Abstract:A new axially modified silicon phthalocyanine, di [5′-(2′, 3 ′-O-isopropyl)-5-methyl cytidineoxy] silicon phthalocyanine (SiPcG), was prepared and characterized by 1H NMR and HRMS. This compound is essentially nonaggregated in N,N-dimethyformamide and 1% cremophor EL aqueous solution. It shows a Q-band at 676 nm and fluorescence emission at 685 nm in DMF, and exhibits a Q-band at 679 nm and fluorescence emission at 689 nm in 1% cremophor EL aqueous solution. The SiPcG shows a high photodynamic activity against human hepatoma cells HepG2 with an IC50 value down to 7.8×10-8mol·L-1. Fluorescence confocal microscopy study indicated that the SiPcG locates preferentially in the mitochondria of cells. The research results show that the SiPcG is highly potential as a new anti-cancer photosensitizer.
[1] Dolmans D E, Fukumura D, Jain R K, et al. Nature. Rev. Cancer, 2003, 3: 380. [2] Detty M R, Gibson S L, Wagner S J, et al. J. Med. Chem., 2004, 47: 3897. [3] Allen C M, Sharman W M, Vanlier J E, et al . J. Porphyr. Phthalocya., 2001, 5∶ 161. [4] MacDonald I J, Dougherty T J. J. Porphyr. Phthalocya., 2001, 5: 105. [5] Jiang X J, Yeung S L, Lo P C, et al. J. Med. Chem., 2011, 54: 320. [6] Farooq F T, Berlin J, Baron E, et al. Castrointest. Endosc., 2007, 65∶147. [7] Jiang X J, Huang J D, Zhu Y J, et al. Bioorg. Med. Chem. Lett., 2006, 16: 2450. [8] Vhet-Boudou V, Didierjean J, Isel C, et al. Cell Mol. Life Sci., 2006, 63(2)∶163. [9] Galmarini C M, Graham K, Thomas X, et al. Blood, 2001, 98(6): 1922. [10] Lowery M K, Starshark A J, Esposito J N. Inorg Chem., 1965, 4(1): 128. [11] Scalise I, Durantini E N. Bioorg. Med. Chem., 2005, 13: 3037. [12] Ke M R, Huang J D, Weng S M, et al. J. Photochem. Photobiol. A, 2009, 201: 23. [13] LUO Zhi-wei,ZHANG Yi-wei, LIN Dong-en(罗枝伟, 张逸伟, 林东恩). Chemistry Online(化学通报), 2006, 6: 454. [14] Li X Y, He X, Ng D K P, et al. Macromolecules 2000, 33: 2119. [15] Oleinick N L, Morris R L, Belichenko I, et al. Photochem. Photobiol. Sci., 2002, 1:1. [16] Zhao Z X, Chan P S, Li H G, et al. Inorg. Chem., 2012, 51: 812.