Citation: Tu Shuangyan, Xu Wushuang, Qi Fen, He Weijiang, Fei Baoli. Interaction of Optically Pure Dehydroabietylamine Heterocyclic Derivatives with DNA and Preliminary Cytotoxic Activity[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3269-3276. doi: 10.6023/cjoc201904003 shu

Interaction of Optically Pure Dehydroabietylamine Heterocyclic Derivatives with DNA and Preliminary Cytotoxic Activity

Tu Shuangyan ^a ,
Xu Wushuang ^a ,
Qi Fen ^d ,
He Weijiang ^d,, ,
Fei Baoli ^a,b,c,,

a.
Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing Forestry University, Nanjing 210037
b.
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin, Gungxi 541006
c.
Collaborative Innovation Center for Efficient Processing and Utilization of Forestry Resources, Nanjing Forestry University, Nanjing 210037
d.
College of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210037

Corresponding author: He Weijiang, hgfbl@njfu.edu.cn Fei Baoli, heweij69@nju.edu.cn
Received Date: 2 April 2019
Revised Date: 28 June 2019
Available Online: 17 November 2019
Fund Project: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University CMEMR2018-B13Project supported by the Major Projects of Natural Science Research in Jiangsu Higher Education Institutions (No. 18KJA150006), and State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University (No. CMEMR2018-B13)the Major Projects of Natural Science Research in Jiangsu Higher Education Institutions 18KJA150006

Figures(4)

