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Synthesis and comparative study on the antibacterial activity organotin(IV) 3-hydroxybenzoate compounds

  • Sutopo Hadi EMAIL logo , Sri Lestari , Tati Suhartati , Hardoko Insan Qudus , Mita Rilyanti , Dian Herasari und Yandri Yandri
Veröffentlicht/Copyright: 7. Juni 2021
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Pure and Applied Chemistry
Aus der Zeitschrift Pure and Applied Chemistry Band 93 Heft 5

Abstract

The synthesis and comparative study on the antibacterial activity of three organotin(IV) compounds, namely dibutyltin(IV) bis-(3-hydroxybenzoate), [Bu2Sn(3-HBz)2] (7), diphenyltin(IV) bis-(3-hydroxybenzoate), [Ph2Sn(3-HBz)2] (8), and triphenyltin(IV) 3-hydroxybenzoate, [Ph3Sn(3-HBz)] (9) which were prepared by the reaction of dibutyltin(IV) oxide, [Bu2SnO] (4), diphenyltin(IV) dihydroxide, [Ph2Sn(OH)2] (5), and triphenyltin(IV) hydroxide, [Ph3SnOH] (6) with 3-hydroxybenzoic acid (3-HBz) has successfully been performed. The characterization of these compounds were done using 1H and 13C NMR, IR, UV spectroscopies and their compositions were determined based on microanalytical data. Antibacterial activity of these compounds was demonstrated at concentrations of 1.89 × 10−4, 1.81 × 10−4, and 1.72 × 10−4 M, respectively by dilution method against Pseudomonas aeruginosa. Similarly, the compounds were active at concentration of 1.87 × 10−4, 1.79 × 10−4, and 1.71 × 10−4 M, respectively, against Bacillus subtilis. These activities are comparable to that of streptomycin at a concentration of 1.70 × 10−4 M as a positive control, but the halozone of compounds 7, 8, and 9 were slightly lower than that of streptomycin’s halozone. The results obtained suggest that the compounds synthesized have potential as antibacterial agents.

Keywords: Antibacterial activity; B. subtilis ; chemistry and its applications; organotin(IV) 3-hydroxybenzoate; P. Aeruginosa ; VCCA-2020

Introduction

Organotin(IV) compounds have been extensively studied not only because their interesting structural features but also they have been known to show strong many biological activities [1], [2], [3], [4]. Their activities mainly are affected by the functional organic ligand attached to the Sn metal center as well the numbers of the ligand present [2], as a result many derivatives have been synthesized and investigated for their biological activity, such as antifungal [1], [5], anticancer and antitumor [6], [7], [8], [9], antiviral [10], antibacterial [11], [12], antimalarial [13], [14], and inhibitor of corrosion [15], [16], [17], [18].

The resistance of bacteria to antibacterial drugs has become a very serious problem in various sectors, thus special attention is needed to overcome the problem [19], [20]. For this reason, attempts to find new antibacterial drug have been extensively conducted [20], [21].

A compound considered as antibacterial if it has the ability inhibit the growth of bacteria. As a result of antibacterial action, the ability of microorganism to infect and cause disease, and damage foodstuffs is prevented [20], [21].

Based on the potential application of organotin(IV) carboxylate compound as describe above, in this work, we report the synthesis and comparative study on the antibacterial activity of three derivative organotin(IV) compounds of dibutyltin(IV), diphenyltin(IV), and triphenyltin(IV) with 3-hydroxybenzoate as ligand against two bacteria, Gram-positive Bacillus subtilis and Gram-negative Pseudomonas aeruginosa.

Experimental

Materials

All reagents used were of AR grade. Dibutyltin(IV) dichloride, ([Bu2SnCl2]), (1), diphenyltin(IV) dichloride ([Ph2SnCl2]) (2), triphenyltin(IV) chloride ([Ph3SnCl]) (3), 3-hydroxybenzoic acid, (3-HBz), and the control drug, streptomycin were obtained from Sigma–Aldrich, sodium hydroxide (NaOH) and methanol (CH3OH) were JT Baker products and they were used as received without further purification. Gram-negative bacteria P. aeruginosa was obtained from Department of Microbiology, University of Indonesia, Jakarta and Gram-positive bacteria B. subtilis ITBCCB148 was obtained from Biochemistry Laboratory, Department of Chemistry, University of Lampung Indonesia.

