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Synthesis, DNA Binding and Cytotoxic Activity of Newcopper(II) Complexes of Trisubstituted Imidazoles

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Pharmaceutical Chemistry Journal Aims and scope

This study was aimed to synthesize and characterize two new copper(II) complexes, [Cu(phen)(Br-impi)]2+ (1) and [Cu(phen)(M-impi)]2+ (2) (where phen is 1,10-phenanthroline; Br-impi is 2-(2-(4-bromophenyl)-4- (pyridin-2-yl)-4,5-dihydro-1H-imidazol-5-yl)pyridine, andM-impi is 2-(2-(4-methoxyphenyl)-4-(pyridin- 2-yl)-4,5-dihydro-1H-imidazol-5-yl)pyridine), and to study their DNAbinding activity and cytotoxic activity. The interaction of complexes with ds-DNA has been investigated by spectroscopic methods, viscosity measurements, and agarose gel electrophoresis. The results indicate that complex 1 can bind to ds-DNA better than doescomplex 2 with binding constants 1.9 × 105M-1 and 3.9 × 104M-1, respectively.According to the UV titration method, complex 1 is capable of extractingethidium bromide molecules from DNA base pairs at lower concentrations than complex 2. In oxidative medium, both complexes produce complete degradationof plasmid DNA. Thecomplexes were screened against five human cell lines, namely A 549, PC-3, BEAS-2B, HCT-116 and MDZ-MB-231, and it was found that copper(II) complexes of trisubstituted imidazoleexhibited cytotoxic activity.

