Heme Complex with the Imidazole Derivatives Included in Cyclodextrin

Kiyoshi Eshima, Yo ichi Matsushita, Mikiya Serine, Hiroyuki Nishide, Eishun Tsuchida

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Abstract

1-Substituted 2-methylimidazoles included in α-cyclodextrin (CyD) were found to form stable penta-eoordinate complexes with iron(II) protoporphyrin K (Scheme 1). When an equivalent amount of CyD-included l-phenethyl-2-methylimidazole (PMI) was added to a hexa-coordinate complex of (imidazole) 2-heme, they were selectively transfered to the penta-coordinate CyD-included PMI-heme complex (Scheme 2). The apparent formation constants (Ky of the heme complexes with these CyD-included imidazoles were measured spectroscopi-cally (Fig. 1). The K values of the CyD-included imidazoles were 15~30 times larger than that of 2-methylimidazole—heme, due to the larger entropy change (Table 1). The fluores-cenece spectrum of the zinc(II) protoporphyrin K complex with CyD-included PMI suggested a hydrophobic interaction between CyD and the porphyrin. CyD-included PMI-heme complex formed a stable oxygen adduct in an aqueous N, N-dimethylformamide solution (1/9) at-30°C.

Original languageEnglish
Pages (from-to)214-218
Number of pages5
JournalNippon Kagaku Kaishi
Volume1983
Issue number2
DOIs
Publication statusPublished - 1983

Fingerprint

Cyclodextrins
Heme
Derivatives
Imidazoles
Dimethylformamide
imidazole
Porphyrins
Zinc
Entropy
Iron
2-methylimidazole
Oxygen

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Heme Complex with the Imidazole Derivatives Included in Cyclodextrin. / Eshima, Kiyoshi; Matsushita, Yo ichi; Serine, Mikiya; Nishide, Hiroyuki; Tsuchida, Eishun.

In: Nippon Kagaku Kaishi, Vol. 1983, No. 2, 1983, p. 214-218.

Research output: Contribution to journalArticle

Eshima, K, Matsushita, YI, Serine, M, Nishide, H & Tsuchida, E 1983, 'Heme Complex with the Imidazole Derivatives Included in Cyclodextrin', Nippon Kagaku Kaishi, vol. 1983, no. 2, pp. 214-218. https://doi.org/10.1246/nikkashi.1983.214
Eshima, Kiyoshi ; Matsushita, Yo ichi ; Serine, Mikiya ; Nishide, Hiroyuki ; Tsuchida, Eishun. / Heme Complex with the Imidazole Derivatives Included in Cyclodextrin. In: Nippon Kagaku Kaishi. 1983 ; Vol. 1983, No. 2. pp. 214-218.
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abstract = "1-Substituted 2-methylimidazoles included in α-cyclodextrin (CyD) were found to form stable penta-eoordinate complexes with iron(II) protoporphyrin K (Scheme 1). When an equivalent amount of CyD-included l-phenethyl-2-methylimidazole (PMI) was added to a hexa-coordinate complex of (imidazole) 2-heme, they were selectively transfered to the penta-coordinate CyD-included PMI-heme complex (Scheme 2). The apparent formation constants (Ky of the heme complexes with these CyD-included imidazoles were measured spectroscopi-cally (Fig. 1). The K values of the CyD-included imidazoles were 15~30 times larger than that of 2-methylimidazole—heme, due to the larger entropy change (Table 1). The fluores-cenece spectrum of the zinc(II) protoporphyrin K complex with CyD-included PMI suggested a hydrophobic interaction between CyD and the porphyrin. CyD-included PMI-heme complex formed a stable oxygen adduct in an aqueous N, N-dimethylformamide solution (1/9) at-30°C.",
author = "Kiyoshi Eshima and Matsushita, {Yo ichi} and Mikiya Serine and Hiroyuki Nishide and Eishun Tsuchida",
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T1 - Heme Complex with the Imidazole Derivatives Included in Cyclodextrin

AU - Eshima, Kiyoshi

AU - Matsushita, Yo ichi

AU - Serine, Mikiya

AU - Nishide, Hiroyuki

AU - Tsuchida, Eishun

PY - 1983

Y1 - 1983

N2 - 1-Substituted 2-methylimidazoles included in α-cyclodextrin (CyD) were found to form stable penta-eoordinate complexes with iron(II) protoporphyrin K (Scheme 1). When an equivalent amount of CyD-included l-phenethyl-2-methylimidazole (PMI) was added to a hexa-coordinate complex of (imidazole) 2-heme, they were selectively transfered to the penta-coordinate CyD-included PMI-heme complex (Scheme 2). The apparent formation constants (Ky of the heme complexes with these CyD-included imidazoles were measured spectroscopi-cally (Fig. 1). The K values of the CyD-included imidazoles were 15~30 times larger than that of 2-methylimidazole—heme, due to the larger entropy change (Table 1). The fluores-cenece spectrum of the zinc(II) protoporphyrin K complex with CyD-included PMI suggested a hydrophobic interaction between CyD and the porphyrin. CyD-included PMI-heme complex formed a stable oxygen adduct in an aqueous N, N-dimethylformamide solution (1/9) at-30°C.

AB - 1-Substituted 2-methylimidazoles included in α-cyclodextrin (CyD) were found to form stable penta-eoordinate complexes with iron(II) protoporphyrin K (Scheme 1). When an equivalent amount of CyD-included l-phenethyl-2-methylimidazole (PMI) was added to a hexa-coordinate complex of (imidazole) 2-heme, they were selectively transfered to the penta-coordinate CyD-included PMI-heme complex (Scheme 2). The apparent formation constants (Ky of the heme complexes with these CyD-included imidazoles were measured spectroscopi-cally (Fig. 1). The K values of the CyD-included imidazoles were 15~30 times larger than that of 2-methylimidazole—heme, due to the larger entropy change (Table 1). The fluores-cenece spectrum of the zinc(II) protoporphyrin K complex with CyD-included PMI suggested a hydrophobic interaction between CyD and the porphyrin. CyD-included PMI-heme complex formed a stable oxygen adduct in an aqueous N, N-dimethylformamide solution (1/9) at-30°C.

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