Biological properties of hexadeca-substituted metal phthalocyanines bearing different functional groups.

This study presents the synthesis of 4-2-(4-ethynyl-N,N-dimethylaniline)pthalonitrile (1) and its new peripherally tetra-substituted metal phthalocyanines {M= Co (2), Zn (3)}. Characterization of the prepared compounds was carried out by performing...

The design and Synthesis of Metallophthalocyanine-Gold Nanoparticle Hybrids as Biological Agents

Fluorination of pharmaceutical agents has afforded crucial modifications to their pharmacological profiles, leading to important advances in medicinal chemistry. On the other hand, metallodrugs are considered to be valuable candidates in the treatment of several diseases, albeit with the caveat that they may exhibit pharmacological disadvantages, such as poor water solubility, low bioavailability and short circulating time. To surmount these limitations, two approaches have been developed: one based on the design of novel metallodrug-delivering carriers and the other based on optimizing the structure of the ligands bound to the metal center. In this context, fluorination of the ligands may bring beneficial changes (physicochemical and biological) that can help to elude the aforementioned drawbacks. Thus, in this review, we discuss the use of fluorinated ligands in the design of metallodrugs that may exhibit potential anticancer activity.

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Relevance of Fluorinated Ligands to the Design of Metallodrugs for Their Potential Use in Cancer Treatment

This study reports the synthesis of three novel axially disubstituted silicon phthalocyanines (1-3-Si) and their quaternized phthalocyanines (1-3-QSi). The resulting compounds were characterized by applying spectroscopic techniques including 1H NMR, FT-IR, UV-vis, and mass spectroscopy. The biological properties of compounds 1-3-QSi, including DNA cleavage activities, DNA binding modes, and topoisomerase enzyme inhibition activities, were investigated using agarose gel electrophoresis. pBR322 plasmid DNA, CT-DNA, and AL-DNA (isolated from apricot leaf) were used for DNA studies. All the quaternized compounds exhibited acceptable DNA cleavage activities. Human topoisomerase I and E. coli topoisomerase enzymes were used for the topoisomerase I inhibition studies. All the quaternized complexes inhibited topoisomerase I activity. Moreover, these compounds were screened for cytotoxic and apoptotic effects against a human colon cancer cell line (DLD-1) by performing MTT and Annexin V assays. They exhibited toxicity and apoptotic effect on the DLD-1 cell line. The findings reveal that the compounds can be utilized for cancer therapy after further investigations.

Anticancer and biological properties of new axially disubstituted silicon phthalocyanines.

Synthesis of a novel axially substituted silicon phthalocyanine sensitizer for efficient singlet oxygen generation by comparing PDT and SPDT studies

This study presents the preparation of a novel tetra-substituted phthalonitrile (1), namely, 3,6-bis(hexyloxy)-4,5-bis(4-(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal-free (2)/metal {M = Zn (3), Cu (4), Co (5), Lu(CH3COO) (6), Lu (7)} phthalocyanines. A series of various spectroscopic methods (UV-vis, FT-IR, mass, and 1H NMR spectroscopy) were performed for the characterization of the newly synthesized compounds. The potential of compounds 2, 3, and 6 as photosensitizing materials for photodynamic and sonophotodynamic therapies was evaluated by photophysical, photochemical, and sonochemical methods. The highest singlet quantum yields were obtained for the zinc phthalocyanine derivative 3 by performing photochemical and sonochemical methods. In addition, several biological activities of the new compounds 1–7 were investigated. The newly synthesized phthalocyanines exhibited excellent DPPH scavenging activity and also DNA nuclease activity. The antimicrobial activity of the new compounds was evaluated by the disc diffusion assay. Effective microbial cell viability inhibition was observed with phthalocyanine macromolecules. The photodynamic antimicrobial therapy of the phthalocyanines showed 100% bacterial inhibition when compared to the control. They also exhibited significant biofilm inhibition activity against S. aureus and P. aeruginosa. These results indicate that new phthalocyanines are promising photodynamic antimicrobial therapies for the treatment of infectious diseases.

Çetin Çelik

Papers

Photophysicochemical, sonochemical, and biological properties of novel hexadeca-substituted phthalocyanines bearing fluorinated groups.