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Active site mapping of trypsin, thrombin and matriptase-2 by sulfamoyl benzamidines.

Abstract：

:The benzamidine moiety, a well-known arginine mimetic, has been introduced in a variety of ligands, including peptidomimetic inhibitors of trypsin-like serine proteases. According to their primary substrate specificity, the benzamidine residue interacts with the negatively charged aspartate at the bottom of the S1 pocket of such enzymes. Six series of benzamidine derivatives (1-73) were synthesized and evaluated as inhibitors of two prototype serine proteases, that is, bovine trypsin and human thrombin. As a further target, human matriptase-2, a recently discovered type II transmembrane serine protease, was investigated. Matriptase-2 represents an important regulatory protease in iron homeostasis by down-regulation of the hepcidin expression. Compounds 1-73 were designed to contain a fixed sulfamoyl benzamidine moiety as arginine mimetic and a linker-connected additional substructure, such as a tert-butyl ester, carboxylate or second benzamidine functionality. A systematic mapping approach was performed with these inhibitors to scan the active site of the three target proteases. In particular, bisbenzamidines, able to interact with both the S1 and S3/S4 binding sites, showed notable affinity. In branched bisbenzamidines 66-73 containing a third hydrophobic residue, opposite effects of the stereochemistry on trypsin and thrombin inhibition were observed.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Dosa S,Stirnberg M,Lülsdorff V,Häußler D,Maurer E,Gütschow M

doi

10.1016/j.bmc.2012.08.042

subject

Has Abstract

pub_date

2012-11-01 00:00:00

pages

6489-505

issue

21

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(12)00664-5

journal_volume

20

pub_type

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