Three optically pure dehydroabietylamine derivatives, acetyldehydroabietylamine-6, 7-(3-mercapto)-1, 2, 4-triazine (5), acetyldehydroabietylamine-6, 7-indole (7) and 12-(2-aminothiazole)-acetyldehydroabietylamine (10), were obtained by introducing different aromatic heterocycles into the B and C rings of optically pure dehydroabietylamine, which is derived from natural product of rosin, according to superposition principle of activity groups. The results of fluorescence spectroscopy and circular dichroism studies indicate that 5, 7 and 10 could interact with DNA, and the binding ability followed the order 5 > 10 > 7. Gel electrophoresis experiments suggest that 5, 7 and 10 could scissor pBR 322 plasmid DNA into single strands and 5 was the strongest cutter. In addition, the inhibitory rates of dehydroabietylamine and its derivatives 5, 7 and 10 combined with copper chloride (32 μmol·L^-1) on the proliferation of human breast cancer cells MCF-7 were 86.0% (1), 86.7% (5), 34.4% (7) and 0 (10), respectively.
- dehydroabietylamine,
- heterocyclic compounds,
- DNA,
- biological activity
1. [1]
  Mo, Q. J.; Duan, W. G.; L, X. R.; Huang, D. P.; Luo, Z. J. Chin. J. Org. Chem. 2011, 31, 1114 (in Chinese).
2. [2]
  Fei, B. L.; Li, W.; Xu, W. S.; Long, J. Y.; Liu, Q. B.; Sun, W. Y.; Anson, C. E.; Powell, A. K. Eur. J. Inorg. Chem. 2013, 34, 5919.
3. [3]
  Fei, B. L.; Xu, W. S.; Gao, W. L.; Zhang, J.; Zhao, Y.; Long, J. Y.; Anson, C. E.; Powell, A. K. J. Photochem. Photobiol. B 2015, 142, 77. doi: 10.1016/j.jphotobiol.2014.11.008
4. [4]
  Jin, X. Y.; Chen, H.; Li, D. D.; Li, A. L.; Wang, W. Y.; Gu, Wen. J. Enzym. Inhib. Med. Chem. 2019, 34, 955.
5. [5]
  Wang, Y. C.; Su, C. H.; Li, F. Y.; Liu, L. Z.; Pan, Y. M.; Wu, X. R.; Wang, H. S. Spectrochim. Acta A. 2010, 76, 328. doi: 10.1016/j.saa.2010.03.014
6. [6]
  Lin, G. S.; Duan, W. G.; Liu, H. Q.; Ma, Y.; Lei, F. H. Chem. Nat. Compd. 2018, 54, 56. doi: 10.1007/s10600-018-2258-6
7. [7]
  Akhtar, J.; Khan, A. A.; Ali, Z.; Haider, R.; Shahar Yar, M. Eur. J. Med. Chem. 2017, 125, 143. doi: 10.1016/j.ejmech.2016.09.023
8. [8]
  Marin-Ocampo, L.; Veloza, L. A.; Abonia, R.; Sepulveda-Arias, J. C. Eur. J. Med. Chem. 2019, 162, 435. doi: 10.1016/j.ejmech.2018.11.027
9. [9]
  Ali, I.; Mukhtar, S. D.; Hsieh, M. F.; Alothman, Z. A.; Alwarthan, A. RSC Adv. 2018, 8, 37905. doi: 10.1039/C8RA07060A
10. [10]
  Khalifa, M. E. Acta Chim. Slov. 2018, 65, 1. doi: 10.17344/acsi.2017.3547
11. [11]
  Hassan, A. A.; Aly, A. A.; Mohamed, N. K.; EI Shaieb, K. M.; Makhlouf, M. M.; Abdelhafez, ESMN.; Brase, S.; Nieger, M.; Dalby, K. N.; Kaoud, T. S. Bioorg. Chem. 2019, 85, 585. doi: 10.1016/j.bioorg.2019.02.027
12. [12]
  Marques, R. A.; Gomes, A. O. C. V.; de Briton, M. V.; dos Santos, A. L. P.; da Silva, G. S.; de Lima, L. B.; Nunes, F. M.; de Mattos, M. C.; de Oliveira, F. C. E.; Pessoa, C. D.; de Moraes, M. O.; de Fatima, A.; Franco, L. L.; Silva, M. D.; Dantas, M. D. D.; Santos, J. C. C.; Figueiredo, I. M.; da Silva, E. F.; de Aquino, T. M.; de Araujo, J. X.; de Oliveira, M. C. F.; Gunatilaka, A. A. L. J. Photochem. Photobiol. B 2018, 179, 156. doi: 10.1016/j.jphotobiol.2018.01.016
13. [13]
  Zhang, F.; Lin, Q. Y.; Li, S. K.; Zhao, Y. L.; Wang, P. P.; Chen, M. M. Spectrochim. Acta, A 2012, 98, 436. doi: 10.1016/j.saa.2012.08.074
14. [14]
  Niroomand, S.; Khorasani-Motlagh, M.; Noroozifar, M.; Moodi, A. J. Photochem. Photobiol. B 2012, 117, 132. doi: 10.1016/j.jphotobiol.2012.09.015
15. [15]
  Bian, L.; Li, L. Z.; Zhang, Q. F.; Liu, H. L; Wang, D. Q. Acta Chim. Sin. 2011, 69, 1661 (in Chinese). doi: 10.3866/PKU.WHXB20110722
16. [16]
  Tiwari, A. D.; Mishra, A. K.; Mishra, S. B.; Mamba, B. B.; Maji, B.; Bhattacharya, S. Spectrochim. Acta A 2011, 79, 1050. doi: 10.1016/j.saa.2011.04.018
17. [17]
  Huang, J. T.; Zhang, Y.; Wang, X. L.; Ji, L. N.; Liu, H. Y. Chin. J Inorg. Chem. 2013, 29, 1649 (in Chinese).
18. [18]
  Alizadeh, R.; Afzal, M.; Arjmand, F. Spectrochim. Acta, A 2014, 131, 625. doi: 10.1016/j.saa.2014.04.051
19. [19]
  Liu, J. J.; Lu, Y. J.; Wang, J.; Bi, L. W.; Zhao, Z. D. Chin. J. Org. Chem. 2017, 37, 731 (in Chinese).
20. [20]
  Chen, Y. Ph.D. Dissertation, Nanjing Forestry University, Nanjing, 2012 (in Chinese).
21. [21]
  Feng, S. B.; Lei, Q.; Zhang, Y.; Wang, H. S.; Pan, Y. M.; Wu, Q.; Tong, B. H. Chin. J. Org. Chem. 2007, 27, 1414 (in Chinese).
22. [22]
  Gan, L. S.; Zhou, C. X. Chin. J. Org. Chem. 2009, 29, 849 (in Chinese).
1. [1]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
6. [6]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
7. [7]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
8. [8]
  Yuxin CHEN , Yanni LING , Yuqing YAO , Keyi WANG , Linna LI , Xin ZHANG , Qin WANG , Hongdao LI , Wenmin WANG . Construction, structures, and interaction with DNA of two Sm^Ⅲ₄ complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1141-1150. doi: 10.11862/CJIC.20240258
9. [9]
  Chang Liu , Tao Wu , Lijiao Deng , Xuzi Li , Xin Fu , Shuzhen Liao , Wenjie Ma , Guoqiang Zou , Hai Yang . Programmed DNA walkers for biosensors. Chinese Chemical Letters, 2024, 35(9): 109307-. doi: 10.1016/j.cclet.2023.109307
10. [10]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
11. [11]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
12. [12]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
13. [13]
  Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
14. [14]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
15. [15]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
16. [16]
  Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
17. [17]
  Yang Qin , Jiangtian Li , Xuehao Zhang , Kaixuan Wan , Heao Zhang , Feiyang Huang , Limei Wang , Hongxun Wang , Longjie Li , Xianjin Xiao . Toeless and reversible DNA strand displacement based on Hoogsteen-bond triplex. Chinese Chemical Letters, 2024, 35(5): 108826-. doi: 10.1016/j.cclet.2023.108826
18. [18]
  Xiaohong Wen , Mei Yang , Lie Li , Mingmin Huang , Wei Cui , Suping Li , Haiyan Chen , Chen Li , Qiuping Guo . Enzymatically controlled DNA tetrahedron nanoprobes for specific imaging of ATP in tumor. Chinese Chemical Letters, 2024, 35(8): 109291-. doi: 10.1016/j.cclet.2023.109291
19. [19]
  Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
20. [20]
  Zhongyu Wang , Lijun Wang , Huaixin Zhao . DNA-based nanosystems to generate reactive oxygen species for nanomedicine. Chinese Chemical Letters, 2024, 35(11): 109637-. doi: 10.1016/j.cclet.2024.109637

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1546)
HTML views(248)

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