Synthesis of fluorescent analogues of the anticancer natural products 4-hydroxyphenylmethylene hydantoin and delta-tocotrienol

Nat Prod Commun. 2010 Oct;5(10):1623-6.

Abstract

4-Hydroxyphenylmethylene hydantoin (PMH, 1), isolated from the Red Sea sponge Hemimycale arabica, and delta-tocotrienol (3), isolated from the tocotrienol-rich fraction of palm oil, are important antimetastatic and antiproliferative natural products that proved effective against metastatic prostate and breast cancers, respectively. New fluorescent derivatives of PMH (2) and delta-tocotrienol (4) were synthesized by Steglich esterification. Both 2 and 4 retained good anti-migratory and antiproliferative activities, respectively. Fluorescent analogues 2 and 4 can be used for the identification of molecular targets of 1 and 3 in tumor cell cultures.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzylidene Compounds / chemistry*
  • Fluorescent Dyes / chemical synthesis
  • Hydantoins / chemistry*
  • Palm Oil
  • Plant Oils / chemistry
  • Porifera
  • Vitamin E / analogs & derivatives*
  • Vitamin E / chemistry

Substances

  • 4-hydroxyphenylmethylene hydantoin
  • Benzylidene Compounds
  • Fluorescent Dyes
  • Hydantoins
  • Plant Oils
  • Vitamin E
  • tocotrienol, delta
  • Palm Oil