Buthionine Sulphoximine | CAS#5072-26-4 | gamma-glutamylcysteine synthetase inhibitor

MedKoo Cat#: 206723 | Name: Buthionine Sulphoximine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Buthionine Sulphoximine, also known as NSC-326231, is a gamma-glutamylcysteine synthetase inhibitor potentially for the treatment of solid tumors.

Chemical Structure

Buthionine Sulphoximine

CAS#5072-26-4 (DL)

Theoretical Analysis

MedKoo Cat#: 206723

Name: Buthionine Sulphoximine

CAS#: 5072-26-4 (DL)

Chemical Formula: C8H18N2O3S

Exact Mass: 222.1038

Molecular Weight: 222.30

Elemental Analysis: C, 43.22; H, 8.16; N, 12.60; O, 21.59; S, 14.42

Price and Availability

Size	Price	Availability
50mg	USD 150.00	Ready to ship
100mg	USD 250.00	Ready to ship
200mg	USD 450.00	2 weeks
500mg	USD 950.00	2 Weeks

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Related CAS #

83730-53-4 (L) 5072-26-4 (DL)

Synonym

NSC-326231; BSO; Buthionine Sulphoximine; DL-Buthionine-(S,R)-sulfoximine.

IUPAC/Chemical Name

2-amino-4-(butylsulfonimidoyl)butanoic acid

InChi Key

KJQFBVYMGADDTQ-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

N[C@@H](CCS(CCCC)(=O)=N)C(O)=O

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C23M03C09

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

DL-Buthionine-(S,R)-sulfoximine is a potent inhibitor of glutamylcysteine synthetase biosynthesis.

In vitro activity:

Thus, this study next examined the modulatory effects of BSO on the mRNA expression of CNS AA transporters that provide L-cys, such as lat1 and eaac1, and L-cys2/glutamate, such as xct, in the striatum. A significant increase in mRNA levels was detected for all the genes evaluated after BSO injection (Figure 5). These results show that BSO treatment modulates the levels of the transcripts encoding AA transporters related to L-cys/L-cys2 availability in the striatum. Reference: Front Cell Neurosci. 2019; 13: 325. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6664075/

In vivo activity:

The present study found that systemic L-buthionine-S-R-sulfoximine (BSO) administration selectively altered GSH homeostasis and EAAT3 levels in the mice cerebellum. Intraperitoneal treatment of mice with 6 mmol/kg of BSO depleted GSH and GSSG in the liver at 2 h of treatment. Reference: Neurochem Int. 2018 Dec;121:8-18. https://pubmed.ncbi.nlm.nih.gov/30300680/

	Solvent	mg/mL	mM
Solubility
	Water	42.8	192.71

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 222.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Valdovinos-Flores C, Limón-Pacheco JH, León-Rodríguez R, Petrosyan P, Garza-Lombó C, Gonsebatt ME. Systemic L-Buthionine -S-R-Sulfoximine Treatment Increases Plasma NGF and Upregulates L-cys/L-cys2 Transporter and γ-Glutamylcysteine Ligase mRNAs Through the NGF/TrkA/Akt/Nrf2 Pathway in the Striatum. Front Cell Neurosci. 2019 Jul 23;13:325. doi: 10.3389/fncel.2019.00325. PMID: 31396052; PMCID: PMC6664075. 2. Vázquez C, Mejia-Tlachi M, González-Chávez Z, Silva A, Rodríguez-Zavala JS, Moreno-Sánchez R, Saavedra E. Buthionine sulfoximine is a multitarget inhibitor of trypanothione synthesis in Trypanosoma cruzi. FEBS Lett. 2017 Dec;591(23):3881-3894. doi: 10.1002/1873-3468.12904. Epub 2017 Nov 27. PMID: 29127710. 3. Garza-Lombó C, Petrosyan P, Tapia-Rodríguez M, Valdovinos-Flores C, Gonsebatt ME. Systemic L-buthionine-S-R-sulfoximine administration modulates glutathione homeostasis via NGF/TrkA and mTOR signaling in the cerebellum. Neurochem Int. 2018 Dec;121:8-18. doi: 10.1016/j.neuint.2018.10.007. Epub 2018 Oct 6. PMID: 30300680. 4. Yu M, Liu Y, Duan Y, Chen Y, Han J, Sun L, Yang X. Inhibition of glutathione production by L-S,R-buthionine sulfoximine activates hepatic ascorbate synthesis - A unique anti-oxidative stress mechanism in mice. Biochem Biophys Res Commun. 2017 Feb 26;484(1):56-63. doi: 10.1016/j.bbrc.2017.01.072. Epub 2017 Jan 20. PMID: 28115164.

