Skip to main content
SpringerLink
Log in

Synthesis, Characterization and Antiproliferative Activity Test of Some Diphenyltin(IV) Hydroxybenzoates Against A549, MCF-7 and HeLa Human Cancer Cell Lines

  • Research
  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

Due to the various side effects of conventional cancer treatment therapy, efforts to find anticancer agents with minimal side effects are in great demand. One of them is the synthesis of organotin(IV) hydroxybenzoate derivatives. Three organotin(IV) compounds, namely diphenyltin(IV) 2-hydroxybenzoate, [Ph2Sn(2-HBz)2] (DPT2-DH) (2), diphenyltin(IV) 3-hydroxybenzoate, [Ph2Sn(3-HBz)2] (DPT3-DH) (3) and diphenyltin(IV) 4-hydroxybenzoate, [Ph2Sn(4-HBz)2] (DPT4-DH) (4), have been successfully synthesized. Compounds 2–4 were obtained by reacting diphenyltin(IV) oxide, [Ph2SnO] (DPTO) (1) with 2-hydroxybenzoic acid (2-HHBz), 3-hydroxybenzoic acid (3-HHBz) and 4-hydroxybenzoic acid (4-HHBz), respectively. The compounds synthesized were fully characterized by UV–Vis, FT-IR, and NMR spectroscopies and microelemental analysis to see the purity of the compounds. The antiproliferative activity of the compounds was tested against three cancer cell lines of lung cancer (A549), breast cancer (MCF-7) and cervical cancer (HeLa), and their activities were compared to normal cell cancer, Vero. The results of the antiproliferative test demonstrated that compound 2 was found to be most active against the A549 cell line. Compounds 2 and 3 are active against MCF-7 while compound 4 was found to be least active against all cancer lines tested. All compounds have also been found to have a good selectivity index (SI) toward the A549 cell line, although their SI values are not good enough against the HeLa cell line.

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

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

Similar content being viewed by others

Data Availability

No datasets were generated or analysed during the current study.

References

  1. M. McCall, M. McDonald, S. Thorne, A. Ward, C. Heneghan, Yoga for health-related quality of life in adult cancer: a randomized controlled feasibility study. Evid.-Based Compl. Altern. Med. (2015). https://doi.org/10.1155/2015/816820

    Article  Google Scholar 

  2. H. Sung, J. Ferlay, R.L. Siegel, M. Laversanne, I. Soerjomataram, A. Jemal, F. Bray, Global Cancer Statistics 2020, GLOBOCAN estimates of incidence and Mortality Worldwide for 36 cancers in 185 countries. CA Cancer J. Clin. 71, 209–249 (2021). https://doi.org/10.3322/caac.21660

    Article  CAS  PubMed  Google Scholar 

  3. Cancer Observatory, Cancer Today, (2021). Accessed on December 25, 2023. https://gco.iarc.fr/Global

  4. World Health Organization (WHO), Global Health Estimates, 2020: Deaths by Cause, Age, Sex, by Country and by Region, 2000–2019. WHO; 2020. Accessed on January 15, 2023. https://www.who.int/data/gho/data/theme%20s/morta%20lity-andgloba%20l-healt%20h-estim%20ates/ghe-leadingcauses-of-death

  5. A. Annissa, T. Suhartati, Y. Yandri, S. Hadi, Antibacterial activity of Diphenyltin(IV) and triphenyltin(IV) 3-Chlorobenzoate against Pseudomonas aeruginosa and Bacillus subtilis. Orient. J. Chem. 33, 1133–1139 (2017). https://doi.org/10.13005/ojc/330310

    Article  CAS  Google Scholar 

  6. M.R. Roner, C.E. Jr Carraher, K. Shahi, K. Barot, Antiviral activity of metal-containing polymers-Organotin and Cisplatin-Like Polymers materials. Mater. (Basel). 4, 91–112 (2011). https://doi.org/10.3390/ma4060991

    Article  CAS  Google Scholar 

  7. C.S. Rocha, B.P. de Morais, B.L. Rodrigues, C.L. Donnici, G.M. de Lima, J.D. Ardisson, J.A. Takahashi, R.S. Bitzer, Spectroscopic and X-ray structural characterization of New Organotin carboxylates and their in Vitro Antifungal activities. Polyhedron. 117, 35–47 (2016). https://doi.org/10.1016/j.poly.2016.05.031

