Citation: Jia-Wen YING, Qun SUN, Li-Fang YANG, Mei-Rong KE, Jian-Dong HUANG. Synthesis, Spectroscopic Properties, and Photodynamic Anticancer Activities of Novel Arginine-modified Silicon(IV) Phthalocyanines[J]. Chinese Journal of Structural Chemistry, ;2020, 39(1): 66-78. doi: 10.14102/j.cnki.0254-5861.2011-2477 shu

Synthesis, Spectroscopic Properties, and Photodynamic Anticancer Activities of Novel Arginine-modified Silicon(IV) Phthalocyanines

College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fujian Provincial Key Laboratory of Cancer Metastasis Chemoprevention and Chemotherapy, Fuzhou University, Fuzhou 350116, China

Corresponding author: Mei-Rong KE, kemeirong@fzu.edu.cn Jian-Dong HUANG, jdhuang@fzu.edu.cn
Received Date: 29 May 2019
Accepted Date: 17 September 2019

Fund Project: the Marine High-Tech Programs of Fujian Province, China 2016–14the Regional Marine Economic Innovation and Development Demonstration Project of Fujian 2012FJ14the National Natural Science Foundation of China 21301031the National Natural Science Foundation of China U1705282the National Natural Science Foundation of China 21473033

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We design and synthesize a series of novel silicon(IV) phthalocyanines (SiPcs, 1a, 2a, 1b, and 2b) axially conjugated with arginine or arginine-containing oligopeptides (Arg-Arg, Cys-Arg, Cys-Arg-Arg) through ester or ether linkers to demonstrate the effects of substituents and coupling ways on the spectral behaviors and photodynamic activities. The ester-linked SiPcs (1a and 2a) show slight red-shift, higher fluorescence emission and singlet oxygen generation compared to the ether-linked analogues (1b and 2b) due to the stronger electron-withdrawing ability of the ester group, suggesting that electronic effect of the linkers plays an important role in their spectral properties. The introduction of arginine could effectively reduce the aggregation of phthalocyanine in aqueous solutions. With higher cellular uptake and plasma membrane localization ability, 1b and 2b exhibit significantly higher photocytotoxicity against both HepG2 and Hela cells. Moreover, the in vivo fluorescence imaging suggests that 2b is the most specific toward H22 tumor-bearing ICR mice, and it shows efficient tumor growth inhibition with the tumor inhibition rate up to 93%. Thus, this work would provide a new reference for the development of phthalocyanine-based photosensitizers.
- photodynamic therapy,
- phthalocyanine,
- arginine,
- spectral property,
- anticancer activity
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