In vitro protocol:

In vivo protocol:

1. Garza-Lombó C, Petrosyan P, Tapia-Rodríguez M, Valdovinos-Flores C, Gonsebatt ME. Systemic L-buthionine-S-R-sulfoximine administration modulates glutathione homeostasis via NGF/TrkA and mTOR signaling in the cerebellum. Neurochem Int. 2018 Dec;121:8-18. doi: 10.1016/j.neuint.2018.10.007. Epub 2018 Oct 6. PMID: 30300680. 2. Yu M, Liu Y, Duan Y, Chen Y, Han J, Sun L, Yang X. Inhibition of glutathione production by L-S,R-buthionine sulfoximine activates hepatic ascorbate synthesis - A unique anti-oxidative stress mechanism in mice. Biochem Biophys Res Commun. 2017 Feb 26;484(1):56-63. doi: 10.1016/j.bbrc.2017.01.072. Epub 2017 Jan 20. PMID: 28115164.

1: Park MH, Kim SY, Moon C, Bae YC, Moon JI, Moon C. Differential cell death and Bcl-2 expression in the mouse retina after glutathione decrease by systemic D,L-buthionine sulphoximine administration. Mol Cells. 2013 Mar;35(3):235-42. doi: 10.1007/s10059-013-2276-y. Epub 2013 Feb 18. PubMed PMID: 23430084; PubMed Central PMCID: PMC3887915. 2: Vukovic V, Nicklee T, Hedley DW. Differential effects of buthionine sulphoximine in hypoxic and non-hypoxic regions of human cervical carcinoma xenografts. Radiother Oncol. 2001 Jul;60(1):69-73. PubMed PMID: 11410306. 3: Hanada K, Mukasa Y, Nomizo Y, Ogata H. Effect of buthionine sulphoximine, glutathione and methimazole on the renal disposition of cisplatin and on cisplatin-induced nephrotoxicity in rats: pharmacokinetic-toxicodynamic analysis. J Pharm Pharmacol. 2000 Dec;52(12):1483-90. PubMed PMID: 11197076. 4: Lockhart B, Jones C, Cuisinier C, Villain N, Peyroulan D, Lestage P. Inhibition of L-homocysteic acid and buthionine sulphoximine-mediated neurotoxicity in rat embryonic neuronal cultures with alpha-lipoic acid enantiomers. Brain Res. 2000 Feb 14;855(2):292-7. PubMed PMID: 10677603. 5: Chattopadhyay A, Deb S, Chatterjee A. Modulation of the clastogenic activity of gamma-irradiation in buthionine sulphoximine-mediated glutathione depleted mammalian cells. Int J Radiat Biol. 1999 Oct;75(10):1283-91. PubMed PMID: 10549605. 6: Li XM, Metzger G, Filipski E, Lemaigre G, Lévi F. Modulation of nonprotein sulphydryl compounds rhythm with buthionine sulphoximine: relationship with oxaliplatin toxicity in mice. Arch Toxicol. 1998 Sep;72(9):574-9. PubMed PMID: 9806429. 7: Nagasaki H, Nakano H, Boudjema K, Jaeck D, Alexandre E, Baek Y, Kitamura N, Yamaguchi M, Kumada K. Efficacy of preconditioning with N-acetylcysteine against reperfusion injury after prolonged cold ischaemia in rats liver in which glutathione had been reduced by buthionine sulphoximine. Eur J Surg. 1998 Feb;164(2):139-46. PubMed PMID: 9537722. 8: Anderson CP, Tsai J, Chan W, Park CK, Tian L, Lui RM, Forman HJ, Reynolds CP. Buthionine sulphoximine alone and in combination with melphalan (L-PAM) is highly cytotoxic for human neuroblastoma cell lines. Eur J Cancer. 1997 Oct;33(12):2016-9. PubMed PMID: 9516845. 