    Article  CAS  Google Scholar 

  8. S. Samsuar, W. Simanjuntak, H.I. Qudus, Y. Yandri, H. Herasari, S. Hadi, In Vitro Antimicrobial Activity Study of some Organotin(IV) Chlorobenzoates against Staphylococcus aureus and Escherichia coli. J. Adv. Pharm. Edu Res. 11(2), 17–22 (2021). https://doi.org/10.51847/kaijZKAFCO

    Article  CAS  Google Scholar 

  9. M. Sirajuddin, S. Ali, M.N. Tahir, Organotin(IV) derivatives based on 2-((2-methoxyphenyl) carbamoyl) Benzoic Acid: synthesis, Spectroscopic characterization, Assessment of Antibacterial, DNA Interaction, Anticancer and Antileishmanial potentials. J. Mol. Struct. 1229, 129600 (2021). https://doi.org/10.1016/j.molstruc.2020.129600

    Article  CAS  Google Scholar 

  10. C.E. Jr Carraher, M.R. Roner, Organotin polymers as anticancer and antiviral agents. J. Organomet. Chem. 751, 67–82 (2014). https://doi.org/10.1016/j.jorganchem.2013.05.033

    Article  CAS  Google Scholar 

  11. L. Pellerito, L. Nagy, Organotin(IV)n+ complexes formed with biologically active ligands: equilibrium and structural studies, and some biological aspects. Coord. Chem. Rev. 224, 111–150 (2002). https://doi.org/10.1016/S0010-8545(01)00399-X

    Article  CAS  Google Scholar 

  12. S. Hadi, M.D. Fenska, N. Noviany, H. Satria, W. Simanjuntak, M.M. Naseer, Synthesis and antimalarial activity of some triphenyltin(IV) aminobenzoate compounds against Plasmodium Falciparum. Main Met. Group. Chem. 44, 256–260 (2021). https://doi.org/10.1515/mgmc-2021-0028

    Article  CAS  Google Scholar 

  13. S. Hadi, T. Suhartati, N. Noviany, K.D. Pandiangan, Y. Yandri, W. Simanjuntak, Disinfecting activity of some diphenyltin(IV) benzoate derivative compounds. Pure Appl. Chem. 94, 799–807 (2022). https://doi.org/10.1515/pac-2021-1106

    Article  CAS  Google Scholar 

  14. J.O. Adeyemi, D.C. Onwudiwe, A.C. Ekennia, R.C. Uwaoma, E.C. Hosten, Synthesis, characterization and antimicrobial studies of organotin(IV) complexes of N-methyl-N-phenyldithiocarbamate. Inorg. Chim. Acta. 477, 148–159 (2018). https://doi.org/10.1016/j.ica.2018.02.034

    Article  CAS  Google Scholar 

  15. D.K. Kovala-Demertzi, V. Dokorou, Z. Ciunik, N. Kourkoumelis, M.A. Demertzis, Organotin mefenamic complexes preparations, spectroscopic studies and crystal structure of a triphenyltin ester of mefenamic acid: Novelanti-Tuberculosis agents. Appl. Organomet. Chem. 16, 360–368 (2002). https://doi.org/10.1002/aoc.308

    Article  CAS  Google Scholar 

  16. S. Hadi, B. Irawan, T. Yandri, Suhartati, Synthesis, characterization and the antifungal activity test of some organotin(IV) benzoates. J. Phys. : Conf. Ser. 1751, 012099 (2021). https://doi.org/10.1088/1742-6596/1751/1/012099

    Article  CAS  Google Scholar 

  17. C. Hansch, R.P. Verma, Larvicidal activities of some Organotin compounds on Mosquito Larvae: a QSAR Study. Eur. J. Med. Chem. 44, 260–273 (2009). https://doi.org/10.1016/j.ejmech.2008.02.040

