Blockade of endothelin-1 with a novel series of 1,3,6-trisubstituted-2-carboxy-quinol-4-ones controls infection-associated preterm birth

Am J Pathol. 2010 Oct;177(4):1929-35. doi: 10.2353/ajpath.2010.100281. Epub 2010 Aug 27.

Abstract

Preterm birth (PTB) currently accounts for 13% of all births in the United States, with the leading cause of PTB being maternal infection. Endothelin-1, an extremely potent vasoconstrictor capable of increasing myometrial smooth muscle tone, has been shown to be up-regulated in the setting of infection in pregnancy, ultimately leading to PTB. In previous work, we have shown that infection-associated PTB is controlled in our murine model by using phospharamidon, an endothelin-converting enzyme-1 inhibitor; knocking down endothelin-converting enzyme-1 mRNA; or blocking the binding of endothelin-1 to the endothelin-A (ET(A)) receptor with either BQ-123 or with HJP-272, the 6-OH compound of our series of novel synthetic (ET(A)) receptor antagonists. In the current study, we show that HJP-272, a highly selective ET(A) receptor antagonist with an IC(50) of 70.1 nmol/L, binds in a noncompetitive manner to the ET(A) receptor. Additionally, we introduce n-propyl (HJP-286) and n-butyl (HJP-278) analogs of HJP-272. We find that the LD(50) of HJP-272, the analog in the series most effective in controlling preterm birth, is more than 20-fold higher than its therapeutic dose. Acute exposure to high doses of these compounds produces no histological changes in any organ, while chronic exposure produces only a rare hepatotoxic effect. These findings may be of clinical significance, as there is currently no FDA-approved therapy for women presenting with threatened preterm delivery.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aspartic Acid Endopeptidases / antagonists & inhibitors
  • Aspartic Acid Endopeptidases / metabolism
  • Benzodioxoles / therapeutic use*
  • Binding, Competitive
  • Endothelin A Receptor Antagonists*
  • Endothelin-1 / antagonists & inhibitors*
  • Endothelin-1 / metabolism
  • Endothelin-Converting Enzymes
  • Female
  • Hydroxyquinolines / therapeutic use*
  • Lipopolysaccharides / pharmacology
  • Metalloendopeptidases / antagonists & inhibitors
  • Metalloendopeptidases / metabolism
  • Mice
  • Mice, Inbred C57BL
  • Pregnancy
  • Pregnancy Complications, Infectious / prevention & control*
  • Pregnancy, Animal
  • Premature Birth / etiology*
  • Premature Birth / prevention & control*
  • Quinolones / therapeutic use*
  • Receptor, Endothelin A / metabolism
  • Swine

Substances

  • 3-(3-carboxybenzyl)-1-((6-ethylbenzo(d)(1,3)dioxol-5-yl)methyl)-6-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acid
  • Benzodioxoles
  • Endothelin A Receptor Antagonists
  • Endothelin-1
  • HJP 278
  • HJP 286
  • Hydroxyquinolines
  • Lipopolysaccharides
  • Quinolones
  • Receptor, Endothelin A
  • Aspartic Acid Endopeptidases
  • Metalloendopeptidases
  • Ece1 protein, mouse
  • Endothelin-Converting Enzymes