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Iron Binding Dendrimers:  A Novel Approach for the Treatment of Haemochromatosis

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    Iron Binding Dendrimers:  A Novel Approach for the Treatment of Haemochromatosis
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    Department of Pharmacy and Drug Control Centre, King's College London, Franklin-Wilkins Building, 150 Stamford Street, London SE1 9NH, U.K.
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2006, 49, 14, 4171–4182
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    https://doi.org/10.1021/jm0600949
    Published June 21, 2006
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    Abstract

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    A range of iron binding dendrimers terminated with hexadentate ligands formed from hydroxypyridinone, hydroxypyranone, and catechol moieties have been synthesized in order to investigate their potential as clinically useful iron(III)-selective chelators capable of removing dietary iron from the gastrointestinal tract and preventing the development of iron overload typical of haemochromatosis and thalassaemia intermedia. The iron chelating abilities of these molecules have been characterized by MALDI-TOF mass spectrometry and UV spectrometry. Hydroxypyridinone-terminated dendrimers were found to possess a high affinity and selectivity for iron(III). A hydroxypyridinone-based dendrimer was demonstrated to be highly efficient at reducing the absorption of iron(III) in rat intestine. This family of dendrimers may find an application in the treatment of iron overload.

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    †

     Department of Pharmacy.

    ‡

     Drug Control Center.

    *

     Corresponding author. Tel.:  (+)44 207 848 6979. Fax:  (+)44 207 848 6394. E-mail:  [email protected].

    Abbreviations:  MALDI-TOF MS, matrix-assisted laser desorption/ionization time-of-light mass spectrometry; DCCI, 1,3-dicyclohexylcarbodiimide; HOBt, 1-hydroxybenzotriazole; DMF, N,N-dimethylformamide; MBT, 2-mercaptobenzothiazole; DCTB, trans-2-[3-{4-tert-butylphenyl}-2-methyl-2- propenylidene]malononitrile; ICP-MS, inductively coupled plasma mass spectrometry; TMS, tetramethylsilane; ESI MS, electrospray ionization mass spectrometry; CHCA, 4-hydroxy-alpha-cyano-cinnamic acid; THAP, trihydroxyacetophenone; NTA, nitrilotriacetic acid; MOPS, 3-(N-morpholino)propane sulphonic acid.

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    Routine spectroscopic data and ICP-MS operating parameters for the analysis of 58Fe in the perfusion samples. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Med. Chem. 2006, 49, 14, 4171–4182
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    https://doi.org/10.1021/jm0600949
    Published June 21, 2006
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