    Article  CAS  PubMed  Google Scholar 

  18. S. Hadi, M. Noviany, Rilyanti, In Vitro Antimalarial activity of some Organotin(IV)2-Nitrobenzoate compounds against Plasmodium Falciparum. Maced J. Chem. Chem. Eng. 37, 185–191 (2018). https://doi.org/10.20450/mjcce.2018.1414

    Article  CAS  Google Scholar 

  19. V.Y. Tyurin, W. Yaouhan, A.A. Prishchenko, D.B. Shpakovsky, Y.A. Gracheva, T.A. Antonenko, V.A. Tafeenko, D.V. Al´bov, L.A. Aslanov, E.R. Milaeva, Complexes of Organotin compounds with bis- and trisphosphonate derivatives of 2,6-ditertbutylphenol having antioxidant activity. Russ Chem. Bull. 64, 1419–1429 (2015). https://doi.org/10.1007/s11172-015-1026-z

    Article  CAS  Google Scholar 

  20. R.R. Arraq, A.G. Hadi, Synthesis, identification, and anti-oxidant activity of Di-Organotin (IV)-Cephalexin complexes. J. Med. Chem. Sci. 6, 392–401 (2023). https://doi.org/10.26655/JMCHEMSCI.2023.2.19

    Article  CAS  Google Scholar 

  21. S. Ramzan, S. Rahim, S.T. Hussain, K.B. Holt, J.K. Cockcroft, N. Muhammad, Z. Ur-Rehman, A. Nawaz, S. Shujah, Synthesis, characterization, X-ray structure, DNA binding, antioxidant and docking study of new organotin(IV) complexes. Appl. Organomet. Chem. 37, e7161 (2023). https://doi.org/10.1002/aoc.7161

    Article  CAS  Google Scholar 

  22. W. Sari, H.I. Qudus, S. Hadi, The chemical reactivity study of organotin(IV) 4-aminobenzoates using cyclic voltammetry and antioxidant activity test by the DPPH method. Rev. Chim. 71(10), 28–37 (2020). https://doi.org/10.37358/RC.20.10.8347

    Article  CAS  Google Scholar 

  23. M. Gielen, An overview of forty years Organotin Chemistry developed at the Free Universities of Brussels ULB and VUB. J. Braz Chem. Soc. 14, 870–877 (2003). https://doi.org/10.1590/S0103-50532003000600003

    Article  CAS  Google Scholar 

  24. S. Hadi, M. Rilyanti, Synthesis and in vitro anticancer activity of some organotin(IV) benzoate compounds. Orient. J. Chem. 26, 775–779 (2010)

    CAS  Google Scholar 

  25. S. Hadi, M. Rilyanti, Suharso, in vitro activity and comparative studies of some organotin (iv) benzoate derivatives against leukemia cancer cell, L-1210. Indo J. Chem. 12, 172–177 (2012). https://doi.org/10.22146/ijc.21359

    Article  CAS  Google Scholar 

  26. N. Uddin, F. Rashid, A. Haider, S.A. Tirmizi, A. Raheel, M. Imran, S. Zaib, P.L. Diaconescu, J. Iqbal, S. Ali, Triorganotin(IV) carboxylates as potential anticancer agents: their synthesis, physiochemical characterization, and cytotoxic activity against HeLa and MCF-7 Cancer Cells. Appl. Organomet. Chem. (2021). https://doi.org/10.1002/aoc.6165

    Article  PubMed  Google Scholar 

  27. S. Hadi, E.K. Winarno, H. Winarno, K.N. Berawi, T. Suhartati, N. Noviany, W. Simanjuntak, Y. Yandri, Synthesis and in vitro activity investigation of some dibutyl-, diphenyl-and triphenyltin (IV) carboxylates against leukemia cancer cell, L-1210. Pure Appl. Chem. 95, 823–832 (2023). https://doi.org/10.1515/pac-2023-0107

    Article  CAS  Google Scholar 

  28. S. Hadi, E.K. Winarno, H. Winarno, K.N. Berawi, T. Suhartati, Y. Yandri, W. Simanjuntak, Synthesis, characterization and in vitro activity study of some organotin(IV) carboxylates against leukemia cancer cell, L-1210. Sustain. Chem. Res. : Chem. Biochem. Aspects (2023). https://doi.org/10.1515/9783111071435-008

