Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units.

Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Research Abstract Details 

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Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Abstract Text:

Rebecca J Abergel,Kenneth N Raymond,

A series of new linear iron chelators containing hydroxypyridinone and terephthalamide (TAMmeg) moieties have been prepared. All are hexadentate ligands composed of a systematically varied combination of methyl-3,2-hydroxypyridinone and 2,3-dihydroxyterephthalamide binding units; most are based on a spermidine scaffold, but one incorporates the bifunctional 2,3-dihydroxyterephthalamide unit as an integral part of the backbone. Protonation and ferric iron complex formation constants have been determined from solution thermodynamic studies, giving log beta(110) values of 25.7, 30.7, 36.3, 43.8, and 45.0, respectively. The ferric complexes display reversible reduction potentials from -276 to -1032 mV (measured relative to the normal hydrogen electrode) in alkaline solution. The incremental replacement of hydroxypyridinone units by terephthalamide binding groups progressively reduces the ligand acidity, markedly increases the iron-chelate stability, and improves the selectivity for the ferric ion over the ferrous ion. While the majority of iron chelators forming very stable ferric complexes are based on a tripodal backbone such as TREN, the ferric 5-LIO(TAMmeg)(2)(TAM) complex, despite its nontripodal scaffold, is one of the most stable iron complexes yet reported. Moreover, the high affinity for the ferric ion of the discussed linear ligands strongly correlates with their ability to remove iron in vivo.

Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Publishing Authors By Initials

RJ Abergel,KN Raymond,

For similar natural sciences: physics: thermodynamics research abstracts see: natural sciences: physics: thermodynamics research

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Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Inorganic chemistry

VOLUME: 45

Page Numbers: 3622-31

Journal Abbreviation:

ISSN: 0020-1669

DAY: 1

MONTH: May

YEAR: 2006

Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 366543

Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Keywords Mesh Terms:

KEYWORDS: Thermodynamics

MESH TERMS: chemistry

Chemical & Substance for Abstract: Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Information

Substance Name: terephthalamidine

Registry Number: 15411-54-8

Grant and Affiliation Information for Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units.

AFFILIATION: Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.

Country: United States

AGENCY: United States NIDDK

GRANT: DK057814

ACRONYM: DK

MEDLINETA: Inorg Chem

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