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Mixed-Ligand Cu(II) Carboxylates: Synthesis, Crystal Structure, FTIR, DNA Binding, Antidiabetic, and Anti-Alzheimer’s Studies

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Abstract—

A series of four new copper(II) complexes [Cu2(2-BrC6H4CH2COO)4(Phen)2] (1), [Cu(2-BrC6H4CH2COO)2(Bipy)] (2), [Cu2(2-BrC6H4CH2COO)4(3-BrPy)2] (3) and [Cu2(2-BrC6H4CH2COO)4(3-MePy)2] (4) where Phen = 1,10-phenenthroline, Bipy = 2,2′-bipyridine, BrPy = bromopyridine and MePy = methylpyridine have been successfully synthesized and analyzed by elemental analysis, FT-IR, UV-Visible, and single crystal XRD. Complexes 1, 3 and 4 are dimeric and crystallize in the monoclinic space groups p21/c and C2/c, respectively. Distorted square pyramidal geometry around each Cu(II) ion in 1 is formed by the two nitrogen atoms from phenenthroline lying equatorially and three oxygen atoms from three monodentately coordinated carboxylate ligands. Two out of three ligands bridged the two metal ions with Cu···Cu intra dimer distance of 3.62 Å. In 3 and 4, four bidentate carboxylate ligands coordinate to two metal atoms which bridge them equatorially to give rise paddlewheel conformation with square pyramidal geometry around each metal atom. The axial positions of a square pyramid and trigonal bipyramid are occupied by nitrogen donor substituted pyridines with Cu···Cu intra dimer distances of 2.66 and 2.69 Å, respectively. The complex 2 being monomeric, crystallizes in the monoclinic space group C2/c with distorted square planar geometry around metal atom. A wide range of hydrogen bonding and π‒π stacking interactions are present throughout the crystal lattice in all complexes. DNA binding study through spectroscopic technique suggested strong capacity of complexes 1–4 to bind with DNA strand preferably through intercalative and groove binding modes with Kb values 6.03 × 103, 1.34 × 104, 3.18 × 104 and 3.14 × 104 M–1 respectively. The α-glucosidase and anticholinesterase enzyme inhibition assays were performed to investigate the potential of 1–4 as anti-diabetic and anti-alzheimer agents. The results revealed anti-diabetic nature of synthesized complexes with IC50 values in following order 1 < 2 < 3 < 4 with acarbose as control in concentration dependent manner. All these complexes exhibited mild activities against anticholinesterases with galantamine hydrobromide as control. The manuscript reports structurally diverse, bio-active complexes.

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REFERENCES

  1. P. Jaividhya, M. Ganeshpandian, R. Dhivya, et al., Dalton Trans. 44, 11 997 (2015).

    Article  Google Scholar 

  2. C. Rajarajeswari, M. Ganeshpandian, M. Palaniandavar, et al., J. Inorg. Biochem. 140, 255 (2014).

    Article  CAS  PubMed  Google Scholar 

  3. W. H. Mahmoud, G. G. Mohamed, and M. M. I. El-Dessouky, Int. J. Electrochem. Sci. 9, 1415 (2014).

    Google Scholar 

  4. A. J. Hallett, T. M. O’Brien, E. Carter, et al., Inorg. Chim. Acta 441, 86 (2016).

    Article  CAS  Google Scholar 

  5. S. Chandralekaa, K. Ramyab, G. Chandramohana, et al., J. Saudi Chem. Soc. 18, 953 (2014).

    Article  Google Scholar 

  6. G. S. Kurdekar, M. P. Sathisha, V. K. Revankar, et al., Eur. J. Med. Chem. 45, 455 (2010).

    Article  PubMed  CAS  Google Scholar 

  7. J. Sun and H. Xu, Molecules 15, 8349 (2010).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. J. Boonmak, S. Youngme, T. Chotkhun, and J. Reedijk, Inorg. Chem. Commun. 11, 1231 (2008).

    Article  CAS  Google Scholar 

  9. M. Devereux, M. McCann, V. Leon, et al., Met. Based Drugs 7, 275 (2000).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. B. H. Ye, X. Y. Li, I. D. Williams, and X. M. Chen, Inorg. Chem. 41, 6426 (2002).

