| Identification | Back Directory | [Name]
S-4-bromobenzylglutathione cyclopentyl diester | [CAS]
166038-00-2 | [Synonyms]
BrBzGCp2
S-4-bromobenzylglutathione cyclopentyl diester
S-p-Bromobenzylglutathione cyclopentyl diester
S-p-Bromobenzylglutathione cyclopentyl diester >=98% (HPLC)
Glycine, N-[S-[(4-bromophenyl)methyl]-N-L-γ-glutamyl-L-cysteinyl]-, dicyclopentyl ester (9CI) | [Molecular Formula]
C27H38BrN3O6S | [MDL Number]
MFCD28976196 | [MOL File]
166038-00-2.mol | [Molecular Weight]
612.58 |
| Chemical Properties | Back Directory | [Boiling point ]
790.6±60.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 250 mg/mL (408.11 mM) | [form ]
powder | [pka]
12.84±0.46(Predicted) | [color ]
white to beige | [InChIKey]
QIFSPGPRHFNZNN-GOTSBHOMSA-N | [SMILES]
BrC1=CC=C(CSC[C@H](NC(CC[C@H](N)C(OC2CCCC2)=O)=O)C(NCC(OC3CCCC3)=O)=O)C=C1 |
| Hazard Information | Back Directory | [Uses]
S-p-Bromobenzylglutathione cyclopentyl diester has been used as an inhibitor of glyoxalase 1?(GLO-1) enzyme to treat HL-1 cardiomyocytes for stimulating aging-based glycative stress. It has also been used as an inhibitor of GLO-1 in hepatic stellate cells. | [Biochem/physiol Actions]
S-p-Bromobenzylglutathione cyclopentyl diester (BBGC) is a cell-permeable inhibitor of Glyoxalase 1 (GLO1), an enzyme that detoxifies methylglyoxal, a toxic side-product of glycolysis that induces apoptosis at high levels and has been linked to arterial atherogenesis in diabetics. However, tumors use GLO as well and overexpression of GLO1 has been reported in a number of cancers, so GLO1 inhibitors including BBCG have been investigated as possible anticancer agents. Recent studies have indicated that methylglyoxal has some beneficial effects at low levels with GABAA receptor agonist activity, and that GLO1 inhibition with BBGC can reduce anxiety-like behavior and decrease antiseizure activity. S-p-bromobenzylglutathione cyclopentyl diester should be an inportant tool to study the glyoxalase system. | [in vivo]
GLO1 inhibition by BrBzGCp2 increases center time in the OF test, without changing distance traveled. GLO1 inhibition increases MG (methylglyoxal) concentration, thus reducing anxiety-like behavior[2].
BrBzGCp2 pre-treatment decreases seizure duration[3].
BrBzGCp2 injection alleviates the level of anxiety in mice, and mice with less anxiety and fear were more likely to explore the unknown area, implying that inhibition of GLO1 activity mitigated anxiety levels[4].
BrBzGCp2 treatment restores the VPA-induced inhibition effect on GABAA receptor activation[4].
BrBzGCp2 significantly lowers the blood pressure and ameliorated endothelial dysfunction in diabetic mice[5].
| Animal Model: | Male CD-1 mice[2]. | | Dosage: | 50 mg/kg. | | Administration: | IP once (Two hours post-injection, mice were sacrificed, and brains were rapidly dissected and flash-frozen on dry ice. MG concentration was measured) | | Result: | Allowed MG levels to accumulate for 2 hours |
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| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|