Citation: Meng Zhi, Shan Bin, Zhang Ling, Han Gui-Yan, Liu Ming-Hui, Jia Ning-Yang, Miao Zhen-Yuan, Zhang Wan-Nian, Sheng Chun-Quan, Yao Jian-Zhong. Amino acid derivatives of pyropheophorbide-α ethers as photosensitizer: Synthesis and photodynamic activity[J]. Chinese Chemical Letters, ;2016, 27(5): 623-626. doi: 10.1016/j.cclet.2016.03.019 shu

Amino acid derivatives of pyropheophorbide-α ethers as photosensitizer: Synthesis and photodynamic activity

a.
Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
b.
Department of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, China
c.
Department of Radiology, Shanghai Eastern Hepatobiliary Surgery Hospital, Second Military Medical University, Shanghai 200438, China

Corresponding author: Zhang Wan-Nian, zhangwnk@hotmail.com Sheng Chun-Quan, shengcq@hotmail.com Yao Jian-Zhong, yaojz@sh163.net
Received Date: 25 January 2016
Revised Date: 21 February 2016
Accepted Date: 8 March 2016
Available Online: 19 May 2016

Figures(2)

Ten new water-soluble amino acid conjugates of pyropheophorbide-α ethers 4a-4j were synthesized and investigated for their in vitro photodynamic antitumor activity. The results showed that all compounds exhibited higher phototoxicity and lower dark toxicity against three kinds of tumor cell lines than BPD-MA. In particular, themost phototoxic compound 4d and 4j individually showed IC₅₀ values of 41 nmol/L and 33 nmol/L against HCT116 cell, which represented 7.8- and 9.7-fold increase of antitumor potency compared to BPD-MA, respectively, suggesting that they were promising photosensitizers for PDT applications because of their strong absorption at long wavelength (λ_max>650 nm), high phototoxicity, low dark cytotoxicity and good water-solubility.
- Photodynamic therapy (PDT),
- Photosensitiser,
- Pyropheophorbide-α,
- Chlorin,
- Antitumor
1. [1]
  Agostinis P., Berg K., Cengel K.A.. Photodynamic therapy of cancer:an update[J]. Cancer J. Clin., 2011,61:250-281.
2. [2]
  Redmond R.W., Kochevar I.E.. Symposium-in-print:singlet oxygen invited review[J]. Photochem. Photobiol., 2006,82:1178-1186.
3. [3]
  Drogat N., Gady C., Granet R., Sol V.. Design and synthesis of water-soluble polyaminated chlorins and bacteriochlorins-with near-infrared absorption[J]. Dyes Pigments, 2013,98:609-614.
4. [4]
  Oliveira K.T., Momo P.B., Assis F.F.. Chlorins:natural sources, synthetic developments and main applications[J]. Curr. Org. Synth., 2014,11:42-58.
5. [5]
  Yao J.Z., Zhang W.N., Sheng C.Q.. Design, synthesis, and in vitro photodynamic activities of benzochloroporphyrin derivatives as tumor photosensitizers[J]. Bioorg. Med. Chem. Lett., 2008,18:293-297.
6. [6]
  Zhang J.L., Deng L., Yao J.Z.. Synthesis and photobiological study of novel chlorin photosensitizer BCPD-18Ma for photodynamic therapy[J]. Bioorg. Med. Chem., 2011,19:5520-5528.
7. [7]
  Kessel D.. Determinants of photosensitization by mono-L-aspartylchlorin e6[J]. Photochem. Photobiol., 2008,49:447-452.
8. [8]
  Allison R.R., Downie G.H., Cuenca R.. Photosensitizers in clinical PDT[J]. Photodiagn. Photodyn., 2004,1:27-42.
9. [9]
  Hitoshi T., Yasuaki I., Takuya T.. Synthesis of chlorophyll-amino acid conjugates as models for modification of proteins with chromo/fluorophores[J]. Bioorg. Med. Chem., 2014,22:1421-1428.
10. [10]
  Roberts W.G., Shiau F.Y., Nelson J.S.. In vitro characterization of monoaspartyl chlorin e6 and diaspartyl chlorin e6 for photodynamic therapy[J]. J. Natl. Cancer Inst., 1998,80:330-336.
11. [11]
  Yao J.Z., Shen W.D., Liu J.F.. Photochemotherapeutic effects of 2-(1-hydroxy1) ethyl chlorin f and its ether derivatives on sarcoma 180 transplanted in mice[J]. Chin. J. Laser Med. Surg, 2001,9(4).
12. [12]
  Yao J.Z., Chen W.H., He X.. Synthesis and photosensitizing abilities as tumorphotobiological activities of chlorine f methyl ether[J]. Acta Pharm. Sin., 2000,35:63-66.
13. [13]
  Yao J.Z., He X., Shen W.D.. Synthesis of tumor-photobiological activity of chlorine f[J]. Chin. Pharm. J., 1999,34:846-848.
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Wenbin Zhou , Yafei Gao , Xinyu Feng , Yanqing Zhang , Cong Yang , Lanxi He , Fenghe Zhang , Xiaoguang Li , Qing Li . Biomimetic nanoplatform integrates FRET-enhanced photodynamic therapy and chemotherapy for cascaded revitalization of the tumor immune microenvironment in OSCC. Chinese Chemical Letters, 2025, 36(1): 109763-. doi: 10.1016/j.cclet.2024.109763
16. [16]
  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
17. [17]
  Liangliang Jia , Ye Hong , Xinyu He , Ying Zhou , Liujiao Ren , Hongjun Du , Bin Zhao , Bin Qin , Zhe Yang , Di Gao . Fighting hypoxia to improve photodynamic therapy-driven immunotherapy: Alleviating, exploiting and disregarding. Chinese Chemical Letters, 2025, 36(2): 109957-. doi: 10.1016/j.cclet.2024.109957
18. [18]
  Jiaqi Huang , Renjiang Kong , Yanmei Li , Ni Yan , Yeyang Wu , Ziwen Qiu , Zhenming Lu , Xiaona Rao , Shiying Li , Hong Cheng . Feedback enhanced tumor targeting delivery of albumin-based nanomedicine to amplify photodynamic therapy by regulating AMPK signaling and inhibiting GSTs. Chinese Chemical Letters, 2024, 35(8): 109254-. doi: 10.1016/j.cclet.2023.109254
19. [19]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
20. [20]
  Jiechen Liu , Xiaoguang Li , Ruiyang Xia , Yuqi Wang , Fenghe Zhang , Yongzhi Pang , Qing Li . Efficient suppression of oral squamous cell carcinoma through spatial dimension conversion drug delivery systems-enabled immunomodulatory-photodynamic therapy. Chinese Chemical Letters, 2024, 35(12): 109619-. doi: 10.1016/j.cclet.2024.109619

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(636)
HTML views(99)

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