    Article  CAS  PubMed  Google Scholar 

  11. M. E. Russell, C. S. Hawes, A. Ferguson, et al., Dalton Trans. 42, 13 576 (2013).

    Article  CAS  Google Scholar 

  12. C. D. Stewart, M. Pedraza, H. Arman, et al., J. Inorg. Biochem. 149, 25 (2015).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. S. Gupta and M. K. Maheshwari, Chem. Sci. Trans. 3, 927 (2013).

    Google Scholar 

  14. P. M. Reddy, R. Rohini, E. R. Krishna, and A. Hu, V. Ravinder, Int. J. Mol. Sci. 13, 4982 (2012).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. N. Nordin, W. Z. Samad, M. R. Yusop, and M. R. Othman, Malays. J. Anal. Sci. 19, 236 (2015).

    Google Scholar 

  16. Q. Wu, N. Xing, X. Liu, et al., Polyhedron 87, 390 (2015).

    Article  CAS  Google Scholar 

  17. Z. N. Kadhim, J. Mater. Environ. Sci. 6, 693 (2015).

    CAS  Google Scholar 

  18. R. Alam, T. Mistri, P. Mondal, et al., Dalton Trans. 43, 2566 (2014).

    Article  CAS  PubMed  Google Scholar 

  19. N. A. Bailey, D. E. Fenton, R. Moody, et al., Dalton Trans. 11, 2519 (1987).

    Article  Google Scholar 

  20. T. I. Kashar and A. H. El-Sehli, Eur. Sci. J. 12, 1857 (2016).

    Google Scholar 

  21. A. K. Jassal, S. Sharma, G. Hundal, and M. S. Hundal, Cryst. Growth Des. 15, 79 (2015).

    Article  CAS  Google Scholar 

  22. G. L. Ellman, K. D. Courtney, V. Andres, and R. M. Featherstone, Biochem. Pharm. 7, 88 (1961).

    Article  CAS  PubMed  Google Scholar 

  23. Ferheen, S. Aziz-Ur-Rehman, N. Afza, et al., J. Enzyme Inhib. Med. Chem. 24, 1128 (2009).

    Article  CAS  PubMed  Google Scholar 

  24. Gorun, V. I. Proinov, V. Baltescu, et al., Anal. Biochem. 86, 324 (1978).

    Article  CAS  PubMed  Google Scholar 

  25. M. E. Owen, E. Carter, G. J. Hutchings, et al., Dalton Trans. 41, 11 085 (2012).

    Article  CAS  Google Scholar 

  26. K. N. Lazarou, V. Psycharis, S. P. Perlepes, and C. P. Raptopoulou, Polyhedron 28, 1085 (2009).

    Article  CAS  Google Scholar 

  27. S. Dey, S. Sarkar, H. Paul, et al., Polyhedron 29, 1583 (2010).

    Article  CAS  Google Scholar 

  28. A. Colette, A. M. Ondoh, D. M. Yufanyi, and D. S. Y. Gaelle, Int. J. Chem. 7, 10 (2015).

    CAS  Google Scholar 

  29. T. Suksrichavalit, S. Prachayasittikul, T. Piacham, et al., Molecules 13, 3040 (2008).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. D. L. Reger, J. J. Horger, A. Debreczeni, and M. D. Smith, Inorg. Chem. 50, 10 225 (2011).

