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)

B S Creaven, D A Egan, D Karcz, K Kavanagh, M McCann, M Mahon, A Noble, B Thati, M Walsh

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Abstract

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.
Original languageEnglish
Pages (from-to)1108-1119
Number of pages12
JournalJournal of Inorganic Biochemistry
Volume101
Issue number8
DOIs
Publication statusPublished - 2007

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Phenanthrolines
Manganese
Copper
Crystal structure
X-Rays
X rays
Methicillin
Acids
Candida
Methicillin-Resistant Staphylococcus aureus
Ligands
Escherichia coli
Metals
Ketoconazole
Antifungal Agents
Coordination Complexes
Chelation
Ultraviolet spectroscopy
Candida albicans
Magnetic susceptibility

Cite this

@article{3597dcc558264671b7b1788b559ed55d,
title = "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)",
abstract = "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.",
author = "Creaven, {B S} and Egan, {D A} and D Karcz and K Kavanagh and M McCann and M Mahon and A Noble and B Thati and M Walsh",
note = "ID number: ISI:000248775400002",
year = "2007",
doi = "10.1016/j.jinorgbio.2007.04.010",
language = "English",
volume = "101",
pages = "1108--1119",
journal = "Journal of Inorganic Biochemistry",
issn = "0162-0134",
publisher = "Elsevier",
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TY - JOUR

T1 - 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)

AU - Creaven, B S

AU - Egan, D A

AU - Karcz, D

AU - Kavanagh, K

AU - McCann, M

AU - Mahon, M

AU - Noble, A

AU - Thati, B

AU - Walsh, M

N1 - ID number: ISI:000248775400002

PY - 2007

Y1 - 2007

N2 - 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.

AB - 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.

U2 - 10.1016/j.jinorgbio.2007.04.010

DO - 10.1016/j.jinorgbio.2007.04.010

M3 - Article

VL - 101

SP - 1108

EP - 1119

JO - Journal of Inorganic Biochemistry

JF - Journal of Inorganic Biochemistry

SN - 0162-0134

IS - 8

ER -