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SML1306
S-p-Bromobenzylglutathione cyclopentyl diester
≥98% (HPLC), powder, Glyoxalase 1 inhibitor
Synonym(s):
BBGC, BBGD, BrBzGCp2, N-[S-[(4-Bromophenyl)methyl]-N-L-γ-glutamyl-L-cysteinyl]-Glycine dicyclopentyl ester, S-p-Bromobenzylglutathione dicyclopentyl ester, S-para-Bromobenzylglutathione cyclopentyl diester
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Select a Size
5 MG
R 2,274.58
25 MG
R 7,597.79
About This Item
Empirical Formula (Hill Notation):
C27H38BrN3O6S
CAS Number:
Molecular Weight:
612.58
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Product Name
S-p-Bromobenzylglutathione cyclopentyl diester, ≥98% (HPLC)
SMILES string
BrC1=CC=C(CSC[C@H](NC(CC[C@H](N)C(OC2CCCC2)=O)=O)C(NCC(OC3CCCC3)=O)=O)C=C1
InChI
1S/C27H38BrN3O6S/c28-19-11-9-18(10-12-19)16-38-17-23(26(34)30-15-25(33)36-20-5-1-2-6-20)31-24(32)14-13-22(29)27(35)37-21-7-3-4-8-21/h9-12,20-23H,1-8,13-17,29H2,(H,30,34)(H,31,32)/t22-,23-/m0/s1
InChI key
QIFSPGPRHFNZNN-GOTSBHOMSA-N
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 20 mg/mL, clear
storage temp.
2-8°C
Quality Level
Related Categories
1 of 4
This Item | |||
|---|---|---|---|
| form powder | form powder | form powder | form solid |
| assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay >90% (HPLC) |
| Quality Level 100 | Quality Level 100 | Quality Level 100 | Quality Level 100 |
| storage temp. 2-8°C | storage temp. −20°C | storage temp. 2-8°C | storage temp. −20°C |
| solubility DMSO: 20 mg/mL, clear | solubility DMSO: 20 mg/mL, clear | solubility DMSO: ≥10 mg/mL | solubility water: 50 mg/mL |
| color white to beige | color white to beige | color white to tan | color white |
Application
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.
S-p-Bromobenzylglutathione cyclopentyl diester (BBGC) is a cell-permeable inhibitor of Glyoxalase 1 (GLO1).
BBGC possesses antiproliferative activity, observed in human leukemia cells.
Glyoxalases are associated with detoxification process. Inhibition of glyoxalases produces an anti-carcinogenic and anti-inflammatory effect.
Glyoxalases are associated with detoxification process. Inhibition of glyoxalases produces an anti-carcinogenic and anti-inflammatory effect.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Curcumin inhibits glyoxalase 1?a possible link to its anti-inflammatory and anti-tumor activity.
Santel T, et al.
PLoS ONE, 3(10), e3508-e3508 (2008)
Structure?activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects.
Takasawa R, et al.
Bioorganic & Medicinal Chemistry, 16(7), 3969-3975 (2008)
Marcus Hollenbach et al.
PloS one, 12(2), e0171260-e0171260 (2017-02-24)
High concentrations of methylglyoxal (MGO) cause cytotoxiticy via formation of advanced glycation endproducts (AGEs) and inflammation. MGO is detoxificated enzymatically by glyoxalase-I (Glo-I). The aim of this study was to analyze the role of Glo-I during the development of cirrhosis.
Marisol Ruiz-Meana et al.
Circulation, 139(7), 949-964 (2018-12-28)
Senescent cardiomyocytes exhibit a mismatch between energy demand and supply that facilitates their transition toward failing cells. Altered calcium transfer from sarcoplasmic reticulum (SR) to mitochondria has been causally linked to the pathophysiology of aging and heart failure. Because advanced
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