Synthesis and dioxygen-binding properties of double-sided porphyrinatoiron(II) complexes bearing covalently bound axial imidazole

Eishun Tsuchida, Teruyuki Komatsu, Kenji Arai, Hiroyuki Nishide

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Abstract

Double-sided porphyrinatoiron(II) complexes bearing covalently bound axial imidazole, 5-[2-(5-imidazolylvaleryloxy)-6-(pivaloyloxy)phenyl]-10,15,20-tris[2,6- bis(pivaloyloxy)phenyl]porphyrinatoiron(II) and 5-[2-(3,3-dimethylbutyryloxy)-6-(5-imidazolylvaleryloxy)phenyl]-10,15,20-tris[2, 6-bis(3,3-dimethylbutyryloxy)phenyl]porphyrinatoiron(II), have been synthesized. On the basis of their absorption and 1H NMR spectra, the axial imidazole group is co-ordinated. The complexes reversibly form stable dioxygen adducts in toluene at 25 °C, and the kinetics of binding of O2 and CO has been investigated. When embedded in phospholipid unilamellar vesicles, the complexes possess the ability to transport dioxygen in an aqueous medium. The binding affinity of the pivaloyloxy derivative [P1/2(O2) = 27 Torr] is equal to that of a red blood cell suspension and the half-life of the dioxygen adduct formed was 1.5 d under physiological conditions (pH 7.4, 37 °C).

Original languageEnglish
Pages (from-to)2465-2469
Number of pages5
JournalJournal of the Chemical Society, Dalton Transactions
Issue number16
DOIs
Publication statusPublished - 1993

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ASJC Scopus subject areas

  • Chemistry(all)

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