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Aminobisphosphonates based on cyclohexane backbone as coordinating agents for metal Ions. Thermodynamic, spectroscopic and biological studies.

Abstract

Single- and double-amino-bisphosphonates were synthesized and tested for coordination capabilities towards Ca2+, Mg2+, Cu2+ and Ni2+ metal ions by means of potentiometry, UV-vis spectroscopy, mass spectrometry (ESI-MS) and isothermal titration calorimetry (ITC), as well as for cytotoxic activity by MTT [(3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay. Half minimal inhibitory concentrations (IC50) were determined with respect to two cell lines (human melanoma A375 and human colorectal adenocarcinoma HT29). Bearing the structure of compounds on cyclohexane ring allowed for a slight reduction of high hydrophilic character of studied bisphosphonates (BPs). The ligands efficiently bind examined metal ions forming complex equilibria with diversified stoichiometry of equimolar, polynuclear species and biscomplexes. Both ligands as well as their Ca2+ and Mg2+ complexes show selective antiproliferative activity toward studied cancer cell lines. Given thermodynamic and biological data, it can be assumed that ligands are good candidates for linking compounds that may be used in the design of new drug delivery systems. In such approach one bisphosphonate moiety acts as a bone-targeting molecule, while another molecule can be readily attached to the second donor function (primary amine or bisphosphonate).

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Publication details

The article was received on 09 Mar 2018, accepted on 05 Apr 2018 and first published on 06 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ01158C
Citation: New J. Chem., 2018, Accepted Manuscript
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    Aminobisphosphonates based on cyclohexane backbone as coordinating agents for metal Ions. Thermodynamic, spectroscopic and biological studies.

    J. Gałęzowska, H. Czapor-Irzabek, E. Chmielewska, P. Kafarski and T. Janek, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ01158C

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