Structural characterization of angiotensin I-converting enzyme in complex with a selenium analogue of captopril

FEBS J. 2011 Oct;278(19):3644-50. doi: 10.1111/j.1742-4658.2011.08276.x. Epub 2011 Sep 8.

Abstract

Human somatic angiotensin I-converting enzyme (ACE), a zinc-dependent dipeptidyl carboxypeptidase, is central to the regulation of the renin-angiotensin aldosterone system. It is a well-known target for combating hypertension and related cardiovascular diseases. In a recent study by Bhuyan and Mugesh [Org. Biomol. Chem. (2011) 9, 1356-1365], it was shown that the selenium analogues of captopril (a well-known clinical inhibitor of ACE) not only inhibit ACE, but also protect against peroxynitrite-mediated nitration of peptides and proteins. Here, we report the crystal structures of human testis ACE (tACE) and a homologue of ACE, known as AnCE, from Drosophila melanogaster in complex with the most promising selenium analogue of captopril (SeCap) determined at 2.4 and 2.35 Å resolution, respectively. The inhibitor binds at the active site of tACE and AnCE in an analogous fashion to that observed for captopril and provide the first examples of a protein-selenolate interaction. These new structures of tACE-SeCap and AnCE-SeCap inhibitor complexes presented here provide important information for further exploration of zinc coordinating selenium-based ACE inhibitor pharmacophores with significant antioxidant activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiotensin-Converting Enzyme Inhibitors / chemistry
  • Angiotensin-Converting Enzyme Inhibitors / metabolism
  • Animals
  • Captopril / analogs & derivatives*
  • Captopril / metabolism
  • Catalytic Domain
  • Drosophila Proteins / chemistry*
  • Drosophila Proteins / metabolism
  • Drosophila melanogaster / enzymology*
  • Humans
  • Male
  • Models, Molecular
  • Molecular Sequence Data
  • Molecular Structure
  • Peptidyl-Dipeptidase A / chemistry*
  • Peptidyl-Dipeptidase A / metabolism*
  • Protein Conformation
  • Selenium / chemistry*
  • Testis / enzymology
  • X-Ray Diffraction

Substances

  • Angiotensin-Converting Enzyme Inhibitors
  • Drosophila Proteins
  • Captopril
  • Peptidyl-Dipeptidase A
  • Selenium

Associated data

  • PDB/2YDM
  • PDB/3ZQZ