Design and synthesis of rhodamine 110 derivative and caspase-3 substrate for enzyme and cell-based fluorescent assay

Bioorg Med Chem Lett. 2001 Jan 8;11(1):39-42. doi: 10.1016/s0960-894x(00)00590-4.

Abstract

N-Octyloxycarbonyl-R110 (1), with enhanced cell penetration and retention properties, was prepared from rhodamine 110. The tetrapeptide substrate N-Ac-DEVD-N'-octyloxycarbonyl-R110 (3) was prepared and shown to be efficiently cleaved by human recombinant caspase-3 and by apoptotic HL-60 cells. This substrate should prove useful in cell-based assays for apoptosis inducers and inhibitors.

MeSH terms

  • Apoptosis
  • Caspase 3
  • Caspases / metabolism*
  • Drug Design*
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / metabolism*
  • HL-60 Cells
  • Humans
  • Microscopy, Fluorescence
  • Molecular Structure
  • Oligopeptides / chemical synthesis
  • Oligopeptides / metabolism
  • Oligopeptides / pharmacology
  • Recombinant Proteins / metabolism
  • Rhodamines / chemical synthesis*
  • Rhodamines / metabolism*
  • Substrate Specificity

Substances

  • Fluorescent Dyes
  • Oligopeptides
  • Recombinant Proteins
  • Rhodamines
  • acetyl-aspartyl-glutamyl-valyl-aspartal
  • rhodamine 110
  • CASP3 protein, human
  • Caspase 3
  • Caspases