Heptapeptide-based modification leading to enhancing the action of MTCA on activated platelets, P-selectin, GPIIb/IIIa

Future Med Chem. 2018 Aug 1;10(16):1957-1970. doi: 10.4155/fmc-2018-0055. Epub 2018 Jul 5.

Abstract

Aim: The modification of platelet inhibitor to enhance its targeting capacity toward platelets is of clinical importance. Thus, (1R, 3S)-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid (MTCA), a platelet inhibitor, was modified with Lys(Pro-Ala-Lys)-Arg-Gly-Asp-Val (KKV), platelet targeting peptide, to form MTCA-KKV.

Materials & methods: MTCA and MTCA-KKV were synthesized to identify the effect of KKV modification on MTCA and platelets.

Results: Atomic force microscopy imaged MTCA-KKV effectively accumulated on activated platelets. UV spectra showed that MTCA-KKV concentration dependently changed P-selectin and GPIIb/IIIa conformations. For platelet aggregation, the IC50 of MTCA-KKV was approximately 1/10 folds of MTCA.

Conclusion: KKV modification led to forming MTCA-KKV that is superior to MTCA in terms of accumulating on activated platelets, targeting P-selectin and GPIIb/IIIa and inhibiting platelet aggregation. MTCA-KKV could be a promising lead for further investigation.

Keywords: GPIIb/IIIa; P-selectin; anti-aggregation; docking; targeting.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Blood Platelets / drug effects
  • Blood Platelets / metabolism
  • Carbolines / chemistry*
  • Carbolines / pharmacology*
  • Humans
  • Molecular Docking Simulation
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology*
  • P-Selectin / metabolism
  • Platelet Activation / drug effects
  • Platelet Aggregation Inhibitors / chemistry*
  • Platelet Aggregation Inhibitors / pharmacology*
  • Platelet Glycoprotein GPIIb-IIIa Complex / metabolism
  • Rats

Substances

  • Carbolines
  • Oligopeptides
  • P-Selectin
  • Platelet Aggregation Inhibitors
  • Platelet Glycoprotein GPIIb-IIIa Complex
  • 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid