Fluorinated Phthalocyanine/Silver Nanoconjugates for Multifunctional Biological Applications.

In this study, a new phthalonitrile derivative namely 4-[(2,4-difluorophenyl)ethynyl]phthalonitrile (1) and its metal phthalocyanines (2 and 3) were synthesized. The resultant compounds were conjugated to silver nanoparticles and characterized using transmission electron microscopy (TEM) images. The biological properties of compounds (1-3), their nanoconjugates (4-6), and silver nanoparticles (7) were examined for the first time in this study. The antioxidant activities of biological candidates (1-7) were studied by applying the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. The highest antioxidant activity was obtained 97.47 % for 200 mg/L manganese phthalocyanine-silver nanoconjugates (6). The antimicrobial and antimicrobial photodynamic therapy (APDT) activities of biological candidates (1-7) were examined using a micro-dilution assay. The highest MIC value was obtained 8 mg/L for nanoconjugate 6 against E. hirae. The studied compounds and their silver nanoconjugates exhibited high APDT activities against all the studied microorganisms. The most effective APDT activities were obtained 4 mg/L for nanoconjugates (5 and 6) against L. pneumophila and E. hirae, respectively. All the studied biological candidates displayed high cell viability inhibition activities against E. coli cell growth. The biofilm inhibition activities of the tested biological candidates were also investigated against S. aureus and P. Aeruginosa. Biological candidates (1-6) can be considered efficient metal nanoparticle-based materials for multi-disciplinary biological applications.

The effect of phthalocyanine's periphery on the biological activities of carbazole-containing metal phthalocyanines.

This study reports the synthesis and characterization of two new mono- and di-substituted phthalonitriles namely 4-((9H-carbazol-3-yl)oxy)-5-chlorophthalonitrile and 4,5-bis((9H-carbazol-3-yl)oxy)phthalonitrile, respectively. Cyclotetramerization of the new phthalonitriles in the presence of zinc(II) acetate resulted in related zinc(II) phthalocyanines. To study the effect of the position and number of substituents on the biological properties of the phthalocyanines, peripherally or non-peripherally tetra-substituted zinc(II) phthalocyanines bearing (9H-carbazol-3-yl)oxy groups, as well as axially di-substituted silicon phthalocyanines containing the same groups, were prepared. Since gold nanoparticles are well-known as efficient drug delivery agents, the surface of these metal nanoparticles was functionalized with all the compounds. This modification also improved the solubility of the phthalocyanines in aqueous media. In this study, the antioxidant, DNA cleavage, and toxic/phototoxic activities of the resultant nanoconjugates were examined. With a combination of metal ion and substituent (nature, number, and position) effects, the silicon(IV) phthalocyanine exhibited the highest biological properties.