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References

  1. B. Rosenberg, L. Vancamp, and T Krigas, Nature, 205, 698 – 699 (1965).

    Article  CAS  PubMed  Google Scholar 

  2. S. Chandra and R. Kumar, Trans. Metal Chem., 29(3), 269 – 275 (2004).

    Article  CAS  Google Scholar 

  3. S. Chandra, R. Gupta, N. Gupta, and S. S. Bawa, Trans. Metal Chem., 31(2), 147 – 151 (2006).

    Article  CAS  Google Scholar 

  4. C. Gurudevaru, M. Gopalakrishnan, H. Hemachandran, et al., Appl. Organomet. Chem., (2018).

  5. R. Uauy, M. Olivarez, and M. Gonzalez, Am. J. Clin. Nutr., 67, 952S – 959S (1998).

    Article  CAS  PubMed  Google Scholar 

  6. K. D. Daniel, P. Gupta, R. H. Harbach, et al., Biochem. Pharmacol., 67(6), 1139 – 1151 (2004).

    Article  CAS  PubMed  Google Scholar 

  7. H. Xie and Y. J. Kank, Curr. Med. Chem., 16(10), 1304 – 1314 (2009).

    Article  CAS  PubMed  Google Scholar 

  8. Z. Xiao, P. S. Donnelli, M. Zimmermann, and A. G. Wedd, Inorg. Chem., 47(10), 4338 – 4347 (2008).

    Article  CAS  PubMed  Google Scholar 

  9. A. Gupte and R. J. Mumper, Cancer Treat. Rev., 35(1), 32 – 46 (2009).

    Article  CAS  PubMed  Google Scholar 

  10. V. Gandin, M. Porshia, F. Tisado, et al., J. Med. Chem., 51(4), 798 – 808 (2009).

    Google Scholar 

  11. E. D. Clercq, M. Cools, J. Balzarini, et al., Antimicrob. Agents Chemother., 35(4), 679 – 684 (1991).

    Article  PubMed  PubMed Central  Google Scholar 

  12. A. M. G. Mawwar, N. M. Grant, Randa, and S. A. M. Elseginy, Der Pharma Chemica, 5(1), 241 – 255 (2013).

    Google Scholar 

  13. S. P. Zala, R. Badmanaban, D. J. Sen, and C. N. Patel, J. Appl. Pharm. Sci., 2(07), 202 – 208 (2012).

    Google Scholar 

  14. F. Hadizadeh, H. Hosseinzadeh, V. S. MotamedShariaty, et al., Iran. J. Pharm. Res., 7(1), 29 – 33 (2008).

    CAS  Google Scholar 

  15. S. G. Dandale, A. S. Sonar, and P.R. Solanki, Int. J. Chem. Environ. Pharm. Res, 3 (1), 47 – 51 (2012).

    CAS  Google Scholar 

  16. G. S. G. De Carvalho, P. A. Machado, D. T. S. de Paula, et al., Sci. World J., 10, 1723 – 1730 (2010).

    Article  Google Scholar 

  17. G. K. Sharma, N. K. Sharma, and D. Pathak, Indian J. Chem, 52, 266 – 272 (2013).

    Google Scholar 

  18. J. M. Rademaker-Lakhai, D. V. D. Bongard, D. Pluim, et al., Clin. Cancer Res., 10, 3717 – 3727 (2004).

    Article  CAS  PubMed  Google Scholar 

  19. A. T. Baviskar, C. Madaan, R. Preet, et al, J. Med. Chem., 54(14), 5013 – 5030 (2011).

    Article  CAS  PubMed  Google Scholar 

  20. C. Santini, M. Pellei, V. Gandin, et al., Chem. Rev., 114(1), 815 – 862 (2014).

    Article  CAS  PubMed  Google Scholar 

  21. X. W. Liu, J. L. Y.-D. Chen, L. Li, and D.-S. Zhang, Inorg. Chim. Acta, 379, 1 – 6 (2011).

    Article  CAS  Google Scholar 

  22. P. Skehan, R. Soreng, D. Scudiero, et al., J. Natl. Cancer Inst., 82(13), 1107 – 1112 (1990).

    Article  CAS  PubMed  Google Scholar 

  23. J. Wang, R. Mason, D. Van Derveer, et al., J. Org. Chem., 68(13), 5415 – 5418 (2003).

    Article  CAS  PubMed  Google Scholar 

  24. G. J. Lombardino and E. H. Wiseman, J. Med. Chem., 17(11), 1182 – 1188 (1974).

    Article  CAS  PubMed  Google Scholar 

  25. S. U. Rehman, T. Sarwar, M. A. Husain, et al., Arch. Biochem. Biophys., 576, 49 – 60 (2015).

    Article  PubMed  Google Scholar 

  26. J. D. McGhee and P. H. V. Hippel, J. Mol. Biol., 86 (2), 469 – 89 (1974).

    Article  CAS  PubMed  Google Scholar 

  27. S. Ramakrishnan and M. Palaniandavar, J. Chem. Sci., 117(2), 179 – 186 (2005).

    Article  CAS  Google Scholar 

  28. S. Ramakrishnan, V. Rajendiran, M. Palaniandavar, et al., Inorg. Chem., 48(4), 1309 – 1322 (2009).

    Article  CAS  PubMed  Google Scholar 

  29. B. Selvakumar, V. Rajendiran, M. Palanaindavar, et al., J. Inorg. Biochem., 99(8), 1717 – 1732 (2006).

    Google Scholar 

  30. A. Terenzi, G. Barone, A. P. Piccionello, et al., Dalton Trans., 39(38), 9140 – 9145 (2010).

    Article  CAS  PubMed  Google Scholar 

  31. M. M. Heravi, K. Bakhtiari, H. A. Oskooie, and S. Taheri, J. Mol. Catal. A: Chem., 263, 279 – 281 (2007).

    Article  CAS  Google Scholar 

  32. J. K. Barton and A. L. Raphael, J. Am. Chem. Soc., 106 (8), 2466 – 2468 (1984).

    Article  CAS  Google Scholar 

  33. M. R. Eftink and C. A. Ghiron, Anal. Biochem., 114(2), 199 – 227 (1981).

    Article  CAS  PubMed  Google Scholar 

  34. S. Satyanarayana, J. C. Dabrowiak, and J. B. Chaires, Biochemistry, 32(10), 2573 – 2584 (1993).

    Article  CAS  PubMed  Google Scholar 

  35. S. Satyanarayana, J. C. Dabrowiak, and J. B. Chaires, Biochemistry, 31(39), 9319 – 9324 (1992).

    Article  CAS  PubMed  Google Scholar 

  36. J. M. Kelly, A. B. Tossi, D. J. McConnell, and C. Ohuigin, Nucl. Acids Res., 13(17), 6017 – 6034 (1985).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Y.-J. Liu, J. F. He, J.-H. Yao, et al., J. Coord. Chem., 62(4), 665 – 675 (2009).

    Article  CAS  Google Scholar 

  38. X.-L. Hong, Z.-H. Liang, and M.-H. Zeng, J. Coord. Chem, 64(21), 3792 – 3807 (2011).

    Article  CAS  Google Scholar 

  39. D. Canakci, I. Koyuncu, et al., J. Enzyme Inhib. Med. Chem., 34(1), 110 – 116 (2019).

    Article  CAS  PubMed  Google Scholar 

  40. A. Hussain, M. F. AlAjmi, et al., Sci. Rep., 9(1), 5237 (2019).

    Article  PubMed  PubMed Central  Google Scholar 

  41. P. R. Inamdar, R. Chauhan, et al., Inorg. Chem. Commun., 67, 67 – 71 (2016).

    Article  CAS  Google Scholar 

  42. L. Goodrich, H. Gerber, E. Marti, and D. F. Antczak, Vet. Clin. North Am. Equine Pract., 14, 607 – 629 (1998).

    Article  CAS  PubMed  Google Scholar 

  43. A. P. Theon, Vet. Clin. North Am. Equine Pract., 14, 659 – 671 (1998).

    Article  CAS  PubMed  Google Scholar 

  44. L. A. Fortier and M. A. MacHarg, J. Am. Vet. Med. Assoc., 205(8), 1183 – 1185 (1994).

    CAS  PubMed  Google Scholar 

  45. S. Peterson, Vet. Rec., 141, 626 – 628 (1997).

    Google Scholar 

Download references

Conflict of Interest

The authors declare that theyhave no conflictstoffinterest

Funding

The authors thank Zonguldak Bulent Ecevit University for sponsoring this project with a grant number 2020-72118496-02.

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Correspondence to Zuhal Gerçek.

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Gerçek, Z., Yıldız, U., Ulukaya, E. et al. Synthesis, DNA Binding and Cytotoxic Activity of Newcopper(II) Complexes of Trisubstituted Imidazoles. Pharm Chem J 55, 1320–1328 (2022). https://doi.org/10.1007/s11094-022-02578-2

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  • DOI: https://doi.org/10.1007/s11094-022-02578-2

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