Citation: LI Jie, XIONG Ping-Ping, BU Huai-Yu, CHEN San-Ping. Syntheses, Structures, Antifungal Activities and DNACleavage of Transition Metal Coordination Compounds with 4-(1H-1,2,4-triazol-1-ylmethyl) Benzoic Acid[J]. Acta Physico-Chimica Sinica, ;2014, 30(7): 1354-1362. doi: 10.3866/PKU.WHXB201405121 shu

Syntheses, Structures, Antifungal Activities and DNACleavage of Transition Metal Coordination Compounds with 4-(1H-1,2,4-triazol-1-ylmethyl) Benzoic Acid

1.
1. Shaanxi Provincial Key Laboratory of Biotechnology, Key Laboratory of Resource Biology and Biotechnology in Western China Ministry of Education, Northwest University, Xi'an 710069, P. R. China;
2. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710069, P. R. China

Received Date: 26 February 2014
Available Online: 12 May 2014
Fund Project:

Three novel transitionmetal compounds [Cu_0.5L]_n (1), {[Ni(L)₂·(H₂O)₂]·(H₂O)₂}_n(2), and {[Co(L)₂·(H₂O)₂]· (H₂O)₂}_n (3), were hydrothermally synthesized with 4-(1H-1,2,4-triazol-1-ylmethyl) benzoic acid (HL) and characterized by infrared spectroscopy, elemental analyses, single-crystal X-ray diffraction, thermal analyses, UV-Vis spectroscopy, and fluorescence spectroscopy. Structural analyses reveal that compound 1 features a one-dimensional (1D) chain, while isomorphic 2 and 3 exhibit a three-dimensional (3D) network structure with interchain hydrogen-bonding. Antifungal activities tests reveal that 1 has the highest antifungal effect on the five fungi (Fusarium graminearum, Vasa mali, Macrophoma kawatsukai, Colletotrichum gloeosporioides, and Alternaria alternate) among the three compounds. Furthermore, DNA cleavage experiments indicate that compound 1 has more efficient DNA (pUC 18) cleavage activity than compounds 2 and 3. The binding properties of the three compounds with DNA were also investigated by absorption. The results show that the three compounds can intercalate into DNA, and the interaction of compound 1 is the strongest.
- Transition metal compound,
- Crystal structure,
- Antifungal activity,
- DNA cleavage activity,
- DNA intercalation
1. [1]
  
