, Huixiang Li, Fei Wang, Yinglin Wang, Quan Zhao.  (2024)  Temperature/redox dual-responsive self-assembled nanogels for targeting delivery of curcumol to enhance anti-tumor and anti-metastasis activities against breast cancer.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2024.105389]

18. Shiyu Zhang, Bowen Gong, Rong Tan, Yufen Liao, Xin Wang, Xu Wang, Ying Liu, Ting Liu, Jun Luo, Weiwei Li, Jia Yu, Ying Peng, Jiang Zheng.  (2025)  8-Epidiosbulbin E acetate triggers apoptosis via metabolic activation-mediated crosstalk between mitochondria and endoplasmic reticulum.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:40627913] [10.1016/j.ecoenv.2025.118614]

19. Xu Han, Le Chang, Zeqian Wang, Xinfang Zhang, Feng Liu.  (2025)  Dual silicon side chain modification of one-component polysulfide adhesives for excellent mechanical properties and solvent resistance.  Polymer Chemistry,      [PMID:] [10.1039/D5PY00665A]

20. Hua Chai, Renpeng Xia, Nan Ouyang, Jingyu Yao, Jiukun Hu, Minxuan Sun, Peng Miao.  (2025)  Membrane Encapsulated Fe3O4@MnO@cGAMP Nanocatalyst for Cancer Therapy: cGAS-STING Immune Pathway Activation.  Advanced Healthcare Materials,      [PMID:40231491] [10.1002/adhm.202501587]

21. Xu Han, Le Chang, Zeqian Wang, Feng Liu.  (2025)  Preparation of high-performance one-component polysulfide adhesives and modification by silane side chains.  Polymer Chemistry,      [PMID:] [10.1039/D5PY00314H]

22. Xin Zheng, Wei Wu, Yurou Li, Wupei Pan, Yinan Xu, Lianwei Zhong, Yinjie Jiang, Jie Zhou.  (2025)  Matrine triggers cardiotoxicity via apoptosis induced by reduction of GSH synthesis through the ATF4/CTH pathway.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:41276026] [10.1016/j.taap.2025.117654]