Conformationally defined retinoic acid analogues. 5. Large-scale synthesis and mammary cancer chemopreventive activity for (2E,4E,6Z,8E)-8-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3,7-dimethyl-2,4,6-octatrienoic acid (9cUAB30).

Academic Article

Abstract

  • Retinoids that activate the nuclear retinoid X receptors (RXRs) display potential for chemoprevention of breast cancer. We previously reported that 9cUAB30 (1) is an RXR-selective retinoid. To explore its in vivo chemopreventive activity, multigram quantities of 1 were needed. Here, we describe a modified synthesis that yields up to 100 g of 1. We further demonstrate that 1 is very effective in the prevention of N-methyl-N-nitrosourea induced mammary cancers in rats without signs of toxicity.
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    Keywords

  • Animals, Anticarcinogenic Agents, Drug Screening Assays, Antitumor, Fatty Acids, Unsaturated, Female, Mammary Neoplasms, Experimental, Naphthalenes, Rats, Rats, Sprague-Dawley, Receptors, Retinoic Acid, Retinoid X Receptors, Stereoisomerism, Transcription Factors, Tretinoin
  • Digital Object Identifier (doi)

    Author List

  • Atigadda VR; Vines KK; Grubbs CJ; Hill DL; Beenken SL; Bland KI; Brouillette WJ; Muccio DD
  • Start Page

  • 3766
  • End Page

  • 3769
  • Volume

  • 46
  • Issue

  • 17