INTRODUCTION:

Based on the World Health Organization (WHO), the Covid-19 was stated as pandemic in March 2020¹. The emergence and spread of this virus is one of the new public health crisis that threatens the world^1-5. This is because of the fast spread of this virus all over the world¹. As of July 18, 2022, based on data obtained from Worldometer, there were more than 567 million incidents with more than 6.37 million deaths spread across 224 countries⁶. Based on the data monitored from this page, the occurrence of the COVID-19 pandemic may not end in the near future. This happens because, so far there is no drug that can completely overcome this disease^7-15, although the vaccination has proven to increase the body immune thus decreasing the possibility to get caught this virus.

Many studies have reported that chloroquine and hydroxychloroquine which are antimalarial drugs can be used for treating diseases generated byCOVID-19^7,8,10-15. Meanwhile, organotin(IV) carboxylate has also been found to have activity as both antimalarial and antiviral^16-21, so research is needed to test whether organotin(IV) compounds can be used as metal-based materials that can be used for healing due to Covid-19.

Organotin(IV) compounds consists of several biological applications due to their strong influence even at very low concentration^22-24. These compounds’ biological activities are dependent on the anion bearing and organic functional groups bound and attached to Sn²², as a complementary factor^22,24. According to results from recent studies, some organotin(IV) carboxylates compounds exhibited advantageous activities as biological agents. These include antifungal²³, antibacterial^25-27, antitumor and anticancer^28-30, corrosion inhibitor^29,30, ntioxidant activities³¹.

Docking different types of ligands to the protein of interest followed by evaluating the score function is a very important aspect in the contex of drug discovery^32-39. This technique is very useful to determine the binding affinity of the ligand to the protein and the strength of interaction between the two.

Several derivatives of organotin(IV) compound which are interesting to be tested are triphenyltin (IV) aminobenzoates. The synthesis of these compounds has long been reported by some researchers^40-45, however, no work has been reported so far on molecular docking with protein of SARS-Cov-2, therefore this study reports the molecular docking results of a protein selected from SARS-Cov-2 with several triphenyltin (IV) aminobenzoates.

MATERIALS AND METHODS:

Materials:

The AR reagent obtained from popular suppliers was used to conduct this research. Triphenyltin(IV) hydroxide ((C₆H₅)₃OH) (1), 2-, 3-, 4-aminobenzoic acids, boceprevir, as well as methanol (CH₃OH) wereacquired from Sigma-Aldrich (Germany), biomol (Germany) and JT Baker company (United Kingdom).

Characterization:

The UV spectra were produced from a Shimadzu UV-245 Spectrophotometer (Japan), by measuring the samples of 1.0x10^-4 M dissolved in methanol with a 1 mL quartz-cuvette. Furthermore, the elemental analyzerwas manufactured by Carlo Erba (Fisons) EA 1108 CHNS-O. The chemical compositions (CHNS) of the samples were determined by the Elemental Analyser. KBr pellet procedure was used to characterize FTIR using Bruker VERTEX 70 FT-IR spectrophotometer (Germany) and the spectrums were obtained through scanning the sample in a 4000-400cm^-1wavenumber. Bruker AV 600 MHz NMR spectrometer, manufactured in Germany at frequencies of 600 MHz for ¹H as well as 150 MHz for ¹³C was used to collect NMR data consisting of ¹H and ¹³C spectra. Measurements were carried out at 298K with DMSO-D₆, using 32 scans for ¹H as well as DMSO signal at 2.5 ppm as a reference as well as 1000-4000 scans for ¹³C at 39.5 ppm. Gallenkamp Melting Point Apparatus at 300°Cwas used to determine the meeting points.

The Preparation of Triphenyltin (IV) Aminobenzoates:

Triphenyltin (IV) aminobenzoates were prepared using the method applied in previous studies^18-20,25-27. One of such methods includes dissolving compound 1 (0.5505g or 1.5mmol) in methanol (50mL) as well as mixing it with 1 mole equivalent of 2-aminobenzoic acid (0.206 g). This was continued by a 4 hour refluxing at a temperature of 60 – 62°C with the water removed utilizing a Dean-Stark apparatus. Subsequently, a rotary evaporation process was used to remove the solvent, and the solid [(C₆H₅)₃Sn(2-OOCC₆H₄NH₂] (2) yielded was vacuum dried. The solid obtained had a 0.671g mass that equals 92% yield. Furthermore, the samples were examined as well as employed to conduct a study on molecular docking.

Triphenyltin(IV) 3-aminobenzoate, [(C₆H₅)₃Sn(3-OOCC₆H₄NH₂)] (3) and triphenyltin(IV) 4-aminobenzoate, [(C₆H₅)₃Sn(4-OOCC₆H₄NH₂)] (4) used similar technique implemented in the previous experimentation to synthesize a compound (2).

