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
1. [1]
  P. Agostinis, K. Berg, K.A. Cengel, et al., Cancer J. Clin. 61(2011) 250-281. doi: 10.3322/caac.v61:4
2. [2]
  R.W. Redmond, I.E. Kochevar, Photochem. Photobiol. 82(2006) 1178-1186. doi: 10.1562/2006-04-14-IR-874
3. [3]
  N. Drogat, C. Gady, R. Granet, V. Sol, Dyes Pigment. 98(2013) 609-614. doi: 10.1016/j.dyepig.2013.03.018
4. [4]
  K.T. Oliveira, P.B. Momo, F.F. Assis, et al., Curr. Org. Synth. 11(2014) 42-58. doi: 10.2174/15701794113106660085
5. [5]
  J.Z. Yao, W.N. Zhang, C.Q. Sheng, et al., Bioorg. Med. Chem. Lett. 18(2008) 293-297. doi: 10.1016/j.bmcl.2007.10.086
6. [6]
  J.L. Zhang, L. Deng, J.Z. Yao, et al., Bioorg. Med. Chem. 19(2011) 5520-5528.
7. [7]
  D. Kessel, Photochem. Photobiol. 49(2008) 447-452.
8. [8]
  R.R. Allison, G.H. Downie, R. Cuenca, et al., Photodiagn. Photodyn. 1(2004) 27-42. doi: 10.1016/S1572-1000(04)00007-9
9. [9]
  H. Abrahamse, M.R. Hamblin, J. Biochem, 473 (2016) 347-364.
10. [10]
  T. Hitoshi, I. Yasuaki, T. Takuya, et al., Bioorg. Med. Chem. 22(2014) 1421-1428.
11. [11]
  W.G. Roberts, F.Y. Shiau, J.S. Nelson, et al., J. Natl. Cancer Inst. 80(1988) 330-336. doi: 10.1093/jnci/80.5.330
12. [12]
  M. Kwitniewski, A. Juzeniene, L.W. Ma, et al., J. Photochem. Photobiol. B 94(2009) 214-222. doi: 10.1016/j.jphotobiol.2008.11.005
13. [13]
  Z. Meng, B. Yu, G.Y. Han, et al., J. Med. Chem. 59(2016) 4999-5010. doi: 10.1021/acs.jmedchem.6b00352
14. [14]
  Z. Meng, B. Shan, L. Zhang, et al., Chin. Chem. Lett. 27(2016) 623-626. doi: 10.1016/j.cclet.2016.03.019
15. [15]
  J.Z. Yao, W.H. Chen, X. He, et al., Acta Pharm. Sin. 35(2000) 63-66.
16. [16]
  J.Z. Yao, D.Y. Xu, W.H. Chen, et al., Chin. J. Pharm. 30(1999) 403-406.
17. [17]
  J.Z. Yao, J.F. Liu, W.N. Zhang, et al., Chin. J. Org. Chem. 21(2001) 458-462.
1. [1]
  Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
2. [2]
  Zhe Li , Ping-Zhao Liang , Li Xu , Fei-Yu Yang , Tian-Bing Ren , Lin Yuan , Xia Yin , Xiao-Bing Zhang . Three positive charge nonapoptotic-induced photosensitizer with excellent water solubility for tumor therapy. Chinese Chemical Letters, 2024, 35(8): 109190-. doi: 10.1016/j.cclet.2023.109190
3. [3]
  Huijie An , Chen Yang , Zhihui Jiang , Junjie Yuan , Zhongming Qiu , Longhao Chen , Xin Chen , Mutu Huang , Linlang Huang , Hongju Lin , Biao Cheng , Hongjiang Liu , Zhiqiang Yu . Luminescence-activated Pt(Ⅳ) prodrug for in situ triggerable cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109134-. doi: 10.1016/j.cclet.2023.109134
4. [4]
  Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
5. [5]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
6. [6]
  Zhaomin Tang , Qian He , Jianren Zhou , Shuang Yan , Li Jiang , Yudong Wang , Chenxing Yao , Huangzhao Wei , Keda Yang , Jiajia Wang . Active-transporting of charge-reversal Cu(Ⅱ)-doped mesoporous silica nanoagents for antitumor chemo/chemodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109742-. doi: 10.1016/j.cclet.2024.109742
7. [7]
  Xin Lv , Hongxing Zhang , Kaibo Duan , Wenhui Dai , Zhihui Wen , Wei Guo , Junsheng Hao . Lighting the Way Against Cancer: Photodynamic Therapy. University Chemistry, 2024, 39(5): 70-79. doi: 10.3866/PKU.DXHX202309090
8. [8]
  Jing Zhang , Charles Wang , Yaoyao Zhang , Haining Xia , Yujuan Wang , Kun Ma , Junfeng Wang . Application of magnetotactic bacteria as engineering microrobots: Higher delivery efficiency of antitumor medicine. Chinese Chemical Letters, 2024, 35(10): 109420-. doi: 10.1016/j.cclet.2023.109420
9. [9]
  Zhipeng Li , Qincong Feng , Jianliang Shen . A β-lactamase-activatable photosensitizer for the treatment of resistant bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109602-. doi: 10.1016/j.cclet.2024.109602
10. [10]
  Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099
11. [11]
  Jin Wang , Xiaoyan Pan , Junyu Zhang , Qingqing Zhang , Yanchen Li , Weiwei Guo , Jie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187
12. [12]
  Wenjuan Jin , Zelong Chen , Yi Wang , Jiaxuan Li , Jiahui Li , Yuxin Pei , Zhichao Pei . Nano metal-photosensitizer based on Aza-BODIPY-Cu complex for CDT-enhanced dual phototherapy. Chinese Chemical Letters, 2024, 35(7): 109328-. doi: 10.1016/j.cclet.2023.109328
13. [13]
  Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
14. [14]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
15. [15]
  Jia-Qi Feng , Xiang Tian , Rui-Ge Cao , Yong-Xiu Li , Wen-Long Liu , Rong Huang , Si-Yong Qin , Ai-Qing Zhang , Yin-Jia Cheng . An AIE-based theranostic nanoplatform for enhanced colorectal cancer therapy: Real-time tumor-tracking and chemical-enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(12): 109657-. doi: 10.1016/j.cclet.2024.109657
16. [16]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
17. [17]
  Yu Qin , Mingyang Huang , Chenlu Huang , Hannah L. Perry , Linhua Zhang , Dunwan Zhu . O₂-generating multifunctional polymeric micelles for highly efficient and selective photodynamic-photothermal therapy in melanoma. Chinese Chemical Letters, 2024, 35(7): 109171-. doi: 10.1016/j.cclet.2023.109171
18. [18]
  Hao Cai , Xiaoyan Wu , Lei Jiang , Feng Yu , Yuxiang Yang , Yan Li , Xian Zhang , Jian Liu , Zijian Li , Hong Bi . Lysosome-targeted carbon dots with a light-controlled nitric oxide releasing property for enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(4): 108946-. doi: 10.1016/j.cclet.2023.108946
19. [19]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
20. [20]
  Wenkai Liu , Yanxian Hou , Weijian Liu , Ran Wang , Shan He , Xiang Xia , Chengyuan Lv , Hua Gu , Qichao Yao , Qingze Pan , Zehou Su , Danhong Zhou , Wen Sun , Jiangli Fan , Xiaojun Peng . Se-substituted pentamethine cyanine for anticancer photodynamic therapy mediated using the hot band absorption process. Chinese Chemical Letters, 2024, 35(12): 109631-. doi: 10.1016/j.cclet.2024.109631

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(868)
HTML views(71)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142