Synthesis of novel octa-cationic and non-ionic 1,2-ethanediamine substituted zinc (Ⅱ) phthalocyanines and their in vitro anti-cancer activity comparison

• DOI: 10.1016/j.ejmech.2012.09.038
• Publication Date: 2012-10-02T01:01:37Z
• Authors: Ao Wang; Li Zhou; Kelong Fang; Lin Zhou; Yun Lin; Jiahong Zhou; Shaohua Wei
• Keywords: Indoles; Dose-Response Relationship, Drug; Molecular Structure; Cell Survival; Antineoplastic Agents; Isoindoles; Ethylenediamines; 01 natural sciences; 3. Good health; 0104 chemical sciences; Structure-Activity Relationship; Zinc; Spectrometry, Fluorescence; Cations; Organometallic Compounds; Humans; Spectrophotometry, Ultraviolet; Drug Screening Assays, Antitumor; Reactive Oxygen Species; HeLa Cells

Novel tetra-substituted zinc phthalocyanines (Pcs) bearing 1,2-ethanediamine group and the quaternized derivatives were synthesized and characterized. The photophysical and cellular properties of these Pcs were investigated. The results indicated that the quaternized ionic effect can greatly improve the water-solubility of Pcs and reduce their aggregation degree in aqueous solution. Comparative studies with quaternized phthalocyanine and its unquaternized counterpart have also demonstrated that the quaternary action on the molecules significantly enhances the fluorescence quantum yields, fluorescence lifetimes, efficiency of singlet oxygen production and, thereby, the in vitro photodynamic therapy efficacy.