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Molecules 2014, 19(1), 550-567; doi:10.3390/molecules19010550
Article

[15]aneN4S: Synthesis, Thermodynamic Studies and Potential Applications in Chelation Therapy

1
, 1
, 2
, 1
, 3,4
, 1
, 1
, 1,†
 and 1,†,*
1 Instituto de Investigação do Medicamento (iMed.ULisboa), Faculdade de Farmácia, Universidade de Lisboa, Av. Prof. Gama Pinto, Lisboa 1649-003, Portugal 2 CBIOS, Universidade Lusófona Research Center in Biosciences & Health Technologies, Campo Grande 376, Lisboa 1749-024, Portugal 3 CQE, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisboa 1049-001, Portugal 4 DQB, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-001, Portugal These authors contributed equally to the senior authorship.
* Author to whom correspondence should be addressed.
Received: 2 December 2013 / Revised: 23 December 2013 / Accepted: 24 December 2013 / Published: 3 January 2014
(This article belongs to the Special Issue Macrocyclic Chemistry)
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Abstract

The purpose of this work was to synthesize and characterize the thiatetraaza macrocycle 1-thia-4,7,10,13-tetraazacyclopentadecane ([15]aneN4S). Its acid-base behaviour was studied by potentiometry at 25 °C and ionic strength 0.10 M in KNO3. The protonation sequence of this ligand was investigated by 1H-NMR titration that also allowed the determination of protonation constants in D2O. Binding studies of [15]aneN4S with Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Hg2+ and Pb2+ metal ions were further performed under the same experimental conditions. The results demonstrated that this compound has a higher selectivity and thermodynamic stability for Hg2+ and Cu2+, followed by Ni2+. The UV-visible-near IR spectroscopies and magnetic moment data for the Co(II) and Ni(II) complexes indicated a tetragonal distorted coordination geometry for both metal centres. The value of magnetic moment and the X-band EPR spectra of the Cu(II) complex are consistent with a distorted square pyramidal geometry.
Keywords: macrocyclic compounds; thiatetraaza; stability constants; spectroscopic studies; chelation therapy; mercury(II) chelator; copper(II) chelator macrocyclic compounds; thiatetraaza; stability constants; spectroscopic studies; chelation therapy; mercury(II) chelator; copper(II) chelator
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.

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MDPI and ACS Style

Torres, N.; Gonçalves, S.; Fernandes, A.S.; Machado, J.F.; de Brito, M.J.V.; Oliveira, N.G.; Castro, M.; Costa, J.; Cabral, M.F. [15]aneN4S: Synthesis, Thermodynamic Studies and Potential Applications in Chelation Therapy. Molecules 2014, 19, 550-567.

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