Basic Description

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	≥98%
Biochemical and Physiological Mechanisms	DL-Buthionine-sulfoximine inhibits the biosynthesis of Glutathione (GSH) in liver and other peripheral organs. It does not have any effect on GSH in the CNS. It augments the antiproliferative action of reactive oxygen species (e.g., hydrogen peroxide), an
Storage Temp	Store at 2-8°C,Desiccated
Shipped In	Wet ice This product requires cold chain shipping. Ground and other economy services are not available.
Note	Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description	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.

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
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

Names and Identifiers

IUPAC Name	2-amino-4-(butylsulfonimidoyl)butanoic acid
INCHI	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)
InChIKey	KJQFBVYMGADDTQ-UHFFFAOYSA-N
Smiles	CCCCS(=N)(=O)CCC(C(=O)O)N
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=

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):

Analytical Chart:

Find and download the COA for your product by matching the lot number on the packaging.

10 results found

Lot Number	Certificate Type	Date	Item
D2408122	Certificate of Analysis	Jun 17, 2025	D275570
D2408123	Certificate of Analysis	Jun 17, 2025	D275570
D2408140	Certificate of Analysis	Jun 17, 2025	D275570
D2408141	Certificate of Analysis	Jun 17, 2025	D275570
D2408137	Certificate of Analysis	Jan 14, 2025	D275570
D2408149	Certificate of Analysis	Jan 14, 2025	D275570
J2417600	Certificate of Analysis	Sep 19, 2024	D275570
J2417601	Certificate of Analysis	Sep 19, 2024	D275570
D2408138	Certificate of Analysis	Mar 12, 2024	D275570
D2408139	Certificate of Analysis	Mar 12, 2024	D275570

Chemical and Physical Properties

Solubility	Water
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 Å²
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

Citations of This Product

How to Cite Aladdin Scientific Products?

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).
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).
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).
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, 419 (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).
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, 169 (53).
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, 31 (11): (1230–1239).
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).
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-e423).
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, 67 (211).
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).
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).
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,
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, (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, 18 (32): (21156-21170).
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, (2408580).
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, 92 (105389).

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SKU	Size	Availability	Price
D275570-10mg	10mg	2	$17.90
D275570-25mg	25mg	2	$35.90
D275570-50mg	50mg	2	$56.90
D275570-100mg	100mg	1	$89.90

D,L-Buthionine-(S,R)-sulfoximine - 98%, high purity , CAS No.5072-26-4