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Mannose–pepstatin conjugates as targeted inhibitors of antigen processing

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Organic & Biomolecular Chemistry Vol - 4 Issue - 8

Organic & Biomolecular Chemistry Vol - 4 Issue - 7

Organic & Biomolecular Chemistry Vol - 4 Issue - 6

Organic & Biomolecular Chemistry Vol - 4 Issue - 5

Organic & Biomolecular Chemistry Vol - 4 Issue - 4

Organic & Biomolecular Chemistry Vol - 4 Issue - 3

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Mannose–pepstatin conjugates as targeted inhibitors of antigen processing

Content Provider	Royal Society of Chemistry (RSC)
Author	Free, Paul Hurley, Christopher A. Kageyama, Takashi Chain, Benjamin M. Tabor, Alethea B.
Copyright Year	2006
Abstract	The molecular details of antigen processing, including the identity of the enzymes involved, their intracellular location and their substrate specificity, are still incompletely understood. Selective inhibition of proteolytic antigen processing enzymes such as cathepsins D and E, using small molecular inhibitors such as pepstatin, has proven to be a valuable tool in investigating these pathways. However, pepstatin is poorly soluble in water and has limited access to the antigen processing compartment in antigen presenting cells. We have synthesised mannose–pepstatin conjugates, and neomannosylated BSA–pepstatin conjugates, as tools for the in vivo study of the antigen processing pathway. Conjugation to mannose and to neomannosylated BSA substantially improved the solubility of the conjugates relative to pepstatin. The mannose–pepstatin conjugates showed no reduction in inhibition of cathepsin E, whereas the neomannosylated BSA–pepstatin conjugates showed some loss of inhibition, probably due to steric factors. However, a neomannosylated BSA–pepstatin conjugate incorporating a cleavable disulfide linkage between the pepstatin and the BSA showed the best uptake to dendritic cells and the best inhibition of antigen processing.
Starting Page	1817
Ending Page	1830
Page Count	14
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	4
Issue Number	9
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b600060f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Antigen BSA Dendritic cell Cathepsin Pepstatin Antigen processing Disulfide Mannose
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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Mannose–pepstatin conjugates as targeted inhibitors of antigen processing

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