88191-84-8

Basic information

• Product Name: CALPAIN INHIBITOR III
• Synonyms: CALPAIN INHIBITOR III;CARBOBEZOXY-VALINYL-PHENYLALANINALZ-VAL-PHE-CHO;CARBOBENZOXY-VALINYL-PHENYLALANINAL;MDL 28170;Z-VAL-PHE-ALDEHYDE;Z-VAL-PHE-CHO;MDL 28170, Z-Val-Phe-al;Cbz-L-Val-L-Phe-OH
• CAS NO: 88191-84-8
• Molecular Formula: C17H17NO3
• Molecular Weight: 283.32
• EINECS: 618-124-4
• Product Categories: inhibitor
• Mol File: 88191-84-8.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 595.6 °C at 760 mmHg
• Flash Point: 314 °C
• Appearance: /
• Density: 1.153 g/cm³
• Vapor Pressure: 3.74E-14mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 2-8°C
• Solubility: DMSO: 26 mg/mL
• PKA: 11.05±0.46(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• CAS DataBase Reference: CALPAIN INHIBITOR III(CAS DataBase Reference)
• NIST Chemistry Reference: CALPAIN INHIBITOR III(88191-84-8)
• EPA Substance Registry System: CALPAIN INHIBITOR III(88191-84-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 88191-84-8(Hazardous Substances Data)

Usage

Description

CALPAIN INHIBITOR III, also known as MDL-28170, is a potent and selective cell-permeable calpain inhibitor. It is a dipeptide resulting from the formal condensation of the carboxy group of N-benzyloxycarbonyl-L-valine with the amino group of L-phenylalanine aldehyde. CALPAIN INHIBITOR III exhibits neuroprotective effects and inhibits oxidative damage-induced apoptosis in various cell types.

Uses

Used in Neuroprotection:
CALPAIN INHIBITOR III is used as a neuroprotective agent for reducing hypoxia in ischemic-retinopathy and exhibiting neuroprotective effects against glutamate-induced toxicity. It also displays neuroprotective effects in neurotrauma rodent models.
Used in Inhibition of Calpain Proteolysis:
CALPAIN INHIBITOR III is used as an inhibitor of calpain proteolysis, which plays a crucial role in various cellular processes. It is a potent inhibitor of calpain I and II (Ki = 8 nM) and also inhibits brain cysteine protease activity after systemic administration.
Used in Pharmaceutical Industry:
CALPAIN INHIBITOR III is used as a research compound in the pharmaceutical industry for studying the role of calpain enzymes in various diseases and developing potential therapeutic agents targeting these enzymes.
Used in Cell Culture Studies:
CALPAIN INHIBITOR III is used as a tool in cell culture studies to investigate the effects of calpain inhibition on cell death, neurite outgrowth, and apoptosis in different cell types, such as PC12 cells and dorsal root ganglion neurons.

Biological Activity

Potent, selective inhibitor of calpain and cathepsin B (K i values are 10 and 25 nM respectively) that does not inhibit trypsin-like serine proteases. Rapidly penetrates the blood-brain barrier following systemic administration and displays neuroprotective effects in vivo .

Biochem/physiol Actions

Cell permeable: yes

References

1) Chard?et al.?(1995),?Capsaicin-induced neurotoxicity in cultured dorsal root ganglion neurons: involvement of calcium-activated proteases; Neuroscience,?65?1099 2) Li?et al.?(1998),?Postischemic treatment with calpain inhibitor MDL28170 ameliorates brain damage in a gerbil model of global ischemia; Neurosci. Lett.,?247?17 3) Thompson?et al. (2010),?A pharmacological analysis of the neuroprotective efficacy of the brain- and cell-permeable calpain inhibitor MDL-28170 in the mouse controlled cortical impact traumatic brain injury model; J. Neurotrauma,?27?2233 4) Chatterjee?et al.?(1998),?D-amino acid containing, high-affinity inhibitors of recombinant human calpain I; J. Med. Chem.,?41?2663

InChI:InChI=1/C22H26N2O4/c1-16(2)20(24-22(27)28-15-18-11-7-4-8-12-18)21(26)23-19(14-25)13-17-9-5-3-6-10-17/h3-12,14,16,19-20H,13,15H2,1-2H3,(H,23,26)(H,24,27)/t19-,20-/m0/s1