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
Douglass, I.B., J. Am. Chem. Soc., 1937, vol. 59, no. 4, pp. 740–742.
Schwarz, K. and Foltz, C.M., J. Am. Chem. Soc., 1957, vol. 79, no. 12, pp. 3292–3293.
Mugesh, G., du Mont, W.-W., and Sies, H., Chem. Rev., 2001, vol. 101, no. 7, pp. 2125–2180.
Hussain, R.A., Badshah, A., Sohail, M., Lal, B., and Akbar, K., J. Mol. Str., 2013, vol. 1048, no. 0, pp. 367–374.
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.
Hussain, R.A., Badshash, A., Sohail, M., Lal, B., and Altaf, A.A., Inorg. Chim. Acta, 2013, vol. 402, no. 0, pp. 133–139.
Mishra, B., Hassan, P.A., Priyadarsini, K.I., and Mohan, H., J. Phy. Chem. B, 2005, vol. 109, no. 26, pp. 12718–12723.
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.
Xiao, H. and Parkin, K.L., Nutrition and Cancer, 2006, vol. 55, no. 2, pp. 210–223.
Hussain, R.A., Badshah, A., and Shah, A., Appl. Organomet. Chem., 2014, vol. 28, no. 2, pp. 61–73.
Lal, B., Badshah, A., Altaf, A.A., Khan, N., and Ullah, S., Appl. Organomet. Chem., 2011, vol. 25, no. 12, pp. 843–855.
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.
Tabassum, A., Bristow, R.G., and Venkateswaran, V., Can. Treat. Rev., 2010, vol. 36, no. 3, pp. 230–234.
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.
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.
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.
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.
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.
Gaussian 03, Revision C.02, Frisch, M.J., et al., Gaussian, Inc., Wallingford CT, 2004.
Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, pp. 5648–5652.
Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, no. 2, pp. 785–789.
Miehlich, B., Savin, A., Stoll, H., and Preuss, H., Chem. Phys. Lett., 1989, vol. 157, no. 3, pp. 200–206.
Ali, S., Badshah, A., Ataf, A.A., Lal, B., and Khan, K.M., Med. Chem. Res., pp. 1–6.
Hussain, R.A., Badshah, A., Marwat, S., Yasmin, F., and Tahir, M.N., J. Organomet. Chem., 2014, vol. 769, no. 0, pp. 58–63.
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.
Hussain, R.A., Badshah, A., Younis, A., Khan, M.D., and Akhtar, J., Thin Solid Films, 2014, vol. 567, pp. 58–63.
Feng, Q., Li, N.-Q., and Jiang, Y.-Y., Anal. Chim. Acta, 1997, vol. 344, nos. 1–2, pp. 97–104.
Aslanoglu, M. and Ayne, G., Anal. Bioanal. Chem., 2004, vol. 380, no. 4, pp. 658–663.
Shah, A., Qureshi, R., Janjua, N.K., Haque, S., and Ahmad, S., Anal. Sci., 2008, vol. 24, no. 11, pp. 1437–1441.
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.
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.
Oliveira-Brett, A.M., Diculescu, V., and Piedade, J.A.P., Bioelectrochem., 2002, vol. 55, nos. 1–2, pp. 61–62.
Waring, M.J., J. Mol. Biol. 1965, vol. 13, no. 1, pp. 269–282.
Shahabadi, N., Mohammadi, S., and Alizadeh, R., Bioinorg. Chem. Appl., 2011, vol. 2011.
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.
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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