Skip to main content
SpringerLink
Log in

Comparative Analysis of Structure and Biopotency of Di- and Triorganotin(IV) Carboxylates with Hexyl Backbone

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Chemists are pretty much acquainted with coordination compounds bearing carboxylate moieties. Nevertheless comprehensive literature on the subject correlating activity and toxicity with varied organotin(IV) carboxylates containing a diverse array of ligand moieties under identical experimental parameters is lacking. In view of the exciting structural and biological importance attributed to organotin(IV) compounds, the current research work involved synthesizing di- and triorganotin(IV) analogues of carboxylate ligand with hexyl aliphatic, aromatic and alicyclic backbone. The new organotin(IV) complexes with cyclohexane carboxylic acid (L1), benzoic acid (L2), and heptanoic acid (L3) were synthesized by the reaction of di- and triorganotin(IV) salts in the presence of trimethylamine as base. The coordination mode of ligand, structural confirmation and geometry assignment of complexes were established using FT-IR, 1H NMR and 13C NMR spectra. The IR data implied that in both di- and triorganotin(IV) carboxylates, the ligand moiety—(COO) acted as a bidentate group in solid state. 1H and 13C NMR data revealed that tri and diorganotin(IV) complexes occurred as monomeric entities with tetrahedral geometry around tin in solution. The synthesized complexes were also evaluated for their antibacterial and antifungal activity. The results showed that synthesized complexes have greater inhibition potential against different strains of bacteria and fungi compared with the corresponding free ligands. Triorganotin(IV) compounds were found to be more potent against tested bacterial and fungal strains than that of diorganotin(IV) derivatives, having moderate antioxidant activity. Most of the organotin(IV) complexes of benzoic acid were found to be more potent against strains of bacteria and fungi than that of corresponding complexes of other ligands showing that for a biological activity to be shown by a complex, the role of ligand was crucial.

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.

Similar content being viewed by others

REFERENCES

  1. Hussain, S., Ali, S., Shahzadi, S., Sharma, K.S., Qanungo, K., and Shahid, K., Bioinorg. Chem. Appl., 2014, vol. 2014, p. 1. https://doi.org/10.1155/2014/959203

    Article  Google Scholar 

  2. Matela, G., and Aman, R., Cent. Eur. J. Chem., 2012, vol. 10, p. 1. https://doi.org/10.2478/s11532-011-0107-6

    Article  CAS  Google Scholar 

  3. Rehman, Z., Barsan, M.M., Wharf, I., Muhammad, N., Ali, S., Meetsma, A., and Butler, I.S., Inorganica Chim. Acta., 2008, vol. 361, p. 3322. https://doi.org/10.1016/j.ica.2008.05.006

    Article  CAS  Google Scholar 

  4. Chilwal, A., Malhotra, P., and Narula, K., J. Therm. Anal. Calorim., 2013, vol. 114, p. 345. https://doi.org/10.1007/s10973-012-2880-7

    Article  CAS  Google Scholar 

  5. Kumar, M., Abbas, Z., Tuli, H. S., and Rani, A., Curr. Pharmacol. Rep., 2020, vol. 6, p. 167. https://doi.org/10.1007/s40495-020-00222-9

    Article  CAS  Google Scholar 

  6. Rehman, A., Hussain, M., Rehman, Z., Ali, S., Rauf, A., Nasim, F.H., and Helliwell, M., Inorganica Chim. Acta, 2011, vol. 370, p. 27. https://doi.org/10.1016/j.ica.2011.01.007

    Article  CAS  Google Scholar 

  7. Mazhar, M., Khan, M.K., Mahon, M.F., and Molloy, K.C., J. Organomet. Chem., 2004, vol. 689, p. 899. https://doi.org/10.1016/j.jorganchem.2003.12.019

    Article  CAS  Google Scholar 

  8. Shaheen, F., Ali, S., Rosario, S., and Shah, N.A., J. Coord. Chem., 2014, vol. 67, p. 1851. https://doi.org/10.1080/00958972.2014.908187

    Article  CAS  Google Scholar 

  9. Attanzio, A., D’Agostino, S., Busà, R., Frazzitta, A., Rubino, S., Girasolo, M. A., Sabatino, P., and Tesoriere, L., Molecules, 2020, vol. 25, p. 859. https://doi.org/10.3390/molecules25040859

    Article  CAS  Google Scholar 

  10. Gielen, M., Biesemans, M., and Willem, R., Appl. Organomet. Chem., 2005, vol. 19, p. 440. https://doi.org/10.1002/aoc.771

    Article  CAS  Google Scholar 

  11. Hosseiny, M.S., Rounaghi, G.H., and Sadeghian, H., Russ. J. Inorg. Chem., 2011, vol. 56, p. 816. https://doi.org/10.1134/S0036023611050093

    Article  CAS  Google Scholar 

  12. Rehman, A., Choudhary, M. I., Thomsen, W.J., Bioassay Techniques for Development, Amsterdam: Harwood Academic Publishers, 2001, p. 9

  13. Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically: Approved Standard, 2015, 10th ed Wayne, PA: Clinical & Laboratory Standards Institute; CLSI document M7-A10.

