SML1306

S-p-Bromobenzylglutathione cyclopentyl diester

≥98% (HPLC), powder, Glyoxalase 1 inhibitor

• Synonym(e): 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
• Empirische Formel (Hill-System): C₂₇H₃₈BrN₃O₆S
• CAS-Nummer: 166038-00-2
• Molekulargewicht: 612.58
• MDL-Nummer: MFCD28976196
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 329825773
• NACRES: NA.77

Eigenschaften

• product name: S-p-Bromobenzylglutathione cyclopentyl diester, ≥98% (HPLC)
• Qualitätsniveau: 100
• Assay: ≥98% (HPLC)
• Form: powder
• Farbe: white to beige
• Löslichkeit: DMSO: 20 mg/mL, clear
• Lagertemp.: 2-8°C
• 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
• InChIKey: QIFSPGPRHFNZNN-GOTSBHOMSA-N

Beschreibung

Anwendung

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. Wirkung

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.

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.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable