Comparative Bioactivity Study of some Organotin (IV) 2-Chlorobenzoate compounds as Disinfectant agent

 

Sutopo Hadi1*, Cindy Moyna Clara1, Yandri Yandri1, Asep Sukohar2, Tati Suhartati1

1Department of Chemistry, Universitas Lampung, Bandar Lampung, 35415, Indonesia.

2Faculty of Medicine, Universitas Lampung, Bandar Lampung, 35415, Indonesia.

*Corresponding Author E-mail: sutopo.hadi@fmipa.unila.ac.id

 

ABSTRACT:

This research was carried out to study the bioactivitytest as disinfectant of two derivatives of organotin(IV) carboxylate compounds; diphenyltin(IV) di-2-chlorobenzoate (DPT2-CBz) (2) and triphenyltin(IV) 2-chlorobenzoate (TPT2-CBz) (4), against two pathogenic bacteria. Compounds 2 and 3 were successfully prepared by reactingdiphenyltin(IV) oxide (DPTO) (1) and triphenyltin(IV) hydroxide (TPTOH) (3) with 2-chlorobenzoic acid(2-HCBz)with yieldsof 87.71% and 88.73%, respectively. The characterization of the synthesized compounds was performed with several spectroscopy techniques such as UV, IR, 1HNMR, 13CNMR, and microelemental analyzer. The optical density (OD) test for both compounds measured using UV-Vis at 600 nm showeda goodbioactivity against two bacteria, Gram-negative Salmonella sp. and Gram-positive Staphylococcus aureus. The data revealed that compound 4 has bigger bioactivity than compound 2 and the positive control ofcommercial disinfectant (2.5% pine oil). The bioactivity of compound 4was optimum at concentration of 5x10-4 M and contact timeof 15 minutes.These data corresponding to the decrease of absorbance from 0.6640 to 0.0955 for Salmonella sp., and 0.6565 to 0.1295 for S. aureus, whereas although compound 2reached the optimum activityat the same concentration and contact time with compound 4, but the decrease of absorbance was less namely 0.6640 to 0.1305 for Salmonella sp., and 0.6565 to 0.196 for S. aureus. The decrease of absorbance in the measurement of OD implies that both compounds are potential to be used as disinfectant agent.

 

KEYWORDS: Disinfectant, organotin (IV) carboxylate, optical density, Salmonella sp., S. aureus.

 

 

INTRODUCTION: 

Infection is the entry of pathogenic microorganisms, such as bacteria, into the human body and causes disease1. Pathogenic bacteria Salmonella sp.become a worldwide major health problem, with amount of infection reaching 1.9 billion people per year, and 715.000 of them died2. Salmonella sp. causes typhoid fever, diarrhea, sepsis (a complication that makes blood pressure drop dramatically thus causes death)3. S. aureus is also the majorpathogenic bacteriafor human, since it infects at least 30% of human population4-7. S. aureus bacteria causes skin infections, poisoning, endocartisis (heart infection) which is very lethal6,8.

 

Chemical disinfectant used with the aim to inhibit microorganism growth, or kill microorganism until certain amount of their safety limit9-14.

 

Disinfectant might be sprayed on the object surface, liquids, or surrounding area which is suspected being contamined by bacteria or viruses, to reduce the risk of its exposure through human skin or mucous membrane11, 12,15. Methanol, ethanol, and isopropanol are types of alcohol that widely contained in commercial disinfectant. It has been prove effective against bacteria, viruses, and fungi but excessive use in the long term might causes irritation and poisoning16.

 

Based on previous bioactivity studies, other compounds that have great potential to be an active agent for disinfectant are derivative of organotin (IV) carboxylate compounds17. These compounds, are non toxic or slightly toxic to mammals, and have a good activity as antibacterial18-21, anticancer and antitumor22-26, antiviral27,28, antimalaria29-32 and antifungal agents33,34. The longer alkyl chain of organotin(IV) compund and the presence of halogen groups can increase its biological activity35. Based on the fact the derivatives of organotin (IV) compounds have shown many interesting biological activities, in this work we reported the synthesis and disinfectant bioactivity study of two organotin (IV) compounds.