    Article  Google Scholar 

  29. S. Ramasamy, N. Abdul Wahab, N. Zainal Abidin, S. Manickam, Z. Zakaria, Growth inhibition of human gynecologic and Colon cancer cells by Phyllanthus watsonii through apoptosis induction. PLoS ONE. 7, e34793 (2012). https://doi.org/10.1371/journal.pone.0034793D

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. A. Szorcsik, L. Nagy, K. Gadja-Schrantz, L. Pellerito, E. Nagy, E.T. Edelmann, Structural studies on organotin(IV) complexes formed with ligands containing {S, N, O} donor atoms. J. Radioanal Nucl. Chem. 252, 523–530 (2002). https://doi.org/10.1023/A:1015802820423

    Article  CAS  Google Scholar 

  31. E.K. Winarno, H. Winarno, Susanto, Antiproliferative activity of extracts and fractions from irradiated Curcuma zanthorrhiza rhizomes against mouse leukemia and human cancer cell lines. Atom Indo. 45, 159–164 (2009). https://doi.org/10.17146/aij.2019.957

    Article  Google Scholar 

  32. R.A. Turner, Screening Methods in Pharmacology (Academic, New York, 1972), p. 255

    Google Scholar 

  33. Dachriyanus (2004) Spectroscopic Analysis of the Structure of Organic Compounds. LPTIK, Universitas Andalas, Padang, Indonesia, p.132. 

  34. M. López-Lázaro, A simple and reliable approach for assessing anticancer activity in vitro. Curr. Med. Chem. 22, 1324–1334 (2015). https://doi.org/10.2174/0929867322666150209150639

    Article  CAS  PubMed  Google Scholar 

  35. M.K. Amir, S. Khan, Z. Rehman, A. Shah, I.S. Butlerc, Anticancer activity of organotin(IV) carboxylates. Inorg. Chim. Acta. 423, 14–25 (2014). https://doi.org/10.1016/j.ica.2014.07.053

    Article  CAS  Google Scholar 

  36. Z.A. Siddiqi, M. Shahid, S. Kumar, M. Khalid, S. Noor, Synthesis, crystal structure and in vitro antitumor activity of carboxylate bridged dinuclear organotin(IV) complexes. J. Organomet. Chem. 694, 3768–3774 (2009). https://doi.org/10.1016/j.jorganchem.2009.07.030

    Article  CAS  Google Scholar 

  37. N. Awang, N.F. Kamaludin, I. Baba, K.M. Chan, N.F. Rajab, A. Hamid, Synthesis, characterization and Antitumor Activity of New Organotin(IV) Methoxyethyldithiocarbamate Complexes. Orient. J. Chem. 32, 101–107 (2016). https://doi.org/10.13005/ojc/320110

    Article  CAS  Google Scholar 

  38. A. Mohammed, R. Makia, M. Ali, R. Raheem, E. Yousif, Cytotoxic effects of Valsartan Organotin(IV) complexes on human Lung Cancer cells. Biointer Res. Appl. Chem. 11, 8156–8164 (2021). https://doi.org/10.33263/BRIAC111.81568164

    Article  CAS  Google Scholar 

  39. J.C. Pritchetta, L. Naesens, J. Montoya, Treating HHV-6 infections, the laboratory efficacy and clinical use of anti-HHV-6 agents, in Human Herpes Viruses HHV-6A, HHV-6B, and HHV-7. Diagnosis and Clinical Management, 3rd edn., ed. by L. Flamand, I. Lautenschlager, G. Krueger, D. Ablashi (Elsevier, Amsterdam, 2014), pp. 311–331. https://doi.org/10.1016/B978-0-444-62703-2.00019-7

    Chapter  Google Scholar 

  40. G. Indrayanto, G.S. Putra, F. Suhud, Validation of in-vitro bioassay methods: application in herbal drug research. Profiles Drug Subst. Excip Relat. Methodol. 46, 273–307 (2021). https://doi.org/10.1016/bs.podrm.2020.07.005

