In vitro antimalarial activity of some organotin(IV)2-nitrobenzoate compounds against Plasmodium falciparum

Authors

DOI:

https://doi.org/10.20450/mjcce.2018.1414

Keywords:

antimalaria activity, IC50, organotin(IV) nitrobenzoate, P. falcifarum

Abstract

Antimalarial activity study of organotin(IV) derivatives with nitrobenzoic acid derivatives used as ligands has been performed. The targeted compounds were prepared from their organotin(IV) chlorides via dibutyltin(IV) oxide, diphenyltin(IV) dihydroxide, and triphenyltin(IV) hydroxide intermediate products, followed by reacting the intermediate products with 2-nitrobenzoic acid. The antimalarial activity was performed against P. falciparum. The results showed that the IC50values of dibutyiltin(IV) di-2-nitrobenzoate, diphenyltin(IV) di-2-nitrobenzoate, and triphenyltin(IV) 2-nitrobenzoate were in 8.4 × 10‑3, 5.3 × 10–2, and 9.1 × 10–3 µg/ml, respectively. The IC50 values were slightly higher than the value for chloroquine (2 × 10–3 µg/ml) used as the positive control; however, one advantage is that all prepared organotin(IV) compounds were not resistant to Plasmodium, making the use of organotin(IV) as an antimalarial is possible. The results indicated that the derivative of triphenyltin(IV) was more potent when used as an antimalarial, as expected, and has potential to be developed as an antimalarial drug in the future.

Author Biographies

Sutopo Hadi, University of Lampung

Professor of Chemistry

Noviany Noviany, Universitas Lampung

Associate Professor of Organic Chemistry

Mita Rilyanti, Universitas Lampung

Associate Professor of Inorganic Chemistry

References

E. R. T. Tiekink, Structural chemistry of organotin car-boxylates: A review of the crystallographic literature, App. Organomet. Chem. 5, 1–30 (1991).

K. Shahid, S. Ali, S. Shahzadi, Z. Akhtar, Organotin(IV) complexes on aniline derivaties, Part II: Synthesis and spectroscopic characterization of organotin(IV) deriva-tives of 2-[4-bromoanailine)carboxyl]benzoic acid, Turk. J. Chem., 27, 209–215 (2003).

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).

B. Gleeson, J. Claffey, D. Ertler, M. Hogan, H. Müller-Bunz, F. Paradisi, D. Wallis, and M. Tacke, Novel organotin antibacterial and anticancer drugs, Polyhedron, 27, 3619–3624 (2008).

W. Rehman, A. Badshah, S. Khan, L. T. A. Tuyet, Syn-thesis, characterization, antimicrobial and antitumor screening of some diorganotin(IV) complexes of 2-[(9H-Purin-6-ylimino)]-phenol, Eur. J. Med. Chem., 44, 3981–3985(2009).

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

S. Hadi, M. Rilyanti, Suharso, In Vitro activity and comparative studies of some organotin(IV) benzoate de-rivatives against leukemia cancer cell: L-1210, Indo. J. Chem., 12, 172–177 (2012).

S. Hadi, B. Irawan, Efri, The antifungal activity test of some organotin(IV) carboxylates, J. Appl. Sci. Res., 4, 1521–1525(2008).

S. Hadi, M. Rilyanti, Nurhasanah, Comparative study on the antifungal activity of some di- and tributyltin(IV) carboxylate compounds, Modern Appl. Sci.,3 (2), 12–17 (2009).

R. Singh, P. Chaudary, N. K. Khausik, A Review: Organotin compounds in corrosion inhibition, Rev. Inorg. Chem., 30, 275–294 (2010).

R. B. Rastogi, M. M. Singh, K. Singh, M. Yadav, Organotin dithiobiurets as corrosion inhibitors for mildsteel-dimethyl sulfoxide containing HCl, Afr. J. Pure Appl. Chem.,5(2), 19–33(2011).

H. Kurniasiah, M. Nurissalam, B. Iswantoro, H. Afiyani, H. I. Qudus, S. Hadi., The Synthesis, characterization and comparative anticorrosion study of some organotin(IV) 4-chlorobenzoates, Orient. J. Chem., 31, 2377–2383 (2015).

S. Hadi, H. Afriyani, W. D. Anggraini, H. I. Qudus, T. Suhartati, 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., 27, 1509–1512 (2015).

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).

WHO, Roll Back Malaria Program. Available at. http://www.who.int/malaria/en/. 2011. [Verified April 20, 2011]

A. A. James, Mosquito molecular genetics: the hands that feed bite back, Science, 257, 37–38 (1992).

I. R. F. Elyazar, S. I. Hay, J. K. Baird, Malaria distribution, prevalence, drug resistance and control in Indonesia, Adv Parasitol., 74, 41–175 (2011).

WHO. Malaria Profile of Indonesia. http://www.who. int/malaria/publications/country-profiles/profile_idn_en. pdf. 2016 (Verifed on October 5, 2018)

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).

M. Nath, R. Yadav, M. Gielen, H. Dalil, D. de Vos, G. Eng, Synthesis, characteristic spectral studies and in vitro antimicrobial and antitumour activities of organotin(IV) complexes of Schiff bases derived from amino-acids, Appl. Organometal. Chem., 11, 727–736 (1997).

Sudjadi, The Structure Determination of Organic Com-pounds. Ghalia Publishers, 1985. (In Indonesian).

M. Rilyanti, S. Hadi, Synthesis, characterization and thermal stability of complex cis-[Co(bipy)2(CN)2] and its interaction with NO2 gas, Russ. J. Inorg. Chem., 56, 418–421 (2011).

S. Hadi, T. G. Appleton, G. A. Ayoko, Reactions of fac-[PtMe2(OMe)(H2O)3]+ with halide ions: effect of halide trans effect on methoxide hydrolysis, Inorg. Chim. Acta., 352, 201–207 (2003).

S. Hadi, T. G. Appleton, Reactions of cisplatin hydro-lytes, cis-[Pt(15NH3)2(H2O)2]2+, with N-acetyl-L-cysteine, Russ. J. Inorg. Chem., 55, 223–228 (2010).

Z. H. Chohan, A. Rauf, Some biologically active mixed ligand complexes of Co(II), Cu(II) and Ni(II) with ONO, NNO and SNO donor nicotinoylhydrazine-derived lig-ands, Synth. React. Inorg. Met.-Org. Chem., 26, 591–604 (1996).

H. Gershon, Antifungal activity of bischelates of 5-, 7-, and 5,7-halogenated 8-quinols with copper(II). Determi-nation of the long and short acces of the pores in the fungal spore wall, J. Med. Chem., 17, 824–827 (1974).

A. J. Crowe, The antitumour activity of tin compounds; in Gielen M., (Ed.) Metal-Based Drugs, 1, 103–149 (1989).

Downloads

Published

2018-11-07

How to Cite

Hadi, S., Noviany, N., & Rilyanti, M. (2018). In vitro antimalarial activity of some organotin(IV)2-nitrobenzoate compounds against Plasmodium falciparum. Macedonian Journal of Chemistry and Chemical Engineering, 37(2), 185–191. https://doi.org/10.20450/mjcce.2018.1414

Issue

Vol. 37 No. 2 (2018)

Section

Inorganic Chemistry

License

The authors agree to the following licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)

  • Adapt — remix, transform, and build upon the material
  • for any purpose, even commercially.
The licensor cannot revoke these freedoms as long as you follow the license terms.

 Under the following terms:

  • Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.

  • NonCommercial — You may not use the material for commercial purposes.