  (1) Yaghi, O. M.; Davis, C. E.; Li, G. M.; Li, H. L. J. Am. Chem. Soc. 1997, 119, 2861. doi: 10.1021/ja9639473
2. [2]
  (2) Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K. Nature 2000, 404, 982. doi: 10.1038/35010088
3. [3]
  (3) Datta, A.; Karan, N. K.; Mitra, S.; Gramlich, V. J. J. Chem. Cryst. 2003, 33, 579. doi: 10.1023/A:1024299005045
4. [4]
  (4) Gillon, B.; Mathoniere, C.; Ruiz, E.; Alvarez, S.; Cousson, A.; Kahn, T. M. J. Am. Chem. Soc. 2002, 124, 14433. doi: 10.1021/ja020188h
5. [5]
  (5) Kozlov, I. A.; Kubareva, E. A.; Ivanovskaya, M. G. Antisense Nucleic A 1997, 7, 279. doi: 10.1089/oli.1.1997.7.279
6. [6]
  (6) Purmal, A. A.; Shabarv, T. V.; Gumport, R. I. Nucleic Acids Res. 1998, 20, 3713.
7. [7]
  (7) Trawick, B. N.; Daniher, A. T.; Bashkin, J. K. Chem. Rev. 1998, 98, 939. doi: 10.1021/cr960422k
8. [8]
  (8) Budrìa, J. G.; Raugei, S.; Cavallo, L. J. Inorg. Chem. 2006, 22, 1732.
9. [9]
  (9) Liu, J.; Mei,W. J.; Xu, A.W.; Shi, S.; Tan, C. P.; Ji, L. N. Antivir. Res. 2004, 62, 65. doi: 10.1016/j.antiviral.2003.12.004
10. [10]
  (10) Chabner, B. A.; Roberts, T. G. Nat. Rev. Cancer 2005, 5, 65.
11. [11]
  (11) Chen, L. M.; Liu, J.; Chen, J. C.; Shi, S. J. Mol. Struct. 2008, 881, 156. doi: 10.1016/j.molstruc.2007.09.010
12. [12]
  (12) Li, V. S.; Choi, D.;Wang, Z.; Jimenez, L. S.; Tang, M. S.; Kohn, H. J. Am. Chem. Soc. 1996, 18, 2326.
13. [13]
  (13) Zuber, G.; James, C. Q.; Hecht, S. M. J. Am. Chem. Soc. 1998, 120, 9368. doi: 10.1021/ja981937r
14. [14]
  (14) Hecht, S. M. J. Nat. Prod. 2000, 63, 158. doi: 10.1021/np990549f
15. [15]
  (15) Liu, J. G.; Ye, B. H.; Li, H.; Zhen, Q. X.; Ji, L. N.; Fu, Y. H. J. Inorg. Biochem. 1999, 76, 265. doi: 10.1016/S0162-0134(99)00154-3
16. [16]
  (16) Strekowski, L.;Wilson, B. Mutat. Res. 2007, 623, 3. doi: 10.1016/j.mrfmmm.2007.03.008
17. [17]
  (17) Zhou, C. Y.; Zhao, J.;Wu, Y. B.; Yin, C. X.; Yang, P. J. Inorg. Biochem. 2007, 101, 10. doi: 10.1016/j.jinorgbio.2006.07.011
18. [18]
  (18) Gao, F.; Chao, H.; Zhou, F.; Yuan, Y. X.; Peng, B.; Ji, L. N. J. Inorg. Biochem. 2006, 100, 1487. doi: 10.1016/j.jinorgbio.2006.04.008
19. [19]
  (19) Cater, D. C.; Ho, J. X. Adv. Protein Chem. 1994, 45, 153. doi: 10.1016/S0065-3233(08)60640-3
20. [20]
  (20) He, X. M.; Cater, D. C. Nature 1992, 358, 209. doi: 10.1038/358209a0
21. [21]
  (21) Curry, S.; Brick, P.; Frank, N. P. Biochim. Biophys. A 1999, 1141, 131.
22. [22]
  (22) Shen, X. C.; Yuan, Q.; Liang, H. Sci. Chin. Ser. B-Chem. 2003, 46, 387. doi: 10.1360/02yb0062
23. [23]
  (23) Wang, Y. M.; Song, Y.; Kong, D. L. Chin. Sci. Bull. 2005, 50, 1839. doi: 10.1360/982004-405
24. [24]
  (24) Mehra, R. K.; Tran, K.; Scott, G.W.; Mulchandani, P.; Saini, S. S. J. Inorg. Biochem. 1996, 61, 125. doi: 10.1016/0162-0134(95)00046-1
25. [25]
  (25) Koh, L. L.; Ranford, J. O.; Robinson,W. T.; Swensson, J. O.; Tan, A. L.;Wu, D. Inorg. Chem. 1996, 35, 6466. doi: 10.1021/ic9606441
26. [26]
  (26) Zhang, P. Z.; Fu, Q. Y.; Chi, R. X.; Yang, C. X.; Xu, J. G. J. Zhejiang Univ. Sci. Technol. 2003, 15, 143.
27. [27]
