Ömeroğlu İpek, Kaya Esra Nur, Göksel Meltem, Kussovski Vesselin, Mantareva Vanya, Durmuş Mahmut
Department of Chemistry, Gebze Technical University, Kocaeli 41400, Turkey.
Department of Chemistry, Gebze Technical University, Kocaeli 41400, Turkey; Kosekoy Vocational School, Kocaeli University, Kocaeli 41135, Turkey.
Bioorg Med Chem. 2017 Oct 15;25(20):5415-5422. doi: 10.1016/j.bmc.2017.07.065. Epub 2017 Aug 1.
Axially di-(alpha,alpha-diphenyl-4-pyridylmethoxy) silicon(IV) phthalocyanine (3) and its quaternized derivative (3Q) were synthesized and tested as photosensitizers against tumor and bacterial cells. These new phthalocyanines were characterized by elemental analysis, and different spectroscopic methods such as FT-IR, UV-Vis, MALDI-TOF and H NMR. The photophysical properties such as absorption and fluorescence, and the photochemical properties such as singlet oxygen generation of both phthalocyanines were investigated in solutions. The obtained values were compared to the values obtained with unsubstituted silicon(IV) phthalocyanine dichloride (SiPcCl). The addition of two di-(alpha,alpha-diphenyl-4-pyridylmethanol) groups as axial ligands showed an improvement of the photophysical and photochemical properties and an increasement of the singlet oxygen quantum yield (Φ) from 0.15 to 0.33 was determined. The photodynamic efficacy of synthesized photosensitizers (3 and 3Q) were evaluated with promising photocytotoxicity (17% cell survival for 3 and 28% for 3Q) against the cervical cancer cell line (HeLa). The photodynamic inactivation of pathogenic bacterial strains Streptococcus mutans, Staphylococcus aureus, and Pseudomonas aeruginosa suggested a high susceptibility with quaternized derivative (3Q). The both Gram-positive bacterial strains were fully photoinactivated with 11μM 3Q and mild light dose 50J.cm. In case of P. aeruginosa the effect was negligible for concentrations up to 22μM 3Q and light dose 100J.cm. The results suggested that the novel axially substituted silicon(IV) phthalocyanines have promising characteristic as photosensitizer towards tumor cells. The quaternized derivative 3Q has high potential for photoinactivation of pathogenic bacterial species.
轴向二 -（α，α - 二苯基 - 4 - 吡啶基甲氧基）硅（IV）酞菁（3）及其季铵化衍生物（3Q）被合成并作为针对肿瘤细胞和细菌细胞的光敏剂进行测试。这些新型酞菁通过元素分析以及不同的光谱方法如傅里叶变换红外光谱（FT - IR）、紫外 - 可见光谱（UV - Vis）、基质辅助激光解吸电离飞行时间质谱（MALDI - TOF）和核磁共振氢谱（H NMR）进行表征。在溶液中研究了两种酞菁的光物理性质如吸收和荧光，以及光化学性质如单线态氧的产生。将获得的值与未取代的二氯硅（IV）酞菁（SiPcCl）获得的值进行比较。作为轴向配体添加两个二 -（α，α - 二苯基 - 4 - 吡啶基甲醇）基团显示出光物理和光化学性质的改善，并且单线态氧量子产率（Φ）从0.15增加到0.33。合成的光敏剂（3和3Q）对宫颈癌细胞系（HeLa）具有有前景的光细胞毒性（3为17％细胞存活，3Q为28％），评估了其光动力功效。致病性细菌菌株变形链球菌、金黄色葡萄球菌和铜绿假单胞菌的光动力失活表明季铵化衍生物（3Q）具有高敏感性。两种革兰氏阳性细菌菌株用11μM 3Q和50J.cm的轻度光剂量完全光失活。对于铜绿假单胞菌，在浓度高达22μM 3Q和100J.cm的光剂量下效果可忽略不计。结果表明，新型轴向取代的硅（IV）酞菁作为针对肿瘤细胞的光敏剂具有有前景的特性。季铵化衍生物3Q对致病性细菌物种的光失活具有很高的潜力。
