Evidence of Intercalation of trans-Diethylstilbestrol and Its Methyl Ether Derivatives in Multibilayers of Egg Phosphatidylcholine by High-Power Deuterium Nuclear Magnetic Resonance (2H-NMR) Spectroscopy

Taiko Oda; Yoshihiro Sato; Masahiko Kodam; Hazime Saito

doi:10.1248/cpb.38.2397

Evidence of Intercalation of trans-Diethylstilbestrol and Its Methyl Ether Derivatives in Multibilayers of Egg Phosphatidylcholine by High-Power Deuterium Nuclear Magnetic Resonance (²H-NMR) Spectroscopy

Taiko Oda, Yoshihiro Sato, Masahiko Kodam, Hazime Saito

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

The mode of incorporation of 2 H-labeled trans-diethylstilbestrol (DES) (lb) and its methyl ether derivatives (2a, 2b, and 3) into multibilayers of egg phosphatidylcholine was analyzed by means of deuterium nuclear magnetic resonance. A clear distinction was found between DES or its methyl ether derivatives incorporated into lipid bilayers and those precipitated in the aqueous phase, by taking into account the extent of the motionally averaged quadrupole interaction. Thus, it was found that the relative proportion of these compounds incorporated into multibilayers decreased in the following order: DES (1b) > DES monomethyl ether (2a and 2b) > DES dimethyl ether (3). In addition, we demonstrated that the mode of intercalation in the multibilayers differs greatly among these compounds.

Original language	English
Pages (from-to)	2397-2399
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	38
Issue number	9
DOIs	https://doi.org/10.1248/cpb.38.2397
Publication status	Published - 1990 Jan 1

Keywords

H-NMR
diethylstilbestrol
egg phosphatidylcholine
lipid bilayer
microtubule inhibitor
multibilayer
synthetic estrogen

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.38.2397

Cite this

Evidence of Intercalation of trans-Diethylstilbestrol and Its Methyl Ether Derivatives in Multibilayers of Egg Phosphatidylcholine by High-Power Deuterium Nuclear Magnetic Resonance (²H-NMR) Spectroscopy. / Oda, Taiko; Sato, Yoshihiro; Kodam, Masahiko et al.

In: Chemical and Pharmaceutical Bulletin, Vol. 38, No. 9, 01.01.1990, p. 2397-2399.

Research output: Contribution to journal › Article › peer-review

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abstract = "The mode of incorporation of 2 H-labeled trans-diethylstilbestrol (DES) (lb) and its methyl ether derivatives (2a, 2b, and 3) into multibilayers of egg phosphatidylcholine was analyzed by means of deuterium nuclear magnetic resonance. A clear distinction was found between DES or its methyl ether derivatives incorporated into lipid bilayers and those precipitated in the aqueous phase, by taking into account the extent of the motionally averaged quadrupole interaction. Thus, it was found that the relative proportion of these compounds incorporated into multibilayers decreased in the following order: DES (1b) > DES monomethyl ether (2a and 2b) > DES dimethyl ether (3). In addition, we demonstrated that the mode of intercalation in the multibilayers differs greatly among these compounds.",

keywords = "H-NMR, diethylstilbestrol, egg phosphatidylcholine, lipid bilayer, microtubule inhibitor, multibilayer, synthetic estrogen",

author = "Taiko Oda and Yoshihiro Sato and Masahiko Kodam and Hazime Saito",

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AU - Oda, Taiko

AU - Sato, Yoshihiro

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AU - Saito, Hazime

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AB - The mode of incorporation of 2 H-labeled trans-diethylstilbestrol (DES) (lb) and its methyl ether derivatives (2a, 2b, and 3) into multibilayers of egg phosphatidylcholine was analyzed by means of deuterium nuclear magnetic resonance. A clear distinction was found between DES or its methyl ether derivatives incorporated into lipid bilayers and those precipitated in the aqueous phase, by taking into account the extent of the motionally averaged quadrupole interaction. Thus, it was found that the relative proportion of these compounds incorporated into multibilayers decreased in the following order: DES (1b) > DES monomethyl ether (2a and 2b) > DES dimethyl ether (3). In addition, we demonstrated that the mode of intercalation in the multibilayers differs greatly among these compounds.

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