Synthesis, Characterization, and Comparison of Disinfectant Bioactivity Test of Two Triphenyltin(IV) Compounds

Year 2022, Volume: 9 Issue: 4, 1047 - 1054, 30.11.2022

Aisyah Larasaty Susangka , Sutopo Hadı , Noviany Noviany , Agung A. Kiswandono , Nurhasanah Nurhasanah , Kamisah D. Pandiangan

https://doi.org/10.18596/jotcsa.1097465

Cited By: 5

Abstract

This paper aims to report the synthesis of two new organotin(IV) carboxylate derivatives, triphenyltin(IV) 4-aminobenzoate (2) and triphenyltin(IV) 4-nitrobenzoate (3) and to examine their antibacterial activity as a disinfectant. These compounds were prepared by reacting triphenyltin(IV) hydroxide (1) with 4-aminobenzoic acid and 4-nitrobenzoic acid, respectively. Compound (2) was obtained as a yellow solid with a yield of 84.09% and compound (3) in the form of a white solid with a yield of 80.70%. These compounds were well characterized using UV-Vis spectrometry, FT-IR spectrometry and NMR spectroscopy. The bioactivity test as a disinfectant was tested against Salmonella typhosa and Staphylococcus aureus. The activity test was carried out by measuring the optical density (OD) of the tested compounds with concentration variations of 5x10-3, 1x10-3, and 5x10-4 M in methanol and 5% dimethyl sulfoxide (DMSO), commercial Wipol (2.5% pine oil) was used as a positive control with observations monitored at contact times of 0, 5, 10, and 15 minutes. The results showed that of both compounds were active against the two bacteria compared to the positive control with compound 3 found to be more active than compound 2.

Keywords

antibacterial, disinfectant, S. typhosa, S. aureus, triphenyltin(IV) compounds

Supporting Institution

Directorate of Research and Community Services, The Ministry of Education, Cultural, Research and Technology, Indonesia