Triphenyltin(IV) 2-aminobenzoate (2): white-yellowish solid; UV l_max. (MeOH) nm (log e): 236 and 290; IR n_max. (KBr) cm^-1: 1633.4 (COO asym), 1428.7 (COO sym),; 729.4 (phen), 1243.4 (Sn-O-C), 365.6 (Sn-O); ¹H-NMR (in DMSO-D₆, 600 MHz) d (ppm): H₂and H₆= 7.59 (d, 6H); H₃and H₅= 7.48 (t, 6H); H₄= 7.35 (t, 3H), H in benzoate = H₁₀ = 7.84 (d) , H₁₁=7.65 (t) and H₁₂= 7.63 (t)H₁₃ = 7.72 (d); ¹³C-NMR (in DMSO-D₆, 150 MHz): d (ppm): C(phen) C₂and C₆= 131.7, C₃and C₅= 129.3 , C₄= 126.9; C₇: 166.7; C₈: 139.5; C₉133.2; C₁₀= 129.1; C₁₁= 128.5; C₁₂= 128.3; C₁₃= 130.1; microelemental analysis: found : C 61.65 (61.73), H 4.29 (4.32), N 2.86 (2.88). M.p. 109-111°C (Literature values: 108-109°C⁴¹; 110-112°C⁴²; 106-107°C⁴³).

Triphenyltin(IV) 3-aminobenzoate (3): white solid; UV l_max. (MeOH) nm (log e): 236 and 289; IR n_max. (KBr) cm^-1: 1630.2 (COO asym), 1427.6 (COO sym),; 728.8 (phen), 1242.8 (Sn-O-C), 363.9 (Sn-O); ¹H-NMR (in DMSO-D₆, 600 MHz) d (ppm): H₂= H₆ 7.59 (d, 6H); H₃and 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): d (ppm): C(phen) C₂and C₆= 131.7, C₃and 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 : C 61.67 (61.73), H 4.29 (4.32), N 2.87 (2.88). M.p. 105-106°C (Literature value: 105°⁴³).

Triphenyltin(IV) 4-aminobenzoate (4): white solid; UV l_max. (MeOH) nm (log e): 236 and 286; IR n_max. (KBr) cm^-1: 1629.8 (COO asym); 1426.5 (COO sym); 727.6 (phen), 1241.3 (Sn-O-C), 362.8 (Sn-O); ¹H-NMR (in DMSO-D₆, 600 MHz) d (ppm): H₂and H₆ 7.57 (d, 6H); H₃and H₅ 7.45 (t, 6H); H₄: 7.32 (t, 3H), H in benzoate: H₉and H₁₃ = 7.78 (d) , H₁₀and H₁₂= 7.80 (d); ¹³C-NMR (in DMSO-D₆, 150 MHz): d (ppm): C(phen) C₂and C₆= 131.6, C₃and C₅= 129.1, C₄= 126.9; C₇= 163.8; C₈= 137.0; C₉and C₁₃= 130.2; C₁₀and C₁₂= 129.1; C₁₁: 129.5; microelemental analysis: found: C 61.69 (61.73), H 4.31 (4.32), N 2.88 (2.88). M.p. 157-158°C (Literature values: 158-159°C⁴¹; 156-157°C⁴³).

Molecular Docking Activity Study:

The hardware used was an Acer Laptops with Intel® Celeron® processors 2955U 1.4 GHz with 2MB L3 cache, two gigabytes of RAM (Random Access Memory), with the Original Windows 7 Operating System. AutoDock 4 and AutoDock Vina software were used for all calculation of the addition of molecules and scores. The compounds extracted from database PubChem were converted to SDF format, combined in a file and then imported into Auto Dock. Furthermore, the atomic coordinates of the crystal structure in the Mpro protein were extracted on the PDB (Protein Data Bank) as well as made through extracting all solvents with the addition of hydrogen and minimization of ligands bound using the Protein Preparation Wizard. Ionizers were used to produce the ionized state of all compounds on the pH 7 target. Conformer these made low-energy ligands were taken as input for induced addition of molecules. The molecular addition protocol induced-fit incrementally using the AutoDock 4 and device Auto Dock Vina. The results of each device are used to provide rank on the target compound based on its predicted binding energy. The capabilities of AutoDock 4 and AutoDock Vina were preferentially evaluated to determine the active compound classified by the DSF and conformation consistent^32-39.