Instrumentations

Elemental analyses (CHNS) were conducted on Fision EA 1108 series elemental analyzer. IR spectra were recorded on a Bruker VERTEX 70 FT-IR spectrophotometer with KBr discs in the range of 4000–400 cm−1. 1H and 13C NMR spectra were recorded on a Bruker AV 600 MHz NMR (600 MHz for 1H and 150 MHz for 13C). All experiments were run in DMSO-d6 at 298 K. The number of runs used for 1H experiments were 32 with reference at DMSO signal at 2.5 ppm, while the 13C were 1000–4000 scans with the reference DMSO signal at 39.5 ppm. The UV spectra were recorded in the UV region and were measured using a UV-Shimadzu UV-245 Spectrophotometer. Measurements were performed in 1 mL quartz-cells. Solutions were prepared using methanol as the solvent with concentration of 1.0 × 10−4 M.

Preparation of organotin(IV) 3-hydroxybenzoate

The organotin(IV) 3-hydroxybenzoate compounds used in this work were prepared based on the procedures previously reported [8, 9, 12, 14, 16–18], adapted from the work available in the literature [3]. For example the procedure in the preparation of [Ph3Sn(3-HBz)] (9) was as follows:

A mass of 3.855 g (0.01 mol) [Ph3SnCl] (3) in 50 mL methanol was added 0.4 g (0.01 mol) NaOH. The reaction mixtures were stirred for about 60 min. Compound [Ph3SnOH] (6) was precipitated out as white solid, filtered off, washed with double distilled water then with methanol three times and dried in vacuo till they are ready for analysis and further reaction. The yield was 3.42 g (93 %).

A mass of 0.5505 g (1.5 mmol) compound 6 in 30 mL of methanol was added with 1 mol equivalent of 3-HBz (0.207 g) and was refluxed for 4 h at 60–61 °C. After removal of the solvent by rotary evaporator, the compound [[Ph3Sn(3-HBz)] (9) which was obtained was dried in vacuo until they are ready for analysis and further use for antibacterial activity test. The yield was 0.672 g (92 %). The same procedure was also used in the synthesis of [Bu2Sn(3-HBz)2] (7) from compound 4 and Ph2Sn(3-HBz)2] (8) from compound 5 where 2 mol equivalents of 3-HBz acid were added. The compounds synthesized obtained were as follows:

[Bu2Sn(3-HBz)2] (7): white-yellowish solid; UV λmax. (MeOH) nm (log ε): 294; IR νmax. (KBr) cm−1: 2925.63 (Bu), 1584.07 (C=O), 1506.87 (CO2 asym), 1243.4 (Sn–O–C), 778.7 (Sn–Bu), 435.7 (Sn–O); 1H NMR (in DMSO-d6, 600 MHz) δ (ppm): Hα: 1.6 (t), Hβ:1.4 (m); Hγ: 1.29 (t); Hδ: 0.93 (t), H in benzoate = 7.34–783 (m); 13C NMR (in DMSO-d6, 150 MHz): δ (ppm): Cα: 26.2, Cβ: 25.4, Cγ: 21.8, Cδ: 14.1, C1: 165.0; C2: 139.3, C3: 132.2, C4: 138.4, C5: 125.1, C6: 128.6, C7: 129.7; microelemental analysis: found (calculated): C 51.76 (52.07), H 5.48 (5.52).

[Ph2Sn(3-HBz)2] (8): white solid; UV λmax. (MeOH) nm (log ε): 210 and 297; IR νmax. (KBr) cm−1: 1597.2 (C=O), 1690.1 (CO2 sym), 1479.3; 725.7 (phen), 1289.2 (Sn–O–C), 598.4 (Sn–O); 1H NMR (in DMSO-d6, 600 MHz) δ (ppm): H2 & H6 7.52 (d, 4H); H3 & H5 7.56 (t, 4H); H4 7.42 (t, 2H), H in benzoate: 7.70–7.90 (m); 13C NMR (in DMSO-d6, 150 MHz): δ (ppm): C(phen) C1: 129.3, C2 & 6: 129.1, C3 & 5: 128.9, C4: 128.1, C7 165.7, C8 131.4, C9 130.2, C10 134.0, C11 133.8, C12 130.0, C13 128.4; microelemental analysis: found (calculated): C 56.65 (57.04), H 3.61 (3.66).

