Buthionine sulfoximine

Manufactured by Merck Group

Sourced in United States

Buthionine sulfoximine is a synthetic organic compound used as a lab reagent. It is a potent inhibitor of the enzyme gamma-glutamylcysteine synthetase, which is involved in the biosynthesis of the antioxidant glutathione. This compound is commonly used in research settings to study the role of glutathione in various biological processes.

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Buthionine sulfoximine (BSO) (34 citations) L-Buthionine-sulfoximine (34 citations) L-buthionine-sulfoximine (BSO) (17 citations) L-buthionine sulfoximine (L-BSO, (3 citations) DL-Buthionine-sulfoximine (3 citations) DL-buthionine-sulfoximine (BSO, (3 citations)

23 protocols using buthionine sulfoximine

Malaria Parasite Cytotoxicity Assay

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Fast Blue BB salt, hypoxanthine, Triton X-100, thiobarbituric acid, trichloroacetic acid, dimethyl sulfoxide (DMSO), bovine serum albumin, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl bromide (MTT), phosphate-buffered saline (PBS), D-sorbitol, acridine orange, ethidium bromide, buthionine sulfoximine (BSO), glutathione disulfide, glutathione reductase, o-phthalaldehyde, nicotinamide adenine dinucleotide phosphate (NADPH), chloroquine diphosphate, artesunate, and clotrimazole were purchased form Sigma-Aldrich (St. Louis, MO, United States), and Albumax II, Roswell Park Memorial Institute 1,640 (RPMI-1640), Dulbecco’s modified eagle medium (DMEM), fetal bovine serum (FBS), and fungizone were purchased from Gibco (Grand Island, United States). Griess reagent kit, chloromethyl-2′,7′-dichlorodihydrofluorescein diacetate (CM-H₂DCFDA), and SYBR Green qPCR super mix were purchased from Invitrogen (Carlsbad, CA, United States). MitoScreen Flow Cytometry kit (Cat No.551302) and APO-BrdU apoptosis detection kit (Cat No. 556381) were obtained from BD Biosciences (Franklin Lakes, NJ, United States).

Kumar S., Mina P.R., Kumar R., Pal A., Ahmad A., Tandon S, & Darokar M.P. (2021). 4-Chlorothymol Exerts Antiplasmodial Activity Impeding Redox Defense System in Plasmodium falciparum. Frontiers in Pharmacology, 12, 628970.

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Comprehensive Cell Autophagy Assay

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H2DCFDA, rapamycin, pyronin Y, and buthionine sulfoximine were obtained from Sigma-Aldrich Co. (USA). Bafilomycin A1 and pepstatin A were obtained from Sangon Biotech Co. (China). D-Luciferin was obtained from Goldbio Co. (USA). Polybrene, Hoechst 33342, and propidium iodide (PI) were obtained from Yeasen Biotech Co. (China). Transfection reagents DharmaFECT, Lipofectamine 2000, and Alexa Fluor 488 and 567 secondary antibodies were obtained from Thermo Fisher Scientific Inc. (USA, 1:500). Anti-LC3 (#3868, 1:1000), anti-Beclin (#3495, 1:1000), anti-ATG5 (#12994, 1:1000), anti-Oct-4 (#2750, 1:1000), and anti-p62/SQSTM1 (#7695, 1:1000) antibodies were obtained from Cell Signaling Technology (USA). Anti-RB1CC1 (sc-22709, 1:100), anti-Ki-67 (sc-23900, 1:100), and HRP-conjugated goat anti-rabbit secondary antibodies were obtained from Santa Cruz Biotechnology (USA). Anti-vimentin, HRP-conjugated goat anti-mouse, and rabbit anti-goat secondary antibodies were obtained from Boster Co. (China). Anti-β-tubulin (1:1000) and anti-β-actin (1:1000) antibodies were obtained from Transgene Biotech Co. (China). Anti-NRF2 (WL02135, 1:2000), anti-NOTCH1 (WL01991, 1:500), and anti-Lamin B (WL01775, 1:500) antibodies were obtained from Wanleibio Co. (China).

