B. Şebnem Sesalan

The synthesis and investigation of binding properties of a new water soluble hexadeca zinc(II) phthalocyanine with bovine serum albumin and DNA

The synthesis and biological properties of a novel, hexadeca substituted zinc phthalocyanine (3) bearing 6-quinolinoxy units on the periphery together with hexyloxy chains on the non-periphery and its quaternized derivative (3Q) have been reported. The new quinolinoxy substituted zinc phthalocyanine (3) was synthesized and quaternized with the excess of methyl iodide to obtain the compound 3Q. The binding of quaternized 3Q with calf thymus DNA was investigated by UV-vis and fluorescence spectrophotometric methods. The quenching effect of quaternized phthalocyanine on the fluorescence intensity of the SYBR Gold–DNA complex was determined. The interaction between 3Q and bovine serum albumin was investigated. The quenching effect of 3Q on the fluorescence of the acridine orange–BSA complex was determined. The results indicated that this water soluble zinc phthalocyanine can be used for biological and medicinal applications.

Synthesis of Novel Maleonitrile Derivatives

The synthesis of four novel maleonitrile derivatives are described. New maleonitriles have been prepared by the reaction of different alkylhalides such as 3-bromopropionitrile, 1,3-dichloroacetone, α, α′-dibromoxylene, and p-nitrobenzylbromide with dithiomaleonitrile disodium salt. All novel compounds have cis-cyano groups and are characterized by IR, NMR spectroscopy, and elemental analysis. This work was supported by the Research Fund of İstanbul Technical University.

Photophysicochemical, calf thymus DNA binding and in vitro photocytotoxicity properties of tetra-morpholinoethoxy-substituted phthalocyanines and their water-soluble quaternized derivatives

In this study, morpholinoethoxy-substituted metal-free (3), zinc(II) (4) and indium(III) (5) phthalocyanines were synthesized. These phthalocyanines were converted to their water-soluble quaternized derivatives (3Q–5Q) using excess methyl iodide as a quaternization agent. All these phthalocyanines (Pcs) were characterized by elemental analysis and different spectroscopic methods such as FT-IR, 1H NMR, UV–Vis and mass spectrometry. The photophysical and photochemical properties such as fluorescence and generation of singlet oxygen were investigated for determination of these phthalocyanines as photosensitizers in photodynamic therapy (PDT) applications. The binding properties of quaternized phthalocyanines (3Q–5Q) to calf thymus DNA (CT-DNA) were investigated by UV–Vis and fluorescence spectrophotometric methods. The quenching effect of all quaternized phthalocyanines on the fluorescence intensity of SYBR Green–DNA complex was determined. The mixtures of 3Q, 4Q or 5Q and DNA solutions were used to determine the change in Tm of double helix DNA with thermal denaturation profile. In addition, thermodynamic parameters considering their aggregation in buffer solution, which shows the spontaneity of the reactions between DNA and quaternized Pcs were investigated. On the other hand, in vitro phototoxicity and cytotoxicity behavior of the quaternized water-soluble phthalocyanine photosensitizers (3Q–5Q) were tested against the cervical cancer cell line named HeLa for evaluation of their suitability for treatment of cancer by PDT method.Graphical abstractPeripherally tetra-substituted neutral and quaternized metal-free and metallophthalocyanines (MPcs) (Zn, In) bearing morpholinoethoxy groups were prepared. The binding of quaternized compounds (3Q–5Q) to CT-DNA were examined using UV–Vis, fluorescence spectra, thermal denaturation profiles and KSV values. Besides, thermodynamic studies indicated that binding of 3Q–5Q to DNA was spontaneous. On the other hand, in vitro phototoxicity and cytotoxicity behavior of the quaternized water-soluble phthalocyanine photosensitizers (3Q–5Q) were tested against the cervical cancer cell line named HeLa for evaluation of their suitability for treatment of cancer by PDT method.

A novel of PEG-conjugated phthalocyanine and evaluation of its photocytotoxicity and antibacterial properties for photodynamic therapy

A poly(ethylene glycol) (PEG)-conjugated silicon(IV) phthalocyanine axially substituted with (PEG1000) chains (SiPc-PEG) was synthesized, and this novel phthalocyanine was characterized by 1H-NMR, FT-IR and UV-Vis spectrophotometric methods. Elemental analysis data were beneficial for the evaluation of the chemical structure of the new compound. The total number of (O–CH2–CH2 units was calculated as 44 and the structure of the new PEG-conjugated silicon phthalocyanine was determined by the use of integral areas in 1H-NMR spectrum and the ratio of SiPc:PEG1000 was found as 1:2. The photophysical and photochemical properties were determined in both DMSO and aqueous solutions. In addition, the photocytotoxicity of the novel PEG-conjugated silicon(IV) phthalocyanine wasalso examined by testing against human cervical-carcinoma (HeLa) and hepato-carcinoma cells (HuH-7). The IC50 value for the SiPc-PEG compound was determined as 0.28 μM for HeLa cells and 0.4μM for HuH-7 cells. These results imply that HeLa cell...