Synthesis and Structure of Cu(II) Complex of 4’,4’’-Diacetylcurcumin
Main Article Content
Abstract
Reaction of 4’,4’’-diacetylcurcumin (HL) with CuCl2 ∙ 2H2O in the solvent mixture of MeOH and CH2Cl2 gives rise to the corresponding complex. The composition and structure of the resulting complex are characterized and determined by the IR spectroscopy and the Single Crystal X-ray Diffraction (SC-XRD) method. The results reveal the composition [Cu(L)2] of the complex, in which 4’,4’’-diacetylcurcumin serves as monoanionic bidentate ligands with the donor sets (O,O) of the β-diketone moieties.
Keywords:
Curcumin derivatives, Cu(II) complexes, X-ray structure.
References
[1] F. Kühlwein, K. Polborn, W. Beck, Metallkomplexe von Farbstoffen. VIII Übergangsmetallkomplexe des Curcumins und seiner Derivate, Z. Anorg. Allg. Chem. 623 (1997) 1211-1219. https://doi. org/10.1002/zaac. 19976230806.
[2] X. Fang, L. Fang, S. Gou, L. Cheng, Design and synthesis of dimethylaminomethyl-substituted curcumin derivatives/analogues: Potent antitumor and antioxidant activity, improved stability and aqueous solubility compared with curcumin, Bioorg. Med. Chem. Lett. 23 (2013) 1297-1301. https://doi.org/10.1016/j.bmcl.2012. 12.098.
[3] J. Wang, D. Wei, B. Jiang, T. Liu, J. Ni, S. Zhou, Two copper(II) complexes of curcumin derivatives: synthesis, crystal structure and in vitro antitumor activity, Transition Met. Chem. 39 (2014) 553-558. https://doi.org/10.1007/s11 243-014-9831-z.
[4] M. Asti, E. Ferrari, S. Croci, G. Atti, S. Rubagotti, M. Iori, P.C. Capponi, A. Zerbini, M. Saladini, A. Versari, Synthesis and Characterization of 68Ga-Labeled Curcumin and Curcuminoid Complexes as Potential Radiotracers for Imaging of Cancer and Alzheimer’s Disease, Inorg. Chem. 53 (2014) 4922-4933. https://doi.org/10.1021/ic403113z.
[5] P.T. Thuy, P.C. Thang, N.V. Ha, T.T. Nguyet, Synthesis, Structural Characterization of 4’,4’’-Dibenzoylcurcumin and Assessment of its Complexation with Fe3+ and Cu2+ (in Vietnamese), VNU Journal of Science: Natural Sciences and Technology 35 (2019) 22-28. https://doi.org/10.25073/2588-1140/vnunst.4900.
[6] P.T. Thuy, P.C. Thang, N.H. Huy, N.V. Ha, T.T. Nguyet, Synthesis, structural characterization of 4’,4’’-Diacetylcurcumin and its complexes with Fe(III), Co(II) (in Vietnamese), Vietnam Journal of Chemistry 55 (2017) 33-37.
[7] P.T. Thuy, P.C. Thang, V.T.B. Ngoc, T.T. Nguyet, Synthesis and Structural Characterization of a Heteroleptic Pd(II) Complex with 4,4’-Diacetylcurcumin (in Vietnamese), Vietnam Journal of Chemistry 56 (2018) 119-123.
[8] M.C. Foti, A. Slavova-Kazakova, C. Rocco, V.D. Kancheva, Kinetics of curcumin oxidation by 2,2-diphenyl-1-picrylhydrazyl (DPPH∙): an interesting case of separated coupled proton-electron transfer, Org. Biomol. Chem. 14 (2016) 8331-8337. https://doi.org/10.1039/C6OB01439A.
[9] G. Sheldrick, SHELXT - Integrated space-group and crystal-structure determination, Acta Crystallogr. Sect. A71 (2015) 3-8. https://doi.org/10.1107/ S2053273314026370.
[10] G. Sheldrick, Crystal structure refinement with SHELXL, Acta Crystallogr. Sect. C 71 (2015) 3-8. https://doi.org/10.1107/S2053229614024218.
[11] O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program, J. Appl. Crystallogr. 42 (2009) 339-341. https://doi.org/10.1107/S0021889 808042726.
[12] K. Mohammadi, K.H. Thompson, B.O. Patrick, T. Storr, C. Martins, E. Polishchuk, V.G. Yuen, J.H. McNeill, C. Orvig, Synthesis and characterization of dual function vanadyl, gallium and indium curcumin complexes for medicinal applications, J. Inorg. Biochem. 99 (2005) 2217-2225. https:// doi.org/10.1016/j.jinorgbio.2005.08.001.
[13] K. Priyadarsini, The Chemistry of Curcumin: From Extraction to Therapeutic Agent, Molecules 19 (2014) 20091-20112. https://doi.org/10.3390/ molecules191220091.
