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 Table of Contents  
Year : 2019  |  Volume : 8  |  Issue : 2  |  Page : 155-160

Comparative antibacterial activity of synthetic N,S-Heterocyclic derivatives, MgO nanoparticles, and glycine on zoonotic Vibrio fluvialis

1 Torbat Jam Faculty of Medical Sciences, Torbat Jam, Iran
2 Department of Chemistry, Faculty of Science, University of Zabol, Zabol, Iran
3 Department of Clinical Sciences, Faculty of Veterinary Medicine, University of Zabol, Zabol, Iran

Date of Web Publication30-Oct-2019

Correspondence Address:
Dr. Behzad Ghasemi
Torbat Jam Faculty of Medical Sciences, Torbat Jam.
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Source of Support: None, Conflict of Interest: None

DOI: 10.4103/jrptps.JRPTPS_49_18

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Background: Vibrio fluvialis is an emerging zoonotic pathogen that its antibiotic-resistant strains are rapidly expanding. Discovering new antibacterial agents is one way to control it.Aims and Objectives: In this research, inhibitory potentials of glycine, magnesium oxide nanoparticles (NPs), and some synthesized thiazole, imidazolidine-2-thione, and tetrahydropyrimidine-2-thione derivatives were studied against V. fluvialis in an in vitro manner.Materials and Methods: Thiazoles were prepared through Hantzsch reaction. Cyclic thioureas were synthesized from the reaction of diaminoalkanes and carbon disulfde. MgO NPs were created in 23.7–25.7nm by sol–gel processing. Antibacterial properties of all compounds as inhibition zone diameter, the minimum inhibitory concentration, and the minimum bactericidal concentration values were assessed through both disk diffusion and broth microdilution methods.Results: No inhibitory activity on V. fluvialis was observed with MgO NPs and glycine. Among thiazole derivatives, only compound 7e could effciently block the growth of this pathogen. All thioureas except derivative 6c showed antibacterial properties. The best results belonged to imidazolidine-2-thione 7a.Conclusion: Significant inhibitory potentials were observed with some synthetic thiazoles and cyclic thioureas. If antibacterial activates of these heterocycles are proved on resistant strains and their toxic effects are desirable, an important step will be taken in the introduction of these new antibacterial agents.

Keywords: Antibacterial effect, glycine, heterocyclic compound, mgO nanoparticle, vibrio fluvialis

How to cite this article:
Abdollahi M, Beyzaei H, Hashemi SH, Ghasemi B. Comparative antibacterial activity of synthetic N,S-Heterocyclic derivatives, MgO nanoparticles, and glycine on zoonotic Vibrio fluvialis. J Rep Pharma Sci 2019;8:155-60

How to cite this URL:
Abdollahi M, Beyzaei H, Hashemi SH, Ghasemi B. Comparative antibacterial activity of synthetic N,S-Heterocyclic derivatives, MgO nanoparticles, and glycine on zoonotic Vibrio fluvialis. J Rep Pharma Sci [serial online] 2019 [cited 2020 Aug 7];8:155-60. Available from: http://www.jrpsjournal.com/text.asp?2019/8/2/155/269942

  Introduction Top

Vibrio fluvialis is a Gram-negative, oxidase-positive, and nitrate-positive bacterium that has been found in both human and animal feces.[1] Its strains have been isolated from patients with diarrhea, bacteremia, and food poisoning. This pathogen, like Vibrio cholera, causes bacterial gastroenteritis. In addition, symptoms such as severe diarrhea, vomiting, palpitations, fever, dehydration, hypovolemic shock, skin lesions, and tissue necrosis have been found with the diseases caused by this bacterium.[2] Fish farming centers and untreated drinking water and wastewater are the most important contaminating agents.[3] Several cases of child mortality have been reported in countries including Bahrain, Bangladesh, America, Mexico, and Brazil.[4]V. fluvialis strains were resistant to many common antibiotics such as ampicillin, chloramphenicol, streptomycin, gentamicin, and furazolidone due to gene mutation or drugs transport. The drug-resistant strains of this bacterium threaten public health, which increases the cost of treatment. For these reasons, new antibacterial agents must be identified and designed to inhibit V. fluvialis strains.

