ABSTRACT
The syntheses of two zinc(II) phthalocyanines (ZnPcs) having either imidazole (ZnPc 1) or pyridiloxy (ZnPc 2) moieties as their macrocycle substituents are reported. Quaternization of the ZnPcs with methyl iodide afforded water soluble cationic phthalocyanines. The photophysical, photochemical properties and photodynamic therapy (PDT) activity of the ZnPcs were studied in solution. The fluorescence quantum yield and lifetime of ZnPc 1 were higher as compared to ZnPc 2. ZnPc 2 afforded higher triplet state (ΦT) and singlet oxygen quantum yields (ΦΔ) in comparison to ZnPc 1. The PDT activity of ZnPcs was investigated against human breast adenocarcinoma cells (MCF-7). The two compounds afforded a very minimal in vitro dark cytotoxicity with 85% viable cells at concentration ≤80⯵M. On irradiation of the cells having the ZnPcs, ≥50% cell death was recorded for ZnPc 1 which was also evidenced by the cells photo-micrograph.
Subject(s)
Chemical Phenomena , Indoles/chemistry , Photochemotherapy , Water/chemistry , Zinc/chemistry , Dimethyl Sulfoxide/chemistry , Humans , Indoles/chemical synthesis , Isoindoles , MCF-7 Cells , Quantum Theory , Singlet Oxygen/chemistry , Solubility , Spectrometry, Fluorescence , Spectrophotometry, UltravioletABSTRACT
BACKGROUND AND OBJECTIVE: Pancreatic cancer is very common and difficult to diagnose in early stage. Imaging systems for diagnosing cancer have many disadvantages. However, combining different imaging modalities offers synergistic advantages. Optical imaging is the most multidirectional and widely used imaging modality in both clinical practice and research. METHODS: In present study, Zinc(II) phthalocyanine [Zn(II)Pc] was synthesized, labeled with iodine- 131 and in vitro study was carried out. The intracellular uptake studies of radiolabeled Zn(II)Pc were performed in WI-38 [ATCC CCL-75™, tissue: human fibroblast lung] and MIA PaCa-2 [ATCC CRL-1420™, tissue: human epithelial pancreas carcinoma] cell lines. RESULTS: The intracellular uptake efficiency of radiolabeled Zn(II)Pc in MIA PaCa-2 cells was determined two times higher than WI-38 cells. Also, fluorescence imaging (FI) efficiency of synthesized Zn(II)Pc was investigated in MIA PaCa-2 cells and significant uptake was observed. CONCLUSION: Zn(II)Pc might be used as a new agent for dual fluorescence/nuclear imaging for pancreatic cancer.
Subject(s)
Diagnostic Imaging/methods , Indoles/chemistry , Indoles/pharmacology , Organometallic Compounds/chemistry , Organometallic Compounds/pharmacology , Pancreatic Neoplasms/diagnostic imaging , Radiopharmaceuticals/chemistry , Radiopharmaceuticals/pharmacology , Cell Line, Tumor , Fluorescence , Humans , In Vitro Techniques , Indoles/chemical synthesis , Iodine Radioisotopes , Isoindoles , Organometallic Compounds/chemical synthesis , Radiochemistry , Radiopharmaceuticals/chemical synthesis , Zinc CompoundsABSTRACT
A near IR absorbing phthalocyanine bearing four binaphtyl group has been synthesized in order to investigate its cytotoxicity and intracellular uptake of sensitizer on MCF-7 (human breast cancer), MDAH (ovarian cancer), HeLa (human epitheloid cervix carcinoma), EMT-6 (mouse breast cancer) and WI-38 (human fibroblast lung) cell lines. ZnPc showed four time higher intracellular uptake in carcinoma cells (MCF-7) than normal (WI-38) cell lines. With the aim of studying in detail the biodistribution feature and tumor nuclear imaging capacity, ZnPc was also labeled with I-131. The efficiency of radiolabeled compound was 95±4.6%. In addition, ZnPc reveals to be very efficient singlet oxygen generators (ΦΔ=0.612 in DMSO) and promising PS for PDT application. In vitro fluorescence imaging study with MCF-7 cells showed that ZnPc localized in cytoplasm of the cells. This results showed that synthesized ZnPc is promising candidate for dual fluorescence/nuclear imaging breast cancer and shows potential PS for PDT application.
Subject(s)
Indoles/administration & dosage , Organometallic Compounds/administration & dosage , Photochemotherapy/methods , Photosensitizing Agents/administration & dosage , Animals , Breast Neoplasms/metabolism , Cell Line, Tumor , Cytoplasm/metabolism , Female , Humans , Indoles/chemical synthesis , Indoles/pharmacokinetics , Iodine Radioisotopes , Isoindoles , MCF-7 Cells , Mice , Optical Imaging/methods , Organometallic Compounds/chemical synthesis , Organometallic Compounds/pharmacokinetics , Photosensitizing Agents/chemical synthesis , Photosensitizing Agents/pharmacokinetics , Singlet Oxygen/metabolism , Tissue Distribution , Zinc CompoundsABSTRACT
A series of six new subphthalocyanines (SubPcs) bearing an ethynylcarboxyphenyl anchoring unit and decorated with a variety of substituents at the peripheral position of the macrocycle have been synthesized in order to investigate the effect of the peripheral substituent on the performance of dye-sensitized solar cells.