 

MATERIALS AND METHODS:

Materials:

All reagents used were of Analytical Reagent grade. Diphenyltin (IV) oxide (DPTO) (1), triphenyltin(IV) hydroxide (TPTOH) (3), and 2-chlorobenzoic acid (2-HCBz) were obtained from Sigm-Aldrich (MA, USA). Methanol and dimethylsulfoxide (DMSO) were obtained from Merck Millipore (MA, USA). All of these reageants were used as received and without any further purification. Nutrient agar and nutrient broth were obtained from Himedia Laboratories Private Limited (Mumbai, India). A commercial disinfectant was used as a positive control containingactive agent of2.5% pine oil. Gram-negative bacteria Salmonella sp. and Gram-positive bacteria S. aureus were obtained from Laboratory of Vetereiner Center. Directorate General of Livestock and Animal Health, Ministry of Agriculture, Lampung, Indonesia.

 

Instrumentations:

UV spectra were recorded in the UV region and measured using Shidmadzu UV-245 Spectrophotometer (Japan). Measurements were performed in 1 mL quartz-cells. Solutions were prepared using methanol-DMSO 5% as solvent with concentration 1x10-5 M. IR Spectra were recorded on Bruker VERTEX 70 FT-IR Spectrophotometer (Germany) with using KBr discs at range of 4000-400 cm-1. 1H dan 13C NMR spectra were recorded on Bruker AV 600 MHz NMR (Germany) (600 MHz for 1H and 150 MHz for 13C), all measurements runsusing DMSO-D6 at 298K. Number of runs used in 1H were 32 with reference of TMS signal at 0 ppm, while 13C were 1000-4000 with DMSO reference signal at 39.5ppm. Elemental analysis (CHNS) were conducted usingFision EA 1108 Elemental Analyzer (Italy).

 

Synthesis of Organotin(IV) 2-chlorobenzoate:

Synthesis of organotin(IV) 2-chlorobenzoate compounds were carried out in this study following previously reported procedures17-21,26, 29,31,32.

 

The following procedure was applied inthe synthesis of DPT2-CBz (2), and as follows: 0.8667g (0.003mol) of DPTO(1) was added with 2 moles equivalent of 2-HCBz (0.9394g), in 30mL of methanol. These mixtures were refluxed for 4 hours at 60-6°C under stirring condition. The water produced was removed by Dean-Stark apparatus. DPT2-CBz (2) compound was then separated from the solvent using vacuum desiccator until constant and ready to be analyzed and tested for its bioactivity. The yield obtained was 87.71%. The same procedure also adapted in the synthesis of TPT2-CBz (4), using TPTOH (3)withthe addition of onlyone mole equivalent of 2-HCBz.

 

DPT2-CBz (2): soft pink solid; UV lmax. (MeOH) nm (log e): 235 and 282;   IR nmax. (KBr) cm-1:2855.1, 2922.2, 3041.5 (C-C in phen),1684.8 (C=O),  1580.4 (CO2asym), 1386.8 (C=C in phen), 1155.5 (Sn-O-C), 693.3 (Sn-O); 1H-NMR (in DMSO-d6, 600 MHz) d (ppm): H2& H6: 7.44 (d, 4H); H3& H5= 7.46 (t, 4H), H4: 7.47 (t, 2H), H in benzoate:  H10&H11: 7.786-7.03 (t), H12&H13: 7.55-7.56 (t);  13C-NMR (in DMSO-d6, 150 MHz): d (ppm):  C(phen) C1: 131.05,C2 & C6: 129.37, C3 & C5: 128.16, C4: 127.04,C(benzoate) C7: 167.0, C8: 131.23, C9:132.84, C10: 133.54, C11: 134.74, C12: 135.33, C13: 136.82; microelemental analysis: found (calculated): C 53.21 (53.43), H 3.02 (3.09).

 

TPT2-CBz(4): pink solid; UV lmax. (MeOH) nm (log e): 234 and 289;   IR nmax. (KBr) cm-1:2855.1, 2922.2, 3041.5 (C-C in phen),1699.7 (C=O),  1580.4 (CO2asym), 1394.0 (C=C in phen), 1155.5 (Sn-O-C), 693.3 (Sn-O),1H-NMR (in DMSO-d6, 600 MHz) d (ppm): H2 - H6: 7.470-7.518 (m),H in benzoate:  H10: 7.84 (d), H11: 7.65 (t), H12: 7.63 (t),H13: 7.72 (d); 13C-NMR (in DMSO-d6, 150 MHz): d (ppm):  C(phen)  C1: 128.38, C2& C6:128.07, C3& C5: 127.59, C4: 126.61;  C(benzoate)C7:166.34,C8:129.105,C9:131.852;C10:131.113,C11: 136.365,C12: 137.018,C13:137.812; microelemental analysis: found (calculated): C 59.22 (59.39), H 3.71 (3.79).

