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

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

Edité par CCSD ; Wiley-VCH Verlag -

International audience. 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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