Wang Q., Bu S., Xin D., Li B., Wang L, & Lai D. (2018). Autophagy Is Indispensable for the Self-Renewal and Quiescence of Ovarian Cancer Spheroid Cells with Stem Cell-Like Properties. Oxidative Medicine and Cellular Longevity, 2018, 7010472.

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Transfection and Oxidative Stress Assays

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Tissue culture media and supplements were purchased from Lonza (Walkersville, MD, USA). Phenol red-free keratinocyte basal media (KBM) with or without glucose was acquired from Cell Applications, Inc. (San Diego, CA, USA). X-tremeGENE 9 DNA Transfection Reagent was obtained from Roche Applied Science (Indianapolis, IN, USA). Adenoviral vectors were obtained from the Gene Therapy Center Virus Vector Core Facility (University of North Carolina at Chapel Hill, USA). The following chemicals were purchased from Sigma-Aldrich (St. Louis, MO, USA): hydrogen peroxide (H₂O₂), aldrithiol-2 (A-2), dithiothreitol (DTT), 2-mercaptopyridine N-oxide sodium salt (Pyrithione, PYRI), zinc sulfate (Zn²⁺), 2-acetylamino-3-[4-(2-acetylamino-2-carboxyethylsufanylthio-carbonylamino) phenylthiocarbamoylsufanyl] propionic acid (2-AAPA), and buthionine sulfoximine (BSO). Basic laboratory supplies were obtained from Fisher Scientific (Raleigh, NC, USA).

Wages P.A., Silbajoris R., Speen A., Brighton L., Henriquez A., Tong H., Bromberg P.A., Simmons S.O, & Samet J.M. (2014). Role of H2O2 in the oxidative effects of zinc exposure in human airway epithelial cells. Redox Biology, 3, 47-55.

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Prostanoid Compound Acquisition and Characterization

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15-Deoxy-Δ^12,14-prostaglandin J2 (15d-PGJ2), CAY10410 (9,10-dihydro-15-deoxy-Δ^12,14-prostaglandin J2), prostaglandin D2, prostaglandin E2, prostaglandin F2α, rosiglitazone, and T0070907 were purchased from Cayman Chemical (Ann Arbor, MI). Prostaglandin A1, prostaglandin J2, 4-cyclopentene-1,3-dione, 2-cyclopentenone, cycloheximide, actinomycin D, indomethacin, buthionine sulfoximine, and N-acetylcysteine and uric acid were from Sigma-Aldrich (St Louis, MO). Cyclopentanone and cyclopentene were obtained from Tokyo Chemical Industry (TCI, Portland, OR). Structures of these prostanoids are shown in Table I. Nigericin, lactacystin, and ultrapure lipopolysaccharide (LPS) were purchased from Calbiochem (San Diego, CA).

Maier N.K., Leppla S.H, & Moayeri M. (2015). The cyclopentenone prostaglandin 15d-PGJ2 inhibits the NLRP1 and NLRP3 inflammasomes. Journal of immunology (Baltimore, Md. : 1950), 194(6), 2776-2785.

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Purification and Characterization of DIOB

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DIOB was purified from DB rhizomes based on a reported protocol [29 (link)], followed by structural characterization using mass spectrometry and NMR. The purity of DIOB (λ_max = 210 nm) was >98% determined by an HPLC system equipped with a diode array detector. 4-Bromobenzylamine (BBA, >98%) and 4-Bromobenzylmercaptan (BBM, >98%) were purchased from Shanghai Darui Chemical Co., Ltd. (Shanghai, China) and Aladdin Industrial Co., Ltd. (Shanghai, China), respectively. Oxone, reduced nicotinamide adenine dinucleotide phosphate (NADPH), L-lysine (Lys), L-cysteine (Cys), ketoconazole (KTC, >99%), S-hexylglutathione (>99%), chymotrypsin, dexamethasone (DEX, >99%), DL-dithiothreitol (DTT), and buthioninesulfoximine (BSO, >99%) were obtained from Sigma-Aldrich Co. (St. Louis, MO, USA). Pronase E (>98%) was provided by Shanghai Yuanye Biological Technology Co., Ltd. (Shanghai, China). All organic solvents were of HPLC grade and supplied by Fisher Scientific (Springfield, NJ, USA).

