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Comparative DNA binding and antioxidant studies of acetyl and benzoyl substituted ferrocene incorporated selenoureas

Abstract

In this article we have reported synthesis, chemical characterization (1H and 13C NMR, FTIR, CHNS, AAS), DNA binding (with cyclic voltammetry, UV-vis spectroscopy, viscometry and molecular docking) and antioxidant (1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging) activities of two ferrocene incorporated selenoureas namely 1-benzoyl-3-(4-ferrocenylphenyl)selenourea (PB) and 1-acetyl-3-(4-ferrocenylphenyl)selenourea (PA). PA has a DNA binding constant value of 4.510 × 104 M−1 which is lower than DNA binding constant of PB (7.691 × 104 M−1). DNA binding constant was calculated by a decrease in the peak current of compound-DNA adduct relative to the free compound in cyclic voltammetry. Diffusion coefficient of free PA is 1.14 × 10−5 cm2 s−1 which is greater than diffusion coefficient of PA-DNA adduct (2.1 × 10−6 cm2 s−1) and same is the case with free PB (5.41 × 10−5 cm2 s−1) and PB-DNA adduct (4.57 × 10−5 cm2 s−1). IC50 value of PA (50 μM) was found lower than PB (130 μM) for DPPH scavenging.

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References

  1. Douglass, I.B., J. Am. Chem. Soc., 1937, vol. 59, no. 4, pp. 740–742.

    Article  CAS  Google Scholar 

  2. Schwarz, K. and Foltz, C.M., J. Am. Chem. Soc., 1957, vol. 79, no. 12, pp. 3292–3293.

    Article  CAS  Google Scholar 

  3. Mugesh, G., du Mont, W.-W., and Sies, H., Chem. Rev., 2001, vol. 101, no. 7, pp. 2125–2180.

    Article  CAS  Google Scholar 

  4. Hussain, R.A., Badshah, A., Sohail, M., Lal, B., and Akbar, K., J. Mol. Str., 2013, vol. 1048, no. 0, pp. 367–374.

    Article  CAS  Google Scholar 

  5. Hussain, R.A., Badshah, A., Tahir, M.N., Lal, B., and Khan, I.A., Aust. J. Chem., 2013, vol. 66, no. 6, pp. 626–634.

    Article  CAS  Google Scholar 

  6. Hussain, R.A., Badshash, A., Sohail, M., Lal, B., and Altaf, A.A., Inorg. Chim. Acta, 2013, vol. 402, no. 0, pp. 133–139.

    Article  CAS  Google Scholar 

  7. Mishra, B., Hassan, P.A., Priyadarsini, K.I., and Mohan, H., J. Phy. Chem. B, 2005, vol. 109, no. 26, pp. 12718–12723.

    Article  CAS  Google Scholar 

  8. Desai, D., Madhunapantula, S.V., Gowdahalli, K., Sharma, A., Chandagaludoreswamy, R., El-Bayoumy, K., Robertson, G.P., and Amin, S., Bioorg. Med. Chem. Lett., 2010, vol. 20, no. 6, pp. 2038–2043.

    Article  CAS  Google Scholar 

  9. Xiao, H. and Parkin, K.L., Nutrition and Cancer, 2006, vol. 55, no. 2, pp. 210–223.

    Article  CAS  Google Scholar 

  10. Hussain, R.A., Badshah, A., and Shah, A., Appl. Organomet. Chem., 2014, vol. 28, no. 2, pp. 61–73.

    Article  CAS  Google Scholar 

  11. Lal, B., Badshah, A., Altaf, A.A., Khan, N., and Ullah, S., Appl. Organomet. Chem., 2011, vol. 25, no. 12, pp. 843–855.

    Article  CAS  Google Scholar 

  12. Asghar, F., Badshah, A., Shah, A., Rauf, M.K., Ali, M.I., Tahir, M.N., Nosheen, E., Zia ur, R., and Qureshi, R., J. Organomet. Chem., 2012, vol. 717, no. 0, pp. 1–8.

    Article  CAS  Google Scholar 

  13. Tabassum, A., Bristow, R.G., and Venkateswaran, V., Can. Treat. Rev., 2010, vol. 36, no. 3, pp. 230–234.

    Article  CAS  Google Scholar 

  14. Sirajuddin, M., Ali, S., Shah, N.A., Khan, M.R., and Tahir, M.N., Spectrochim. Acta Part A: Molecular and Biomolecular Spectroscopy, 2012, vol. 94, no. 0, pp. 134–142.

    Article  CAS  Google Scholar 

  15. Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., and Olson, A.J., J. Comp. Chem., 2009, vol. 30, no. 16, pp. 2785–2791.