 

Bioactivity Test of Disinfectant:

Disinfectant bioactivity test was carried out using the modification of the optical density (OD) method based on the work of others10-14,17,36,37. In this study, 5mL solution containing compounds 2 and 4 with concentration variations of 5x10-3, 1x10-3, and 5x10-4 M were used as the disinfectant. Each of these disinfectants was observed for their bioactivity against 0.5 μL pathogenic bacteria Salmonella sp. and S. aureus with contact times of 0, 5, 10, and 15 minutes and was monitored with Spectrophotometer UV-Visible at 600 nm38.

 

RESULT AND DISCUSIONS:

The synthesis of two derivatives of organotin(IV) carboxylates compound 2 and 4 has successfully been carried out by reacting DPTO (1) and TPTOH (3) with 2-HCBzusing the procedures available in the      literature17-21,26,29,31,32. As an example, in thereaction scheme in the preparation of compound 2 is shown in Figure 1.

 

Fig. 1:The reaction scheme in the preparation of (a)compound 2; (b) compound 4

 

Compound 2 was successfully synthesized forming soft pink solid with a totalyield  of 87.71%, while compound 4forming pink solid with a total yield 88.73%. The results of characterization from several spectroscopies such as UV, IR, 1H-NMR, 13C-NMR providing good spectra and the elemental analysis data values ​​are very good as close to the theoretical values which are evidence of the success in the synthesis of the compounds studied.

 

The UV spectroscopy analysis of compounds2 and 4, producedcharacteristic absorption values with ​specificλmax. The synthesized compounds 2 and 4 had two characteristic peaks with transitions π→π* and n→π*, while in the starting materials 1 and 3, they hadonly one characteristic peak with the transition π→π*. For example, in compound 1 the transition of π→π* occurred at 203 nm which is due to the delocalization of phenyl electron. Upon reaction of 1 with 2-chlorobenzoic acid ligand to produce compound 2, bathochromic shifting occurs due to the influence chromophore groupfromcarbonyl group and addition of benzenerings. In compound 2 there was alson→π* transition at 282 nm due to the presence of a lone pair electron from chlorine group. Similar shifts changewas also observed in the formation of compound4from 3.

 

FT-IR absorption data show finger print area of each functional group present in the compounds 2 and4 prepared. Both compounds gave a characteristic absorption of C-H group at wave number 2922,2 cm-1. Stronger absorption of C=O group appeared at 1684.8 cm-1 and 1699.7 cm-1 in the compounds 2 and 4 was obtained from the ligand 2-HCBz, while C=C group at 1580.4 cm-1 from the sp2 hybridized phenyl in the benzene rings. The ligand 2-HCBz successfully bound incompounds 2 and 4was proven by the presence of Sn-O-C group at 1155.5 cm-1, Sn-Ph group at 1051.1 cm-1, and Sn-O group at 693.3 cm-1. As an example of data changes in the FT-IR spectra for the conversion of compound 1 to compound 2 isshown  in Figure 2.

 

Fig.2: FT-IR spectra of (a) DPTO (1); (b) DPT2-CBz (2)

 

The synthesized compounds were well characterizedusing1H and 13C NMR spectroscopy. By careful analysis, the data for compounds prepared have been compared with the previous similar                compounds17-21,26,29,31,32. In 1H NMR, the chemical shift (δ) of phenyl proton bound to Sn atom as expected appeared in the range of 7.44-7.47 ppm, while the chemical shift of proton benzote were at 7.79-7.81ppm. The 13C NMR of the phenyl bound to Sn atom gave δ at 126.9-130.5ppm and the carbon benzoate at 137. The chemical shift (δ) of carbon carbonyl as exptected appeared ad 166-167 ppm17-21,26,29,31,32. The 1H and 13C NMR spectra of compound 4 are shown in Figure 3.

 

Fig. 3: The spectrumof (a) 1H NMR; (b) 13C-NMR of compound TPT2-CBz (4)

 

Table 1 shows bioactivity tests results of compounds 2 and 4 against pathogenic bacteria Salmonella sp. and S. aureus measured using optical density method. This method was used to determine the density of bacteria before and after the addition of disinfectantand based on the absorbance value measured with UV-Vis at 600nm. The decrease of absorbance value on the optical density method, is equivalent withthe decrease ofthe number of bacteria36.

