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HemoCD as a Totally Synthetic Artificial Oxygen Carrier: Improvements in the Synthesis and O 2 /CO Discrimination
Author(s) -
Kitagishi Hiroaki,
Mao Qiyue,
Kitamura Naoya,
Kita Takahiro
Publication year - 2017
Publication title -
artificial organs
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.684
H-Index - 76
eISSN - 1525-1594
pISSN - 0160-564X
DOI - 10.1111/aor.12870
Subject(s) - porphyrin , chemistry , dimer , selectivity , pyridine , yield (engineering) , oxygen , carboxylate , aqueous solution , linker , combinatorial chemistry , hemoglobin , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , materials science , catalysis , computer science , metallurgy , operating system
HemoCD, which is composed of an iron(II)porphyrin such as 5,10,15,20‐tetrakis(4‐sulfonatophenyl)porphinatoiron(II) (Fe(II)TPPS) and a cyclodextrin (CD) dimer having a pyridine linker, represents a synthetic hemoglobin (Hb) model compound that exhibits reversible oxygen (O 2 ) binding ability in aqueous solution at an ambient temperature. Therefore, hemoCD has the potential to be used as a totally synthetic artificial oxygen carrier. In this article, we describe the improvements of hemoCD related to its synthesis and O 2 /CO selectivity. The synthesis procedure of the CD dimer of hemoCD was re‐examined, and the CD dimer was successively synthesized from inexpensive β‐CD with a 38% yield (three‐steps), which enabled us to obtain the CD dimer in gram‐quantities. The O 2 /CO selectivity of hemoCD was also markedly improved using an iron(II)porphyrin having a carboxylate group at the distal site of hemoCD.