Chromogenic betaine lariates for highly selective calcium ion sensing in aqueous environment

Daniel Citterio, Mio Omagari, Takashi Kawada, Shin Ichi Sasaki, Yoshio Suzuki, Koji Suzuki

研究成果: Article査読

13 被引用数 (Scopus)

抄録

This paper describes the design, synthesis, and the characterization of the two new chromogenic crown ethers 2,2′-[1,4,10,13-tetraoxa-7,16- diazacyclooctadecane-7,16-diylbis(methylene)]bis[4-[(1-methyl-4-(1H) -pyridinylidene)ethylidene]-2,5-cyclohexadien-1-one (KBC-001) and the lipophilic derivative 2,2′-[1,4,10,13-tetraoxa-7,16-diazacyclooctadecane- 7,16-diylbis(methylene)]bis[4-[(1-dodecyl-4-(1H)-pyridinylidene)ethylidene]-2, 5-cyclohexadien-1-one (KBC-002). A merocyanine dye that forms a betainic structure upon intramolecular charge transfer and shows solvent polarity dependent spectral sensitivity was selected as the chromophore system to develop the new chromoionophores. This approach allows the design of overall electrically neutral ligands bearing charged groups without the need of external counter ions. A proton ionizable group in the dye moiety acts as a charged ion-binding site and is an integral part of a lariat crown ether ionophore. A chromoionophore for calcium ion sensing has been developed, which combines the size-selective binding character of a crown ether with strong electrostatic attraction between the positively charged calcium ion and two negatively charged lariat side arms in the overall neutral compound. This water-soluble dye selectively responds to the presence of calcium ions in water at pH 8.5 with a dynamic response range between 10μM and 10mM. The binding event can be monitored both by absorption spectrometry and by fluorescence spectrometry. No cross-sensitivity was found for the physiologically important cations Mg2+, Li+, Na+, and K+ up to concentrations of 0.1M under the same experimental conditions. In contrast to the water-soluble reagent KBC-001, the lipophilized derivative KBC-002 having two long alkyl chains was successfully applied to ion-exchange type optode membranes made from plasticized poly(vinyl chloride) (PVC). The dynamic response range of the optode at pH 9.0 was between 10μM and 10mM while retaining the high calcium selectivity.

本文言語English
ページ(範囲)227-234
ページ数8
ジャーナルAnalytica Chimica Acta
504
2
DOI
出版ステータスPublished - 2004 2 23
外部発表はい

ASJC Scopus subject areas

  • 分析化学
  • 生化学
  • 環境化学
  • 分光学

フィンガープリント

「Chromogenic betaine lariates for highly selective calcium ion sensing in aqueous environment」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル