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Organotin(IV) O-butyl carbonodithioates: Synthesis, characterization, in vitro bioactivities, and interaction with SS-DNA

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Abstract

Organotin(IV) O-butyl carbonodithioates [Me2SnL2], [Bu2SnL2], [Ph2SnL2], [Bu3SnL], and [Ph3SnL], where L = C4H9OCS –2 , have been successfully synthesized and characterized by FT-IR, 1H and 13C NMR, and single crystal X-ray analysis. The ligand coordinates to the tin atom via the carbonodithioate group. According to the X-ray diffraction data, the tin atom in [Me2SnL2] has distorted tetrahedral geometry. The synthesized compounds were screened in vitro for antibacterial, antifungal, antileishmanial, cytotoxic, and protein kinase inhibitory activities. The complexes [Bu3SnL] and [Ph3SnL] exhibited the highest anti-leishmanial activity that exceeded the activity of the reference drug amphotericin B, probably by blocking the function of parasitic mitochondria due to which it restricts further growth of the organisms. The ligand and the complexes have been shown to bind to DNA via intercalative interactions resulting in hypochromic effect with a minor red shift as confirmed by UV-Vis spectroscopic studies.

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References

  1. Pellerito, L. and Nagy, L., Coord. Chem. Rev., 2002, vol. 224, no. 1, p. 111. doi 10.1016/S0010-8545(01)00399-X

    Article  CAS  Google Scholar 

  2. Nath, M., Pokharia, S., and Yadav, R., Coord. Chem. Rev., 2001, vol. 215, no. 1, p. 99. doi 10.1016/S0010- 8545(00)00404-5

    Article  CAS  Google Scholar 

  3. Al-Najjar, A.A., Shehata, M.R., Mohamed, M., and Shoukry, M.M., Main Group Met. Chem., 1999, vol. 22, no. 4, p. 253. doi 10.1515/MGMC.1999.22.4.253

    Article  CAS  Google Scholar 

  4. Tiekink, E.R.T., Appl. Organomet. Chem., 2008, vol. 22, no. 9, p. 533. doi 10.1002/aoc.1441

    Article  CAS  Google Scholar 

  5. Yin, H.D. and Xue, S.C., Appl. Organomet. Chem., 2006, vol. 20, no. 4, p. 283. doi 10.1002/aoc.1048

    Article  CAS  Google Scholar 

  6. Tiekink, E.R.T., Main Group Met. Chem., 1992, vol. 15, p. 161. doi 10.1002/chin.199321265

    CAS  Google Scholar 

  7. Hussain, H., Ahmad, V.U., Green, I.R., Krohn, K., Hussain, J., and Badshah, A., Arkivoc, 2007, vol. 2007, part 14, p. 289. http.10.2298/JSC0802179H.

    Article  Google Scholar 

  8. Khan, S., Nami, S.A., and Siddiqi, K.S., J. Organomet. Chem., 2008, vol. 693, no. 6, p. 1049. doi 10.1016/j.jorganchem.2007.12.026

    Article  CAS  Google Scholar 

  9. Menezes, D.C., Vieira, F.T., de Lima, G.M., Wardell, J.L., Cortés, M.E., Ferreira, M.P., and Vilas Boas, A., Appl. Organomet. Chem., 2008, vol. 22, no. 4, p. 221. doi 10.1002/aoc.1375

    Article  CAS  Google Scholar 

  10. Muhammad, N., Shuja, S., Ali, S., Butler, I.S., Meetsma, A., and Khan, M., Polyhedron, 2009, vol. 28, no. 16, p. 3439. doi 10.1016/j.poly.2009.07.025

    Article  Google Scholar 

  11. Javed, F., Ali, S., Shah, M.W., Munawar, K.S., Shahzadi, S., Sharma, S.K., and Qanungo, K., J. Coord. Chem., 2014, vol. 67, no. 16, p. 2795. doi 10.1080/00958972.2014.947967

    Article  CAS  Google Scholar 

  12. Armarego, W.L. and Chai, C.L.L., Purification of Laboratory Chemicals, London: Butterworth Heinemann, 2003, 5th ed.

    Google Scholar 

  13. Sirajuddin, M., Ali, S., Shah, N.A., Khan, M.R., and Tahir, M.N., Spectrochim. Acta, Part A, 2012, vol. 94, p. 134. doi 10.1016/j.saa.2012.03.068

    Article  CAS  Google Scholar 

  14. Shaheen, F., Ali, S., Rehman, Z.U., and Meetsma, A., Polyhedron, 2012, vol. 31, no. 1, p. 697. doi 10.1016/j.poly.2011.10.025

    Article  CAS  Google Scholar 

  15. Domazetis, G., Magee, R.J., and James, B.D., J. Organomet. Chem., 1977, vol. 141, no. 1, p. 57. doi 10.1016/S0022-328X(00)90667-3

    Article  CAS  Google Scholar 

  16. Gómez-Ortiz, L.A., Cea-Olivares, R., Garcia-Montalvo, V., and Hernández-Ortega, S., J. Organomet. Chem., 2002, vol. 654, no. 1, p. 51. doi 10.1016/S0022-328X(02) 01373-6

    Article  Google Scholar 

  17. Nadvornik, M., Holecek, J., Handlír, K., and Lycka, A., J. Organomet. Chem., 1984, vol. 275, no. 1, p. 43. doi 10.1016/0022-328X(84)80576-8

    Article  CAS  Google Scholar 

  18. Eng, G., Song, X., Duong, Q., Strickman, D., Glass, J., and May, L., Appl. Organomet. Chem., 2003, vol. 17, no. 4, p. 218. doi 10.1002/aoc.423