    Article  CAS  Google Scholar 

  16. Drew, H.R., Wing, R.M., Takano, T., Broka, C., Tanaka, S., Itakura, K., and Dickerson, R.E., Proceedings of the National Academy of Sciences, 1981, vol. 78, no. 4, pp. 2179–2183.

    Article  CAS  Google Scholar 

  17. Hanwell, M.D., Curtis, D.E., Lonie, D.C., Vandermeersch, T., Zurek, E., and Hutchison, G.R., J. Cheminform., 2012, vol. 4, no. 1, pp. 1–17.

    Article  Google Scholar 

  18. Rappe, A.K., Casewit, C.J., Colwell, K., Goddard Iii, W., and Skiff, W., J. Am. Chem. Soc., 1992, vol. 114, no. 25, pp. 10024–10035.

    Article  CAS  Google Scholar 

  19. Gaussian 03, Revision C.02, Frisch, M.J., et al., Gaussian, Inc., Wallingford CT, 2004.

    Google Scholar 

  20. Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, pp. 5648–5652.

    Article  CAS  Google Scholar 

  21. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, no. 2, pp. 785–789.

    Article  CAS  Google Scholar 

  22. Miehlich, B., Savin, A., Stoll, H., and Preuss, H., Chem. Phys. Lett., 1989, vol. 157, no. 3, pp. 200–206.

    Article  CAS  Google Scholar 

  23. Ali, S., Badshah, A., Ataf, A.A., Lal, B., and Khan, K.M., Med. Chem. Res., pp. 1–6.

  24. Hussain, R.A., Badshah, A., Marwat, S., Yasmin, F., and Tahir, M.N., J. Organomet. Chem., 2014, vol. 769, no. 0, pp. 58–63.

    Article  CAS  Google Scholar 

  25. Hussain, R.A., Badshah, A., Tahir, M.N., Hassan, T.U., and Bano, A., J. Biochem. Mol. Toxicol., 2014, vol. 28, no. 2, pp. 60–68.

    Article  CAS  Google Scholar 

  26. Hussain, R.A., Badshah, A., Younis, A., Khan, M.D., and Akhtar, J., Thin Solid Films, 2014, vol. 567, pp. 58–63.

    Article  CAS  Google Scholar 

  27. Feng, Q., Li, N.-Q., and Jiang, Y.-Y., Anal. Chim. Acta, 1997, vol. 344, nos. 1–2, pp. 97–104.

    Article  CAS  Google Scholar 

  28. Aslanoglu, M. and Ayne, G., Anal. Bioanal. Chem., 2004, vol. 380, no. 4, pp. 658–663.

    Article  CAS  Google Scholar 

  29. Shah, A., Qureshi, R., Janjua, N.K., Haque, S., and Ahmad, S., Anal. Sci., 2008, vol. 24, no. 11, pp. 1437–1441.

    Article  CAS  Google Scholar 

  30. Shah, A., Zaheer, M., Qureshi, R., Akhter, Z., and Faizan Nazar, M., Spectrochim. Acta Part A: Molecular and Biomolecular Spectroscopy, 2010, vol. 75, no. 3, pp. 1082–1087.

    Article  Google Scholar 

  31. Lal, B., Badshah, A., Altaf, A.A., Tahir, M.N., Ullah, S., and Huq, F., Dalton Trans., 2012, vol. 41, no. 48, pp. 14643–14650.

    Article  CAS  Google Scholar 

  32. Oliveira-Brett, A.M., Diculescu, V., and Piedade, J.A.P., Bioelectrochem., 2002, vol. 55, nos. 1–2, pp. 61–62.

    Article  CAS  Google Scholar 

  33. Waring, M.J., J. Mol. Biol. 1965, vol. 13, no. 1, pp. 269–282.

    Article  CAS  Google Scholar 

  34. Shahabadi, N., Mohammadi, S., and Alizadeh, R., Bioinorg. Chem. Appl., 2011, vol. 2011.

  35. Barone, G., Terenzi, A., Lauria, A., Almerico, A.M., Leal, J.M., Busto, N., and García, B., Coord.Chem. Rev., 2013, vol. 257, nos. 19–20, pp. 2848–2862.

    Article  CAS  Google Scholar 

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Correspondence to Amin Badshah.

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Published in Russian in Elektrokhimiya, 2015, Vol. 51, No. 3, pp. 235–247.

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Hussain, R.A., Badshah, A. & Akbar, K. Comparative DNA binding and antioxidant studies of acetyl and benzoyl substituted ferrocene incorporated selenoureas. Russ J Electrochem 51, 198–208 (2015). https://doi.org/10.1134/S1023193515030088

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  • DOI: https://doi.org/10.1134/S1023193515030088

Keywords

  • ferrocene
  • selenourea
  • DNA binding
  • antioxidant
  • cyclic voltammetry
  • 1,1-diphenyl-2-picrylhydrazyl