[Ph3Sn(3-HBz)] (9): white solid; UV λmax. (MeOH) nm (log ε): 234 and 293; IR νmax. (KBr) cm−1: 3437.3 (OH), 1624.7 (C=O), 1632.9 (CO2 asym), 1551.8; 730.8 (phen), 1290.1 (Sn–O–C), 726.4 (Sn–O); 1H NMR (in DMSO-d6, 600 MHz) δ (ppm): H2 = H6 7.59 (d, 6H); H3 & H5 7.46 (t, 6H); H4: 7.33 (t, 3H), H in benzoate: H9 = 7.83 (s); H11 = 7.60 (d); H12 = 7.60 (d); H13 = 7.60 (d); 13C NMR (in DMSO-d6, 150 MHz): δ (ppm): C(phen) C2 & C6 = 131.7, C3 & C5 = 129.2, C4 = 126.9; C7 = 165.3; C8 = 137.2; C9 = 132.9; C10 = 129.5; C11 = 128.4; C12 = 128.2; C13 = 130.0; microelemental analysis: found (calculated): C 60.79 (61.60), H 4.02 (4.11).

Antibacterial activity test

Antibacterial activity test by diffusion test

Nutrient agar (NA) was used as the media for the antibacterial activity test. In 100 mL aquadest was dissolved 2.8 g of NA, heated and sterilized by autoclave at 121 °C, pressure of 1 atm for 15 min Fifteen milliliters of sterile media was placed on sterilized petri disc. The preparation of the media was conducted at laminar air flow, and left the media to solidify.

The diffusion test method was performed based on the procedure available in the literature [22], [23] and as follows: one ose of B. subtilis and P. aeruginosa was diluted with 2 mL of saline solution (NaCl 0.85 %) and was used as bacteria suspension. One milliliter of the suspension was then inoculated on NA, flattened with spreader. Four paper discs were prepared. The first paper disc was for the positive control (streptomycin), the second was for negative control containing the DMSO, solvent used for the test, the third and fourth paper discs containing the organotin(IV) compounds tested. All paper discs were then placed on the surface of media. They were then incubated for one day at 37 °C and were monitored to see the inhibition zone. Each experiment was repeated at least three times. The compounds giving the most effective inhibition were then chosen for the dilution method.

Antibacterial activity test with dilution test

The most effective concentration inhibition zones obtained for all organotin(IV) 3-hydroxybenzoate compounds tested with diffusion test, then were tested with dilution test. They were dissolved with aquadest-DMSO and the volumes were varied for dilution test based on the procedure described by other [22], [23].The compounds tested with certain volume were then placed to liquid NA media, homogenized with vortex and then pour to petri disc, left them until solidified. The bacteria suspensions of P. aeruginosa and B. subtilis were then inoculated on the media at temperature of 37 °C for 2–3 days. The growth of bacteria was then monitored every day. The volume of the compound tested was varied into 0.5; 1.0; 1.5; 2.0, and 2.5 mL where each of them was mixed with 15 mL of liquid NA media, homogenized with shaker. The most effective compounds tested were a compound which was the compound with the smallest concentration but the inhibition zone was the biggest [22], [23].

Results and discussion

The syntheses of [Bu2Sn(3-HBz)2] (7), [Ph2Sn(3-HBz)2] (8), and [Ph3Sn(3-HBz)] (9) were conducted by reacting the compounds of [Bu2SnO] (4), [Ph2Sn(OH)2] (5), and [Ph3SnOH] (6) with 3-HBz acid by the use of the procedures previously reported [5, 8, 9, 12, 14, 16–18]. The elemental compositions of all synthesized compounds, as revealed by the results of microanalysis for each compound, are very reliable and in accordance with the calculated data. An example on the preparation of compound 9 was shown in Fig. 1.

Fig. 1: The preparation of triphenyltin(IV) 3-hydroxybenzoate, [Ph3Sn(3-HBz)] (9).
Fig. 1:

The preparation of triphenyltin(IV) 3-hydroxybenzoate, [Ph3Sn(3-HBz)] (9).

Several spectroscopic techniques were used to justify the successful synthesis of the targeted compounds. The FT-IR of compound 3 has characteristic stretch for Sn–Cl bond at 448.2 cm−1, upon conversion of 3–6, the new stretch at 726.4 cm−1 appeared, this peak is a characteristic for Sn–O bond which indicated that this bond has been formed, while Sn–Cl disappeared and also the presence of wide peak at 3437.3 cm−1 is an indication the presence of hydroxyl group in the tin atom. After the reaction of 6 and 3-hydrobenzoic acid to form compound 9, the new vibration of Sn–O–C appeared at 1290.1 cm−1, which indicated that oxygen from carboxyl group is bound to Sn atom, and the presence of vibration at 1624.7 cm−1, which is specific for C=O stretch indicated that carbonyl in the carboxyl is now present in the compound. The other vibrations are still present in the region close to the starting material [1, 8, 9, 12, 14, 16–18, 24].