Wang K., Lin D., Guo X., Huang W., Zheng J, & Peng Y. (2017). Chemical Identity of Interaction of Protein with Reactive Metabolite of Diosbulbin B In Vitro and In Vivo. Toxins, 9(8), 249.

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Metabolic Flux Analysis Reagents

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Glutamate pyruvate transaminase, glucose-6-phosphate dehydrogenase (G6PDH), lactate dehydrogenase, nicotinamide adenine dinucleotide phosphate (NADP(H)), nicotinamide adenine dinucleotide (NAD), adenosine triphosphate (ATP), and α-ketoglutarate were purchased from Calzyme (San Luis Obispo, CA). Hexokinase, microbial glutamate dehydrogenase, 3-nitrophenylhydrazine, N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide, buthionine sulfoximine, C75, and CBR-5884 were purchased from Sigma (St. Louis, MO). Glutaminase was purchased from Megazyme (Chicago, IL). [5-¹³C] glutamine, [1,2-¹³C] glucose, and [3-¹³C] lactate were purchased from Cambridge Isotopes (Tewksbury, MA). 6-Aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) was purchased from Toronto Research Chemicals (Toronto, Canada). Cell culture media, fetal bovine serum, and cell culture supplies were purchased from Fisher Scientific (Pittsburg, PA). Buffers and other general reagents were purchased from Sigma.

Jekabsons M.B., Merrell M., Skubiz A.G., Thornton N., Milasta S., Green D., Chen T., Wang Y.H., Avula B., Khan I.A, & Zhou Y.D. (2023). Breast cancer cells that preferentially metastasize to lung or bone are more glycolytic, synthesize serine at greater rates, and consume less ATP and NADPH than parent MDA-MB-231 cells. Cancer & Metabolism, 11, 4.

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Evaluating Antioxidant Effects on DNA Damage

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The cells were treated either with 1 μM doxorubicin, 20 nM Taxol (Paclitaxel), 6 μg/ml MMC (all Sigma-Aldrich), or with different concentrations of N-acetyl-cysteine, l-cysteine, cystine, reduced glutathione and buthionine sulfoximine (Sigma-Aldrich). The primary antibodies used were anti-p53 DO-1 mouse monoclonal (Santa Cruz Biotechnology, Santa Cruz, CA, USA, Cat. # sc-126), anti-GAPDH FL-335 rabbit monoclonal (Santa Cruz, Cat. # sc-25778) and anti-phospho-Histone H2AX Ser139 (Merck Millipore, Stockholm, Sweden, Cat. # 05-636 clone JBW301).

Cheteh E.H., Augsten M., Rundqvist H., Bianchi J., Sarne V., Egevad L., Bykov V.J., Östman A, & Wiman K.G. (2017). Human cancer-associated fibroblasts enhance glutathione levels and antagonize drug-induced prostate cancer cell death. Cell Death & Disease, 8(6), e2848-.

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Ferroptosis Regulation in Cancer Cells