RESULTS AND DISCUSSION:

Three triphenyltin(IV) aminobenzoates, compounds 2, 3, as well as 4, shown in Figure 1,were synthesized through reacting [(C₆H₅)₃SnOH] (1) using 2-, 3-, 4-aminobenzoic acids, with the directions contained on the preliminary studies^18-20,
25-27. The synthesized compounds' elemental microanalyses were in line with the estimated data.

Fig. 1: The compounds studied structure

Some spectroscopic strategies were utilized to determine thecompounds’ identity. A 726.36 cm^-¹wave number was used to characterize the compound 1 FT-IR spectrum which indicates the existence of the Sn–O bond. In the 3437.29 cm^-¹wave number, this band was given to the Sn-OH bond and with [(C₆H₅)₃Sn(2-OOCC₆H₄NH₂] formation (2), the hydroxyl stretching vibration lose. Furthermore, intense bands were obtained from asymmetric and the carboxylate symmetric stretching at 1530 cm^-1 as well as 1634 cm^-1. This showed that the aminobenzoate ligand istied to the Sn centre as well as substituted OH^- group at compound 1. This extension is due to the absorption band at 1240 cm^-1, that connected with Sn-O-C stretching. The absorption bands examined in FTIR spectrum showed theformation ofcompounds 23,as well as 4^{18-20, 25-27}.

Some important signals were used to synthesize the ¹H and ¹³C NMR spectra for the compounds. Furthermore, the presence of phenyl protons bound to central atom Sn and benzoate are due to the chemical shifts in 7.30 – 7.59 ppm and 7.6 – 7.9ppm. Signals in the range of 131 – 126 ppm and 140 – 130ppm, representing carbon atoms of the phenyl ligand, and aminobenzoate were found on the NMR spectra. These values are in accordance with preliminary studies and the additional support is given through the signals within the 163 – 166ppm region, thereby signifying the presence of carboxyl group^{18-20,25-27, 46}. The chemical shifts generated from the compound are in accordance with the data for the compounds formerly analysed^{18-20, 25-27, 46}.

The results in Table 1 indicate that the synthesized triphenyltin (IV) aminobenzoates showed smaller energy binding than the drug standard used. Thus it is an indication that the three compounds docked with MPro protein were more active as antivirus drug. Their strong activity against antivirus was also supported their very low of estimation of inhibition constant (K_i) which were 7.2 x 10^-2, 5.0 x 10^-2, as well as 2.3 x 10^-2‑µM^{47, 48}. An example of docking interaction between compound 4 and MPro protein is shown in Figure 2.

Fig. 2: The interaction of triphenyltin(IV) 4-aminobenzoate with MPro protein isolated from SARS-Cov-2

The experimental results obtained showed that both the carbon atom number and the ligand type play essential roles in performance of triphenyltin(IV) compounds investigated as an anti-malaria agent⁴⁹. These results are in line with the features of numerous biologically active compounds, whereby the complex ones are higher than the non-complex forms⁵⁰.

Table1: The energy binding and estimation of inhibition constant (K_i) of the compounds investigated

Compounds	Energy binding (Kcal.mol)	Estimation of inhibition constant (K_i) x 10^-2µM
Boceprevir	-9.60	9.5
2-aminobenzoic acid (2-(NH₂)C₆H₄COOH)	-1.22	22
[(C₆H₅)₃SnOH] (1)	-2.51	19
[(C₆H₅)₃Sn(2-OOCC₆H₄NH₂] (2)	-9.74	7.2
[(C₆H₅)₃Sn(3-OOCC₆H₄NH₂] (3)	-9.97	5.0
[(C₆H₅)₃Sn(4-OOCC₆H₄NH₂] (4)	-10.42	2.3

CONCLUSIONS:

In conclusion, this research successfully prepared three triphenyltin(IV) aminobenzoate compounds, and the molecular docking has been successfully conducted against a protein isolated from SARS-Cov-2 virus. The result of energy binding clearly indicated that the compounds synthesized were more active and stronger than the positive control drug used in the testing. The results were also supported with the low estimation of inhibition constants of compounds 2-4. It is suggested to evaluate further a molecular docking on other proteins from SARS-Cov-2 such as RdRp as well as Plpro to see their potential used as antivirus agent.

ACKNOWLEDGMENTS:

The authors expresses gratitude to the Research and Community Services Directorate, and Education, Cultural, Research, and Technology Ministry for funding this research through Penelitian Terapan 2021, with the contract of 3973/UN26.21/PN/2021 and 276/E4.1/AK.04.PT/2021 and 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.

CONFLICT OF INTEREST:

The authors declare no conflict of interest.

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Received on 09.08.2022 Modified on 31.12.2022

Research J. Pharm. and Tech 2023; 16(9):4032-4036.

DOI: 10.52711/0974-360X.2023.00661