Development of specific CXCR4 inhibitors possessing high selectivity indexes as well as complete stability in serum based on an anti-HIV peptide T140

Bioorg Med Chem Lett. 2001 Jul 23;11(14):1897-902. doi: 10.1016/s0960-894x(01)00323-7.

Abstract

We previously reported a truncated polyphemusin peptide analogue, T140, which efficiently inhibits infection of target cells by T-cell line-tropic strains of HIV-1 (X4-HIV-1) through its specific binding to a chemokine receptor, CXCR4. We have found that T140 is not stable in feline serum due to the cleavage of the C-terminal Arg,(14) indispensable for anti-HIV activity. On the other hand, a C-terminally amidated analogue of T140, TZ14004, has been found to be completely stable in incubation in the serum for 2 days. The C-terminal amide is thought to be needed for stability in serum. However, TZ14004 does not have fairly strong anti-HIV activity, but has relatively strong cytotoxicity, probably due to an increase by +1 charge from total +7 charges of T140. In our previous study, the number of total +6 charges seemed to be a suitable balance between activity and cytotoxicity. In this study, we have conducted a double-L-citrulline (Cit)-scanning study on TZ14004 based on the C-terminally amidated form in due consideration of the total net charges in the whole molecule to find novel effective CXCR4 inhibitors, TN14003 ([Cit(6)]-T140 with the C-terminal amide) and TC14012 ([Cit(6), D-Cit(8)]-T140 with the C-terminal amide), which possess high selectivity indexes (SIs) and complete stability in feline serum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-HIV Agents / blood
  • Anti-HIV Agents / chemistry*
  • Anti-HIV Agents / pharmacology*
  • Anti-HIV Agents / toxicity
  • Cats
  • Cell Survival / drug effects
  • Circular Dichroism
  • Citrulline / chemistry*
  • Drug Stability
  • HIV-1 / drug effects*
  • Humans
  • Inhibitory Concentration 50
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Peptides / pharmacology
  • Receptors, CXCR4 / antagonists & inhibitors*

Substances

  • Anti-HIV Agents
  • Oligopeptides
  • Peptides
  • Receptors, CXCR4
  • Citrulline
  • T140 peptide