4-(1H-1,2,4-三唑-1-亚甲基)苯甲酸过渡金属配合物的合成、结构、抑菌活性及DNA裂解活性

doi:10.3866/PKU.WHXB201405121

Abstract

Abstract:

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.

Key words: Transition metal compound, Crystal structure, Antifungal activity, DNA cleavage activity, DNA intercalation

Click here to download Supporting Info material in PDF type

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 Phys. -Chim. Sin. 2014, 30(7), 1354-1362. doi: 10.3866/PKU.WHXB201405121

References

(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) 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) Datta, A.; Karan, N. K.; Mitra, S.; Gramlich, V. J. J. Chem. Cryst. 2003, 33, 579. doi: 10.1023/A:1024299005045
(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) Kozlov, I. A.; Kubareva, E. A.; Ivanovskaya, M. G. Antisense Nucleic A 1997, 7, 279. doi: 10.1089/oli.1.1997.7.279
(6) Purmal, A. A.; Shabarv, T. V.; Gumport, R. I. Nucleic Acids Res. 1998, 20, 3713.
(7) Trawick, B. N.; Daniher, A. T.; Bashkin, J. K. Chem. Rev. 1998, 98, 939. doi: 10.1021/cr960422k
(8) Budrìa, J. G.; Raugei, S.; Cavallo, L. J. Inorg. Chem. 2006, 22, 1732.
(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) Chabner, B. A.; Roberts, T. G. Nat. Rev. Cancer 2005, 5, 65.
(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) Li, V. S.; Choi, D.;Wang, Z.; Jimenez, L. S.; Tang, M. S.; Kohn, H. J. Am. Chem. Soc. 1996, 18, 2326.
(13) Zuber, G.; James, C. Q.; Hecht, S. M. J. Am. Chem. Soc. 1998, 120, 9368. doi: 10.1021/ja981937r
(14) Hecht, S. M. J. Nat. Prod. 2000, 63, 158. doi: 10.1021/np990549f
(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) Strekowski, L.;Wilson, B. Mutat. Res. 2007, 623, 3. doi: 10.1016/j.mrfmmm.2007.03.008
(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) 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) Cater, D. C.; Ho, J. X. Adv. Protein Chem. 1994, 45, 153. doi: 10.1016/S0065-3233(08)60640-3
(20) He, X. M.; Cater, D. C. Nature 1992, 358, 209. doi: 10.1038/358209a0
(21) Curry, S.; Brick, P.; Frank, N. P. Biochim. Biophys. A 1999, 1141, 131.
(22) Shen, X. C.; Yuan, Q.; Liang, H. Sci. Chin. Ser. B-Chem. 2003, 46, 387. doi: 10.1360/02yb0062
(23) Wang, Y. M.; Song, Y.; Kong, D. L. Chin. Sci. Bull. 2005, 50, 1839. doi: 10.1360/982004-405
(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) 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) Zhang, P. Z.; Fu, Q. Y.; Chi, R. X.; Yang, C. X.; Xu, J. G. J. Zhejiang Univ. Sci. Technol. 2003, 15, 143.
(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) Zhao, X. X.; Ma, J. P.; Dong, Y. B.; Huang, R. Q. Cryst. Growth Des. 2007, 7, 1058. doi: 10.1021/cg060583+
(29) Qin, J.; Ma, J. P.; Liu, L. L.; Huang, R. Q.; Dong, Y. B. Acta Cryst. 2009, 65, 66.
(30) Sheldrick, G. M. SHELXS-97, Program for Solution of Crystal Structures; University of Göttingen: Göttingen, Germany, 1990.
(31) Sheldrick, G. M. SHELXK-97, Program for Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
(32) Mann, A.; Banso, A.; Clifford, L. C.; Tan. J. Health. Res. 2008, 10, 34.
(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) Zhang, J. P.; Chen, X. M. Chem. Commun. 2006, 1689.
(35) Ouellette,W.; Hudson, B. S.; Zubieta, J. Inorg. Chem. 2007, 46, 4887. doi: 10.1021/ic062269a
(36) Zheng, L. L.; Li, H. X.; Leng, J. D.;Wang, J.; Tong, M. L. Eur. J. Inorg. Chem. 2008, 213.
(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) 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) 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) Zavitsanos, K.; Nunes, A. M.; Malandrinos, G.; Hadjiliadis, N. J. Inorg. Biochem. 2011, 105, 1329. doi: 10.1016/j.jinorgbio.2011.07.014
(41) Barton, J. K.; Raphael, A. L. J. Am. Chem. Soc. 1984, 106, 2466. doi: 10.1021/ja00320a058
(42) Scheppler, J. A.; Cassin, P. E.; Gambier, R. M. Biotechnology Explorations: Applying the Fundamentals; ASM Press: Washington DC, 2000.
(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) Li, Y. T.; Liu, Z. Q.;Wu, Z. Y. J. Inorg. Biochem. 2008, 102, 1790. doi: 10.1016/j.jinorgbio.2008.05.011
(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) Khoramdareh, Z. K.; Yazdi, S. A.; Spingler, H. B.; Khandar, A. A. Inorg. Chim. Acta 2014, 415. 7.
(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) Melnik, M. Coord. Chem. Rev. 1982, 42, 259. doi: 10.1016/S0010-8545(00)80537-8
(49) Kato, M.; Muto, Y. Coord. Chem. Rev. 1988, 92, 45. doi: 10.1016/0010-8545(88)85005-7
(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

