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ProductsBack/Leupeptin . hemisulfate [103476-89-7]
Chemical Structure
Chemical Structure
Chemical Structure

Leupeptin . hemisulfate [103476-89-7]

Research Use Only
AG-CP3-7000
AdipoGen Life Sciences
CAS Number103476-89-7
DownloadMSDS
Product group Chemicals
Estimated Purity>97%
Molecular Weight426.6 . 49.0
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Leupeptin . hemisulfate [103476-89-7]
  • Delivery Days Customer
    10
  • CAS Number
    103476-89-7
  • Certification
    Research Use Only
  • Estimated Purity
    >97%
  • Molecular Formula
    C20H38N6O4 . 0.5 H2SO4
  • Molecular Weight
    426.6 . 49.0
  • Scientific Description
    Chemical. CAS: 103476-89-7. Formula: C20H38N6O4 . 0.5 H2SO4. MW: 426.6 . 49.0. Synthetic. Potent, competitive and reversible cysteine, serine and threonine protease inhibitor. Inhibits calpain, kallikrein, trypsin, plasmin, papain and cathepsin B. Does not inhibit pepsin, elastase, renin, cathepsins A and D, thrombin or alpha-chymotrypsin. Used to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin. Shown to inhibit activation-induced programmed cell death. Antioxidant and anti-inflammatory agent. Widely used as a protein purification tool to prevent proteases present in tissue samples from degrading the protein of interest. - Potent, competitive and reversible cysteine, serine and threonine protease inhibitor. Inhibits calpain, kallikrein, trypsin, plasmin, papain and cathepsin B. Does not inhibit pepsin, elastase, renin, cathepsins A and D, thrombin or alpha-chymotrypsin. Used to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin. Shown to inhibit activation-induced programmed cell death. Antioxidant and anti-inflammatory agent. Widely used as a protein purification tool to prevent proteases present in tissue samples from degrading the protein of interest. Molecular docking and molecular dynamics simulation of leupeptin with the transmembrane serine protease TMPRSS2, show strong interactions with the key amino acids Ser186, His41 and Asp180 of catalytic triad present in the active site of TMPRSS2. This interaction causes the inhibition of the function of TMPRSS2, which is essential for SARS-CoV-2 viral entry and infection. As an inhibitor of TMPRSS2 this agent could be repurposed for treatment of COVID-19.
  • SMILES
    OS(O)(=O)=O.[H]C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(C)=O.[H]C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(C)=O
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

References

  • Leupeptins, new protease inhibitors from actinomycetes: T. Aoyagi, et al.; J. Antibiot. (Tokyo) 22, 283 (1969)
  • Biological activities of leupeptins: T. Aoyagi; J. Antibiot. (Tokyo) 22, 558 (1969)
  • Mechanism of association of a specific aldehyde inhibitor, leupeptin, with bovine trypsin: H. Kuramochi, et al.; J. Biochem. 86, 1403 (1979)
  • The slow, tight-binding inhibition of cathepsin B by leupeptin. A hysteretic effect: A. Baici, et al.; Eur. J. Biochem. 129, 33 (1982)
  • Leupeptin, a thiol proteinase inhibitor, causes a selective impairment of spatial maze performance in rats: U. Staubli, et al.; Behav. Neural. Biol. 40, 58 (1984)
  • Leupeptin selectively inhibits human platelet responses induced by thrombin and trypsin; a role for proteolytic activation of phospholipase C: M. Ruggiero & E.G. Lapetina; BBRC 131, 1198 (1985)
  • Protease-inhibitory activities of leupeptin analogues: T. Saino, et al.; J. Antibiot. (Tokyo) 41, 220 (1988)
  • New leupeptin analogues: synthesis and inhibition data: R.M. McConnell, et al.; J. Med. Chem. 33, 86 (1990)
  • Developing selective inhibitors of calpain: K.K. Wang, et al.; TIPS 11, 139 (1990)
  • Cell-penetrating inhibitors of calpain: S. Mehdi, et al.; TIBS 16, 150 (1991)