    Article  CAS  Google Scholar 

  31. L. F. Marquesa, M. V. Marinhoa, C. C. Correaa, et al., Inorg. Chim. Acta 368, 242 (2011).

    Article  CAS  Google Scholar 

  32. B. Chen, F. R. Fronczek, B. H. Courtney, and F. Zapata, Cryst. Growth Des. 6, 825 (2006).

    Article  CAS  Google Scholar 

  33. S. J. Jennifer and P. T. Muthiah, Chem. Cent. J. 42, 1 (2014).

    Google Scholar 

  34. P. M. Selvakumara, S. Nadellaa, J. Sahooa, et al., J. Coord. Chem. 66, 287 (2013).

    Article  CAS  Google Scholar 

  35. C. S. Liu, J. J. Wang, L. F. Yan, et al., Inorg. Chem. 46, 6299 (2007).

    Article  CAS  PubMed  Google Scholar 

  36. M. Devereux, D. O’Shea, M. O’Connor, et al., Polyhedron 26, 4073 (2007).

    Article  CAS  Google Scholar 

  37. A. N. Wein, R. Cordeiro, N. Owens, et al., J. Fluorine Chem. 130, 197 (2009).

    Article  CAS  Google Scholar 

  38. V. Paredes-Garcia, R. C. Santana, R. Madrid, et al., Inorg. Chem. 15, 8369 (2013).

    Article  CAS  Google Scholar 

  39. M. Iqbal, I. Ahmad, S. Ali, and M. Sohail, Polyhedron 50, 524 (2012).

    Article  CAS  Google Scholar 

  40. Z. D. Matovic, V. D. Miletic, G. Samardzic, et al., Inorg. Chim. Acta 358, 3135 (2005).

    Article  CAS  Google Scholar 

  41. P. J. K. Inba, B. Annaraj, S. Thalamuthu, and M. A. Neelakantan, Bioinorg. Chem. App. 2013, 1 (2013).

    Article  CAS  Google Scholar 

  42. J. P. Barbier, A. El Biyyadh, C. Kappenstein, et al., Inorg. Chem. 24, 3615 (1985).

    Article  CAS  Google Scholar 

  43. L. Zhang, L. Liu, G. F. Liu, et al., J. Chem. Crystallogr. 35, 583 (2005).

    Article  CAS  Google Scholar 

  44. U. Mukhopadhyay, D. Choquesillo-Lazarte, J. Niclos-Gutierrez, and I. Bernal, Cryst. Eng. Commun. 6, 627 (2004).

    Article  CAS  Google Scholar 

  45. J. C. Garcia-Ramos, A. Tovar-Tovar, J. Hernandez-Lima, et al., Polyhedron 30, 2697 (2011).

    Article  CAS  Google Scholar 

  46. C. Hou, J. M. Shi, Y. M. Sun, et al., Dalton Trans. 43, 5970 (2008).

    Article  CAS  Google Scholar 

  47. K. Miyamura, A, Mihara, T. Fujii, et al., J. Am. Chem. Soc. 117, 2377 (1995).

    Article  CAS  Google Scholar 

  48. J. Sun, X. Tong, and H. Xu, Inorg. Chem. Commun. 13, 645 (2010).

    Article  CAS  Google Scholar 

  49. E. N. M. Yusof, T. S. A. Ravoof, E. R. T. Tiekink, et al., J. Mol. Sci. 16, 11034 (2015).

    Article  CAS  Google Scholar 

  50. D. S. Leela, B. Ushaiah, G. Anupama, et al., J. Fluoresc. 25, 185 (2015).

    Article  CAS  PubMed  Google Scholar 

  51. K. Khorsandi, R. Hosseinzadeh, and M. Gheshlagi, J. Appl. Sol. Chem. Model. 2, 105 (2013).

    CAS  Google Scholar 

  52. N. Shahabadi and S, Mohammadi, Bioinorg. Chem. App. 2012, 1 (2012).

    Google Scholar 

  53. M. Chikira, C. Hee Ng, and M. Palaniandavar, Int. J. Mol. Sci. 16, 22 754 (2015).

    Article  CAS  Google Scholar 

Download references

Funding

A.M. is thankful to Higher Education Commission of Pakistan for providing financial support.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, 45320, Islamabad, Pakistan

    Afifa Mushtaq, Saqib Ali & Ali Haider

  2. Department of Physics, University of Sargodha, Sargodha, Pakistan

    Muhammad Nawaz Tahir

  3. Department of Biochemistry, University of Gujrat, 50700, Gujrat, Pakistan

    Hammad Ismail

  4. Department of Chemistry, Bacha Khan University, 24420, Charsadda, KPK, Pakistan

    Muhammad Iqbal

Authors
  1. Afifa Mushtaq
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  2. Saqib Ali
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  3. Muhammad Nawaz Tahir
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Correspondence to Saqib Ali or Muhammad Iqbal.

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Afifa Mushtaq, Ali, S., Tahir, M.N. et al. Mixed-Ligand Cu(II) Carboxylates: Synthesis, Crystal Structure, FTIR, DNA Binding, Antidiabetic, and Anti-Alzheimer’s Studies. Russ. J. Inorg. Chem. 64, 1365–1378 (2019). https://doi.org/10.1134/S0036023619110147

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