Synthesis, characterization, and antimicrobial activity of silver(I) and copper(II) complexes of phosphate derivatives of pyridine and benzimidazole.
Two silver(I) complexes--[Ag(4-pmOpe)]NO₃}(n) and [Ag(2-bimOpe)₂]NO₃--and three copper(II) complexes--[Cu₄Cl₆O(2-bimOpe)₄], [CuCl₂(4-pmOpe)₂], and [CuCl₂(2-bis(pm)Ope]--were synthesized by reaction of silver(I) nitrate or copper(II) chloride with phosphate derivatives of pyridine and benzimidazole, namely diethyl (pyridin-4-ylmethyl)phosphate (4-pmOpe), 1H-benzimidazol-2-ylmethyl diethyl phosphate (2-bimOpe), and ethyl bis(pyridin-2-ylmethyl)phosphate (2-bis(pm)Ope). These compounds were characterized by ¹H, ¹³C, and ³¹P NMR as well as IR spectroscopy, elemental analysis, and ESIMS spectrometry. Additionally, molecular and crystal structures of {[Ag(4-pmOpe)]NO₃}n and [Cu₄Cl₆O(2-bimOpe)₄] were determined by single-crystal X-ray diffraction analysis. The antimicrobial profiles of synthesized complexes and free ligands against test organisms from the ATCC and clinical sources were determined. Silver(I) complexes showed good antimicrobial activities against Candida albicans strains (MIC values of ∼19 μM). [Ag(2-bimOpe)₂]NO₃ was particularly active against Pseudomonas aeruginosa and methicillin-resistant Staphylococcus epidermidis, with MIC values of ∼5 and ∼10 μM, respectively. Neither copper(II) complexes nor the free ligands inhibited the growth of test organisms at concentrations below 500 μg mL⁻¹.
Department of Bioinorganic Chemistry, Medical University of Łódź, Muszyńskiego 1, 90-151 Łódź (Poland). urszula.kalinowska-lis@umed.lodz.pl.
Urszula
U
Kalinowska-Lis
Eligia M
EM
Szewczyk
Lilianna
L
Chęcińska
Jakub M
JM
Wojciechowski
Wojciech M
WM
Wolf
Justyn
J
Ochocki
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001562:Benzimidazoles / Q000737:chemistry*; D002176:Candida albicans / Q000187:drug effects; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D016106:Methicillin Resistance; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010710:Phosphates / Q000737:chemistry*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D011725:Pyridines / Q000737:chemistry*; D012834:Silver / Q000737:chemistry; D013212:Staphylococcus epidermidis / Q000187:drug effects
D000890:Anti-Infective Agents; D001562:Benzimidazoles; D056831:Coordination Complexes; D010710:Phosphates; D011725:Pyridines; D012834:Silver; D003300:Copper; C031000:benzimidazole; C023666:pyridine
N,O ligands; X-ray diffraction; antimicrobial activity; copper(II) complexes; silver(I) complexes