  (27) Xiong, P. P.; Li, J.; Bu, H. Y.;Wei, Q.; Zhang, R. L.; Chen, S. P. J. Solid State Chem. 2014, 215, 292. doi: org/10.1016/j.jssc.2014.04.012
28. [28]
  (28) Zhao, X. X.; Ma, J. P.; Dong, Y. B.; Huang, R. Q. Cryst. Growth Des. 2007, 7, 1058. doi: 10.1021/cg060583+
29. [29]
  (29) Qin, J.; Ma, J. P.; Liu, L. L.; Huang, R. Q.; Dong, Y. B. Acta Cryst. 2009, 65, 66.
30. [30]
  (30) Sheldrick, G. M. SHELXS-97, Program for Solution of Crystal Structures; University of Göttingen: Göttingen, Germany, 1990.
31. [31]
  (31) Sheldrick, G. M. SHELXK-97, Program for Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
32. [32]
  (32) Mann, A.; Banso, A.; Clifford, L. C.; Tan. J. Health. Res. 2008, 10, 34.
33. [33]
  (33) Li, Y. T.; Liu, Z. Q.;Wu, Z. Y. J. Inorg. Biochem. 2008, 102, 1790. doi: org/10.1016/j.jinorgbio.2008.05.011
34. [34]
  (34) Zhang, J. P.; Chen, X. M. Chem. Commun. 2006, 1689.
35. [35]
  (35) Ouellette,W.; Hudson, B. S.; Zubieta, J. Inorg. Chem. 2007, 46, 4887. doi: 10.1021/ic062269a
36. [36]
  (36) Zheng, L. L.; Li, H. X.; Leng, J. D.;Wang, J.; Tong, M. L. Eur. J. Inorg. Chem. 2008, 213.
37. [37]
  (37) AbouEl, E. S.; El, S. A.; Emam, S. M.; Ell, S. M. A. Spectrochim. Acta Part A 2008, 71, 421. doi: 10.1016/j.saa.2007.12.031
38. [38]
  (38) Valent, A.; Melnik, M.; Hudecova, D.; Dudova, B.; Kivekas, R.; Sundberg, M. R. Inorg. Chim. Acta 2002, 340, 15. doi: 10.1016/S0020-1693(02)01062-9
39. [39]
  (39) Song, Y. M.;Wu, Q.; Yang, P. J.; Luan, N. N. J. Inorg. Biochem. 2006, 100, 1685. doi: 10.1016/j.jinorgbio.2006.06.001
40. [40]
  (40) Zavitsanos, K.; Nunes, A. M.; Malandrinos, G.; Hadjiliadis, N. J. Inorg. Biochem. 2011, 105, 1329. doi: 10.1016/j.jinorgbio.2011.07.014
41. [41]
  (41) Barton, J. K.; Raphael, A. L. J. Am. Chem. Soc. 1984, 106, 2466. doi: 10.1021/ja00320a058
42. [42]
  (42) Scheppler, J. A.; Cassin, P. E.; Gambier, R. M. Biotechnology Explorations: Applying the Fundamentals; ASM Press: Washington DC, 2000.
43. [43]
  (43) Xi, P. X.; Xu, Z. H.; Chen, F. J.; Zeng, Z. Z. J. Inorg. Biochem. 2009, 103, 210. doi: 10.1016/j.jinorgbio.2008.10.010
44. [44]
  (44) Li, Y. T.; Liu, Z. Q.;Wu, Z. Y. J. Inorg. Biochem. 2008, 102, 1790. doi: 10.1016/j.jinorgbio.2008.05.011
45. [45]
  (45) Rajendiran, V.; Karthik, R.; Palaniandavar, M.; Evans, S. H.; Periasamy, V. S.; Akbarsha, M. A.; Srinag, B. S.; Krishnamurthy, H. Inorg. Chem. 2007, 46, 8208. doi: 10.1021/ic700755p
46. [46]
  (46) Khoramdareh, Z. K.; Yazdi, S. A.; Spingler, H. B.; Khandar, A. A. Inorg. Chim. Acta 2014, 415. 7.
47. [47]
  (47) Jiang, J.; Tang, X. L.; Dou,W.; Zhang, H. H.; Liu,W. S.;Wang, C. X.; Zheng, J. R. J. Inorg. Biochem. 2010, 104, 583. doi: 10.1016/j.jinorgbio.2010.01.011
48. [48]
  (48) Melnik, M. Coord. Chem. Rev. 1982, 42, 259. doi: 10.1016/S0010-8545(00)80537-8
49. [49]
  (49) Kato, M.; Muto, Y. Coord. Chem. Rev. 1988, 92, 45. doi: 10.1016/0010-8545(88)85005-7
50. [50]
  (50) Weder, J. E.; Dillon, C. T.; Hambley, T.W.; Kennedy, B. J.; Lay, P. A.; Biffin, J. R.; Regtop, H. L.; Davies, N. M. Coord. Chem. Rev. 2002, 232, 95. doi: 10.1016/S0010-8545(02)00086-3
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