  14. Shahzadi, S., Shahid, K., and Ali, S., Russ. J. Coord. Chem., 2007, vol. 33, p. 403. https://doi.org/10.1134/S1070328407060048

    Article  CAS  Google Scholar 

  15. Yin, H.D. and Sheng, C.X., Appl. Organomet. Chem., 2006, vol. 20, p. 283. https://doi.org/10.1002/aoc.1048

    Article  CAS  Google Scholar 

  16. Shah, F.A., Shahzadi, S., Ali, S., Molloy, K.C., and Ahmad, S., Russ. J. Coord. Chem., 2009, vol. 35, p. 896. https://doi.org/10.1134/S1070328409120069

    Article  CAS  Google Scholar 

  17. Rehman, W., Baloch, M.K., Badshah, A., and Ali, S., Russ. J. Coord. Chem., 2005, vol. 31, p. 856. https://doi.org/10.1007/s11173-005-0181-4

    Article  CAS  Google Scholar 

  18. Matela, G. and Aman, R., Cent. Eur. J. Chem., 2012, vol. 10, p. 1. https://doi.org/10.2478/s11532-011-0107-6

    Article  CAS  Google Scholar 

  19. Sirajuddin, M., Ali, S., McKee, V., Zaib, S., and Iqbal, J., RSC Adv., 2014, vol. 4, p. 57505. https://doi.org/10.1039/C4RA10487K

    Article  CAS  Google Scholar 

  20. Waseem, D., Butt, A.F., Haq, I., Bhatti, M.H., and Khan, G.M., DARU J. Pharm. Sci., 2017, vol. 25, p. 1. https://doi.org/10.1186/s40199-017-0174-0

    Article  CAS  Google Scholar 

  21. Lockhart, T.P., Manders, W.F., and Holt, E.M., J. Am. Chem. Soc., 1986, vol. 108, p. 6611. https://doi.org/10.1021/ja00281a026

    Article  CAS  Google Scholar 

  22. Lockhart, T.P. and Manders, W.F., Inorg. Chem., 1986, vol. 25, p. 892. https://doi.org/10.1021/ic00227a002

    Article  CAS  Google Scholar 

  23. Sharma, S., Meena, R., Singh, R.V., and Fahmi, N., Main Group Met. Chem., 2016, vol. 39, p. 31. https://doi.org/10.1515/mgmc-2015-0030

    Article  CAS  Google Scholar 

  24. Hussain, S., Ali, S., Shahzadi, S., Tahir, M.N., and Shahid, M., J. Coord. Chem., 2015, vol. 68, p. 2369. https://doi.org/10.1080/00958972.2015.1046849

    Article  CAS  Google Scholar 

  25. Graisa, A.M., Husain, A.A., Al-Mashhadani, M.H., Ahmed, D.S., Adil, H., and Yousif, E., J. Serambi Eng., 2022, vol. 7, p. 2631. https://doi.org/10.32672/jse.v7i1.3825

    Article  Google Scholar 

  26. Liu, K., Chang, G., Yan, H., Li, Z., Hong, M., and Niu, M., Appl. Organomet. Chem., 2018, vol. 32, p. e3973. https://doi.org/10.1002/aoc.3973

  27. Shaheen, F., Sirajuddin, M., Ali, S., Dyson, P.J., Shah, N.A., and Tahir, M.N., J. Organomet. Chem., 2018, vol. 856, p. 13. https://doi.org/10.1016/j.jorganchem.2017.12.010

    Article  CAS  Google Scholar 

  28. Chans, G.M., Muñoz-Hurtado, J., Hernández-Ortega, S., Ramírez-Apan, T., Nieto-Camacho, A., and Gómez, E., J. Coord. Chem., 2015, vol. 68, p. 3741. https://doi.org/10.1080/00958972.2015.1072174

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Allama Iqbal Open University Islamabad, 44310, Islamabad, Pakistan

    Farzana Shaheen & Lubna Riaz

  2. Department of Biology & Environmental Science, Faculty of Sciences, Allama Iqbal Open University Islamabad, 44310, Islamabad, Pakistan

    Samar Naseer

  3. Department of Chemistry, Faculty of Science, University of Wah, The Mall, 47010, Wah Cantt, Pakistan

    Tahira Amir

  4. Healthcare Biotechnology, Atta-Ur-Rehman School of Applied Biosciences (ASAB) National University of Science and Technology (NUST), 44010, Islamabad, Pakistan

    Balquees Kanwal

Authors
  1. Farzana Shaheen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lubna Riaz
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Samar Naseer
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tahira Amir
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Balquees Kanwal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Farzana Shaheen.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shaheen, F., Riaz, L., Naseer, S. et al. Comparative Analysis of Structure and Biopotency of Di- and Triorganotin(IV) Carboxylates with Hexyl Backbone. Russ J Gen Chem 92, 2370–2378 (2022). https://doi.org/10.1134/S1070363222110226

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363222110226

Keywords:

Search

Navigation