 

Tabel 1: Optical Density Data of Disinfectant against Bacteria

Compound

Optical Density at MIC 5x10-4 M

(15 minutes)

Salmonella sp.

(0.6640)

S. aureus

(0.6570)

2

0.1305

0.1960

4

0.0955

0.1295

Positive Control

(2.5% pine oil)

0.4025

0.4600

 

The absorbance data of McFarland's standard solution in Table 2, can be used to calculate bacteria density in units (CFU/mL), through linear regression equation4. The average initial absorbance of Salmonella sp. was 0.6640 and its equivalent to 10.6942 x 108 CFU/mL, while S. aureus was 0.657 its equivalent to 10.5804 x 108 CFU/mL. Bioactivity of compounds 2, 4 and commercial disinfectant as positive control (2.5% pine oil), optimum at 5x10-4 M and contact time with bacteria 15 minutes. Bacteria absorbance of compound 4, decreased from 0.6640 to 0.0955 for Salmonella sp., and 0.6570 to 0.1295 for S. aureus. Bacteria absorbance of compound 2, decreased from 0.6640 to 0.1305 for Salmonella sp., and 0.6570 to 0.196 for S. aureus. Positive control showed adecrease in the absorbance of bacteria from 0.6640 to 0.4025 for Salmonella sp., and 0.6570 to 0.4600 for S. aureus.

 

Table 2: McFarland Nephelometer Standards38

Mc Farland standard No.

 

0.5

 

1

 

2

 

3

 

4

CFU/mL (x108)

1.5

3

6

9

12

Absorbance

0.132

0.257

0.451

0.582

0.669

 

These absorbance values, ​​indicate the ability of compound 4 against pathogenic bacteria better than compound 2, corresponded with the reference state that the longer alkyl chain of organotin(IV) compound can increase its biological activity35. In this study, all disinfectantsshowed a better against Salmonella sp. bacteria (Gram-negative) compared to S. aureus (Gram-positive), caused by the cell wall of Gram-negative bacteria has little peptidoglycan layer, and causes bacterial cells easily break and damage the immune system8,39,40.

 

Other possible mechanism actions of disinfectants were the presence of electronegative chlorine substituents causes peptide bonds in bacteria cells oxidized, so that the proteins constituent denatured20. It proves that organotin(IV) 2-chlorobenzoate compounds are able to act as disinfectants against pathogenic bacteria.

 

CONCLUSIONS:

Synthesis of some organotin(IV) compounds with 2-chlorobenzoic acid ligand has been successfully carried out, as proven by the analysis results of UV, IR, 1H NMR, 13C NMR spectroscopies and microelemental analysis data. The result of bioactivity of compounds 2 and 4 using optical density method also showed goodactivityagainst pathogenic bacteria Salmonella sp. and S. aureus. Compound 4was found to be more effective inkilling bacteria than compound 2 and commercial disinfectant as positive control (2.5% pine oil). The large number of phenyl or benzene rings, and the presence of chlorine substituents in compounds 2 and 4 also increases their bioactivity. Organotin(IV) 2-chlorobenzoate compounds arevery potential to be futuredisinfectant as have been shown by their effectivity against pathogenic bacteria. The study and development of further bioactivity testing methodsfor other derivative of organotin(IV) compounds is required in order to find new compound with stronger bioactivity in disinfectant activity test.

 

ACKNOWLEDGEMENTS:

The authors are grateful to the Institute of Research and Community Services, Universitas Lampung and Directorate of Research and Community Services, The Ministry of Education, Culture, Research, and Technology, Indonesia for the funding given to this research through National Competitive Basic Research Grant Scheme (Penelitian Dasar Kompetitive Nasional) with contract numbers of 027/E5/PG.02.00/PT/2022, dated March 16, 2022 and 2143/UN26.21/PN/2022 dated April 29, 2022.

 

CONFLIC OF INTEREST:

The authors declare no conflict of interest.

 

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Received on 29.06.2022            Modified on 24.11.2022

Accepted on 21.02.2023           © RJPT All right reserved

Research J. Pharm. and Tech 2023; 16(6):2885-2889.

DOI: 10.52711/0974-360X.2023.00475