Citation: Eda Şengül Elif, Cansu Gökçe Topkaya, Tolga Göktürk, Ramazan Gup. Synthesis and Characterization of Copper(Ⅱ) Complexes with Aroylhydrazone Ligands Containing Quaternary Ammonium Salts: in Vitro DNA Binding and Nuclease Activity[J]. Chinese Journal of Inorganic Chemistry, ;2020, 36(7): 1333-1343. doi: 10.11862/CJIC.2020.149 shu

Synthesis and Characterization of Copper(Ⅱ) Complexes with Aroylhydrazone Ligands Containing Quaternary Ammonium Salts: in Vitro DNA Binding and Nuclease Activity

Department of Chemistry, Faculty of Science, Mugla Sıtkı Koçman University, 48000, Kotekli-Mugla, Turkey

Corresponding author: Ramazan Gup, rgup@mu.edu.tr
Received Date: 27 June 2019
Revised Date: 3 March 2020

Fund Project: Supported by the Muğla Sıtkı Koçman University Research Projects Coordination Office through Project (Grant No.15/168)the Muğla Sıtkı Koçman University Research Projects Coordination Office through Project 15/168

Figures(8)

Two new N, N, N-trimethylpropane-1-ammonium and N, N, N-trimethylpentane-1-ammonium conjugated acetophenone-(4-hydroxybenzohydrazone) ligands, (E)-3-(4-(1-(2-(4-hydroxybenzoyl)hydrazono)ethyl)phenoxy)-N, N, N-trimethylpropan-1-ammonium perchlorate (H₂L¹) and (E)-3-(4-(1-(2-(4-hydroxybenzoyl)hydrazono)ethyl)phenoxy)N, N, N-trimethylpentane-1-ammonium perchlorate (H₂L²), and two new copper complexes with the formulation[Cu (HL¹)₂] and[Cu(HL²)₂] were synthesized and their DNA binding and cleavage activities of the compounds were investigated. The mechanism of DNA cleavage and the effect of the compound concentration on the DNA cleavage reaction were also studied. UV-Vis spectroscopy results suggest that all compounds preferably bind to DNA via major groove binding mode. This is also supported that DNA cleavage activity was inhibited in the presence of methyl green, a major groove binder. According to the results of electrophoresis studies, the compounds exhibit significant cleavage activity on the plasmid DNA both in the presence and absence of an oxidative agent (H₂O₂), which strongly depends on the concentration of the compound. The compounds cleavage pBR322 DNA via hydrolytic pathway, which is also supported by the DNA cleavage experiments in the presence of different radical scavengers.
- hydrazone,
- copper(Ⅱ) complex,
- CT-DNA binding,
- pBR322 DNA cleavage
1. [1]
  Hecht S M. J. Nat. Products, 2000, 63(1):158-168
2. [2]
  Zuber G, Quada Jr J, Hecht S M. J. Am. Chem. Soc., 1998, 120:9368-9369
3. [3]
  Johnstone T C, Suntharalingam K, Lippard S J. Chem. Rev., 2016, 116(5):3436-3486
4. [4]
  Woollins J D, Woollins A, Rosenberg B. Polyhedron, 1983, 2:175-178
5. [5]
  Levi J A, Aroney R S, Dalley D N. Br. Med. J., 1981, 282(2):2003-2004
6. [6]
  Montero E I, Pérez J M, Schwartz A, et al. ChemBioChem, 2002, 3:61-67
7. [7]
  Kathiresan S, Mugesh S, Annaraj J, et al. New J. Chem., 2017, 41:1267-1283 doi: 10.1039/C6NJ03501A
8. [8]
  Loehrer P J, Einhorn L H. Ann. Intern. Med., 1984, 100:704713
9. [9]
  Kavanagh J, Tresukosol D, Edwards C. J. Clin. Oncol., 1995, 13(7):1584-1588 doi: 10.1200/JCO.1995.13.7.1584
10. [10]
  Marzano C, Pellei M, Tisato F, et al. Med. Chem., 2009, 9(2):185-211
11. [11]
  Ainscough E W, Brodie A M, Denny W A, et al. Inorg. Biochem., 1999, 77(3):125-133
12. [12]
  Tabassum S, Asim A, Arjmand F, et al. Eur. J. Med. Chem., 2012, 58:308-316 doi: 10.1016/j.ejmech.2012.09.051
13. [13]
  Reddy P R, Shilpa A, Raju N, et al. J. Inorg. Biochem., 2011, 105(12):1603-1612 doi: 10.1016/j.jinorgbio.2011.08.022
14. [14]
  Banerjee S, Mondal S, Sen S, et al. Dalton Trans., 2009, 34:6849-6860