9: Dizdar N, Kullman A, Kågedal B, Arstrand K. Effects on interstitial glutathione, cysteine and 5-S-cysteinyldopa of buthionine sulphoximine in human melanoma transplants. Melanoma Res. 1997 Aug;7(4):322-8. PubMed PMID: 9293482. 10: Chattopadhyay A, Choudhury S, Chatterjee A. Modulation of the clastogenic activity of bleomycin by reduced-glutathione, glutathione-ester and buthionine sulphoximine. Mutagenesis. 1997 Jul;12(4):221-5. PubMed PMID: 9237765. 11: Sarma L, Devasagayam TP, Mohan H, Mittal JP, Kesavan PC. Mechanisms of protection by buthionine sulphoximine against gamma-ray-induced micronuclei in polychromatic erythrocytes of mouse bone marrow. Int J Radiat Biol. 1996 May;69(5):633-43. PubMed PMID: 8648251. 12: Schneider E, Yamazaki H, Sinha BK, Cowan KH. Buthionine sulphoximine-mediated sensitisation of etoposide-resistant human breast cancer MCF7 cells overexpressing the multidrug resistance-associated protein involves increased drug accumulation. Br J Cancer. 1995 Apr;71(4):738-43. PubMed PMID: 7710938; PubMed Central PMCID: PMC2033716. 13: Terradez P, Asensi M, Lasso de la Vega MC, Puertes IR, Viña J, Estrela JM. Depletion of tumour glutathione in vivo by buthionine sulphoximine: modulation by the rate of cellular proliferation and inhibition of cancer growth. Biochem J. 1993 Jun 1;292 ( Pt 2):477-83. PubMed PMID: 8503882; PubMed Central PMCID: PMC1134234. 14: Riley RJ, Spielberg SP, Leeder JS. A comparative study of the toxicity of chemically reactive xenobiotics towards adherent cell cultures: selective attenuation of menadione toxicity by buthionine sulphoximine pretreatment. J Pharm Pharmacol. 1993 Apr;45(4):263-7. PubMed PMID: 8098365. 15: Brittebo EB, Darnerud PO, Eriksson C, Brandt I. Nephrotoxicity and covalent binding of 1,1-dichloroethylene in buthionine sulphoximine-treated mice. Arch Toxicol. 1993;67(9):605-12. PubMed PMID: 8311687. 16: Jin YZ, Ding L, Shen ZF, Cai RM, Xu LM, Yang JK, Jin XQ, Lu WQ, Xu JF. Effects of glutathione depletion using buthionine sulphoximine on the cytotoxicity in mammalian cells and human tumor cells in vitro. Chin Med J (Engl). 1992 Aug;105(8):647-50. PubMed PMID: 1458967. 17: Polhuijs M, Lankhaar G, Mulder GJ. Relationship between glutathione content in liver and glutathione conjugation rate in the rat in vivo. Effect of buthionine sulphoximine pretreatment on conjugation of the two 2-bromoisovalerylurea enantiomers during intravenous infusion. Biochem J. 1992 Jul 15;285 ( Pt 2):401-4. PubMed PMID: 1637334; PubMed Central PMCID: PMC1132802. 18: Mizutani T, Yoshida K, Ito K, Kawazoe S. Sex difference in the nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine. Food Chem Toxicol. 1992 Mar;30(3):247-50. PubMed PMID: 1618448. 19: VanSteenhouse JL, Fettman MJ, Gould DH. The effect of glutathione depletion by buthionine sulphoximine on 1-cyano-3,4-epithiobutane toxicity. Food Chem Toxicol. 1991 Mar;29(3):153-7. PubMed PMID: 2032656. 20: Wong RS, Basas RA, Ling CC. Enhancement of SR 2508 (etanidazole) radiosensitization by buthionine sulphoximine at low-dose-rate irradiation. Int J Radiat Biol. 1991 Jan;59(1):133-43. PubMed PMID: 1671060.