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  Epoxysuccinyl peptide-derived cathepsin B inhibitors: Modulating membrane permeability by conjugation with the C- terminal heptapeptide segment of penetratin

Schaschke, N., Deluca, D., Assfalg-Machleidt, I., Höhneke, C., Sommerhoff, C. P., & Machleidt, W. (2002). Epoxysuccinyl peptide-derived cathepsin B inhibitors: Modulating membrane permeability by conjugation with the C- terminal heptapeptide segment of penetratin. Biological Chemistry, 383(5), 849-852.

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Genre: Journal Article
Alternative Title : Biol. Chem.

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 Creators:
Schaschke, N.1, Author              
Deluca, D.2, Author              
Assfalg-Machleidt, I.2, Author              
Höhneke, C., Author
Sommerhoff, C. P., Author
Machleidt, W.2, Author              
Affiliations:
1Moroder, Luis / Bioorganic Chemistry, Max Planck Institute of Biochemistry, Max Planck Society, ou_1565160              
2External Organizations, ou_persistent22              

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Free keywords: antennapedia; CA074; cathepsin L; MCF-7 cells
 Abstract: Besides its physiological role in lysosomal protein breakdown, extralysosomal cathepsin B has recently been implicated in apoptotic cell death. Highly specific irreversible cathepsin B inhibitors that are readily cellpermeant should be useful tools to elucidate the effects of cathepsin B in the cytosol. We have covalently functionalised the poorly cellpermeant epoxysuccinyl based cathepsin B inhibitor [RGlyGlyLeu(2S, 3S)tEpsLeuProOH; R=OMe] with the Cterminal heptapeptide segment of penetratin (R=[epsilon]AhxArg ArgNleLysTrpLysLysNH(2)). The high inhibitory potency and selectivity for cathepsin B versus cathepsin L of the parent compound was not affected by the conjugation with the penetratin heptapeptide. The conjugate was shown to efficiently penetrate into MCF-7 cells as an active inhibitor, thereby circumventing an intracellular activation step that is required by other inhibitors, such as the prodruglike epoxysuccinyl peptides E64d and CA074Me.

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Language(s): eng - English
 Dates: 2002-05
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 31323
ISI: 000176382200016
 Degree: -

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Title: Biological Chemistry
  Alternative Title : Biol. Chem.
Source Genre: Journal
 Creator(s):
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Publ. Info: -
Pages: - Volume / Issue: 383 (5) Sequence Number: - Start / End Page: 849 - 852 Identifier: ISSN: 1431-6730