title: Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload.
abstract: Iron overload is a clinical problem which can be prevented by using iron chelating agents. An alternative method of relieving iron overload is to reduce iron absorption from the intestine by administering specific iron chelating agents, which can bind iron to form nonabsorbable complexes. Based on this strategy, a series of polymeric ligands containing the chelating moiety 3-hydroxypyridin-4-ones (HPOs) were synthesized. The synthetic route involves the benzylation of hydroxyl group of (2-methyl-3-hydroxypyran-4-one (maltol) and conversion of benzylated maltol to 3-benzyloxypyridin-4-one derivatives by using three suitable primary amines (2,6-diaminohexanoic acid (lysine) and 1,6-diaminohexane and 5-aminopentanol). The resulted compounds incorporated into polymer by copolymerization with acryloyl chloride using 2, 2'-azobisisobutyronitrile (AIBN) as the initiator. Finally, the benzyl groups of polymers were removed by catalytic hydrogenation (Pd/C). In this work, three final polymers of HPO derivatives namely poly-2-propylamido-6-(3- hydroxy -1,4-dihydro-2-methy-4-oxopyrid-1-yl) hexanoic acid, 6-(3-hydroxy-1, 4-dihydro-2-methyl-4-oxopyrid-1-yl) hexyl-1-polypropylamide and 5-(3-hydroxy-1-,4-dihydro-2-methyl-4-oxopyrid-1-yl)-1-polyacrylate pentane were synthesized. Identification and structural elucidation of compounds were achieved by proton nuclear magnetic resonance ((1)H NMR), carbon nuclear magnetic resonance ((13)C NMR) and infrared (IR) spectroscopy.
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmacy and Pharmaceutical Sciences and Isfahan Pharmaceutical Sciences Research Center, Isfahan University of Medical Sciences, Isfahan, I.R. Iran.
authors.forename: Lotfollah
authors.initials: L
authors.lastname: Saghaie
authors.affiliation: Department of Pharmacy, King's College London, London, UK.
authors.forename: Dy
authors.initials: D
authors.lastname: Liu
authors.affiliation: Department of Pharmacy, King's College London, London, UK.
authors.forename: Robert C
authors.initials: RC
authors.lastname: Hider
keywords: 3-Hydroxypyridin-4-ones; Iron chelating agents; Iron overload