Citation: Zhang Chenglu, Li Yizheng, Li Jingyi, Li Yilin, Gong Rongqing, Wang Huayu. Synthesis and Bioactivities of Novel 1, 2, 4-Triazine Scheleton Phenanthroline Derivatives and the Fluorescent Recognition on DNA Using Three Novel Co (Ⅲ) Complexes[J]. Chinese Journal of Organic Chemistry, ;2018, 38(10): 2720-2730. doi: 10.6023/cjoc201803048 shu

Synthesis and Bioactivities of Novel 1, 2, 4-Triazine Scheleton Phenanthroline Derivatives and the Fluorescent Recognition on DNA Using Three Novel Co (Ⅲ) Complexes

School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029

Corresponding author: Zhang Chenglu, zhangchenglu@lnnu.edu.cn
Received Date: 28 March 2018
Revised Date: 7 June 2018
Available Online: 30 October 2018
Fund Project: Project supported by the Science and Technology Research Program of Liaoning Provincial Department of Education (No. 2009A426)the Science and Technology Research Program of Liaoning Provincial Department of Education 2009A426

Figures(9)

Cdc25B has become the important target for curing cancer owing to its over expression in kinds of cancers. Compounds containing phenanthroline moiety have become research objectives on the DNA fluorescence probes or the new curing agents for their excellent fluorescence property and bioactivities. Twelve novel 1, 2, 4-triazine scheleton phenanthroling derivatives ARTP1~ARTP12 were first designed and synthesized, the structures of ARTP1~ARTP12 were characterized successfully by means of IR and NMR. The inhibitory activities of ARTP1~ARTP12 against Cdc25B were evaluated. The results show that nine target molecules exhibit excellent inhibitories, four molecules behave better activities than the contrast reference Na₃VO₄ indicating that they may be used as Cdc25B inhibitors. Meanwhile, three novel complexes Co-ARTP-5, Co-ARTP-6 and Co-ARTP-10 were first afforded by the reaction of the excellent inhibitory active compounds ARTP5, ARTP6 and ARTP10 with Co³⁺ respectively. The structures of the three complexes were confirmed through IR, UV-Vis, ¹H NMR and fluorescence spectra. The interaction modes between the complexes and CT-DNA were explored. As a result, the excitation peaks of the complexes show a red shift and the complexes interact with CT-DNA through the insert mode. The binding constants K_b are (2.12±0.20)×10⁵, (3.29±0.20)×10⁵and (1.50±0.20)×10⁵ L·mol^-1, respectively, and it occurs strong fluorescene quenching. The complexes are expected to be the DNA fluorescence probes.
- 1, 10-phenanthroline,
- 1, 2, 4-triazine,
- Cdc25B,
- Co(Ⅲ) complex,
- fluorescent
1. [1]
  Mak, L. H.; Knott, J.; Scott, K. A.; Scott, C.; Whyte, G. F.; Ye, Y.; Mann, D. J.; Ces, O.; Stivers, J.; Woscholski, R. Bioorg. Med. Chem. 2012, 20, 4371. doi: 10.1016/j.bmc.2012.05.040
2. [2]
  He, X. P.; Deng, Q.; Gao, L. X.; Li, C.; Zhang, W.; Zhou, Y. B.; Tang, Y.; Shi, X. X.; Xie J.; Li J.; Chen, G. R.; Chen, K. X. Bioorg. Med. Chem. 2011, 19, 3892. doi: 10.1016/j.bmc.2011.05.049
3. [3]
  Sarkis, M.; Tran, D. N.; Kolb, S.; Miteva, M. A.; Villoutreix, B. O.; Garbay, C.; Braud, E. Bioorg. Med. Chem. Lett. 2012, 22, 7345. doi: 10.1016/j.bmcl.2012.10.072
4. [4]
  B urle, S.; Blume, T.; Günther, J.; Henschel, D.; Hillig, R. C.; Husemann, M.; Mengel, A.; Parchmann, C.; Schmid, E.; Skuballa, W. Bioorg. Med. Chem. Lett. 2004, 14, 1673. doi: 10.1016/j.bmcl.2004.01.052
5. [5]
  Barton, J. K.; Danishefsky, A.; Goldberg, J. J. Am. Chem. Soc. 1984, 106, 2172. doi: 10.1021/ja00319a043
6. [6]
  Demeunynck, M.; Bailly, C.; Wilson, W. D. DNA and RNA Binders, From Small Molecules to Drugs, Vol. 1, Wiley-VCH, Weinheim, 2003.
7. [7]
  Masood, M. A.; Hodgson, D. J. Inorg. Chem. 1993, 32, 4839. doi: 10.1021/ic00074a031
