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83730-53-4

83730-53-4 structure
83730-53-4 structure
  • Name: L-Buthionine (S,R)-sulfoximine
  • Chemical Name: l-buthionine-(s,r)-sulfoximine
  • CAS Number: 83730-53-4
  • Molecular Formula: C8H18N2O3S
  • Molecular Weight: 222.305
  • Catalog: Research Areas Cancer
  • Create Date: 2018-05-15 08:00:00
  • Modify Date: 2024-01-02 21:06:02
  • L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase and depletes cellular glutathione levels. The IC50 value of L-Buthionine-(S,R)-sulfoximine on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively.
Name l-buthionine-(s,r)-sulfoximine
Synonyms L-BUTHIONINESULPHOXIMINE
L-BUTHIONINE-S,R-SULPHOXIMINE
Butanoic acid, 2-amino-4-(S-butylsulfonimidoyl)-, (2S)-
L-BUTHIONINE-SULFOXIMINE
L-BUTHIONINE-[S,R]-SULFOXIME
MFCD00067000
(2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic acid
dl-S-(n-butyl)-homocystein-DR-sulfoximine
buthionine-<S,R>-sulfoximine
L-Buthionine (S,R)-sulfoximine
D-Buthionine Sulfoximine
D,L-buthionine-(S,R)-sulfoximine
Buthionine sulfoximine
L-BUTHIONINE (R,S)-SULFOXIMINE
L-BSO
DL-buthionine-(S,-R)-sulphoximine
Description L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase and depletes cellular glutathione levels. The IC50 value of L-Buthionine-(S,R)-sulfoximine on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively.
Related Catalog
Target

γ-glutamylcysteine synthetase[1].

In Vitro L-Buthionine-(S,R)-sulfoximine (BSO: 50 μM) treatment for 48 hr results in a 95% decrease in ZAZ and M14 melanoma cell line GSH levels, and a 60% decrease in GST enzyme activity. GST-π protein and mRNA levels are significantly reduced in both cell lines[1]. L-Buthionine-(S,R)-sulfoximine (BSO) induces oxidative stress in a cell by irreversibly inhibiting g-glutamylcysteine synthetase, an essential enzyme for the synthesis of glutathione (GSH)[2].
In Vivo The average number of eye-spots (mean±SEM) is 5.36±0.29 (n=46), 7.79±0.45 (n=34) and 8.78±0.61 (n=32) in untreated controls, 2 mM L-Buthionine-(S,R)-sulfoximine (BSO) and 20 mM BSO treated mice, respectively. The 2 mM BSO treatment results in ~30% more eye-spots, and the 20 mM treatment results in 40% more eye-spots compared with untreated mice. It is showed that BSO causes an elevated frequency of DNA deletions during mouse development. BSO treatment reduced GSH concentration in mouse fetuses by 55% and 70% at 2 mM and 20 mM BSO doses, respectively, compared to untreated mice. Co-treatment with 2 mM BSO and 20 mM NAC depleted GSH to a similar extent as 2 mM BSO, consistent with the function of BSO to inhibit the g-GCS enzyme indispensable for GSH synthesis. Like GSH, cysteine levels dropped following BSO treatment[2].
Animal Admin Mice[2] C57BL/6J pun/pun mice are used in the study. Pregnancy is timed by checking for vaginal plugs. Noon of the day of discovery is counted as 0.5 days post coitum (d.p.c.). Similarly, the time of birth of a litter is timed with the noon of discovery counted as 0.5 days post-partum (d.p.p.). Pregnant dams are given free access to drinking water supplemented by either 2 mM L-Buthionine-(S,R)-sulfoximine (BSO), 20 mM BSO, 2 mM BSO and 20 mM NAC, 20 mM NAC or unsupplemented water for 18 days from 0.5 to 18.5 d.p.c. The pH of supplemented water is as follows: 6.88, 20 mM BSO; 3.37, 2 mM BSO; 2.65, 2 mM BSO plus 20 mM NAC; and 2.58, 20 mM NAC. The pH of regular water used in our facility is ~4. To determine the DNA deletion frequency, 20-day-old offspring (23 mice in the control group and 16-17 mice per exposure group) are sacrificed to visualize eye-spots (DNA deletions) in their RPE[2].
References

[1]. Fruehauf JP, et al. Selective and synergistic activity of L-S,R-buthionine sulfoximine on malignant melanoma is accompanied by decreased expression of glutathione-S-transferase. Pigment Cell Res. 1997 Aug;10(4):236-49.

[2]. Reliene R, et al. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis. 2006 Feb;27(2):240-4.
Density 1.3±0.1 g/cm3
Boiling Point 382.3±52.0 °C at 760 mmHg
Melting Point 224-228ºC (dec.)
Molecular Formula C8H18N2O3S
Molecular Weight 222.305
Flash Point 185.0±30.7 °C
Exact Mass 222.103806
PSA 112.62000
LogP 0.22
Vapour Pressure 0.0±1.9 mmHg at 25°C
Index of Refraction 1.538
Storage condition 2~8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EK7713440
CHEMICAL NAME :
Butanoic acid, 2-amino-4-(S-butylsulfonimidoyl)-, (2S)-
CAS REGISTRY NUMBER :
83730-53-4
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C8-H18-N2-O3-S
MOLECULAR WEIGHT :
222.34

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3552 mg/kg
SEX/DURATION :
female 10-11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Lung
DOSE/DURATION :
10 mmol/L
REFERENCE :
CBTOE2 Cell Biology and Toxicology. (Princeton Scientific Pub., Inc., 301 N. Harrison St., CN 5279, Princeton, NJ 08540) V.1- 1984- Volume(issue)/page/year: 7,249,1991
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn
Risk Phrases R36/37/38
Safety Phrases S22;S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS EK7713440
HS Code 2925290090
Precursor  1

DownStream  0

HS Code 2925290090
Summary 2925290090 other imines and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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