Skip to main content
SpringerLink
Log in

Copper(II) and manganese(II) picrate complexes with the V-shaped ligand 1,3-bis(1-methylbenzimidazol-2-yl)-2-thiapropane: preparation, structure, DNA-binding properties and antioxidant activities

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

A V-shaped ligand, 1,3-bis(1-methylbenzimidazol-2-yl)-2-thiapropane (L), and its copper(II) and manganese(II) picrate complexes have been synthesized and characterized. The compositions of the complexes are [Cu(L)2](pic)2·2DMF (1) and [Mn(L)(pic)2] (2), respectively. The crystal structure of complex 1 reveals a distorted tetrahedral geometry provided by four N donors from two ligands. Complex 2 is six coordinated, with a distorted octahedral geometry. Experimental studies of the DNA-binding properties indicated that the free ligand and both complexes bind to DNA via the intercalation mode, and the order of the binding affinity is L > 1 > 2. Antioxidant tests in vitro show that the Cu(II) complex possesses significant antioxidant activity against superoxide and hydroxyl radicals, with better scavenging effects than mannitol and vitamin C.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Guckian KM, Morales JC, Kool ET (1998) J Org Chem 63:9652

    Article  CAS  Google Scholar 

  2. Morales JC, Kool ET (1998) Nat Struct Biol 5:950

    Article  CAS  Google Scholar 

  3. Wu HL, Wang KT, Kou F, Jia F, Liu B, Yuan JK, Bai Y (2011) J Coord Chem 64:2676

    Article  CAS  Google Scholar 

  4. Wu HL, Huang XC, Yuan JK, Kou F, Jia F, Liu B, Wang KT (2010) Eur J Med Chem 45:5324

    Article  CAS  Google Scholar 

  5. White AW, Almassy R, Calvert AH, Curtin NJ, Griffin RJ, Hostomsky Z, Maegley K, Newell DR, Srinivasan S, Golding BT (2000) J Med Chem 43:4084

