Synthesis, characterization and in vitro activity study of some organotin(IV) carboxylates against leukemia cancer cell, L-1210
-
Sutopo Hadi
,
Ermin Katrin Winarno
Abstract
This paper presents successful resynthesizing of several dibutyl-, diphenyl-, and triphenyltin(IV) carboxylate compounds, and their activity against leukemia cancer cell, L-1210. The compounds were synthesized by reacting the dibutyltin(IV) oxide (DBTO) (1), diphenyltin(IV) oxide (DPTO) (3), and triphenyltin(IV) hydroxide (TPTOH) (5) with 3-hydroxybenzoic acid (3-HHBz). Prior to cancer activity tests, the compounds were characterized by UV–Vis, FT-IR, NMR (both 1H NMR and 13C NMR), and microanalysis to determine elemental composition of the samples. The anticancer tests revealed that triphenyltin(IV) 3-hydroxybenzoate (TPTHBz) (6) displayed significantly higher activity than those exhibited by dibutyltin(IV) di(3-hydroxybenzoate) (DBTHBz) (2) and diphenyltin(IV) di(3-hydroxybenzoate) (DPTHBz) (4).
Acknowledgments
The authors would like to thank to Higher Education, Technology, and Innovation (HETI) Universitas Lampung, Republic of Indonesia, for giving the funding for this project to be undertaken through Domestic Innovation Research and Collaboration with contract number of 9946/UN26/HK.01.03/2022, 1 November 2022. Thank also goes to Dr. Huy Hoang of Institute of Molecular Biosciences (IMB) University of Queensland for NMR experimentation.
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: None declared.
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Devi, J, Kumar, B, Taxak, B. Recent advancements of organotin(IV) complexes derived from hydrazone and thiosemicarbazone ligands as potential anticancer agents. Inorg Chem Commun 2022;139:109208. https://doi.org/10.1016/j.inoche.2022.109208.Search in Google Scholar
2. Salam, MA, Affan, MA, Ahmad, FB, Arafath, MA. Organotin(IV) complexes with pyruvic acid phenylhydrazone (HPAPD): synthesis, spectral characterization, and in vitro antibacterial activity. J Coord Chem 2012;65:1999–2007. https://doi.org/10.1080/00958972.2012.687104.Search in Google Scholar
3. Pellerito, L, Nagy, L. Organotin(IV)n+ complexes formed with biologically active ligands: equilibrium and structural studies, and some biological aspects. Coord Chem Rev 2002;224:111–50. https://doi.org/10.1016/s0010-8545(01)00399-x.Search in Google Scholar
4. Rocha, CS, de Morais, BP, Rodrigues, BL, Donnici, CL, de Lima, GM, Ardisson, JD, et al.. Spectroscopic and X-ray structural characterization of new organotin carboxylates and their in vitro antifungal activities. Polyhedron 2016;117:35–47. https://doi.org/10.1016/j.poly.2016.05.031.Search in Google Scholar
5. Samsuar, S, Simanjuntak, W, Qudus, HI, Yandri, Y, Herasari, H, Hadi, S. In vitro antimicrobial activity study of some organotin(IV) chlorobenzoates against Staphylococcus aureus and Escherichia coli. J Adv Pharm Educ Res 2021;11:17–22. https://doi.org/10.51847/kaijzkafco.Search in Google Scholar
6. Hadi, S, Lestari, S, Suhartati, T, Qudus, HI, Rilyanti, M, Herasari, D, et al.. Synthesis and comparative study on the antibacterial activity organotin (IV) 3-hydroxybenzoate compounds. Pure Appl Chem 2021;93:623–8. https://doi.org/10.1515/pac-2020-1103.Search in Google Scholar
7. Annissa, Suhartati, T, Yandri, HS, Hadi, S. Antibacterial activity of diphenyltin(IV) and triphenyltin(IV) 3-chlorobenzoate against Pseudomonas aeruginosa and Bacillus subtilis. Orient J Chem 2017;33:1133–9. https://doi.org/10.13005/ojc/330310.Search in Google Scholar
8. Hadi, S, Hermawati, E, Noviany, N, Suhartati, T, Yandri, Y. Antibacterial activity test of diphenyltin(IV) dibenzoate and triphenyltin(IV) benzoate compounds against Bacillus substilis and Pseudomonas aeruginosa. Asian J Microbiol Biotechnol Environ Sci 2018;20:113–9.Search in Google Scholar
9. Susangka, AL, Hadi, S, Noviany, N, Kiswandono, AA, Nurhasanah, Pandiangan, KD. Synthesis, characterization, and comparison of disinfectant bioactivity test of two triphenyltin(IV) compounds. J Turk Chem Soc, Sect A: Chem 2022;9:1047–54. https://doi.org/10.18596/jotcsa.1097465.Search in Google Scholar
10. Hadi, S, Suhartati, T, Noviany, N, Pandiangan, KD, Yandri, Y, Simanjuntak, W, et al.. Disinfecting activity of some diphenyltin(IV) benzoate derivative compounds. Pure Appl Chem 2022;94:799–807. https://doi.org/10.1515/pac-2021-1106.Search in Google Scholar
11. Hansch, C, Verma, RP. Larvicidal activities of some organotin compounds on mosquito larvae: a QSAR study. Eur J Med Chem 2009;44:260–73. https://doi.org/10.1016/j.ejmech.2008.02.040.Search in Google Scholar PubMed
