Citation: Xu Guangcan, Liu Qingchuan, Yuan Jie, Hu Zhanxing, Ma Fangfang, Liang Guangyi, Xu Bixue. Synthesis and Anti-Hepatitis B Virus Activities of Galactopyranosyl Derivatives of Matijin-Su[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1617-1625. doi: 10.6023/cjoc201512051 shu

Synthesis and Anti-Hepatitis B Virus Activities of Galactopyranosyl Derivatives of Matijin-Su

Xu Guangcan ^a,c ,
Liu Qingchuan ^b ,
Yuan Jie ^a,d ,
Hu Zhanxing ^a ,
Ma Fangfang ^a,c ,
Liang Guangyi ^a,c,*,, ,
Xu Bixue ^a,*,,

a.
Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550002
b.
302 Hospital of PLA, Beijing 100039
c.
Guiyang College of Traditional Chinese Medicine, Guiyang 550002
d.
College of Pharmacy, Guizhou University, Guiyang 550002)

Corresponding author: Liang Guangyi, guangyi_liang@126.com Xu Bixue, bixue_xu@126.com
Received Date: 31 December 2015
Revised Date: 10 March 2016

Fund Project: the Western Light Talent Culture Project (2014) AAAAthe National Natural Science Foundation of China No. 81360472

Figures(6)

To improve the concentration in liver lesion tissue and increase the anti-hepatitis B virus (HBV) activities of Matijin-Su (MTS) derivatives, five hepatic targeting galactopyranosyl derivatives of MTS were synthesized by indirect connecting the liver targeting galactose ligands to MTS using ethanolamin as a linker and their structures were confirmed by ¹H NMR, ¹³CNMR, ¹H-¹H COSY, HMQC and ESI-MS. The anti-HBV activities of those compounds were evaluated in HepG2 2.2.15 cells. The screening results showed that all target compounds had inhibitory effect on HBV DNA replication in HepG2 2.2.15 cells in a dose-response manner.
- hepatic targeting,
- derivatives of Matijin-Su,
- glacatose,
- anti-hepatitis B virus activity
1. [1]
  Pierre, V.-D.; Zanetti, A.-R.; Shouval, D.; Herck, K.-V. Adv. Exp. Med. Biol. 2010, 659, 175.
2. [2]
  Xu, B.-X.; Huang, Z.-M.; Liu, C.-X.; Cai, Z.-G.; Pan, W.-D.; Cao, P.-X.; Hao, X.-J.; Liang,G.-Y. Bioorg. Med. Chem. 2009, 17, 3118.
3. [3]
  Qiu, J.-Y.; Xu, B.-X.; Huang, Z.-M.; Pan, W.-D.; Cao, P.-X.; Liu, C.-X.; Hao, X.-J.; Song, B.-A.; Liang, G.-Y. Bioorg. Med. Chem. 2011, 19, 5352.
4. [4]
5. [5]
  Morell, A.-G.; Gregoriadis, G.; Scheinberg, I.-H.; Hickman, J.; Ashwell, G. J. Biol. Chem. 1971, 246, 1461.
6. [6]
  Wu, G.-Y.; Wu, C.-H. Adv. Drug Delivery Rev. 1998, 29, 243.
7. [7]
  Yamazaki, N.; KoJima, S.; Bovin, N.-V.; André, S.; Gabius, S.; Gabius, H. J. Adv. Drug Delivery Rev. 2000, 43, 225.
8. [8]
  Cai, G.; Jiang, M.; Zhang, B.; Zhou, Y.; Zhang, L.; Lei, J.; Gu, X.; Cao, G.; Jin, J.; Zhang, R. Biol. Pharm. Bull. 2009, 32, 440.
9. [9]
  Yang, W.; Mou, T.; Peng, C.; Wu, Z.; Zhang, X.; Li, F.; Ma, Y. Bioorg. Med. Chem. 2009, 17, 7510.
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
  Alker, D.; Arrowsmith, J.-E. Eur. J. Med. Chem. 1991, 26, 907.
18. [18]
  Chen, N.; Xie, J. J. Org. Chem. 2014, 79, 10716.
19. [19]
20. [20]
  Pathigoolla, A.; Sureshan, K. M. Chem. Commun. 2014, 50, 317.
21. [21]
  Miyata, O.; Takahashi, S.; Tamura, A.; Ueda, M.; Naito, T. Tetrahedron 2008, 64, 1270.
22. [22]
  Schädel, U.; Sansone, F.; Casnati, A.; Ungaro, R. Tetrahedron 2005, 61, 1149.
1. [1]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
2. [2]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
3. [3]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
4. [4]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
5. [5]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
6. [6]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
7. [7]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
8. [8]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
9. [9]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . 高效靶向示踪钙钛矿纳米系统光电增效抗肿瘤. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-. doi: 10.1016/j.actphy.2024.100042
10. [10]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
11. [11]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
12. [12]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
13. [13]
  Wei Li , Jinfan Xu , Yongjun Zhang , Ying Guan . 共价有机框架整体材料的制备及食品安全非靶向筛查应用——推荐一个仪器分析综合化学实验. University Chemistry, 2025, 40(6): 276-285. doi: 10.12461/PKU.DXHX202406013
14. [14]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
15. [15]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
16. [16]
  Jiayu Gu , Siqi Wang , Jun Ling . Kinetics of Living Copolymerization: A Brief Discussion. University Chemistry, 2025, 40(4): 100-107. doi: 10.12461/PKU.DXHX202406012
17. [17]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
18. [18]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
19. [19]
  Congying Lu , Fei Zhong , Zhenyu Yuan , Shuaibing Li , Jiayao Li , Jiewen Liu , Xianyang Hu , Liqun Sun , Rui Li , Meijuan Hu . Experimental Improvement of Surfactant Interface Chemistry: An Integrated Design for the Fusion of Experiment and Simulation. University Chemistry, 2024, 39(3): 283-293. doi: 10.3866/PKU.DXHX202308097
20. [20]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(972)
HTML views(123)

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