    Article  CAS  Google Scholar 

  6. Horton DA, Bourne GT, Smythe ML (2003) Chem Rev 103:893

    Article  CAS  Google Scholar 

  7. Pan GL, Bai YC, Wang H, Kong J, Shi FR, Zhang YH, Wang XL, Wu HL (2013) Zeitschrift Für Naturforschung B 68:257

    Article  CAS  Google Scholar 

  8. Soderlind KJ, Gorodetsky B, Singh AK, Bachur NR, Miller GG, Lown JW (1999) Anticancer Drug Des 14:19

    CAS  Google Scholar 

  9. Wilhelmsson LM, Westerlund F, Lincoln P, Norden B (2002) J Am Chem Soc 124:12092

    Article  CAS  Google Scholar 

  10. Dandlier PJ, Holmlin RE, Barton JK (1997) Science 274:1465

    Article  Google Scholar 

  11. Sathyaraj G, Nair BU (2010) Eur J Med Chem 45:284

    Article  CAS  Google Scholar 

  12. Manju S, Arun V (2010) J Coord Chem 63:307

    Article  Google Scholar 

  13. Boca M, Boca R, Kickelbick G, Linert W, Svoboda I (2002) Inorg Chim Acta 338:36

    Article  CAS  Google Scholar 

  14. Yang ZY, Wang Y, Wang Y (2007) Bioorg Med Chem Lett 17:2096

    Article  CAS  Google Scholar 

  15. Wu HL, Shi FR, Wang XL, Zhang YH, Bai YC, Kong J, Wang CP (2014) Transit Met Chem 39:261

    Article  CAS  Google Scholar 

  16. Xi PX, Xu ZH, Liu XH, Chen FH, Zeng ZZ, Zhang XW, Liu Y (2009) J Fluoresc 19:63

    Article  CAS  Google Scholar 

  17. Qi GF, Yang ZY, Qin DD, Wang BD, Li TR (2008) Chem Pharm Bull 56:452

    Article  CAS  Google Scholar 

  18. Lakowicz JR, Webber G (1973) Biochemistry 12:4161

    Article  CAS  Google Scholar 

  19. Wu HL, Kou F, Jia F, Liu B, Yuan JK, Bai Y (2011) J Coord Chem 64:3041

    Article  CAS  Google Scholar 

  20. Tan CP, Liu J, Chen LM, Shi S, Ji LN (2008) J Inorg Biochem 102:1644

    Article  CAS  Google Scholar 

  21. Guo ZY, Xing RE, Liu S, Yu HH, Wang PB, Li CP, Li PC (2005) Med Chem Lett 15:4600

    Article  CAS  Google Scholar 

  22. Leonard SS, Keil D, Mehlmanb T, Proper S, Shi X, Harris GK (2006) J Ethnopharmacol 103:288

    Article  CAS  Google Scholar 

  23. Le XY, Liao SR, Liu XP, Feng XL (2006) J Coord Chem 59:985

    Article  CAS  Google Scholar 

  24. Dagdigian JV, Reed CA (1979) Inorg Chem 18:2623

    Article  CAS  Google Scholar 

  25. Bruker (2006) APEX2, SAINT. Bruker AXS Inc., Madison

    Google Scholar 

  26. Sheldrick GM (2004) SADABS, program for empirical absorption correction of area detector data. University of Göttingen, Göttingen

  27. Sheldrick GM (2008) Acta Crystal A 64:112

    Article  CAS  Google Scholar 

  28. Geary WJ (1971) Coord Chem Rev 7:81

    Article  CAS  Google Scholar 

  29. Aghatabay NM, Tulu M, Mahmiani Y, Somer M, Dulger B (2008) Struct Chem 19:71

    Article  CAS  Google Scholar 

  30. Su CY, Kang BS, Du CX, Yang QC (2000) Inorg Chem 39:4843

    Article  CAS  Google Scholar 

  31. Wu HL, Wang KT, Yun RR, Huang XC (2009) Synth React Inorg Met-Org Chem 39:629

    CAS  Google Scholar 

  32. Wu HL, Sun T, Li K, Xu Y, Yun RR, Sun Q (2009) Z Anorg Allg Chem 635:146

    Article  CAS  Google Scholar 

  33. Baldini M, Belicchi-Ferrari M, Bisceglie F, Dall’Aglio PP, Pelosi G, Pinelli S, Tarasconi P (2004) Inorg Chem 43:7170

    Article  CAS  Google Scholar 

  34. Chen AY, Yu C, Gatto B, Liu LF (1993) Proc Natl Acad Sci USA 90:8131

    Article  CAS  Google Scholar 

  35. Dimitrakopoulou A, Dendrinou-Samara C, Pantazaki AA, Alexiou M, Nordlander E, Kessissoglou DP (2008) J Inorg Biochem 102:618

    Article  CAS  Google Scholar 

  36. Mukherjee S, Basu C, Chowdhury S, Chattopadhyay AP, Ghorai A, Ghosh U, Stoeckli-Evans H (2010) Inorg Chim Acta 363:2752

    Article  CAS  Google Scholar 

  37. Baguley BC, LeBret M (1984) Biochemistry 23:937

    Article  CAS  Google Scholar 

  38. Tsai K, Hsu TG, Hsu KM, Cheng H, Liu TY, Hsu CF, Kong CW (2001) Free Radic Biol Med 31:1465

    Article  CAS  Google Scholar 

  39. Udilova N, Kozlov AV, Bieberschulte W, Frei K, Ehrenberger K, Nohl H (2003) Biochem Pharmacol 65:59

    Article  CAS  Google Scholar 

  40. Li TR, Yang ZY, Wang BD, Qin DD (2008) Eur J Med Chem 43:1688

    Article  Google Scholar 

Download references

Acknowledgments

The present research was supported by the National Natural Science Foundation of China (Grant No. 21367017), the Fundamental Research Funds for the Gansu Province Universities (212086), Natural Science Foundation of Gansu Province (Grant No. 1212RJZA037), and ‘Qing Lan’ Talent Engineering Funds for Lanzhou Jiaotong University.

Author information

Authors and Affiliations

  1. School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou, 730070, Gansu, People’s Republic of China

    Huilu Wu, Jin Kong, Zaihui Yang, Xiaoli Wang, Furong Shi, Yanhui Zhang & Cuiping Wang

Authors
  1. Huilu Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jin Kong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zaihui Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiaoli Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Furong Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yanhui Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Cuiping Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Huilu Wu.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, H., Kong, J., Yang, Z. et al. Copper(II) and manganese(II) picrate complexes with the V-shaped ligand 1,3-bis(1-methylbenzimidazol-2-yl)-2-thiapropane: preparation, structure, DNA-binding properties and antioxidant activities. Transition Met Chem 39, 951–960 (2014). https://doi.org/10.1007/s11243-014-9880-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-014-9880-3

Keywords

Search

Navigation