    Article  CAS  Google Scholar 

  19. Lockhart, T.P., Manders, W.F., and Holt, E.M., J. Am. Chem. Soc., 1986, vol. 108, no. 21, p. 6611. doi 10.1021/ja00281a026

    Article  CAS  Google Scholar 

  20. Willem, R., Verbruggen, I., Gielen, M., Biesemans, M., Mahieu, B., Basu Baul, T.S., and Tiekink, E.R.T., Organometallics, 1998, vol. 17, no. 26, p. 5758. doi 10.1021/om980504u

    Article  CAS  Google Scholar 

  21. Mohamed-Ibrahim, M.I., Chee, S.S., Buntine, M.A., Cox, M.J., and Tiekink, E.R.T., Organometallics, 2000, vol. 19, no. 25, p. 5410. doi 10.1021/om000717v

    Article  CAS  Google Scholar 

  22. Ali, S., Muhammed, N., and Meetsma, A., Acta Crystallogr., Sect. E, 2007, vol. 63, p. m431. doi 10.1107/S1600536806056236

  23. Sun, H., Xiang, J., Liu, Y., Li, L., Li, Q., Xu, G., and Tang, Y., Biochimie, 2011, vol. 93, no. 8, p. 1351. doi 10.1016/j.biochi.2011.06.007

    Article  CAS  PubMed  Google Scholar 

  24. Jaumot, J., and Gargallo, R., Curr. Parm. Des., 2012, vol. 18, no. 14, p. 1900. doi 10.2174/138161212799958486

    Article  CAS  Google Scholar 

  25. Wei, C., Wang, J., and Zhang, M., Biophys. Chem., 2010, vol. 148, no. 1, p. 51. doi 10.1016/j.bpc.2010.02.009

    Article  CAS  PubMed  Google Scholar 

  26. Bhadra, K. and Kumar, G.S., Biochim. Biophys. Acta, Gen. Subj., 2011, vol. 1810, no. 4, p. 485. doi 10.1016/j.bbagen.2011.01.011

    Article  CAS  Google Scholar 

  27. Yang, X., Shen, G.L., and Yu, R.Q., Microchem. J., 1999, vol. 62, no. 3, p. 394. doi 10.1006/mchj.1999.1747

    Article  CAS  Google Scholar 

  28. Xu, Z., Bai, G., and Dong, C., Bioorg. Med. Chem., 2005, vol. 13, no. 20, p. 5694. doi 10.1016/j.bmc.2005.06.023

    Article  CAS  PubMed  Google Scholar 

  29. Ibrahim, M.S., Shehatta, I.S., and Al-Nayeli, A.A., J. Pharm. Biomed. Anal., 2002, vol. 28(2), p. 217. doi 10.1016/S0731-7085(01)00624-0

    Article  CAS  PubMed  Google Scholar 

  30. Fritsche, T.R., McDermott, P.F., Shryock, T.R., and Walker, R.D., J. Clin. Microbiol., 2007, vol. 45, no. 8, p. 2758. doi 10.1128/JCM.00569-07

    Article  PubMed  PubMed Central  Google Scholar 

  31. Rehman, Z.U., Muhammad, N., Shah, A., Ali, S., and Khan, E., Heteroatom Chem., 2012, vol. 23, no. 6, p. 560. doi 10.1002/hc.21050

    Article  Google Scholar 

  32. Ferreira, I.P., de Lima, G.M., Paniago, E.B., Rocha, W.R., Takahashi, J.A., Pinheiro, C.B., and Ardisson, J.D., Polyhedron, 2014, vol. 79, p. 161. doi 10.1016/j.poly.2014.05.001

    Article  CAS  Google Scholar 

  33. Shi, Y., Zhang, B.Y., Zhang, R.F., Zhang, S.L., and Ma, C.L., J. Coord. Chem., 2012, vol. 65, no. 23, p. 4125. doi 10.1080/00958972.2012.734814

    Article  CAS  Google Scholar 

  34. Neelakantan, M.A., Esakkiammal, M., Mariappan, S.S., Dharmaraja, J., and Jeyakumar, T., Indian J. Pharm. Sci., 2010, vol. 72, no. 2, p. 216. doi 10.4103/0250- 474X.65015

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. Neelakantan, M.A., Rusalraj, F., Dharmaraja, J., Johnsonraja, S., Jeyakumar, T., and Pillai, M.S., Spectrochim. Acta, Part A, 2008, vol. 71, no. 4, p. 1599. doi 10.1016/j.saa.2008.06.008

    Article  CAS  Google Scholar 

  36. Meyer, B.N., Ferrigni, N.R., Putnam, J.E., Jacobsen, L.B., Nichols, D.J., and McLaughlin, J.L., Planta Med., 1982, vol. 45, no. 5, p. 31. doi 10.1055/s-2007-971236

    Article  CAS  PubMed  Google Scholar 

  37. Saxena, A.K., Appl. Organomet. Chem., 1987, vol. 1, no. 1, p. 39. doi 10.1002/aoc.590010107

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    F. Javed, S. Ali & S. Shahzadi

  2. Department of Physics, University of Sargodha, Sargodha, Pakistan

    M. N. Tahir

  3. Department of Biotechnology, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    S. Tabassum

  4. Chemistry Division, Pakistan Institute of Nuclear Science and Technology, Nilore, Islamabad, Pakistan

    N. Khalid

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  1. F. Javed
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  2. S. Ali
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Correspondence to S. Ali.

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Javed, F., Ali, S., Shahzadi, S. et al. Organotin(IV) O-butyl carbonodithioates: Synthesis, characterization, in vitro bioactivities, and interaction with SS-DNA. Russ J Gen Chem 86, 2768–2776 (2016). https://doi.org/10.1134/S1070363216120380

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