Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload
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 t...
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| Format: | Online |
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Medknow Publications & Media Pvt Ltd
2015
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| Online Access: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4623625/ |
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pubmed-46236252015-11-23 Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload Saghaie, Lotfollah Liu, Dy Hider, Robert C Original Article 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 (1H NMR), carbon nuclear magnetic resonance (13C NMR) and infrared (IR) spectroscopy. Medknow Publications & Media Pvt Ltd 2015 /pmc/articles/PMC4623625/ /pubmed/26600863 Text en Copyright: © 2015 Research in Pharmaceutical Sciences http://creativecommons.org/licenses/by-nc-sa/3.0 This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 License, which allows others to remix, tweak, and build upon the work non-commercially, as long as the author is credited and the new creations are licensed under the identical terms. |
| repository_type |
Open Access Journal |
| institution_category |
Foreign Institution |
| institution |
US National Center for Biotechnology Information |
| building |
NCBI PubMed |
| collection |
Online Access |
| language |
English |
| format |
Online |
| author |
Saghaie, Lotfollah Liu, Dy Hider, Robert C |
| spellingShingle |
Saghaie, Lotfollah Liu, Dy Hider, Robert C Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload |
| author_facet |
Saghaie, Lotfollah Liu, Dy Hider, Robert C |
| author_sort |
Saghaie, Lotfollah |
| title |
Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload |
| title_short |
Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload |
| title_full |
Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload |
| title_fullStr |
Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload |
| title_full_unstemmed |
Synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload |
| title_sort |
synthesis of polymers containing 3-hydroxypyridin-4-one bidentate ligands for treatment of iron overload |
| description |
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 (1H NMR), carbon nuclear magnetic resonance (13C NMR) and infrared (IR) spectroscopy. |
| publisher |
Medknow Publications & Media Pvt Ltd |
| publishDate |
2015 |
| url |
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4623625/ |
| _version_ |
1613494016829030400 |