Studies on the Structures and Antihyperglycemic Effects of Zn2+, Cu2+, Ni2+-Metformin Complexes

Acta Chimica Sinica ›› 2004, Vol. 62 ›› Issue (8): 783-788. Previous Articles Next Articles

Zn²⁺,Cu²⁺及Ni²⁺对二甲双胍的配合作用及降血糖活性研究

朱苗力, 卢丽萍, 杨频

山西大学分子科学研究所, 化学生物学与分子工程教育部重点实验室, 太原, 030006

投稿日期:2003-12-12 修回日期:2004-03-08 发布日期:2014-02-18
通讯作者: 杨频,E-mail:yangpin@sxu.edu.cn E-mail:yangpin@sxu.edu.cn
基金资助:
国家自然科学基金(No.20171031)、山西省青年基金(No.20011007)和2002年山西省归国留学基金资助项目.

Studies on the Structures and Antihyperglycemic Effects of Zn²⁺, Cu²⁺, Ni²⁺-Metformin Complexes

ZHU Miao-Li, LU Li-Ping, YANG Pin

Institute of Molecular Science, Chemical Biology and Molecular Engineering Laboratory of Education Ministry, Shanxi University, Taiyuan 030006

Received:2003-12-12 Revised:2004-03-08 Published:2014-02-18

Abstract

The structures and charge distribution as well as antihyperglycemic effects of 1,1-dimethylbiguanide (metformin) metal (Zn²⁺, Cu²⁺ and Ni²⁺) complexes were investigated. Metformin can complex with Zn²⁺ at bridging N, forming a rare monodentate complex, but complex with Cu²⁺ and Ni²⁺ at terminal N atoms, giving rise to bidentate complexes. The charge distribution calculated by DFT and ab initio methods indicates that the bridging N atom has more negative charge than terminal N atoms. The antihyperglycemic effects of metformin metal complexes show that the monodentate complex has no effect and bidentate complexes still keep the activity but less efficient than metformin alone. This result suggests that the bridging N atom of metformin be important for its antihyperglycemic effect.

Key words: complexes of metal-metformin, charge distribution, antihyperglycemic effect

Cite this article

ZHU Miao-Li, LU Li-Ping, YANG Pin. Studies on the Structures and Antihyperglycemic Effects of Zn²⁺, Cu²⁺, Ni²⁺-Metformin Complexes[J]. Acta Chimica Sinica, 2004, 62(8): 783-788.

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[1] Coulston, L.; Dandona, P. Diabetes 1980, 29(8), 665.
[2] Lynch, C. J.; Patson, B. J.; Goodman, S. A.; Trapolsi, D.; Kimball, S. R. Am. J. Physiol. Endocrinol. Metab. 2001, 281, E25.
[3] Chen, L.-L. Chin. J. Clin. Nutr. 2002, 10(3), 220 (in Chinese). (陈璐璐, 中国临床营养杂志, 2002, 10(3), 220.)
[4] Han, Y.; Tu, S.-Z.; Wang, Q.-J. Chin. New Drugs J. 2000, 9(7), 443 (in Chinese). (韩莹, 屠树滋, 王秋娟, 中国新药杂志, 2000, 9(7), 443.)
[5] Sun, H.-W. Program SCMAR, Central Laboratory, Nankai University, Tianjing, 1997 (in Chinese). (孙宏伟, SCMAR程序, 南开大学实验中心, 天津, 1997.)
[6] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9, Gaussian, Inc., Pittsburgh PA, 1998.
[7] Chen, Q.-M. Acta Pharm. Sinica 1985, 21(16), 410 (in Chinese). (陈其明, 药学学报, 1985, 21(16), 410.)
[8] Xu, S.-Y. Methodology of Pharmacological Experimental, 2nd ed., People's Medical Publishing House, Beijing, 1991, 1269 (in Chinese). (徐叔云, 药理实验方法学(第二版), 人民卫生出版社, 北京, 1991, 1269.)
[9] Ray, P. Chem. Rev. 1961, 61, 313.
[10] Zhu, M.-L.; Lu, L.-P.; Jin, X.-L.; Yang, P. Acta Crystallogr. 2002, C58(3), m158.
[11] Zhu, M.-L.; Lu, L.-P.; Yang, P.; Jin, X.-L. Acta Crystallogr. 2002, E58(5), m217.
[12] Zhu, M.-L.; Lu, L.-P.; Yang, P.; Jin, X.-L. Acta Crystallogr. 2002, E58(6), m272.
[13] Zhu, M.-L.; Lu, L.-P.; Yang, P. Acta Crystallogr. 2003, E59(4), o586.
[14] Hariharan, M.; Rajan, S. S.; Srinivasan, R. Acta Crystallogr. 1989, C45, 911.
[15] Lide, D. R. Tetrahedron 1962, 17, 125.
[16] Zhu, M.-L.; Yang, P.; Lu, L.-P. Acta Crystallogr. 2003, E59(2), m91.
[17] He, Z.-L.; Zhu, M.-L.; Ma, G.-B. Acta Crystallogr. 2002, E58(5), m647.
[18] Lu, L.-P.; Zhu, M.-L.; Yang, P. J. Inorg. Biochem. 2003, 95(1), 31.
[19] Lu, L.-P.; Zhu, M.-L. Acta Crystallogr. 2003, E59(12), m1086.
[20] Lu, L.-P.; Zhu, M.-L.; Yang, P. Acta Crystallogr. 2004, C60(1), m18.
[21] Yang, P.; Zhu, M.-L. Chem. Res. Appl. 1992, 4(3), 20 (in Chinese). (杨频, 朱苗力, 化学研究与应用, 1992, 4(3), 20.)

Zn²⁺,Cu²⁺及Ni²⁺对二甲双胍的配合作用及降血糖活性研究

Studies on the Structures and Antihyperglycemic Effects of Zn²⁺, Cu²⁺, Ni²⁺-Metformin Complexes

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Zn2+,Cu2+及Ni2+对二甲双胍的配合作用及降血糖活性研究