title: Synthesis, structural characterization, antimicrobial and cytotoxic effects of aziridine, 2-aminoethylaziridine and azirine complexes of copper(II) and palladium(II).
abstract: The synthesis, spectroscopic and X-ray structural characterization of copper(II) and palladium(II) complexes with aziridine ligands as 2-dimethylaziridine HNCH(2)CMe(2) (a), the bidentate N-(2-aminoethyl)aziridines C(2)H(4)NC(2)H(4)NH(2) (b) or CH(2)CMe(2)NCH(2)CMe(2)NH(2) (c) as well as the unsaturated azirine NCH(2)CPh (d) are reported. Cleavage of the cyclometallated Pd(II) dimer [μ-Cl(C(6)H(4)CHMeNMe(2)-C,N)Pd](2) with ligand a yielded compound [Cl(NHCH(2)CMe(2))(C(6)H(4)CHMe(2)NMe(2)-C,N)Pd] (1a). The reaction of the aziridine complex trans-[Cl(2)Pd(HNC(2)H(4))(2)] with an excess of aziridine in the presence of AgOTf gave the ionic chelate complex trans-[(C(2)H(4)NC(2)H(4)NH(2)-N,N')(2)Pd](OTf)(2) (2b) which contains the new ligand b formed by an unexpected insertion and ring opening reaction of two aziridines ("aziridine dimerization"). CuCl(2) reacted in pure HNC(2)H(4) or HNCH(2)CMe(2) (b) again by "dimerization" to give the tris-chelated ionic complex [Cu(C(2)H(4)NC(2)H(4)NH(2)-N,N')(3)]Cl(2) (3b) or the bis-chelated complex [CuCl(C(2)H(2)Me(2)NC(2)H(2)Me(2)NH(2)-N,N')(2)]Cl (4c). By addition of 2H-3-phenylazirine (d) to PdCl(2), trans-[Cl(2)Pd(NCH(2)CPh)(2)] (5d) was formed. All new compounds were characterized by NMR, IR and mass spectra and also by X-ray structure analyses (except 3b). Additionally the cytotoxic effects of these complexes were examined on HL-60 and NALM-6 human leukemia cells and melanoma WM-115 cells. The antimicrobial activity was also determined. The growth of Gram-positive bacterial strains (S. aureus, S. epidermidis, E. faecalis) was inhibited by almost all tested complexes at the concentrations of 37.5-300.0 μg mL(-1). However, MIC values of complexes obtained for Gram-negative E. coli and P. aeruginosa, as well as for C. albicans yeast, mostly exceeded 300 μg mL(-1). The highest antibacterial activity was achieved by complexes 1a and 2b. Complex 2b also inhibited the growth of Gram-negative bacteria.
authors.affiliation: Department of Cosmetic Raw Materials Chemistry, Faculty of Pharmacy, Medical University of Lodz, Muszynski Str. 1, 90-151 Lodz, Poland. elzbieta.budzisz@umed.lodz.pl
authors.forename: E
authors.initials: E
authors.lastname: Budzisz
authors.forename: R
authors.initials: R
authors.lastname: Bobka
authors.forename: A
authors.initials: A
authors.lastname: Hauss
authors.forename: J N
authors.initials: JN
authors.lastname: Roedel
authors.forename: S
authors.initials: S
authors.lastname: Wirth
authors.forename: I-P
authors.initials: IP
authors.lastname: Lorenz
authors.forename: B
authors.initials: B
authors.lastname: Rozalska
authors.forename: M
authors.initials: M
authors.lastname: Więckowska-Szakiel
authors.forename: U
authors.initials: U
authors.lastname: Krajewska
authors.forename: M
authors.initials: M
authors.lastname: Rozalski
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001388:Aziridines / Q000737:chemistry*; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D045744:Cell Line, Tumor; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000737:chemistry; D019281:Dimerization; D006801:Humans; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010165:Palladium / Q000737:chemistry*
chemical_list: C575380:2-aminoethylaziridine; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D001388:Aziridines; D009942:Organometallic Compounds; C033132:aziridine; D010165:Palladium; D003300:Copper