Abstract
A new caffeic acid derivative ((E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylic acid, HL1)) is synthesized from caffeic acid, followed by the preparation of a Cu(II) complex, [Cu2(L1)4DMSO2]·2DMSO. The structure is determined by single crystal X-ray diffraction, and the urease inhibitory activity of the complex is studied. The results show that IC50 of the complex is 0.56 μmol/L, which is superior to positive control acetohydroxamic acid (AHA, IC50 was 10.95 μmol/l), i.e., the complex has strong inhibitory activity towards urease.
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H. L. Mobley and R. P. Hausinger, Microbiol. Rev., 53, No. 1, 85–108 (1989).
H. L. T. Mobley, M. D. Island, and R. P. Hausinger, Microbiol. Rev., 59, No. 3, 451–480 (1995).
L. E. Zonia, N. E. Stebbins, and J. C. Polacco, Plant Physiol., 107, No. 4, 1097–1103 (1995).
C. M. Collins and S. E. F. D′Orazio, Mol. Microbiol., 9, No. 5, 907–913 (1993).
C. Montecucco and R. Rappuoli, Nature Rev. Mol. Cell Biology., 2, No. 6, 457–466 (2001).
Z. Wang, et al., Biol. Fertil. Soils., 11, No. 1, 43–47 (1991).
International Agency for Research on Cancer. IARC Monograph on the Evaluation of the Carcinogenic Risks to Humans, Vol. 61, Schistosomes, Liver flukes and Helicobacter pylori. International Agency for Research on Cancer, Lyon (1994).
B. Krajewska, J. Mol. Catal. B Enzym., 59, Nos. 1-3, 22–40 (2009).
B. J. Marshall, Gastroenterology Clinics of North America, 22, No. 1, 183–198 (1993).
U. Ermler, W. Grabarse, and S. Shima, Curr. Opin. Struct. Biol., 8, No. 6, 749–758 (1998).
M. Salamatazar, et al., Pak. J. Nutr., 11, No. 6, 224–234 (2004).
J.-W. Liang, et al., J. Inorg. Biochem., 141, 17–27 (2014).
I. Ali, et al., Polyhedron, 56, No. 1, 134–143 (2013).
H. Chiririwa, et al., Polyhedron, 49, No. 1, 29–35 (2013).
X. Liu, et al., Bioorg. Med. Chem. Lett., 23, No. 13, 3780–3784 (2013).
Z. Yao, et al., Eur. J. Med. Chem., 86, 449–455 (2014).
Y. Li, et al., Inorg. Chim. Acta, 360, No. 9, 2881–2889 (2007).
D. H. Shi, et al., Inorg. Chem. Commun., 10, No. 4, 404–406 (2007).
Y.-M. Cui, Y.-G. Li, Y.-J. Cai, W. Chen, and H.-L. Zhu, J. Coord. Chem., 64, 610–616 (2011).
W. Chen, et al., Europ. J. Med. Chem., 45, No. 10, 4473–4478 (2010).
Z. L. You, X. Han, and G. N. Zhang, Z. Anorg. Chem., 634, No. 1, 142–146 (2008).
C. V. Rao, et al., Chem.-Biol. Interact., 84, No. 3, 277–290 (1992).
S. Y. Yang, et al., Food Chem. Toxicol., 55, No. 3, 92–99 (2013).
G. İlhami, Toxicol., 217, Nos. 2/3, 213–220 (2006).
M. Cárdenas, et al., Bioorgan. Med. Chem., 14, No. 9, 2966–2971 (2006).
M. Kartal, et al., J. Ethnopharmacol., 86, No. 1, 69–73 (2003).
M. Sugiura, et al., Chem. Pharm. Bull., 37, No. 4, 1039–1043 (1989).
P. Michaluart, et al., Cancer Res., 59, No. 10, 2347–2352 (1999).
S. Son and B. A. Lewis, J. Agric. Food Chem., 50, No. 3, 468–472 (2002).
Z. Otwinowski and W. Minor, Methods in Enzymology, in: C. W. Carter Jr., R. M. Sweet (eds.), Macromolecular Crystallography, Part A, Vol. 276, Academic Press, Part A, New York (1997), pp. 307–326.
A. Altomare, et al., J. Appl. Crystallogr., 32, No. 1, 115–119 (1999).
G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany (1997).
T. Tanaka, M. Kawase, and S. Tani, Life Sci., 73, No. 23, 2985–2990 (2003).
C. Y. Wang, J. Coord. Chem., 62, 2860–2868 (2009).
W. Zaborska, B. Krajska, and Z. Olech, J. Med. Chem., 19, 65–69 (2004).
D. D. Van Slyke and R. M. Archibald, J. Biolog. Chem., 154, No. 3, 623–642 (1944).
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Original Russian Text © 2017 X.-F. Chen, C.-F. Wang, S. Kong, C. Li, X. Zhou, C.-Y. Zhang, G.-H. Sheng, H.-L. Zhu.
The text was submitted by the authors in English.
Zhurnal Strukturnoi Khimii, Vol. 58, No. 4, pp. 827–833, July–August, 2017.
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Chen, XF., Wang, CF., Kong, S. et al. Structure and urease inhibitory activity of copper(II) complex with (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylic acid. J Struct Chem 58, 797–803 (2017). https://doi.org/10.1134/S0022476617040229
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DOI: https://doi.org/10.1134/S0022476617040229