Newly synthesized curcumin analog has improved potential to prevent colorectal carcinogenesis in vivo

Cancer Sci. 2009 May;100(5):956-60. doi: 10.1111/j.1349-7006.2009.01127.x.

Abstract

Curcumin (diferuloylmethane) has chemopreventive and chemotherapeutic potentials against various types of cancers. We have developed a series of curcumin analogs to improve its low bioavailability by enhancing its potentials. The newly synthesized analog GO-Y030 [(1E, 4E)-1,5-bis-(3,5(-bismethoxymethoxyphenyl) penta-1,4-dien-3-one] showed a 30-fold greater growth suppression in vitro via similar molecular mechanisms to curcumin. The availability of this analog was examined by using a mouse model harboring the germ-line mutation of Apc, Apc(580D/+), in vivo. Apc(580D/+) mice had a very limited survival time with an intestinal obstruction due to polyposis. The average tumor number in mice fed GO-Y030 was reduced to 61.2% of those that were fed the basal diet (P < 0.05). Compared with Apc(580D/+) mice fed the basal diet (median survival time = 166.5 days), a significantly prolonged lifespan (213 days) was observed in Apc(580D/+) mice fed GO-Y030. The chemopreventive effect with GO-Y030 was improved, compared with curcumin (191 days). The survival benefit corresponded to the diminished intestinal tumor incidence in Apc(580D/+) mice fed GO-Y030. No adverse reactions were observed, judging from body weight or biochemical data concerning liver and renal damage. Degradation of accumulated beta-catenin with curcumin is one of the major mechanisms of chemoprevention in colorectal carcinogenesis. It was demonstrated that the number of beta-catenin-positive adenoma cells in Apc(580D/+) mice fed GO-Y030 was reduced.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenoma / metabolism
  • Adenoma / pathology
  • Animals
  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Benzene Derivatives / pharmacology*
  • Cell Transformation, Neoplastic / metabolism
  • Cell Transformation, Neoplastic / pathology*
  • Colorectal Neoplasms / metabolism
  • Colorectal Neoplasms / pathology*
  • Colorectal Neoplasms / prevention & control*
  • Curcumin / chemical synthesis*
  • Curcumin / chemistry
  • Curcumin / pharmacology*
  • Disease Models, Animal
  • Genetic Predisposition to Disease
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Ketones / pharmacology*
  • Mice
  • Molecular Structure
  • Survival Rate
  • beta Catenin / metabolism

Substances

  • 1,5-bis(3,5-bis(methoxymethoxy)phenyl)penta-1,4-dien-3-one
  • Benzene Derivatives
  • Ketones
  • beta Catenin
  • Curcumin