Design and total synthesis of a fluorescent phorboxazole A analog for cellular studies

Bioorg Med Chem Lett. 2006 Feb 15;16(4):901-4. doi: 10.1016/j.bmcl.2005.10.109. Epub 2005 Nov 21.

Abstract

To enable studies to elucidate the intracellular processing and targeting of the potent cytostatic/apoptotic anticancer natural products phorboxazoles A and B, a fluorescent derivative has been developed. This involved the total syntheses of the terminal alkyne 33-O-Me-45,46-dehydrobromophorboxazole A (MDHBPA) and a terminal vinyl iodide derivative of the blue fluorescent dye N,N,-dimethyl-7-aminocoumarin (DMC). Sonogashira coupling of these partners provided enyne DMC-MDHBPA in high yield.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aminocoumarins / chemical synthesis
  • Aminocoumarins / chemistry
  • Aminocoumarins / pharmacology
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Fluorescent Dyes* / chemical synthesis
  • Fluorescent Dyes* / chemistry
  • Fluorescent Dyes* / pharmacology
  • Heterocyclic Compounds, 4 or More Rings* / chemical synthesis
  • Heterocyclic Compounds, 4 or More Rings* / chemistry
  • Heterocyclic Compounds, 4 or More Rings* / pharmacology
  • Humans
  • Molecular Conformation
  • Oxazoles* / chemical synthesis
  • Oxazoles* / chemistry
  • Oxazoles* / pharmacology
  • Structure-Activity Relationship

Substances

  • Aminocoumarins
  • Antineoplastic Agents
  • Fluorescent Dyes
  • Heterocyclic Compounds, 4 or More Rings
  • Oxazoles
  • phorboxazole A