The structure-function relationship between peptide aldehyde derivatives on initiation of neurite outgrowth in PC12h cells

Neurosci Lett. 1990 Nov 27;120(1):1-4. doi: 10.1016/0304-3940(90)90153-z.

Abstract

We have previously shown that, among many protease inhibitors examined, only a leupeptin analogue, Ac-Leu-Leu-Nle-al (ALLNal), induces neurite outgrowth in PC12h cells. Since this neurite outgrowth is different from that induced by nerve growth factor (NGF) in terms of morphology and persistence, the existence of a specific protease which regulates neurite formation in PC12h cells was expected. A set of 10 ALLNal analogue peptide protease inhibitors was synthesized and examined for their potency in inducing neurite outgrowth in PC12h cells. Substitution of the N-terminal acetyl residue in ALLNal by benzyloxycarbonyl (Z) increased the activity by about 4 times. For Z-Leu-Leu-X-al, neurite outgrowth was induced in the following order: Leu greater than Phe greater than Nva greater than Val = Ile = Nle greater than Ala greater than Gly at the X residue. The potency of Z-Leu-Leu-Leu-al (ZLLLal) was 50-fold stronger than that of ALLNal. ZLLLal provides a strong tool for characterizing this new type of protease.

Publication types

  • Comparative Study

MeSH terms

  • Adrenal Gland Neoplasms
  • Aldehydes / pharmacology
  • Amino Acid Sequence
  • Animals
  • Axons / drug effects
  • Axons / physiology*
  • Axons / ultrastructure
  • Cell Line
  • Molecular Sequence Data
  • Nerve Growth Factors / pharmacology
  • Oligopeptides / pharmacology*
  • Pheochromocytoma
  • Rats
  • Structure-Activity Relationship

Substances

  • Aldehydes
  • Nerve Growth Factors
  • Oligopeptides