Physicochemical Properties
| Molecular Formula | C27H38N3O6SBR |
| Molecular Weight | 612.57612 |
| Exact Mass | 849.18 |
| CAS # | 166038-00-2 |
| PubChem CID | 127939 |
| Appearance | White to off-white solid powder |
| Density | 1.38g/cm3 |
| Boiling Point | 790.6ºC at 760 mmHg |
| Flash Point | 431.9ºC |
| Vapour Pressure | 5.64E-25mmHg at 25°C |
| Index of Refraction | 1.596 |
| LogP | 2.987 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 16 |
| Heavy Atom Count | 38 |
| Complexity | 783 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C1CCC(C1)OC(=O)CNC(=O)[C@H](CSCC2=CC=C(C=C2)Br)NC(=O)CC[C@@H](C(=O)OC3CCCC3)N |
| InChi Key | QIFSPGPRHFNZNN-GOTSBHOMSA-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)/t22-,23-/m0/s1 |
| Chemical Name | cyclopentyl (2S)-2-amino-5-[[(2R)-3-[(4-bromophenyl)methylsulfanyl]-1-[(2-cyclopentyloxy-2-oxoethyl)amino]-1-oxopropan-2-yl]amino]-5-oxopentanoate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vivo | BrBzGCp2 inhibits GLO1, which lengthens the center of the OF test without altering the travel distance. Methylglyoxal (MG) concentrations are raised by GLO1 inhibition, which decreases anxiety-like behaviors [2]. Seizure duration is shortened by BrBzGCp2 pretreatment [3]. Mice that receive injections of BrBzGCp2 have lower anxiety levels, and since less fearful and anxious mice are more inclined to explore new places, it follows that GLO1 activity inhibition lowers anxiety levels [4]. The suppression of GABAA receptor activation caused by VPA can be restored by BrBzGCp2 therapy [4]. In diabetic mice, BrBzGCp2 improves endothelial dysfunction and lowers blood pressure considerably [5]. |
| Animal Protocol |
Animal/Disease Models: Male CD-1 mouse [2]. Doses: 50 mg/kg. Route of Administration: One intraperitoneal (ip) injection (Two hrs (hrs (hours)) after injection, mice were sacrificed, brains were rapidly dissected and snap frozen on dry ice. MG concentration was measured) Experimental Results: MG levels were allowed to accumulate for 2 hrs (hrs (hours)) |
| References |
[1]. Antitumor activity of S-(p-bromobenzyl)glutathione diesters in vitro: a structure-activity study. J Med Chem. 1996 Aug 16;39(17):3409-11. [2]. Glyoxalase 1 increases anxiety by reducing GABAA receptor agonist methylglyoxal. J Clin Invest. 2012 Jun;122(6):2306-15. [3]. GLO1 inhibitors for neuropsychiatric and anti-epileptic drug development. Biochem Soc Trans. 2014 Apr;42(2):461-7. [4]. Glyoxalase 1 and its substrate methylglyoxal are novel regulators of seizure susceptibility. Epilepsia. 2013 Apr;54(4):649-57. [5]. GW29-e0826 ARC Regulates Programmed Necrosis and Myocardial Ischemia/Reperfusion Injury through Preventing the Opening of mPTP. J Am Coll Cardiol. 2018 Oct, 72 (16_Supplement) C27. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~408.11 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 20 mg/mL (32.65 mM) in 8% DMSO 18% Tween80 + 74% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (3.40 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (3.40 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6324 mL | 8.1622 mL | 16.3244 mL | |
| 5 mM | 0.3265 mL | 1.6324 mL | 3.2649 mL | |
| 10 mM | 0.1632 mL | 0.8162 mL | 1.6324 mL |