8. [8]
  Kalyanasundaram, K.; Gratzel, M. Coord. Chem. Rev. 1998, 77, 347.
9. [9]
  Barton, J. K.; Danishefsky, A. T.; Goldberg, J. M. J. Am. Chem. Soc. 1984, 106, 2172. doi: 10.1021/ja00319a043
10. [10]
  Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; Von Zelewsky, A. Coord. Chem. Rev. 1988, 84, 85. doi: 10.1016/0010-8545(88)80032-8
11. [11]
  Balzani, V.; Juris, A.; Venturi, M.; Campagna, S.; Serroni, S. Chem. Rev. 1996, 96, 759. doi: 10.1021/cr941154y
12. [12]
  Cola, L. D.; Belser, P. Coord. Chem. Rev. 1998, 177, 301. doi: 10.1016/S0010-8545(98)00198-2
13. [13]
  Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553. doi: 10.1021/cr990376z
14. [14]
  Chao, H.; Ji, L. N. Bioinorg. Chem. Appl. 2005, 3, 15. doi: 10.1155/BCA.2005.15
15. [15]
  Vos, J. G.; Kelly, J. M. J. Chem. Soc., Dalton Trans. 2006, 41, 4869.
16. [16]
  Tan, L. F.; Liu, J. H.; Wang, F.; Zhang, S. Chem. Biodiversity 2007, 4, 2863. doi: 10.1002/(ISSN)1612-1880
17. [17]
  Liu, Y. J.; Wang, N.; Mei, W. J.; Chen, F.; He, L. X.; Jian, L. Q.; Wang, R. J. Transition. Met. Chem. 2007, 32, 332. doi: 10.1007/s11243-006-0172-4
18. [18]
  Xu, H.; Deng, H.; Zhang, Q. L.; Huang, Y.; Liu, J. Z.; Li, L. L. Inorg. Chem. Commun. 2003, 6, 766. doi: 10.1016/S1387-7003(03)00079-0
19. [19]
  Tan, L. F.; Chao, H.; Liu, Y. J.; Li, H.; Sun, B.; Ji, L. N. Inorg. Chim. Acta 2005, 358, 2191. doi: 10.1016/j.ica.2004.10.030
20. [20]
  Cédric, M. R.; Eddy, D.; Francis, S. Chem. Commun. 2005, 345.
21. [21]
  Mahajan, S. S.; Scian, M.; Sripathy, S.; Posakony, J.; Lao, U.; Loe, T. K.; Leko, V.; Thalhofer, A.; Schuler, A. D.; Bedalov, A.; Simon, J. A. J. Med. Chem. 2014, 57, 3283. doi: 10.1021/jm4018064
22. [22]
  Wang, Z. N.; Xue, S. J. Chin. J. Org. Chem. 2002, 22, 174(in Chinese). doi: 10.3321/j.issn:0253-2786.2002.03.004
23. [23]
  Paul, K.; Sharma, A.; Luxami, V. Bioorg. Med. Chem. Lett. 2014, 24, 624. doi: 10.1016/j.bmcl.2013.12.005
24. [24]
  Khoshneviszadeh, M.; Ghahremani, M. H.; Foroumadi, A.; Miri, R.; Firuzi, O.; Madadkar-Sobhani, A.; Edraki, N.; Parsa, M.; Shafiee, A. Bioorg. Med. Chem. 2013, 21, 6708. doi: 10.1016/j.bmc.2013.08.009
25. [25]
  El-Sayed Ali, T. S. Eur. J. Med. Chem. 2009, 44, 4385. doi: 10.1016/j.ejmech.2009.05.031
26. [26]
  Stefek, M.; Soltesova Prnova, M.; Majekova, M.; Rechlin, C.; Heine, A.; Klebe, G. J. Med. Chem. 2015, 58, 2649. doi: 10.1021/jm5015814
27. [27]
  Luo, R.; Liu, L.; Si, Y.; Fang, J. J.; Xu, H. R.; Zhao, L. L.; An, D. M.; Mu, J. Mod. Prev. Med. 2011, 38, 4550(in Chinese).
28. [28]
  Guo, X. X.; Du, X. X.; Xue, S. S. Chin. J. Pharmacovigilance 2011, 8, 212(in Chinese). doi: 10.3969/j.issn.1672-8629.2011.04.007
29. [29]
  Li, J.; Li, X. M.; Wang, H. Y. Int. J. Intern. Med. 1999, 26, 107(in Chinese).
30. [30]
  Cui, X. Y.; Cao, M. F.; Sun, H.; Yu, B. L. Med. Lab. Sci. Clin. 2008, 16, 71(in Chinese).
31. [31]
  Sangshetti, J. N.; Shinde, D. B. Bioorg. Med. Chem. Lett. 2010, 20, 742. doi: 10.1016/j.bmcl.2009.11.048
32. [32]
  Misra, U.; Hitkari, A.; Saxena, A. K.; Gurtu, S.; Shanker, K. Eur. J. Med. Chem. 1996, 31, 629. doi: 10.1016/0223-5234(96)89559-6
33. [33]
  Lindsley, C. W.; Wisnoski, D. D.; Wang, Y.; Leister, W. H.; Zhao, Z. J. Tetrahedron Lett. 2003, 44, 4495. doi: 10.1016/S0040-4039(03)01019-0
34. [34]
  Thirumurugan, P.; Perumal, P. T. Dyes Pigm. 2011, 88, 403. doi: 10.1016/j.dyepig.2010.07.013
35. [35]
  Ghazvini Zadeh, E. H.; El-Gendy, B. E. M.; Popa, A. G.; Katritzky, A. R. Med. Chem. Commun. 2012, 3, 52. doi: 10.1039/C1MD00177A
36. [36]
  Chai, J. H.; Wang, Y.; Xu, D. Q.; Wang, X.; Zhu, C. A.; Guo, Y.; Zhang, C. L. Chem. J. Chin. Univ. 2014, 35, 750(in Chinese). doi: 10.7503/cjcu20130759
