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Synthesis 2005(20): 3555-3564  
DOI: 10.1055/s-2005-918442
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and in vitro Enzyme Hydrolysis of Trioxadiaza- and Tetraoxadiaza-Crown Ether-Based Complexing Agents with Disposable Ester Pendant Arms

Tímea Iványi, István Lázár*
University of Debrecen, Department of Inorganic and Analytical Chemistry, Egyetem tér 1, Debrecen 4032, Hungary
Fax: +36(52)489667; e-Mail: lazar@delfin.unideb.hu;
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Publication History

Received 23 February 2005
Publication Date:
27 October 2005 (online)

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Abstract

New disposable ester derivatives of the complexing agents N,N′-bis(carboxymethyl)piperazine, -homopiperazine, -1,7-diaza-15-crown-5 and -1,10-diaza-18-crown-6 were synthesized with a variety of synthetic methods and fully characterized. Hydrolytic properties of the pendant arms were studied under different pH conditions as well as in the presence and absence of porcine liver esterase enzyme and approximate hydrolysis half lives were determined by 1H NMR technique. In vitro studies on pig liver cell homogenates and living thin chicken liver slices proved that the selected double ester 4b can penetrate liver tissues spontaneously, liberate the free complexing agent N,N′-bis(carboxymethyl)-18-ane-N2O4 (ODDA) inside the cells and are potentially capable of removing lead and other toxic metal ions from the liver.

Key words

crown compounds - complexes - esters - enzymes - hydrolyses

1

LEAD Action News Vol. 3, No. 3 Winter 1995; Adulteration of Paprika in Hungary http://www.zip.com.au/˜djrat/lanv3n3/lanv3n3-6.html.