3-O-phosphate ester conjugates of 17-β-O-{1-[2-carboxy-(2-hydroxy-4-methoxy-3-carboxamido)anilido]ethyl}1,3,5(10)-estratriene as novel bone-targeting agents.
A series of 3-O-phosphorylated analogs (4-10) of a novel bone-targeting estradiol analog (3) were synthesized after a thorough study of the reaction of 3 with a selection of phosphoryl chlorides under a variety of reaction conditions. Evaluation of these novel phosphate analogs for affinity for hydroxyapatite revealed that they bind with equal or higher affinity when compared to the bone tissue accumulator, tetracycline.
Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.
Shama
S
Nasim
Ashish P
AP
Vartak
William M
WM
Pierce
K Grant
KG
Taylor
Ned
N
Smith
Peter A
PA
Crooks
D001842:Bone and Bones / Q000737:chemistry*; D017886:Durapatite / Q000737:chemistry; D004952:Esters; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004963:Estrenes / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*; D013752:Tetracycline / Q000737:chemistry
C556359:17-beta-O-(1-(2-carboxy-(2-hydroxy-4-methoxy-3-carboxamido)anilido)ethyl)1,3,5(10)-estratriene; D004952:Esters; D004963:Estrenes; D010710:Phosphates; D004958:Estradiol; D017886:Durapatite; D013752:Tetracycline