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

Chemistry Central Journal

Mehmet Karakus²  Yuksel Ikiz³  Halil Ibrahim Kaya¹  Omer Simsek¹ 

[1] Department of Food Engineering, Faculty of Engineering, Pamukkale University, Kinikli 20075, Denizli, Turkey

[2] Department of Chemistry, Faculty of Arts&Sciences, Pamukkale University, Kinikli 20075, Denizli, Turkey

[3] Department of Textile Engineering, Faculty of Engineering, Pamukkale University, Kinikli 20075, Denizli, Turkey

关键词: Antibacterial;    Electrospinning;    Nanofiber;    Copper(I) and Silver(I) complexes;    Triphenylphosphine;    Dithiophosphonates;   

Others  :  787793
DOI  :  10.1186/1752-153X-8-18

 received in 2013-12-17, accepted in 2014-03-05,  发布年份 2014

【 摘 要 】

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.

【 授权许可】

   
2014 Karakus et al.; licensee Chemistry Central Ltd.

【 图 表 】

Scheme 1

Scheme 2

Scheme 3

Figure 1.

Figure 2.

Figure 3.

Figure 4.

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