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Syntheses of isotopically labeled 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid (LGD1069), a potent retinoid x receptor-selective ligand

✍ Scribed by Lin Zhang; Beth Ann Badea; Debra Enyeart; Elaine M. Berger; Dale E. Mais; Marcus F. Boehm

Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
576 KB
Volume
36
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

LGD1069, 4‐[1‐(3,5,5,8,8‐pentamethyl‐5,6,7,8‐tetrahydro‐2‐naphthyl)ethenyl] benzoic acid, is the first retinoid X receptor (RXR) selective retinoid to enter clinical trials for treatment of dermatological diseases and cancer. In order to examine biological properties such as receptor binding, metabolism and bioavailability, [^13^C]‐, [^14^C]‐, and [^3^H]‐labeled LGD1069 is required. Herein, we describe synthetic methods for preparing isotopically labeled homologs of LGD1069 as well as comparative competition binding data for [6,7‐^3^H]‐LGD1069 and [^3^H]‐9‐cis retinoic acid with RXR active retinoids. The final radiolabeled products, [6,7‐^3^H]‐LGD1069 and 3‐[^14^C]‐LGD1069 have specific activities of 56 Ci/mmol and 49 mCi/mmol, respectively. Radiochemical purities are 99.5% for [6,7‐^3^H]‐LGD1069 and 99.0% for 3‐[^14^C]‐LGD1069. The chemical purity is 99.0% for 3‐[^13^CD~3~]‐LGD1069. Competition binding studies with known retinoids show similar K~d~ values when either [6,7‐^3^H]‐LGD1069 or [^3^H]‐9‐cis retinoic acid is used as the radioligand.

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## Abstract The synthesis of [1′,3′‐^3^H]4‐(4′‐azido‐5′,6′,7′,8′‐tetrahydro‐5′,5′,8′,8′‐tetramethyl ‐2′‐anthracenyl)benzoic acid is described. This retinoid was designed as a photoaffinity probe of the receptor sites of cellular retinoic acid‐binding protein and the nuclear retinoic acid receptor p