PMID- 21520419
OWN - NLM
STAT- MEDLINE
DCOM- 20110819
LR  - 20131121
IS  - 1860-7187 (Electronic)
IS  - 1860-7179 (Linking)
VI  - 6
IP  - 5
DP  - 2011 May 2
TI  - Synthesis, structure, and biological activity of des-side chain analogues of 
      1alpha,25-dihydroxyvitamin D3 with substituents at C18.
PG  - 788-93
LID - 10.1002/cmdc.201100021 [doi]
AB  - An improved synthetic route to 1alpha,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-1alpha,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 1alpha,25-dihydroxyvitamin D(3).
CI  - Copyright (c) 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
FAU - Verlinden, Lieve
AU  - Verlinden L
AD  - Laboratorium voor Experimentele Geneeskunde en Endocrinologie, Katholieke 
      Universiteit Leuven, Leuven, Belgium.
FAU - Verstuyf, Annemieke
AU  - Verstuyf A
FAU - Eelen, Guy
AU  - Eelen G
FAU - Bouillon, Roger
AU  - Bouillon R
FAU - Ordonez-Moran, Paloma
AU  - Ordonez-Moran P
FAU - Larriba, Maria Jesus
AU  - Larriba MJ
FAU - Munoz, Alberto
AU  - Munoz A
FAU - Rochel, Natacha
AU  - Rochel N
FAU - Sato, Yoshiteru
AU  - Sato Y
FAU - Moras, Dino
AU  - Moras D
FAU - Maestro, Miguel
AU  - Maestro M
FAU - Seoane, Samuel
AU  - Seoane S
FAU - Dominguez, Fernando
AU  - Dominguez F
FAU - Eduardo-Canosa, Silvina
AU  - Eduardo-Canosa S
FAU - Nicoletti, Daniel
AU  - Nicoletti D
FAU - Moman, Edelmiro
AU  - Moman E
FAU - Mourino, Antonio
AU  - Mourino A
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20110329
PL  - Germany
TA  - ChemMedChem
JT  - ChemMedChem
JID - 101259013
RN  - 0 (Receptors, Calcitriol)
RN  - FXC9231JVH (Calcitriol)
SB  - IM
MH  - Animals
MH  - Binding Sites
MH  - Calcitriol/chemical synthesis/*chemistry/pharmacology
MH  - Cell Line, Tumor
MH  - Computer Simulation
MH  - Humans
MH  - Receptors, Calcitriol/chemistry/genetics/metabolism
MH  - Swine
EDAT- 2011/04/27 06:00
MHDA- 2011/08/20 06:00
CRDT- 2011/04/27 06:00
PHST- 2011/01/21 00:00 [received]
PHST- 2011/02/24 00:00 [revised]
PHST- 2011/04/27 06:00 [entrez]
PHST- 2011/04/27 06:00 [pubmed]
PHST- 2011/08/20 06:00 [medline]
AID - 10.1002/cmdc.201100021 [doi]
PST - ppublish
SO  - ChemMedChem. 2011 May 2;6(5):788-93. doi: 10.1002/cmdc.201100021. Epub 2011 Mar 
      29.