[1]	Xianhong Chen, Pengchao Ruan, Xianwen Wu, Shuquan Liang, Jiang Zhou. Crystal Structures, Reaction Mechanisms, and Optimization Strategies of MnO₂ Cathode for Aqueous Rechargeable Zinc Batteries [J]. Acta Phys. -Chim. Sin., 2022, 38(11): 2111003-.
[2]	Zijun Jing, Chen Tan Khai, Teng He, Yang Yu, Qijun Pei, Jintao Wang, Hui Wu, Ping Chen. Synthesis, Characterization, and Crystal Structure of Lithium Pyrrolide [J]. Acta Phys. -Chim. Sin., 2021, 37(11): 2009039-.
[3]	Mengxue Zhou, Ning Ren, Jianjun Zhang. Crystal Structure, Thermal Decomposition Mechanism and Properties of Lanthanide Supramolecular Complexes Based on 2, 4, 6-Trimethylbenzoic Acid and 5, 5'-Dimethyl-2, 2'-bipyridine [J]. Acta Phys. -Chim. Sin., 2021, 37(10): 2004071-.
[4]	Jian Li,Cong Lin,Jianhua Lin,Junliang Sun. Application of Combining X-ray Diffraction and Electron Crystallography for Determination of Complex Inorganic Crystal Structure [J]. Acta Physico-Chimica Sinica, 2020, 36(1): 1907052-.
[5]	An XIE,Zhi WANG,Qiaoyu WU,Liping CHENG,Genggeng LUO,Di SUN. [Ag₂₅(SC₆H₄Prⁱ)₁₈(dppp)₆](CF₃SO₃)₇·CH₃CN (HSC₆H₄Prⁱ = 4-t-isopropylthiophenol, and dppp = 1, 3-bis(diphenyphosphino)propane) Cluster Containing a Sandwich-like Skeleton: Structural Characterization and Optical Properties [J]. Acta Phys. -Chim. Sin., 2018, 34(7): 776-780.
[6]	Youkun ZHENG,Hui JIANG,Xuemei WANG. Multiple Strategies for Controlled Synthesis of Atomically Precise Alloy Nanoclusters [J]. Acta Phys. -Chim. Sin., 2018, 34(7): 740-754.
[7]	Xue HAN,Jin YANG,Yingying LIU,Jianfang MA. Syntheses and Luminescent Properties of Coordination Polymers Based on 1, 2, 4-Triazole-Substituted Resorcin[4]arene [J]. Acta Phys. -Chim. Sin., 2018, 34(5): 476-482.
[8]	Shun-Sheng ZHAO,Lan-Lan LI,Xiang-Rong LIU,Zuo-Cheng DING,Zai-Wen YANG. Crystal Structure, Thermal Decomposition and Interaction with CT-DNA of Three 2-Hydroxy-1-naphthaldehyde Acyl Hydrazones [J]. Acta Phys. -Chim. Sin., 2017, 33(2): 356-363.
[9]	Shi CAO,Li-Li ZENG,Jing XIE,Shi-Gang WAN,Dan Li,Hui ZHANG. Supramolecular Helical Chirality of Schiff Base Copper(Ⅱ) Complexes and Their Chiroptical Spectroscopy [J]. Acta Phys. -Chim. Sin., 2017, 33(12): 2480-2490.
[10]	Jian-Xia HUO,Su-Wei SONG,Cheng-Wei JIN,Ning REN,Li-Na GENG,Jian-Jun ZHANG. Synthesis, Characterization, Thermal Decomposition Mechanism and Properties of the [Eu(4-MOBA)₃(terpy)(H₂O)]₂ Complex [J]. Acta Phys. -Chim. Sin., 2016, 32(4): 901-906.
[11]	Jing. LI,Li-Zhen. CHEN,Jian-Long. WANG,Guan-Chao. LAN,Huan. HOU,Man. LI. Crystal Structure and Thermal Decomposition Kinetics of Byproduct of Synthesis of RDX: 3, 5-Dinitro-1-oxygen-3, 5-diazacyclohexane [J]. Acta Phys. -Chim. Sin., 2015, 31(11): 2049-2056.
[12]	ZHANG Xiang-Xiong, CHEN Min. Influence of Homogeneous Electric Field on the Structure and Growth of Ice [J]. Acta Phys. -Chim. Sin., 2014, 30(7): 1208-1214.
[13]	CHEN Lai, CHEN Shi, HU Dao-Zhong, SU Yue-Feng, LI Wei-Kang, WANG Zhao, BAO Li-Ying, WU Feng. Crystal Structure and Electrochemical Performance of Lithium-Rich Cathode Materials xLi₂MnO₃·(1-x)LiNi_0.5Mn_0.5O₂ (x=0.1-0.8) [J]. Acta Phys. -Chim. Sin., 2014, 30(3): 467-475.
[14]	YANG Jian-Hui, JI Jia-Lin, LI Lin, WEI Shi-Hao. Hydrogen Chemisorption and Physisorption on the Two-Dimensional TiC Sheet Surface [J]. Acta Phys. -Chim. Sin., 2014, 30(10): 1821-1826.
[15]	ZHU Yan-Yan, LIU Yan-Fang, LÜ Yan-Hui, WANG Hua, LING Qiang, ZHU Yong-Fa. Reflux Preparation and Photocatalytic Performance of Bismuth Phosphate Nanorods [J]. Acta Phys. -Chim. Sin., 2013, 29(03): 576-584.

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

PDF

Like

Knowledge

Abstract

Supporting Info

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0