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B2640

Sigma-Aldrich

DL-Buthionine-(S,R)-sulfoximine

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10 μG
1 402,00 MYR

About This Item

Linear Formula:
CH3(CH2)3S(O)(=NH)CH2CH2CH(NH2)CO2H
CAS Number:
5072-26-4
Molecular Weight:
222.31
MDL number:
MFCD00070309
UNSPSC Code:
12161501
PubChem Substance ID:
24278264
NACRES:
NA.77

1 402,00 MYR

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biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (TLC)

form

powder

mp

215 °C (dec.) (lit.)

solubility

water: 50 mg/mL, clear to very slightly hazy, colorless to yellow

storage temp.

2-8°C

SMILES string

CCCCS(=N)(=O)CCC(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)

InChI key

KJQFBVYMGADDTQ-UHFFFAOYSA-N

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Stainless Steel - AISI 316L alloy, FeCr18Ni10Mo3

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Stainless Steel - AISI 316L alloy, FeCr18Ni10Mo3

Stainless Steel - AISI 316L alloy, FeCr18Ni10Mo3 foil, 50 x 50mm, 0.38mm thickness, annealed

GF27553833

Stainless Steel - AISI 316L alloy, FeCr18Ni10Mo3

form

powder

form

powder

form

powder

form

foil (annealed)

manufacturer/tradename

Goodfellow 775-107-07

manufacturer/tradename

Goodfellow 688-465-52

manufacturer/tradename

Goodfellow 433-650-01

manufacturer/tradename

Goodfellow 275-538-33

weight

200 g

weight

50 g

weight

100 g

weight

-

max. part. size

3 μm

max. part. size

3 μm

max. part. size

-

max. part. size

-

General description

DL-buthionine-SR-sulfoximine (BSO) is an amino acid analogue,[1] which acts as an inhibitor of γ-glutamylcysteine synthetase.[2] BSO increases the sensitivity of Trypanosoma cruzi to antiparasitic drugs, such as nifurtimox or benznidazole.[1]

Application

DL-Buthionine-(S,R)-sulfoximine has also been used:
  • to induce oxidative stress in Starlings[3]
  • to deplete choroidal glutathione (GSH) in two-day-old rat pups[4]
  • to test its inhibitory effect on the enzymes, γ-glutamylcysteine synthetase and trypanothione synthetase (TryS) from T. cruzi[5]

DL-Buthionine-(S,R)-sulfoximine has been used to deplete cellular glutathione levels in retinal ganglion cell 5 (RGC-5) cell line.[6]

Biochem/physiol Actions

Depletes cellular glutathione and downregulates GST level.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000289464
    0000289463
    0000289464
    0000289463
    SLCM0182

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    Sergei V Kotenko
    Cytokine & growth factor reviews, 13(3), 223-240 (2002-12-19)
    Five novel cytokines (IL-19, IL-20, IL-22 (IL-TIF), IL-24 (human MDA-7, mouse FISP, rat C49A/Mob-5), and IL-26 (AK155)) demonstrating limited primary sequence identity and probable structural homology to IL-10 have been identified. These cellular cytokines, as well as several cytokines encoded
    María J Loera-Arias et al.
    Biotechnology letters, 36(12), 2489-2494 (2014-09-13)
    Interleukin-22 (IL-22) participates in the modulation of innate immunity and inflammation. This cytokine has important therapeutic potential, such as with ulcerative colitis, liver and lung injury, and infection, in different animal models. We generated a Lactococcus lactis strain that secretes
    Yi Zhao et al.
    International journal of clinical and experimental medicine, 8(6), 9580-9584 (2015-08-27)
    The interleukin (IL)-23/IL-17A/IL-22 cytokine axis plays a critical role in the pathogenesis of psoriasis, wherein IL-22 effects on epidermal alternations by inhibiting differentiation and inducing keratinocyte proliferation. In this study, we investigated effects of curcumin on IL-22-induced proliferation in a
    H Fukui et al.
    British journal of cancer, 111(4), 763-771 (2014-06-18)
    Interleukin-22 (IL-22) has been recently highlighted owing to its biological significance in the modulation of tissue responses during inflammation. However, the role of IL-22 in carcinogenesis has remained unclear. Here, we investigated the pathophysiological significance of IL-22 expression in gastric
    P Conti et al.
    Immunology letters, 88(3), 171-174 (2003-08-28)
    It has been reported that the CD4+ T cell is a very important source of interleukin 10 (IL-10), while CD8+ cells produce low amounts. IL-10 exerts several immune stimulating, as well as inhibitory effects. There are at least five novel
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