A rational approach to the design and synthesis of a new bradykinin B(1) receptor antagonist

J Med Chem. 2000 Jun 15;43(12):2387-94. doi: 10.1021/jm990962k.

Abstract

We have previously synthesized a potent and selective B(1) bradykinin receptor antagonist, JMV1645 (H-Lys-Arg-Pro-Hyp-Gly-Igl-Ser-D-BT-OH), containing a dipeptide mimetic ((3S)-amino-5-carbonylmethyl-2,3-dihydro-1, 5-benzothiazepin-4(5H)-one (D-BT) moiety) at the C-terminal. Analogues of this potent B(1) bradykinin receptor antagonist in which the central Pro(2)-Hyp(3)-Gly(4)-Igl(5) tetrapeptide has been replaced by constrained N-1-substituted-1,3,8-triazaspiro¿4. 5decan-4-one ring system were synthesized. Among these analogues, compound JMV1640 (1) was found to have an affinity of 24.10 +/- 9.48 nM for the human cloned B(1) receptor. It antagonized the ¿des-Arg(10)-kallidin-induced contraction of the human umbilical vein (pA(2) = 6.1 +/- 0.1). Compound 1 was devoid of agonist activity at the kinin B(1) receptor. Moreover, it did not bind to the human cloned B(2) receptor. Therefore, JMV1640 constitutes a lead compound for the rational search of nonpeptide B(1) receptor analogues based on the BK sequence.

MeSH terms

  • Animals
  • Bradykinin Receptor Antagonists*
  • CHO Cells
  • Cricetinae
  • Drug Design
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy
  • Muscle Contraction / drug effects
  • Muscle, Smooth, Vascular / drug effects
  • Muscle, Smooth, Vascular / physiology
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / metabolism
  • Oligopeptides / pharmacology
  • Receptor, Bradykinin B1
  • Structure-Activity Relationship
  • Thiazepines / chemical synthesis*
  • Thiazepines / chemistry
  • Thiazepines / metabolism
  • Thiazepines / pharmacology
  • Transfection
  • Umbilical Veins / drug effects
  • Umbilical Veins / physiology

Substances

  • Bradykinin Receptor Antagonists
  • JMV 1640
  • Oligopeptides
  • Receptor, Bradykinin B1
  • Thiazepines