p-BrBzGSH(Cp)2 | CAS#166038-00-2 | GLO1 inhibitor

MedKoo Cat#: 562203 | Name: p-BrBzGSH(Cp)2

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

p-BrBzGSH(Cp)2 is an inhibitor of glyoxylase 1 (GLO1). It acts by increasing DNA-AGEs, stimulating RAGE expression, and inhibiting brain tumor growth in orthotopic mouse models. p-BrBzGSH(Cp)2 is an inhibitor of multiple small molecules.

Chemical Structure

p-BrBzGSH(Cp)2

CAS#166038-00-2

Theoretical Analysis

MedKoo Cat#: 562203

Name: p-BrBzGSH(Cp)2

CAS#: 166038-00-2

Chemical Formula: C27H38BrN3O6S

Exact Mass: 611.1665

Molecular Weight: 612.58

Elemental Analysis: C, 52.94; H, 6.25; Br, 13.04; N, 6.86; O, 15.67; S, 5.23

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Synonym

p-BrBzGSH(Cp)2; p BrBzGSH(Cp)2; pBrBzGSH(Cp)2; BBGC; BBGD;

IUPAC/Chemical Name

S-(p-Bromobenzyl) glutathione dicyclopentyl ester

InChi Key

QIFSPGPRHFNZNN-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=C(C(NC(CCC(C(OC1CCCC1)=O)N)=O)CSCC2=CC=C(Br)C=C2)NCC(OC3CCCC3)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

BrBzGCp2 is a Glyoxalase 1 (GLO1) inhibitor, with a GC50 of 4.23 μM in HL-60 cells.

In vitro activity:

GLO1 inhibition in GBM cell lines and in an orthotopic xenograft GBM mouse model was examined using both small molecule and short hairpin RNA (shRNA) approaches. Inhibition of GLO1 with S-(p-bromobenzyl) glutathione dicyclopentyl ester (p-BrBzGSH(Cp)₂) increased levels of the DNA-AGE N²-1-(carboxyethyl)-2'-deoxyguanosine (CEdG), a surrogate biomarker for nuclear MG exposure; substantially elevated expression of the immunoglobulin-like receptor for AGEs (RAGE); and induced apoptosis in GBM cell lines. Reference: Int J Mol Sci. 2018 Jan 30;19(2):406. https://pubmed.ncbi.nlm.nih.gov/29385725/

In vivo activity:

This study aims to evaluate the roles of glyoxalase 1 (GLO1)-methylglyoxal (MG)-γ-aminobutyric acid (GABA) signaling in ASD using a valproic acid (VPA)-induced animal model of autism. Administration of S-p-bromobenzylglutathione cyclopentyl diester (BrBzGCp2), a GLO1 inhibitor, was beneficial for alleviating anxiety, reducing repetitive behavior, and improving the impaired sociability and nociceptive threshold of VPA mice. BrBzGCp2 treatment may be developed as a promising therapeutic strategy for patients with ASD. Reference: ACS Chem Neurosci. 2020 Nov 18;11(22):3786-3792. https://pubmed.ncbi.nlm.nih.gov/33166134/

	Solvent	mg/mL	mM
Solubility
	DMSO	250.0	408.11

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 612.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jandial R, Neman J, Lim PP, Tamae D, Kowolik CM, Wuenschell GE, Shuck SC, Ciminera AK, De Jesus LR, Ouyang C, Chen MY, Termini J. Inhibition of GLO1 in Glioblastoma Multiforme Increases DNA-AGEs, Stimulates RAGE Expression, and Inhibits Brain Tumor Growth in Orthotopic Mouse Models. Int J Mol Sci. 2018 Jan 30;19(2):406. doi: 10.3390/ijms19020406. PMID: 29385725; PMCID: PMC5855628. 2. Wang K, Li N, Xu M, Huang M, Huang F. Glyoxalase 1 Inhibitor Alleviates Autism-like Phenotype in a Prenatal Valproic Acid-Induced Mouse Model. ACS Chem Neurosci. 2020 Nov 18;11(22):3786-3792. doi: 10.1021/acschemneuro.0c00482. Epub 2020 Nov 9. PMID: 33166134.

In vitro protocol:

In vivo protocol:

1. Wang K, Li N, Xu M, Huang M, Huang F. Glyoxalase 1 Inhibitor Alleviates Autism-like Phenotype in a Prenatal Valproic Acid-Induced Mouse Model. ACS Chem Neurosci. 2020 Nov 18;11(22):3786-3792. doi: 10.1021/acschemneuro.0c00482. Epub 2020 Nov 9. PMID: 33166134.

1: Jandial R, Neman J, Lim PP, Tamae D, Kowolik CM, Wuenschell GE, Shuck SC, Ciminera AK, De Jesus LR, Ouyang C, Chen MY, Termini J. Inhibition of GLO1 in Glioblastoma Multiforme Increases DNA-AGEs, Stimulates RAGE Expression, and Inhibits Brain Tumor Growth in Orthotopic Mouse Models. Int J Mol Sci. 2018 Jan 30;19(2). pii: E406. doi: 10.3390/ijms19020406. PubMed PMID: 29385725.