Citation: Zhang Xingjie, Meng Zhi, Ma Zhiqiang, Liu Junhong, Han Guiyan, Ma Fujia, Jia Ningyang, Miao Zhenyuan, Zhang Wannian, Sheng Chunquan, Yao Jianzhong. Design and synthesis of novel water-soluble amino acid derivatives of chlorin p6 ethers as photosensitizer[J]. Chinese Chemical Letters, ;2019, 30(1): 247-249. doi: 10.1016/j.cclet.2018.04.029 shu

Design and synthesis of novel water-soluble amino acid derivatives of chlorin p6 ethers as photosensitizer

Zhang Xingjie ^a,1 ,
Meng Zhi ^a,1 ,
Ma Zhiqiang ^a,1 ,
Liu Junhong ^a ,
Han Guiyan ^a ,
Ma Fujia ^b ,
Jia Ningyang ³ ,
Miao Zhenyuan ^a ,
Zhang Wannian ^a,, ,
Sheng Chunquan ^a,, ,
Yao Jianzhong ^a,,

a.
Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
b.
Department of Pharmacy, 455 th Hospital of Chinese People's Liberation Army, Shanghai 200052, China
c.
Department of Radiology, Shanghai Eastern Hepatobiliary Surgery Hospital, Second Military Medical University, Shanghai 200438 China

Corresponding author: Zhang Wannian, zhangwnk@hotmail.com Sheng Chunquan, shengcq@hotmail.com Yao Jianzhong, yaojz6601@sina.com

Received Date: 27 March 2018
Revised Date: 24 April 2018
Accepted Date: 24 April 2018
Available Online: 27 January 2018

Figures(2)

Eight new water-soluble amino acid conjugates 6a-h of chlorin p₆ ethers (5a-d) were synthesized and preliminarily investigated for their in vitro PDT antitumor activity and structure-activity relationship (SAR). The results showed that all compounds exhibited much higher phototoxicity against tumor cells than talaporfin. SAR analysis indicated that PDT antitumor effect enhanced with the increase of carbon chain length of alkoxyl ether bonds at 3¹-position, and L-aspartic acid was superior to L-glutamic acid. In particular, the IC₅₀ values of most phototoxic compound 6d were 0.20 mmol/L against A549 cell and 0.41 mmol/L against B16-F10 cell, which individually represented 31-and 24-fold increase of antitumor potency compared to talaporfin, suggesting that it was a promising candidate photosensitizer (PS) for PDT applications due to its strong absorption at long wavelength, high phototoxicity, low dark cytotoxicity and good water-solubility.
- Photodynamic therapy (PDT),
- Photosensitizer,
- Silkworm excrement,
- Chlorin p₆,
- Antitumor
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