The λmax. of all compounds were obtained by UV spectroscopy analyses. From the data obtained for each compound, it is clear that there was some important shifting change in the λmax for each compound. For example in compounds 8, the λmax observed were 220 and 258 nm. In 9, there were large shift in both π→π* and n-л* transitions, due to the replacement of OH group by 3-hydroxybenzoate. The 3-hydroxybenzoate ligand is a strong chromophore group due to the present –C=O– and –C=C– bonds. The large shifts observed in 9 were due to the increase of conjugate bond in these compounds causing the energy difference between HOMO and LUMO orbitals were decreased making the λmax. absorbs were increased [5, 8, 9, 12, 14, 16–18, 25]. These observations were also found for compounds 7 and 8.

The 1H and 13C NMR data of the organotin(IV) compounds synthesized were carefully analyzed to prove the successful of synthesis. The characteristic chemical shift in the spectra of the compounds prepared were characterized carefully and compared to the data available in the literatures [5, 8, 9, 12, 14, 16–18, 24]. Based on the data of 1H NMR spectrum for compound 9, the chemical shifts of phenyl protons attached to tin metal appeared as expected in the range from 7.33 for H4 to 7.59 ppm for H2 and H6, while the protons in benzoate ring appeared at 7.60–7.83 ppm. The 13C NMR values of the compounds synthesized were close to the values reported by others [5, 8, 9, 12, 14, 16–18, 24]. The analyses are as follows the carbon in the carboxyl group as expected appeared in the region of 165–166 ppm. The δ of carbons in the phenyl ligand in compounds 8 and 9 are at 126.9–131.7 ppm and the carbons in the benzoate are in δ range of 128.2–1329 ppm [5, 8, 9, 12, 14, 16–18, 24].

The results of antibacterial activity test by diffusion method and then followed with dilution test for the compounds synthesized are shown in Table 1. The halozone was observed in all concentrations from compounds 7–9, while for the starting materials (1–3) and intermediate products (4–6) the halozone observed were very small or no halozone were observed. This result indicated that the synthesized compounds tested have antibacterial activity and have ability to disturb the metabolism in the bacteria.

Table 1:

MIC values of all compounds tested compared with streptomycin.

Compound Minimum inhibitory concentration (MIC) (x 10−4 M)
B. subtilis P. aeruginosa
Streptomycin 1.70 1.71
[Bu2Sn(3-HBz)2] (7) 1.87 1.89
[Ph2Sn(3-HBz)2] (8) 1.79 1.81
[Ph3Sn(3-HBz)] (9) 1.71 1.72

The microorganism inhibition mechanism by antibacterial substances may be caused by some factors, namely (1) the disturbance in the compound composition of cell wall; (2) the increase of cell membrane permeability which cause the loss of component cell structure; (3) the inactivation of enzyme; and (4) destruction or damaging the function of genetic materials [21], [22], [23].

In this biological activity test, the compounds 8 and 9 where their molecules are more electropositive than 7, were able to disturb the electronegative bacteria cell wall, thus the interaction cause the disruption of bacteria growth. This is because the bacteria wall cell is composed by macromolecule of peptidoglycan which was composed by tetrapeptideglycan that functioned to feed the cell and to give strength, protect the cell and carry out intracellular material exchange with their environment. When the cell wall is disrupted, it will cause the cell inside is not protected as a result the bacteria will die due to the disruption of the tested compounds [21], [22], [23].

Conclusions

The preparation of three organotin(IV) compounds, dibutyltin(IV)-, diphenyltin(IV)-, and triphenyltin(IV) with 3-Hbz acid have successfully been carried out and successfully tested as antibacterial. Based on the results obtained, all compounds synthesized are potentially to be used as antibacterial agents. The data also indicated that the triphenyltin(IV) has stronger antibacterial activities. The result also showed that this finding directly proportional with to the number of carbon atom present in each compound. The data also reveal that it correlates with the ability of phenyl ligand to draw electron from the metal center as a result the metal became more positive and reacted actively with electronegative cell of bacteria, thus the growth of bacteria was disrupted. Further investigations with other bacteria both Gram-positive and Gram-negative are now still on going in our laboratory. It will also be interesting to test the activity of these compounds as antifungal.

