HemoCD as a Totally Synthetic Artificial Oxygen Carrier: Improvements in the Synthesis and O2/CO Discrimination.
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 (O2) 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 O2/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 O2/CO selectivity of hemoCD was also markedly improved using an iron(II)porphyrin having a carboxylate group at the distal site of hemoCD.
Department of Molecular Chemistry and Biochemistry, Faculty of Science and Engineering, Doshisha University, Kyotanabe, Kyoto, Japan.
Hiroaki
H
Kitagishi
Department of Molecular Chemistry and Biochemistry, Faculty of Science and Engineering, Doshisha University, Kyotanabe, Kyoto, Japan.
Qiyue
Q
Mao
Department of Molecular Chemistry and Biochemistry, Faculty of Science and Engineering, Doshisha University, Kyotanabe, Kyoto, Japan.
Naoya
N
Kitamura
Department of Molecular Chemistry and Biochemistry, Faculty of Science and Engineering, Doshisha University, Kyotanabe, Kyoto, Japan.
Takahiro
T
Kita
D001802:Blood Substitutes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002248:Carbon Monoxide / Q000378:metabolism*; D003505:Cyclodextrins / Q000737:chemistry*; D006454:Hemoglobins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008665:Metalloporphyrins / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D010100:Oxygen / Q000378:metabolism*; D011108:Polymers / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry
C466420:5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrinato iron(III) chloride; D001802:Blood Substitutes; D003505:Cyclodextrins; D006454:Hemoglobins; D008665:Metalloporphyrins; D011108:Polymers; D011725:Pyridines; D002248:Carbon Monoxide; C023666:pyridine; D010100:Oxygen
Artificial oxygen carrier; Cyclodextrin; Hemoglobin; Porphyrin; Synthesis