Metal-Based Drugs
Volume 6 (1999), Issue 2, Pages 101-110
http://dx.doi.org/10.1155/MBD.1999.101

Functionalized Derivatives of Benzo-Crown Ethers. Part 4. Antifungal Macrocyclic Supramolecular Complexes of Transition Metal Ions Acting as Lanosterol-14-α -Demethylase Ihibitors

1Universitatea Politehnica Bucuresti, Dept. of Analytical Chemistry, 1, Polizu, Bucuresti R-78126, Romania
2Laboratoire des Matériaux et procédés Membranaires, Ecole Nationale Supérieure de Chimie Montpelier 8, rue de I'Ecole Normale, Montpellier,Cedex 5 F-34296, France
3Università degli Studi, Dipartamento di Chimica, Laboratoiro di Chimica Inorganica e Bioinorganica, Via Gino Capponi 7, Firenze I-50121, Italy
4Universitatea Politehnica Bucuresti, Dept of lnorganic Chemistry, 1,Polizu, Bucuresti R-78126, Romania

Received 27 January 1999; Accepted 11 February 1999

Copyright © 1999 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Poly- and mononuclear metal complexes of 2,3,11,12-bis[4-(10-aminodecylcarbonyl)]benzo-18- crown-6 (L) and Cu(II); Ni(II); Co(II) and Cr(III) have been synthesized and characterized by standard physico-chemical procedures. In the newly prepared complexes the crown moiety oxygen atoms of the macrocyclic host did not generally interact with metal ions, whereas the two amino groups of the ligand always did. Several of the newly synthesized compounds act as effective antifungal agents against Aspergillus and Candida spp., some of them showing activities comparable to ketoconazole, with minimum inhibitory concentrations in the range of 0.30.5μg/mL . The mechanism of antifungal action of these coordination compounds is probably connected to an inhibition of lanosterol-14-α -demethylase, a metallo-enzyme playing a key role in sterol biosynthesis in fungi, bacteria and eukariotes.