Project Number

Penelitian Dasar

Thanks

Institute of Research and Community Services, Universitas Lampung

References

• 1. Sirajuddin M, Ali S, Tahir MN. Organotin(IV) derivatives based on 2-((2-methoxyphenyl)carbamoyl)benzoic acid: Synthesis, spectroscopic characterization, assessment of antibacterial, DNA interaction, anticancer and antileishmanial potentials. Journal of Molecular Structure. 2021 Apr;1229:129600.
• 2. 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 [Internet]. 2021 Apr [cited 2022 Sep 14];35(4). Available from: https://onlinelibrary.wiley.com/doi/10.1002/aoc.6165
• 3. 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 Oct;117:35–47.
• 4. Pellerito L. Organotin(IV)n+ complexes formed with biologically active ligands: equilibrium and structural studies, and some biological aspects. Coordination Chemistry Reviews. 2002 Jan;224(1–2):111–50.
• 5. Tiekink ERT. Structural chemistry of organotin carboxylates: a review of the crystallographic literature. Appl Organometal Chem. 1991 Jan;5(1):1–23.
• 6. Szorcsik A, Nagy L, Gajda-Schrantz K, Pellerito L, Nagy E, Edelmann F. Structural studies on organotin(IV) complexes formed with ligands containing S,N,O donor atoms. Journal of Radioanalytical and Nuclear Chemistry. 2002;252(3):523–30.
• 7. Ahmed S, Ali S, Ahmed F, Bhatti MH, Badshah A, Mazhar M, et al. Synthesis, spectroscopic characterization, and biological applications of organotin(iv) derivatives of 2-(n-maleoyl)-3-phenylpropanoic acid. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 2002 Sep 26;32(8):1521–36.
• 8. Rocha C, De Morais B, Rodrigues B, Donnici C, De Lima G, Ardisson J, et al. Spectroscopic and X‐ray structural characterization of new polymeric organotin (IV) carboxylates and their in vitro antifungal activities: Part II. Applied Organometallic Chemistry. 2017;31(7):e3645.
• 9. Muhammad N, Shah NA, Ali S, Elahi SN, Rehman W, Shujah S, et al. Theoretical and Experimental in vitro Antifungal and Antitumor Activities of Organotin(IV) Derivatives of 3-(4-nitrophenyl)-2-methylacrylic acid. Pharmaceutical Chemistry Journal. 2019 Nov 1;53(8):689–96.
• 10. Sari W, Qudus HI, Hadi S. The chemical reactivity study of organotin (IV) 4-aminobenzoates using cyclic voltammetry and antioxidant activity test by the DPPH method. Revista de Chimie. 2020;71(10):28–37.
• 11. Tyurin VYu, Yaohuan W, Prishchenko AA, Shpakovsky DB, Gracheva YuA, Antonenko TA, et al. Complexes of organotin compounds with bis- and trisphosphonate derivatives of 2,6-di-tert-butylphenol having antioxidant activity. Russian Chemical Bulletin. 2015 Jun 1;64(6):1419–29.
• 12. Hadi S, Qudus HI, Wattana-Amorn P. The Potency Study of Organotin (IV) 3-Nitrobenzoate Compounds as Antimalarial Agents. In IOP Publishing; 2019. p. 012012.
• 13. Hansch C, Verma RP. Larvicidal activities of some organotin compounds on mosquito larvae: A QSAR study. European Journal of Medicinal Chemistry. 2009 Jan;44(1):260–73.
• 14. Hadi S, Noviany N, Rilyanti M. In vitro antimalarial activity of some organotin (IV) 2-nitrobenzoate compounds against Plasmodium falciparum. Macedonian Journal of Chemistry and Chemical Engineering. 2018;37(2).
• 15. 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 Group Metal Chemistry. 2021;44(1):256–60.
• 16. Roner MR, Carraher Jr CE, Shahi K, Barot G. Antiviral activity of metal-containing polymers—Organotin and cisplatin-like polymers. Materials. 2011;4(6):991–1012.
• 17. Roner MR, Carraher CE, Miller L, Mosca F, Slawek P, Haky JE, et al. Organotin polymers as antiviral agents including inhibition of Zika and Vaccinia viruses. Journal of Inorganic and Organometallic Polymers and Materials. 2020;30(3):684–94.
• 18. Rehman W, Badshah A, Khan S. Synthesis, characterization, antimicrobial and antitumor screening of some diorganotin (IV) complexes of 2-[(9H-Purin-6-ylimino)]-phenol. European journal of medicinal chemistry. 2009;44(10):3981–5.
• 19. Hadi S, Rilyanti M, Suharso S. In vitro activity and comparative studies of some organotin (iv) benzoate derivatives against leukemia cancer cell, l-1210. Indonesian Journal of Chemistry. 2012;12(2):172–7.
• 20. Syed Annuar SN, Kamaludin NF, Awang N, Chan KM. Cellular basis of organotin (IV) derivatives as anticancer metallodrugs: a review. Frontiers in chemistry. 2021;522.
• 21. Singh R, Chaudhary P, Kaushik N. A Review: Organotin compounds in corrosion inhibition. Reviews in Inorganic Chemistry. 2010;30(4):275–94.
• 22. Hadi S. The anticorrosion activity of dibutyltin (IV) and diphenyltin (IV) dihydroxybenzoate compounds towards HRP mild steel in NaCl. Journal of Chemical and Pharmaceutical Research. 2016;8(8):975–80.
• 23. 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. Journal of Electrochemical Science and Technology. 2019;10(1):29–36.
• 24. 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 and Applied Chemistry. 2021;93(5):623–8.
• 25. Hadi S, Simanjuntak W, Qudus HI, Yandri Y, Herasari D. In vitro antimicrobial activity study of some organotin (IV) chlorobenzoates against Staphylococcus aureus and Escherichia coli. Journal of Advanced Pharmacy Education & Research [JAPER]. 2021;11(2):17–22.
• 26. Hadi S, Qudus HI, Simanjuntak W. In vitro antibacterial activity of some of dibutyltin (IV) chlorobenzoate derivatives against Staphylococcus aureus and Escherichia coli. ARPN Journal of Engineering and Applied Sciences. 2021;16(15):1623–9.
• 27. Hadi S, Irianti NT, Noviany N. Sintesis, Karakterisasi, dan Uji Aktivitas Antibakteri Senyawa Organotimah (IV) 4-Nitrobenzoat. ALCHEMY Jurnal Penelitian Kimia. 2022;18(1):19–29.
• 28. 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 Journal of Microbiology, Biotechnology & Environmental Sciences. 2018;20(1):113–9.
• 29. Annissa A, Suhartati T, Yandri Y. Antibacterial Activity of Diphenyltin (IV) and Triphenyltin (IV) 3-Chlorobenzoate Againts Pseudomonas aeruginosa and Bacillus subtilis. Oriental Journal of Chemistry. 2017;33(3):1133–9.
• 30. Hadi S, Suhartati T, Noviany N, Pandiangan KD, Yandri Y, Simanjuntak W, et al. Disinfecting activity of some diphenyltin (IV) benzoate derivative compounds. Pure and Applied Chemistry. 2022;
• 31. Chan ECS, Pelczar MJ. Instructor’s manual to accompany Elements of microbiology. McGraw-Hill Book Company; 1981.
• 32. Lorian V, editor. In: Antibiotics in Laboratory Medicine. Baltimore: William and Wilkins co.; 1980. p. 1–22.
• 33. Lorian V, editor. In: Antibiotics in Laboratory Medicine. Baltimore: William and Wilkins co.; 1980. p. 170–8.
• 34. Lorian V, editor. In: Antibiotics in Laboratory Medicine. Baltimore: William and Wilkins co.; 1980. p. 511–2.
• 35. Amsterdam D. In: Antibiotics in Laboratory Medicine. 6th edition. Philadelphia: LWW Publishers; 2014. p. 807.
• 36. Noviany N, Sialdian D, Setiawan A, Irawan B, Azmi MN, Sutopo H. Bioassay-guided separation approach for characterization of new antibacterial fractions from the stem roots extracts of Archidendron jiringa. Journal of the Turkish Chemical Society Section A: Chemistry. 2021;8(2):391–402.
• 37. Sulaiman M, Hassan Y, TOK TT, Noundou XS. Synthesis, antibacterial activity and docking studies of benzyl alcohol derivatives. Journal of the Turkish Chemical Society Section A: Chemistry. 2020;7(2):481–8.