Synthesis, characterization, electrospinning and antibacterial studies on triphenylphosphine-dithiphosphonates Copper(I) and Silver(I) complexes

Abstract

Background: The novel amido and O-ferrocenyldithiophosphonates [FcP(S)(SH)(NHR1)] (Fc = Fe(η5-C5H5)(η5-C5H4), R1 = 1-(4-fluorophenylethyl and benzyloxycyclopentyl) and [FcP(S)(OR2)S-][H3N+C(CH3)3] (R2 = myrtanyl) were synthesized by the reaction of [(FcPS2)]2 (Fc = Fe(η5-C5H5)(η5-C5H4)) and chiral amines, such as (S)-(-)-1-(4-fluorophenylethyl) amine and (1S,2S)-(+)-benzyloxycyclopentyl amine, and of (1S), (2S), (5S)-myrtanol in toluene. The reaction of ferrocenyldithiophosphonates and [Cu(PPh3)2]NO3 or AgNO3 and PPh3 gave rise to copper(I) and silver(I) complexes in THF. [Ag2{FcP(OMe)S2}2(PPh3)2] and [Cu(PPh3)2]NO3 were embedded into nanofibers and their antimicrobial activities on fibers were also investigated.Results: The compounds have been characterized by elemental analyses, IR, NMR (1H-, 31P-) spectroscopy as well as MS measurements. Nanofibers were obtained by electrospinning method which is the simplest and most effective method to produce nanoscale fibers under strong electrical field. Antimicrobial activity of the compound 5, [Ag2{FcP(OMe)S2}2(PPh3)2], and [Cu(PPh3)2]NO3 on fibers were studied.Conclusions: In this study, the new dithiophosphonate ligands were synthesized and utilized in the preparation of copper(I) and silver(I) complexes with ferrocenyldithiophosphonate and triphenylphosphine. Then, the compounds [Ag2{FcP(OMe)S2}2(PPh3)2] and [Cu(PPh3)2]NO3 were added into the PAN solutions (Co-PAN dissolved in dimethylacetamide) and the solutions were electrospun onto microscope slides and PP meltblown surfaces. Antimicrobial activity of the compounds [Ag2{FcP(OMe)S2}2(PPh3)2] and [Cu(PPh3)2]NO3 on fibers were determined in vitro against two indicator strains; M. luteus NCIB and E. coli ATCC25922. The obtained results indicated that these metals showed moderate level antimicrobial activities. © 2014 Karakus et al.; licensee Chemistry Central Ltd.