15. [15]
  Raja D S, Ramachandran E, Bhuvanesh N S P, et al. Eur. J. Med. Chem., 2013, 64:148-159
16. [16]
  Todorovic T R, Rychlewska U, Warzajtis B, et al. Polyhedron, 2009, 28:2397-2402
17. [17]
  Marzano C, Pellei M, Colavito D, et al. J. Med. Chem., 2006, 49:7317-7324
18. [18]
  Li M X, Zhang L Z, Chen C L, et al. J. Inorg. Biochem., 2012, 106(1):117-125
19. [19]
  Maheswari P U, Barends S, Özalp-Yaman S, et al. Chem. Eur. J., 2007, 13(18):5213-5222
20. [20]
  Itoh T, Hisada H, Sumiya T, et al. Chem. Commun., 1997, 7:677-678
21. [21]
  Tisato F, Marzano C, Porchia M, et al. Med. Res. Rev., 2010, 30(4):708-749
22. [22]
  Vutey V, Castelli S, D'Annessa I, et al. Arch. Biochem. Biophys., 2006, 606:34-40
23. [23]
  Chaviara A T, Christidis P C, Papageorgiou A, et al. J. Inorg. Biochem., 2005, 99(11):2102-2109 doi: 10.1016/j.jinorgbio.2005.07.011
24. [24]
  Fahmi N, Shrivastava S, Meena R, et al. New J. Chem., 2013, 37:1445-1453 doi: 10.1039/c3nj40907d
25. [25]
  Sparatore F, Pirisino G, Alamanni M P, et al. Boll. Chim. Farm., 1978, 117:638-651
26. [26]
  Singh W M, Dash B C. Pesticides, 1998, 22:33-37
27. [27]
  Baseer M A, Jadhav V D, Phule R M, et al. Orient. J. Chem., 2000, 16:553-556
28. [28]
  Sathyadevi P, Krishnamoorthy P, Alagesan M, et al. Polyhedron, 2012, 31(1):294-306
29. [29]
  Fan C, Su H, Zhao J, et al. Eur. J. Med. Chem., 2010, 45(4):1438-1446 doi: 10.1016/j.ejmech.2009.12.048
30. [30]
  Gokce C, Gup R. J. Photochem. Photobiol. B, 2013, 122:1523
31. [31]
  Krishnamoorthy P, Sathyadevi P, Cowley A H, et al. Eur. J. Med. Chem., 2011, 46(8):3376-3387
32. [32]
  Shtyrlin N V, Sapozhnikov S V, Galiullina A S, et al. Biomed. Res. Int., 2016:3864193
33. [33]
  Minbiole K P C, Jennings M C, Ator L E, et al. Tetrahedron, 2016, 72:3559-3566 doi: 10.1016/j.tet.2016.01.014
34. [34]
  Kowalczyk I. Molecules, 2008, 13:379-390
35. [35]
  Reddy P R, Shilpa A, Raju N, et al. J. Inorg. Biochem., 2011, 105(12):1603-1612
36. [36]
  Tabassum S, Al-Asbahy W M, Afzal M, et al. Dalton Trans., 2012, 41(16):4955-4964 doi: 10.1039/c2dt12044e
37. [37]
  Kala U L, Suma S, Kurup M R P, et al. Polyhedron, 2007, 26(7):1427-1435 doi: 10.1016/j.poly.2006.11.035
38. [38]
  Gup R, Kırkan B. Spectrochim. Acta Part A, 2006, 64(3):809815
39. [39]
  Mendes I C, Moreira J P, Speziali N L, et al. J. Braz. Chem. Soc., 2006, 17(8):1571-1577 doi: 10.1590/S0103-50532006000800013
40. [40]
  Gokce C, Gup R. Appl. Organomet. Chem., 2012, 27(5):263268
41. [41]
  Dinda P, Sengupta P, Ghosh S, et al. Inorg. Chem., 2002, 41(6):1684-1688
42. [42]
  Zhi L L, Zhao C, Xu T, et al. J. Inorg. Biochem., 2005, 99(5):1076-1082
43. [43]
  Lamour E, Routier S, Bernier J L, et al. J. Am. Chem. Soc., 1999, 121:1862-1869 doi: 10.1021/ja982221z
44. [44]
  Ghosh K, Kumar P, Tyagi N. Inorg. Chem. Acta, 2011, 375:77-83 doi: 10.1016/j.ica.2011.04.035
45. [45]
  Gup R, Erer O, Dilek N. Bioorg. Chem., 2017, 71:325-334 doi: 10.1016/j.bioorg.2017.03.003
46. [46]
  Gup R, Erer O, Dilek N. J. Mol. Struct., 2017, 1129:142-151 doi: 10.1016/j.molstruc.2016.09.066
47. [47]
  Show C, Barton J K. Methods Enzymol., 1992, 212:219-242
48. [48]
  Xiao Y N, Zhan C X. J. Appl. Polym. Sci., 2002, 84(5):887893
49. [49]
  Ozawa T, Hanaki A, Onodera K. Polyhedron, 1992, 11(7):735-738 doi: 10.1016/S0277-5387(00)86004-0
50. [50]
  Massoud S S, Perkins R S, Louka F R, et al. Dalton Trans., 2014, 43(26):10086-10103
51. [51]
  Gup R, Gökçe C, Dilek N. J. Supramol. Chem., 2015, 27(10):629-641 doi: 10.1080/10610278.2015.1051978
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