Oligopyridine ligands derived from amino acid precursors: Their Zn2+ complexation and effects on hepatic stellate cell functions

Hiroshi Tsukube; Yuki Noda; Yumiko Kataoka; Hiroyuki Miyake; Satoshi Shinoda; Akiko Kojima-Yuasa; Yoshitake Nishida; Isao Matsui-Yuasa

doi:10.1039/B806548A

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Oligopyridine ligands derived from amino acid precursors: Their Zn²⁺ complexation and effects on hepatic stellate cell functions†

Hiroshi Tsukube,*^a Yuki Noda,^a Yumiko Kataoka,^a Hiroyuki Miyake,^a Satoshi Shinoda,^a Akiko Kojima-Yuasa,*^b Yoshitake Nishida^b and Isao Matsui-Yuasa^b

Author affiliations

* Corresponding authors

^a Department of Chemistry, Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka, Japan
E-mail: tsukube@sci.osaka-cu.ac.jp
Fax: +81-6-6605-2560
Tel: +81-6-6605-2560

^b Department of Food and Human Health Sciences, Graduate School of Human Life Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka, Japan
E-mail: kojima@life.osaka-cu.ac.jp
Fax: +81-6-6605-2810
Tel: +81-6-6605-2810

Abstract

A series of oligopyridine ligands were derived from amino acid amides in which amide oxygen and ternary nitrogen atoms were combined with pyridine moieties. ¹H NMR and circular dichroism spectroscopic characterizations revealed that they formed stable Zn²⁺ complexes in neutral aqueous solutions and caused Zn²⁺ deficiency in the hepatic stellate cell systems. Since collagen synthesis was effectively promoted in the cells, the present oligopyridine derivatives worked as biocompatible ligands for Zn²⁺ complexation and cell activation.

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Supplementary files

¹H NMR spectral changes of 3b upon Zn(ClO ₄) ₂ complexation in aqueous solution, ESI-MS spectrum of an equimolar mixture of 3b and Zn(ClO ₄) ₂ in H ₂O, CD spectral changes and titration curves for log K'; determination of 2, 3a, 3c and 4a, ¹H and ¹³C NMR spectra of 3a?3c and 4b PDF (529K)

Article information

DOI: https://doi.org/10.1039/B806548A
Article type: Paper
Submitted: 17 Apr 2008
Accepted: 12 May 2008
First published: 24 Jun 2008

Download Citation

Dalton Trans., 2008, 4038-4043

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Oligopyridine ligands derived from amino acid precursors: Their Zn²⁺ complexation and effects on hepatic stellate cell functions

H. Tsukube, Y. Noda, Y. Kataoka, H. Miyake, S. Shinoda, A. Kojima-Yuasa, Y. Nishida and I. Matsui-Yuasa, Dalton Trans., 2008, 4038 DOI: 10.1039/B806548A

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Dalton Transactions