Article note

A collection of invited papers based on presentations at the Virtual Conference on Chemistry and its Applications (VCCA-2020) held on-line, 1–31 August 2020.

Corresponding author: Sutopo Hadi, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Lampung, Bandar Lampung35145, Indonesia, e-mail:

Funding source: Institute of Research and Community Services, Universitas Lampung

Funding source: Directorate of Research and Community Services, The Ministry of Research, Technology and Higher Education, Indonesia

Award Identifier / Grant number: 858/UN26.21/PN/2019

Award Identifier / Grant number: 179/SP2H/ADM/LT/DRPM/2020

Acknowledgment

Special thanks must go to Directorate of Intellectual Property Right (DPKI), Directorate General of Strengthening Research and Development for giving SH support to present the paper in the international conference, International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin and Lead (ICCOC-GTL) September 1-6, 2019 Saitama, Japan.

  1. Research funding: The authors are grateful to Directorate of Research and Community Services, The Ministry of Research, Technology and Higher Education, Indonesia that provided fund for this project to be undertaken through Penelitian Disertasi Doktor (Doctoral Research Grant Scheme) 2019 and 2020 with contract number 858/UN26.21/PN/2019 and 179/SP2H/ADM/LT/DRPM/2020, respectively.

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Published Online: 2021-06-07
Published in Print: 2021-05-26

© 2021 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/

Artikel in diesem Heft

  1. Frontmatter
  2. In this issue
  3. Special topic paper
  4. State-of-the-art progress in tracking plasmon-mediated photoredox catalysis
  5. Invited papers
  6. Leading by example
  7. A blueprint for green chemists: lessons from nature for sustainable synthesis
  8. Synthetic approaches to 2,5-bis(hydroxymethyl)furan (BHMF): a stable bio-based diol
  9. Conference papers
  10. Virtual Conference on Chemistry and its Applications VCCA-2020
  11. Comparison of P- and As-core-modified porphyrins with the parental porphyrin: a computational study
  12. Data curation to improve the pattern recognition performance of B-cell epitope prediction by support vector machine
  13. Molecular insights of metal–metal interactions in transition metal complexes using computational methods
  14. Structure, electronic and optical properties of chalcopyrite-type nano-clusters XFeY2 (X=Cu, Ag, Au; Y=S, Se, Te): a density functional theory study
  15. An efficient nanofiltration system containing mixture of rice husk ash and Fe/CeO2–SiO2 nanocomposite for the removal of azo dye and pesticide
  16. Synthesis and comparative study on the antibacterial activity organotin(IV) 3-hydroxybenzoate compounds
  17. IUPAC Technical Report
  18. Interpretation and use of standard atomic weights (IUPAC Technical Report)
https://doi.org/10.1515/pac-2020-1103
Schlagwörter für diesen Artikel
Antibacterial activity; B. subtilis; chemistry and its applications; organotin(IV) 3-hydroxybenzoate; P. Aeruginosa; VCCA-2020

Artikel in diesem Heft

  1. Frontmatter
  2. In this issue
  3. Special topic paper
  4. State-of-the-art progress in tracking plasmon-mediated photoredox catalysis
  5. Invited papers
  6. Leading by example
  7. A blueprint for green chemists: lessons from nature for sustainable synthesis
  8. Synthetic approaches to 2,5-bis(hydroxymethyl)furan (BHMF): a stable bio-based diol
  9. Conference papers
  10. Virtual Conference on Chemistry and its Applications VCCA-2020
  11. Comparison of P- and As-core-modified porphyrins with the parental porphyrin: a computational study
  12. Data curation to improve the pattern recognition performance of B-cell epitope prediction by support vector machine
  13. Molecular insights of metal–metal interactions in transition metal complexes using computational methods
  14. Structure, electronic and optical properties of chalcopyrite-type nano-clusters XFeY2 (X=Cu, Ag, Au; Y=S, Se, Te): a density functional theory study
  15. An efficient nanofiltration system containing mixture of rice husk ash and Fe/CeO2–SiO2 nanocomposite for the removal of azo dye and pesticide
  16. Synthesis and comparative study on the antibacterial activity organotin(IV) 3-hydroxybenzoate compounds
  17. IUPAC Technical Report
  18. Interpretation and use of standard atomic weights (IUPAC Technical Report)
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