    Article  CAS  PubMed  Google Scholar 

  41. O.A. Peña-Morán, M.L. Villarreal, L. Álvarez-Berber, A. Meneses-Acosta, V. Rodríguez-López, Cytotoxicity, post-treatment recovery, and selectivity analysis of naturally occurring podophyllotoxins from Bursera fagaroides var. fagaroides on breast Cancer cell lines. Molecules. 21, 1013 (2016). https://doi.org/10.3390/molecules21081013

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. M. López-Lázaro, Editorial: how many times should we screen a chemical library to discover an anticancer drug? Drug Discov Today. 20, 167–169 (2015). https://doi.org/10.1016/j.drudis.2014.12.006

    Article  PubMed  Google Scholar 

  43. N. Weerapreeyakul, A. Nonpunya, S. Barusrux, T. Thitimetharoch, B. Sripanidkulchai, Evaluation of the anticancer potential of six herbs against a hepatoma cell line. Chin. Med. 7, 15 (2012). https://doi.org/10.1186/1749-8546-7-15

    Article  PubMed  PubMed Central  Google Scholar 

  44. M. López-Lázaro, Two preclinical tests to evaluate anticancer activity and to help validate drug candidates for clinical trials. Onco Targets Ther. 2, 91–98 (2015). https://doi.org/10.18632/oncoscience.132

    Article  Google Scholar 

  45. C. Pellerito, L. Nagy, L. Pellerito, A. Szorcsik, Biological activity studies on organotin(IV)n + complexes and parent compounds. J. Organomet. Chem. 691, 1733–1747 (2006). https://doi.org/10.1016/j.jorganchem.2005.12.025

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to thank to Higher Education Technology and Innovationa (HETI) Universitas Lampung, Republic of Indonesia for giving the funding for this project to be undertaken. Thank also goes to Dr. Huy Hoang of Institute of Molecular Biosciences (IMB) University of Queensland for NMR experimentation.

Funding

This work was funded by Higher Education Technology and Innovationa (HETI) Universitas Lampung, Republic of Indonesia for giving the funding for this project to be undertaken through Domestic Innovation Research and Collaboration 2023/2024 with contract number of 10629/UN26/HK.01.00/2023, 17 October 2023.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Lampung, Bandar Lampung, 35145, Indonesia

    Sutopo Hadi, Dea A. S. Thian, Muhammad D. Fansang & Tati Suhartati

  2. Research Center for Radiation Process Technology, Research Organization for Nuclear Energy (BATAN) - National Research and Innovation Agency (NRIA), Gedung 90, KST B.J. Habibie, Jl. Puspiptek, Muncul, Kec. Setu, Tangerang Selatan, 15314, Banten, Indonesia

    Ermin K. Winarno, Hendig Winarno & Susanto Susanto

  3. Medical Faculty, University of Lampung, Bandar Lampung, 35145, Indonesia

    Khairun N. Berawi

Authors
  1. Sutopo Hadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ermin K. Winarno
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hendig Winarno
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Susanto Susanto
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dea A. S. Thian
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Muhammad D. Fansang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Khairun N. Berawi
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Tati Suhartati
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

SH, EKW, HW and SS: the primary responsibility for the design of the work. SS, DAST, MDF, KNB and TS: substantial contributions to the work and analysis. SH, EKW and HW: contributed to the interpretation of the data. SH and HW: drafting and revising the work critically for important intellectual content. All authors read and approved the fnal manuscript.

Corresponding author

Correspondence to Sutopo Hadi.

Ethics declarations

Conflict of interest

The authors declare no conflict of interest.

Ethical Approval

Not applicable.

Informed Consent

Not applicable.

Consent for Publication

Not applicable.

Additional information

This paper is dedicated in memory of the late Dr. Charles E. Carraher, Jr. for his invaluable dedication as pioneer in the field of inorganic and organometallic polymers.

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hadi, S., Winarno, E.K., Winarno, H. et al. Synthesis, Characterization and Antiproliferative Activity Test of Some Diphenyltin(IV) Hydroxybenzoates Against A549, MCF-7 and HeLa Human Cancer Cell Lines. J Inorg Organomet Polym (2024). https://doi.org/10.1007/s10904-024-03042-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10904-024-03042-2

Keywords

Search

Navigation