[14] P.C. Thang, P.T. Thuy, T.T.K. Ngan, L.C. Dinh, Đ.T. Dat, T.T. Nguyet, Synthesis, structural characterization of 4’,4’’-dimethoxy-4-methylcurcumin and evaluation of its complexation with Co2+ and Cu2+ (in Vietnamese), Vietnam Journal of Chemistry 56 (2018) 113-117.
[15] J.T. Mague, W.L. Alworth, F.L. Payton, Curcumin and Derivatives, Acta Cryst. C 60 (2004) 608-610. https://doi.org/10.1107/s0108270104015434.
[2] X. Fang, L. Fang, S. Gou, L. Cheng, Design and synthesis of dimethylaminomethyl-substituted curcumin derivatives/analogues: Potent antitumor and antioxidant activity, improved stability and aqueous solubility compared with curcumin, Bioorg. Med. Chem. Lett. 23 (2013) 1297-1301. https://doi.org/10.1016/j.bmcl.2012. 12.098.
[3] J. Wang, D. Wei, B. Jiang, T. Liu, J. Ni, S. Zhou, Two copper(II) complexes of curcumin derivatives: synthesis, crystal structure and in vitro antitumor activity, Transition Met. Chem. 39 (2014) 553-558. https://doi.org/10.1007/s11 243-014-9831-z.
[4] M. Asti, E. Ferrari, S. Croci, G. Atti, S. Rubagotti, M. Iori, P.C. Capponi, A. Zerbini, M. Saladini, A. Versari, Synthesis and Characterization of 68Ga-Labeled Curcumin and Curcuminoid Complexes as Potential Radiotracers for Imaging of Cancer and Alzheimer’s Disease, Inorg. Chem. 53 (2014) 4922-4933. https://doi.org/10.1021/ic403113z.
[5] P.T. Thuy, P.C. Thang, N.V. Ha, T.T. Nguyet, Synthesis, Structural Characterization of 4’,4’’-Dibenzoylcurcumin and Assessment of its Complexation with Fe3+ and Cu2+ (in Vietnamese), VNU Journal of Science: Natural Sciences and Technology 35 (2019) 22-28. https://doi.org/10.25073/2588-1140/vnunst.4900.
[6] P.T. Thuy, P.C. Thang, N.H. Huy, N.V. Ha, T.T. Nguyet, Synthesis, structural characterization of 4’,4’’-Diacetylcurcumin and its complexes with Fe(III), Co(II) (in Vietnamese), Vietnam Journal of Chemistry 55 (2017) 33-37.
[7] P.T. Thuy, P.C. Thang, V.T.B. Ngoc, T.T. Nguyet, Synthesis and Structural Characterization of a Heteroleptic Pd(II) Complex with 4,4’-Diacetylcurcumin (in Vietnamese), Vietnam Journal of Chemistry 56 (2018) 119-123.
[8] M.C. Foti, A. Slavova-Kazakova, C. Rocco, V.D. Kancheva, Kinetics of curcumin oxidation by 2,2-diphenyl-1-picrylhydrazyl (DPPH∙): an interesting case of separated coupled proton-electron transfer, Org. Biomol. Chem. 14 (2016) 8331-8337. https://doi.org/10.1039/C6OB01439A.
[9] G. Sheldrick, SHELXT - Integrated space-group and crystal-structure determination, Acta Crystallogr. Sect. A71 (2015) 3-8. https://doi.org/10.1107/ S2053273314026370.
[10] G. Sheldrick, Crystal structure refinement with SHELXL, Acta Crystallogr. Sect. C 71 (2015) 3-8. https://doi.org/10.1107/S2053229614024218.
[11] O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program, J. Appl. Crystallogr. 42 (2009) 339-341. https://doi.org/10.1107/S0021889 808042726.
[12] K. Mohammadi, K.H. Thompson, B.O. Patrick, T. Storr, C. Martins, E. Polishchuk, V.G. Yuen, J.H. McNeill, C. Orvig, Synthesis and characterization of dual function vanadyl, gallium and indium curcumin complexes for medicinal applications, J. Inorg. Biochem. 99 (2005) 2217-2225. https:// doi.org/10.1016/j.jinorgbio.2005.08.001.
[13] K. Priyadarsini, The Chemistry of Curcumin: From Extraction to Therapeutic Agent, Molecules 19 (2014) 20091-20112. https://doi.org/10.3390/ molecules191220091.
[14] P.C. Thang, P.T. Thuy, T.T.K. Ngan, L.C. Dinh, Đ.T. Dat, T.T. Nguyet, Synthesis, structural characterization of 4’,4’’-dimethoxy-4-methylcurcumin and evaluation of its complexation with Co2+ and Cu2+ (in Vietnamese), Vietnam Journal of Chemistry 56 (2018) 113-117.
[15] J.T. Mague, W.L. Alworth, F.L. Payton, Curcumin and Derivatives, Acta Cryst. C 60 (2004) 608-610. https://doi.org/10.1107/s0108270104015434.