Synthesis and biological activity of modified peptide inhibitors of angiotensin-converting enzyme.

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Roark WH, Tinney FJ, Cohen D, Essenburg AD, Kaplan HR

Synthesis and biological activity of modified peptide inhibitors of angiotensin-converting enzyme.

J Med Chem. 1985 Sep;28(9):1291-5.

PubMed ID

2993618 [ View in PubMed

]

Abstract

A series of non-sulfhydryl modified dipeptides related to CI-906, CI-907, and enalapril was prepared in which various isosteric moieties (O, S, SO, SO2) have been substituted for the amino group and in which the proline residue has been replaced with various hydrophobic amino acids. The compounds were evaluated in vitro for inhibition of angiotensin-converting enzyme and in vivo for antihypertensive activity. Compound 7c, the most potent member of this series, had an in vitro IC50 of 1.4 X 10(-8) M and showed modest oral antihypertensive activity at 30 mg/kg in conscious, two kidney, one clip Goldblatt hypertensive rats. Structure-activity relationships are discussed.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Captopril	Angiotensin-converting enzyme	IC 50 (nM)	1300	N/A	N/A	Details
Enalapril	Angiotensin-converting enzyme	IC 50 (nM)	140	N/A	N/A	Details