Abstract
Two Cu(II) complexes of curcumin derivatives, formulated as CuL a2 (1) and CuL b2 (2) [HLa = 1,7-bis(4-ethyloxy-3-methoxy-phenyl)-1,6-heptadiene-3,5-dione and HLb = 1,7-bis(4-butyloxy-3-methoxy-phenyl)-1,6-heptadiene-3,5-dione], have been synthesized and characterized by single-crystal X-ray diffraction, along with physicochemical and spectroscopic methods. In both complexes, each Cu(II) center is surrounded by four oxygen atoms from two β-diketone ligands in a square planar geometry. Complex 1 forms a 2D layer structure through intermolecular π–π stacking interactions, as well as weak coordination interactions between the Cu and O atoms of the solvent 1,4-dioxane molecules. Complex 2 displays a 1D column structure stabilized by intermolecular π–π stacking interactions. MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assays were used to evaluate the cytotoxicities of these complexes against three human cancer cell lines. The results show that the Cu(II) complexes exhibit more potent inhibition tumor growth in comparison with the free ligands.
Similar content being viewed by others
References
Anand P, Thomas SG, Kunnumakkara AB, Sundaram C, Harikumar KB, Sung B, Tharakan ST, Misra K, Priyadarsini IK, Rajasekharan KN, Aggarwal BB (2008) Biochem Pharmacol 76:1590–1611
Aggarwal BB, Sundaram C, Malani N, Ichikawa H (2007) Adv Exp Med Biol 595:1–75
Goel A, Kunnumakkara AB, Aggarwal BB (2008) Biochem Pharmacol 75:787–809
Aggarwal BB, Harikumar KB (2008) Int J Biochem Cell Biol 41:40–59
Kunnumakkara AB, Guha S, Krishnan S, Diagaradjane P, Gelovani J, Aggarwal BB (2007) Cancer Res 67:3853–3861
Shankar S, Srivastava RK (2007) Int J Oncol 30:905–918
Marin YE, Wall BA, Wang S, Namkoong J, Martino JJ, Suh J (2007) Melanoma Res 17:274–283
Shehzad A, Wahid F, Lee YS (2010) Arch Pharm 343:489–499
Lin YL, Liu YK, Tsai NM, Hsieh JH, Chen CH, Lin CM, Liao KW (2012) Nanomed Nanotechnol Biol Med 8:318–327
Cheng AL, Hsu CH, Lin JK, Hsu MM, Ho YF, Shen TS (2001) Anticancer Res 21:2895–2900
Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB (2007) Mol Pharmacol 4:807–818
Ferrari E, Lazzari S, Marverti G, Pignedoli F, Spagnolo F, Saladini M (2009) Bioorg Med Chem 17:3043–3052
Shi Q, Wada K, Ohkoshi E, Lin L, Huang R, Morris-Natschke SL, Goto M, Lee KH (2012) Bioorg Med Chem 20:4020–4031
Pan YB, Wang MY, Bu XZ, Zuo YL, Wang SM, Wang DJ, Liu Q, Su BJ, Xu T, Wang CH, Claret FX, Yang HL (2013) BMC Cancer 13:323–331
Bayomi SM, El-Kashef HA, El-Ashmawy MB, Nasr MNA, El-Sherbeny MA, Badria FA, Abou-zeid LA, Ghaly MA, Abdel-Aziz NI (2013) Med Chem Res 22:1147–1162
Jeon HS, Jo MH, Kim HJ, Lee MH, Yu SK, Kim CS, Lee SY, Kim SG, Chun HS, Park E, Kim DK (2012) J Korean Soc Appl Biol Chem 55:451–456
Agrawal DK, Misbra PK (2010) Med Res Rev 30:818–860
Fang XB, Fang L, Gou SH, Cheng L (2013) Bioorg Med Chem Lett 23:1297–1301
Caruso F, Rossi M, Benson A, Opazo C, Freedman D, Monti E, Gariboldi MB, Shaulky J, Marchetti F, Pettinari R, Pettinari C (2012) J Med Chem 55:1072–1081
Khalil MI, Al-Zahem AM, Al-Qunaibit MH (2013) Bioinorg Chem Appl 2013:1–5
Valentini A, Conforti F, Crispini A, De Martino A, Condello R, Stellitano C, Rotilio G, Ghedini M, Federici G, Bernardini S, Pucci D (2009) J Med Chem 52:484–491
Pucci D, Bloise R, Bellusci A, Bernardini S, Ghedini M, Pirillo S, Valentini A, Crispini A (2007) J Inorg Biochem 101:1013–1022
Song YM, Xu JP, Ding L, Hou Q, Liu JW, Zhu ZL (2009) J Inorg Biochem 103:396–400
John VD, Kuttan G, Krishnankutty K (2002) J Exp Clin Cancer Res 21:219–224
Balaji B, Somyajit K, Banik B, Nagaraju G, Chakravarty AR (2013) Inorg Chim Acta 400:142–150
Zhou SS, Xue X, Jiang B, Lu CH, Tian YP, Jiang MH (2011) Acta Chim Sinica 69:2335–2340
Zhou SS, Xue X, Jiang B, Tian YP (2012) Sci China Chem 55:334–340
Uauy R, Olivares M, Gonzalez M (1998) Am J Clin Nutr 67:952–959
Xu GY, Wei D, Wang JF, Jiang B, Wang MH, Xue X, Zhou SS, Wu BX, Jiang MH (2014) Dyes Pigm 101:312–317
Clegg JK, Lindoy LF, McMurtriea JC, Schilter D (2005) Dalton Trans 857–864
Shiga T, Ohba M, Ohkawa H (2004) Inorg Chem 43:4435–4446
Christiana AM, Constantinos ED, Christodoulos M (2008) J Inorg Biochem 102:77–86
Sundquist WI, Lippard SJ (1990) Coord Chem Rev 100:293–322
Xu ZH, Zhang YM, Xue ZQ, Yang XL, Wu ZY, Guo ZJ (2009) Inorg Chim Acta 362:2347–2352
Halámiková A, Heringová P, Kašpárková J, Intini FP, Natile G, Nemirovski A, Gibson D, Brabec V (2008) J Inorg Biochem 102:1077–1089
Acknowledgments
This research was financially supported by the Opening Foundation of Anhui Province Key Laboratory of Environment-friendly Polymer Materials (No. 2013KF001), the National Natural Science Foundation of China (No. 21071001), the Natural Science Foundation of Anhui Province (No. 1208085MH173), and the Youth Foundation of Anhui University of Chinese Medicine (No. 2011qn027).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wang, J., Wei, D., Jiang, B. et al. Two copper(II) complexes of curcumin derivatives: synthesis, crystal structure and in vitro antitumor activity. Transition Met Chem 39, 553–558 (2014). https://doi.org/10.1007/s11243-014-9831-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-014-9831-z