37. [37]
  Zhang, C. L.; Wang, X.; Guo, Y.; Wu, Y. F.; Gao, L. N.; Sun, L. J. Chin. J. Org. Chem. 2014, 34, 2331(in Chinese).
38. [38]
  Zhu, C. A.; Wu, F. Y.; Wang, X.; Gao, L. N.; Weng, Q. F.; Shi, L.; Zhang, C. L. Chin. J. Appl. Chem. 2014, 31, 455(in Chinese).
39. [39]
  Zhang, C. L.; Guo, Y.; Chen, Y.; Sun, L. J.; Cheng, A. Q.; Zhao, N.; Zhao, B. C.; Tang, J.; Xi, H. Chin. J. Org. Chem. 2015, 35, 1665(in Chinese).
40. [40]
  Shui, Y. H. J. Chengdu Text. Coll. 2000, 17, 61(in Chinese).
41. [41]
  Wang, G. Z.; Wang, Q. X. Stud. Trace Elem. Health 2004, 21, 54(in Chinese).
42. [42]
  Park, H.; Bahn, Y. H.; Jung, S. K.; Jeong, D. G.; Lee, S. H.; Seo, I.; Yoon, T. S.; Kim, S. J.; Ryu, S. E. J. Med. Chem. 2008, 51, 5533. doi: 10.1021/jm701157g
43. [43]
  Vlček, A. A. Inorg. Chem. 1967, 6, 1425. doi: 10.1021/ic50053a028
44. [44]
  Heinrich W, Milena T. Collect. Czech. Chem. Commun. 2003, 68, 965. doi: 10.1135/cccc20030965
45. [45]
  Akritopoulou-Zanze, I.; Wang, Y.; Zhao, H.; Djuric, S. W. Tetrahedron Lett. 2009, 50, 5773. doi: 10.1016/j.tetlet.2009.07.036
46. [46]
  Zou, X. H.; Ye, B. H.; Li, H.; Liu, J. G.; Xiong, Y.; Ji, L. N. J. Chem. Soc., Dalton Trans. 1999, 9, 1423.
47. [47]
  Pabst, G. R.; Pfüller, O. C.; Sauer, J. Tetrahedron Lett. 1998, 39, 8825. doi: 10.1016/S0040-4039(98)02044-9
48. [48]
  Chao, H.; Qiu, Z. R.; Cai, L. R.; Zhang, H.; Li, X. Y.; Wong, K. S.; Ji, L. N. Inorg. Chem. 2003, 42, 8823. doi: 10.1021/ic034769z
1. [1]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
2. [2]
  Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
3. [3]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
4. [4]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
5. [5]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
6. [6]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
7. [7]
  Yubin Su , Chenyu Yao , Shuyan Chen , Lisha Xu , Min Peng , Yawen Wang , Yu Peng , Jianfeng Zheng . 一种聚集诱导发光荧光探针的合成及其在指纹显影中的应用——本科生综合性化学实验探索. University Chemistry, 2026, 41(5): 70-78. doi: 10.12461/PKU.DXHX202511031
8. [8]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
9. [9]
  Shunping WANG , Chuandong GE , Shuguang QU , Tianduo LI , Shaomin WANG , Qingyuan YANG . Synthesis of a fluorescent probe based on urea-based coordination and Si—O bond cleavage for F^- and Cr(Ⅵ) detection. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 297-308. doi: 10.11862/CJIC.20250214
10. [10]
  Xinrong Wu , Yingying Ren , Jianxue Wang , Lijin Yang , Jia Jia , Nan Li , Na Zhao . 聚光捕胺——高灵敏胺响应型聚集诱导发光探针的合成及传感应用. University Chemistry, 2026, 41(5): 180-189. doi: 10.12461/PKU.DXHX202509129
11. [11]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
12. [12]
  Xiaohong Li , Huanjiang Wang , Fang Tan , Xiaohua Cai , Yingchun Luo , Yanli Leng , Guoyong Zhou , Zhu Wen . Research on the Project-Driven Teaching Model in the Context of New Engineering: A Case Study of the Development of a “Portable Metal ions and Pesticide Residues Intelligent Detection System”. University Chemistry, 2026, 41(1): 204-212. doi: 10.12461/PKU.DXHX202510037
13. [13]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
14. [14]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
15. [15]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
16. [16]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
17. [17]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
18. [18]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
19. [19]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
20. [20]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(1708)
HTML views(227)

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