Two novel coumarin-based ligands, coumarin-6,7-dioxyacetic acid (1) (cdoaH(2))and 4-methylcoumarin-6,7-dioxyacetic acid (2) (4-MecdoaH(2)), were reacted with copper(II) and manganese(II) salts to give [Cu(cdoa)(H2O2)]center dot 1.5H(2)O (3), [Cu(4-Mecdoa)(H2O2)(2)] (4), [Mn(cdoa)(H2O2)(2)] (5) and [Mn(4-Mecdoa)(H2O2)2] center dot 0.5H(2)O (6). The metal complexes, 3-6, were characterised by elemental analysis, IR and UV-Vis spectroscopy, and magnetic susceptibility measurements and were assigned a polymeric structure. 1 and 2 react with Cu(II) in the presence of excess 1,10-phenanthroline (phen) giving [Cu(cdoa)(phen)(2)]center dot 8.8H(2)O (7) and [Cu(4-Mecdoa)(phen)(2)]center dot 13H(2)O (8), respectively. The X-ray crystal structures of 7 and 8 confirmed trigonal bipyramidal geometries, with the metals bonded to the four nitrogen atoms of the two chelating phen molecules and to a single carboxylate oxygen of the dicarboxylate ligand. The complexes were screened for their antimicrobial activity against a number of microbial species, including methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli and Candida albicans. The metal-free ligands 1 and 2 were active against all of the microbes. Complexes 3-6 demonstrated no significant activity whilst the phen adducts 7 and 8 were active against MRSA (MIC80 = 12.1 mu M), E coli (MIC80 = 14.9 M) and Patonea agglumerans (MIC80 = 12.6 mu M). Complex 7 also demonstrated anti-Candida activity (MIC80 = 22 mu M) comparable to that of the commercially available antifungal agent ketoconazole (MIC80 = 25 mu M). (c) 2007 Elsevier Inc. All rights reserved.
Creaven, B. S., Egan, D. A., Karcz, D., Kavanagh, K., McCann, M., Mahon, M., Noble, A., Thati, B., & Walsh, M. (2007). Synthesis, characterisation and antimicrobial activity of copper(II) and manganese(II) complexes of coumarin-6,7-dioxyacetic acid (cdoaH(2)) and 4-methylcoumarin-6,7-dioxyacetic acid (4-MecdoaH(2)): X-ray crystal structures of [Cu(cdoa)(phen)(2)] center dot 8.8H(2)O and [Cu(4-Mecdoa)(phen)(2)] center dot 13H(2)O (phen=1,10-phenanthroline). Journal of Inorganic Biochemistry, 101(8), 1108-1119. https://doi.org/10.1016/j.jinorgbio.2007.04.010