| Identification | Back Directory | [Name]
CALPAIN INHIBITOR III | [CAS]
88191-84-8 | [Synonyms]
CS-1705
Calp III
MDL 28170
Z-Val-Phe-H
Z-VAL-PHE-CHO
Z-L-Val-L-Phe-OH
Cbz-L-Val-L-Phe-OH
Z-VAL-PHE-ALDEHYDE
CALPAIN INHIBITOR III
MDL 28170, Z-Val-Phe-al
CARBOBENZOXY-VALINYL-PHENYLALANINAL
CARBOBEZOXY-VALINYL-PHENYLALANINALZ-VAL-PHE-CHO
Calpain Inhibitor III - CAS 88191-84-8 - Calbiochem
N-[N-[(Phenylmethoxy)carbonyl]-L-valyl]-phenylalaninal
N-[(1S)-1-[[(1-Formyl-2-phenylethyl)amino]carbonyl]-2-methylpropyl]carbamic acid phenylmethyl ester
Carbamic acid, N-[(1S)-1-[[(1-formyl-2-phenylethyl)amino]carbonyl]-2-methylpropyl]-, phenylmethyl ester | [EINECS(EC#)]
618-124-4 | [Molecular Formula]
C22H26N2O4 | [MDL Number]
MFCD00798796 | [MOL File]
88191-84-8.mol | [Molecular Weight]
382.45 |
| Chemical Properties | Back Directory | [Boiling point ]
595.6±50.0 °C(Predicted) | [density ]
1.153±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 26 mg/mL
| [form ]
White lyophilized solid | [pka]
11.05±0.46(Predicted) | [color ]
White | [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. |
| Hazard Information | Back Directory | [Description]
MDL-28170 (88191-84-8) is a potent and selective cell permeable calpain inhibitor. Inhibits oxidative damage-induced apoptosis in PC12 cells and capsaicin-induced apoptosis in dorsal root ganglion neurons.1?It penetrates the blood-brain barrier and inhibits brain cysteine protease activity after systemic administration, ameliorating brain damage in a gerbil model of global ischemia.2?Displays neuroprotective effects in neurotrauma rodent models.3?Calpain I Ki?= 8 nM; Cathepsin B Ki?= 24 nM in isolated enzyme assays. IC50?= 0.3 μM in intact cell assay.4 | [Uses]
MDL 28170 acts as a caplain inhibitor reducing hypoxia in ischemic-retinopathy, and various other neuroprotective effects. | [Definition]
ChEBI: A dipeptide resulting from the formal condensation of the carboxy group of N-benzyloxycarbonyl-L-valine with the amino group of L-phenylalanine aldehyde. It is a potent cell-permeable inhibitor of calpai
I and II, and is also a gamma-secretase inhibitor. | [General Description]
A potent, cell-permeable inhibitor of calpain I and II (Ki = 8 nM) that also reduces capsaicin-mediated cell death in cultured dorsal root ganglion. Reported to block A23187-induced suppression of neurite outgrowth in isolated hippocampal pyramidal neurons. Exhibits neuroprotective effects against glutamate-induced toxicity. | [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 | [storage]
Store at -20°C | [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 |
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