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All chemicals used were of analytical reagent grade. Milli-Q water was used for the preparation of standards and reagents. 0.4% trypan blue solution (Cat. 15250061), C11-Bodipy 581/591 (Cat. D3861), and Hoechst33342 (Cat. H3570) were purchased form Thermo Fisher (Waltham, MA). Erastin (Cat. B1524), RSL3 (Cat. B6095), and ferrostatin-1 (Cat. A4371) were obtained from APExBIO (Boston, MA). Buthionine sulfoximine (Cat. 83730-53-4), dimethyl fumarate (Cat. 242926-25G), TNF-α (Cat. H8916), and cycloheximide (Cat. C7698) propidium iodide (Cat. p4170) were purchased from Sigma-Aldrich (St. Louis, MO). ZVAD-FMK (Cat. FMK001), was purchased from R&D Systems (Minneapolis, MN). Antibody to glutamate-cysteine ligase, catalytic subunit (GCLC) (Cat. EP13475) was obtained from Abcam. Pro-caspase3 (Cat. MA1-91637) and GAPDH (Cat. PA1-987) antibodies were purchased from Thermo Fisher. Cleaved caspase 3 antibody (Cat. #9664S) was purchased from Cell Signaling Technology (Danvers, MA). Iron assay kit (Cat. I7504-60) was obtained from Pointe Scientific (Canton, MI). All other chemicals were obtained from Sigma-Aldrich and Fisher Scientific.

Wei Z., Hao C., Huangfu J., Srinivasagan R., Zhang X, & Fan X. (2021). Aging Lens Epithelium is Susceptible to Ferroptosis. Free radical biology & medicine, 167, 94-108.

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Oxidative Stress Pathway Modulation

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Mercaptosuccinic acid (used at 50 μm), buthionine sulfoximine (used at 40 μm) and EA (used at 50 and 100 μm in PC9 and H1975 cells, respectively) were purchased from Sigma (St Louis, MO, USA), whereas EGFR Inhibitor 324674 was from Santa Cruz (Dallas, TX, USA) and Merck (Kenilworth, NJ, USA), respectively. Antibodies against GSTpi, GPX1, GSS, GSR, GCLC, GSTpi, SQSTM1 and DPP3 were from Abcam (Cambridge, UK); antibodies targeting NRF2 and KEAP1 were from Santa Cruz and anti-PALB2 was from Novus (Abingdon, UK). The specificity of all antibodies employed here was assessed by disappearance of the respective signal following selective targeting of the expression of the corresponding protein by siRNA treatment. Quantitect primers targeting GSTpi, GPX1, GPX1, GSS, GSR and GCLC were from Qiagen (Valencia, CA, USA). All other primers were synthesised by Sigma. SiRNAs were purchased from Dharmacon (Little Chalfont, UK). Dihydroethidine was from Invitrogen (Waltham, MA, USA) and DAF-FM from Sigma.

Li H., Stokes W., Chater E., Roy R., de Bruin E., Hu Y., Liu Z., Smit E.F., Heynen G.J., Downward J., Seckl M.J., Wang Y., Tang H, & Pardo O.E. (2016). Decreased glutathione biosynthesis contributes to EGFR T790M-driven erlotinib resistance in non-small cell lung cancer. Cell Discovery, 2, 16031-.

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Differentiation of Mouse D3 ESCs into Neuronal Precursors

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Mouse D3 ESC (ATCC, Manassas, VA, USA) were cultured and induced to form neuronal precursors, resembling the embryonic neuroepithelium that forms the neural tube, as described [28 (link)]. Briefly, undifferentiated (UD) ESC was grown as monolayers, then were induced to form embryoid bodies, then differentiating (D) neuronal precursors were selected from embryoid bodies in attached cultures. D ESC cultures were terminated after four days cultured with or without 0.25 mmol/L buthionine sulfoximine (BSO), a gamma-glutamylcysteine inhibitor [45 (link)], to inhibit the synthesis of glutathione, or 0.001 µmol/L; antimycin A (AA), a mitochondrial complex III inhibitor to stimulate the production of superoxide (both from Sigma-Aldrich, St. Louis, MO, USA).

Alcala M., Bolado V.E., Sánchez-Vera I., Clapés S., Dasí F., Sáez G., Carrera E., Alvarez-Gallego F., Loeken M.R, & Viana M. (2021). Prevention of Teratogenesis in Pregnancies of Obese Rats by Vitamin E Supplementation. Antioxidants, 10(8), 1173.

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