12. Hadi, S, Noviany, Rilyanti, M. In vitro antimalarial activity of some organotin(IV)2-Nitrobenzoate compounds against Plasmodium falciparum. Maced J Chem Chem Eng 2018;37:185–91. https://doi.org/10.20450/mjcce.2018.1414.Search in Google Scholar
13. Hadi, S, Fenska, MD, Noviany, N, Satria, H, Simanjuntak, W, Naseer, MM. Synthesis and antimalarial activity of some triphenyltin(IV) aminobenzoate compounds against Plasmodium falciparum. Main Met Group Chem 2021;44:256–60. https://doi.org/10.1515/mgmc-2021-0028.Search in Google Scholar
14. Hazani, NN, Mohd, Y, Ghazali, SAISM, Farina, Y, Dzulkifli, NN. Electrochemical studies on corrosion inhibition behaviour of synthesised 2-acetylpyridine 4-ethyl-3-thiosemicarbazone and its tin(IV) complex for mild steel in 1 M HCl solution. J Electrochem Sci Technol 2019;10:29–36.Search in Google Scholar
15. Hadi, S, Afriyani, H, Anggraini, WD, Qudus, HI, Suhartati, T. The synthesis and potency study of some dibutyltin(IV) dinitrobenzoate compounds as corrosion inhibitor for mild steel HRP in DMSO-HCl solution. Asian J Chem 2015;27:1509–12. https://doi.org/10.14233/ajchem.2015.18590.Search in Google Scholar
16. Hadi, S, Rilyanti, M. Synthesis and in vitro anticancer activity of some organotin(IV) benzoate compounds. Orient J Chem 2010;26:775–9.Search in Google Scholar
17. Uddin, N, Rashid, F, Haider, A, Tirmizi, SA, Raheel, A, Imran, M, et al.. 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;35:e6165. https://doi.org/10.1002/aoc.6165.Search in Google Scholar
18. Hadi, S, Rilyanti, M, Suharso, S. In vitro activity and comparative studies of some organotin(IV) benzoate derivatives against leukemia cancer cell: L-1210. Indo J Chem 2012;12:172–7. https://doi.org/10.22146/ijc.21359.Search in Google Scholar
19. Turner, RA. Screening methods in pharmacology. New York: Academic Press; 1972.Search in Google Scholar
20. Hadi, S, Rilyanti, M, Nurhasanah. Comparative study on the antifungal activity of some di- and tributyltin(IV) carboxylate compounds. Mod Appl Sci 2009;3:12–7. https://doi.org/10.5539/mas.v3n1p12.Search in Google Scholar
21. Chohan, ZH, Rauf, A. Some biologically active mixed ligand complexes of Co(II), Cu(II) and Ni(II) with ONO, NNO and SNO donor nicotinoylhydrazine-derived ligands. Synth React Inorg Met Org Chem 1996;26:591–604. https://doi.org/10.1080/00945719608004764.Search in Google Scholar
22. Gershon, H. Antifungal activity of bischelates of 5-7-and 5,7-halogenated 8-quinols with copper(II). Determination of the long and short access of the pores in the fungal spore wall. J Med Chem 1974;17:824–7. https://doi.org/10.1021/jm00254a009.Search in Google Scholar PubMed
23. Crowe, AJ. The antitumour activity of tin compounds. In: Gielen, M, editor. Metal-based drugs. Freund: Freund Publishing House; 1989, vol 1: 103–49 pp.Search in Google Scholar
© 2023 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Reviews
- Biopolymeric composite materials for environmental applications
- Evaluation of phytochemicals and amino acid profiles of four vegetables grown on a glyphosate contaminated soil in Southwestern Nigeria
- Synthesis, characterization and in vitro activity study of some organotin(IV) carboxylates against leukemia cancer cell, L-1210
- Maximizing advantages and minimizing misinterpretation risks when using analogies in the presentation of chemistry concepts: a design challenge
- Computational chemistry in the undergraduate inorganic curriculum
- Phytochemical components and GC–MS analysis of Petiveria alliaceae L. fractions and volatile oils
- Sugar palm (Arenga p innata) thermoplastic starch nanocomposite films reinforced with nanocellulose
- Photoprotection strategies with antioxidant extracts: a new vision
- Light-driven bioprocesses
- A systematic DFT study of arsenic doped iron cluster AsFe n (n = 1–4)
Articles in the same Issue
- Frontmatter
- Reviews
- Biopolymeric composite materials for environmental applications
- Evaluation of phytochemicals and amino acid profiles of four vegetables grown on a glyphosate contaminated soil in Southwestern Nigeria
- Synthesis, characterization and in vitro activity study of some organotin(IV) carboxylates against leukemia cancer cell, L-1210
- Maximizing advantages and minimizing misinterpretation risks when using analogies in the presentation of chemistry concepts: a design challenge
- Computational chemistry in the undergraduate inorganic curriculum
- Phytochemical components and GC–MS analysis of Petiveria alliaceae L. fractions and volatile oils
- Sugar palm (Arenga p innata) thermoplastic starch nanocomposite films reinforced with nanocellulose
- Photoprotection strategies with antioxidant extracts: a new vision
- Light-driven bioprocesses
- A systematic DFT study of arsenic doped iron cluster AsFe n (n = 1–4)
