✦ LIBER ✦

Synthesis, Structure, and Biological Activity of des-Side Chain Analogues of 1α,25-Dihydroxyvitamin D3 with Substituents at C18

✍ Scribed by Dr. Lieve Verlinden; Prof. Annemieke Verstuyf; Dr. Guy Eelen; Prof. Roger Bouillon; Dr. Paloma Ordóñez-Morán; Dr. María Jesús Larriba; Prof. Alberto Muñoz; Dr. Natacha Rochel; Dr. Yoshiteru Sato; Dr. Dino Moras; Dr. Miguel Maestro; Dr. Samuel Seoane; Dr. Fernando Dominguez; Dr. Silvina Eduardo-Canosa; Dr. Daniel Nicoletti; Prof. Edelmiro Moman; Prof. Antonio Mouriño

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 375 KB
Volume: 6
Category: Article
ISSN: 1860-7179
DOI: 10.1002/cmdc.201100021

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✦ Synopsis

Abstract

An improved synthetic route to 1α,25‐dihydroxyvitamin D~3~ des‐side chain analogues 2 a and 2 b with substituents at C18 is reported, along with their biological activity. These analogues display significant antiproliferative effects toward MCF‐7 breast cancer cells and prodifferentiation activity toward SW480‐ADH colon cancer cells; they are also characterized by a greatly decreased calcemic profile. The crystal structure of the human vitamin D receptor (hVDR) complexed to one of these analogues, 20(17→18)‐abeo‐1α,25‐dihydroxy‐22‐homo‐21‐norvitamin D~3~ (2 a) reveals that the side chain introduced at position C18 adopts the same orientation in the ligand binding pocket as the side chain of 1α,25‐dihydroxyvitamin D~3~.

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