Thiazoles as an important class of heterocyclic compounds are present in various enzymes, vitamins, and pharmaceutics.[5] They were used in the treatment of cancer, blood fat, blood pressure, as well as infectious diseases caused by HIV, Candida albicans, anopheles, and trypanosomes.[6] Thiazole derivatives could efficiently block the growth of Gram-positive Staphylococcus aureus, Streptococcus faecalis, and Bacillus subtilis and Gram-negative  Escherichia More Details coli, Pseudomonas aeruginosa, and Enterobacter clavata.[7] Some thiazoles are effective on resistant bacterial strains.[8]

Imidazolidines are present in the chemical structure of drugs such as midazolam, phenytoin, and ketoconazole. They were applied as pain relief, anti-inflammatory, anticancer, antidiabetic, antiparasitic, and antifungal agents.[9],[10],[11],[12],[13],[14] Good to excellent inhibitory activities were observed with some derivatives of imidazolidines against S. aureus, P. aeruginosa, and E. coli.[15],[16]

Inhibitory activities were observed with tetrahydropyrimidine derivatives against enzymes, cancer and tuberculosis cells, Aspergillus niger, C. albicans, and Plasmodium malariae.[17],[18],[19],[20] Pathogenic bacteria such as P. aeruginosa and Klebsiella pneumoniae were also controlled with them.[21]

Metallic nanoparticles (NPs) are attractive chemicals due to their therapeutic effects on parasitic, viral, bacterial, and neurological diseases and blood disorders. Magnesium is the fourth most important element of the body and the second most important element in the cell, which plays a vital role in the activity of the nervous system, muscles and enzymes, energy production, bone and teeth formation. Mg NPs were utilized as broad-spectrum antibacterial agents due to their low toxicity as well as easy and inexpensive preparation.[22]

Protective effects of glycine, the simplest of the amino acids, have been confirmed in alcohol-induced oxidative stress. It could inhibit the growth of Helicobacter pylori under in vitro culture conditions.[23]

In this research, the in vitro inhibitory potential of glycine, magnesium oxide NPs, and some synthesized thiazole, imidazolidine-2-thione, and tetrahydropyrimidine-2-thione derivatives was studied against V. fluvialis.

  Materials and Methods Top

General procedure for the synthesis of thiazole derivatives 3a-f

The reaction of thioamide (1) (1 mmol, 0.23g), sodium bicarbonate (1 mmol, 0.08g), and 1-bromocarbonyl compounds 2a-f in 1ml of N, N -dimethylformamide as the solvent at room temperature for 24 -46h afforded thiazoles 3a-f [Figure 1].[24]
Figure 1: Steps of the synthesis of thiazole derivatives

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3-Methyl -4 -(4-methylthiazol-2-yl) -1-phenyl-1H-pyrazol-5-amine (3a)

m.p. 170°C–172°C; 1H NMR (DMSO-d6, 400 MHz) δ: 2.37 (3H, s), 2.40 (3H, s), 6.71 (1H, d, J = 9.5 Hz), 7.04 (1H, s), 7.39 (1H, m), 7.54–7.56 (3H, m), 7.62 (2H, d, J = 7.8 Hz) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 161.9, 151.1, 146.5, 146.3, 138.7, 129.8, 127.2, 123.2, 109.1, 98.1, 17.3, 14.4ppm; IR (KBr) ν: 3314, 3262, 1620, 1556, 1401, 1200, 641cm−1. Anal. Calcd. for C14H14N4S: C 62.20, H 5.22, N 20.72, S 11.86; found: C 62.23, H 5.23, N 20.70, S 11.84.

1 -(2 -(5-Amino-3-methyl-1 -phenyl-1H-pyrazol-4-yl)-4-methylthiazol-5-yl) ethan-1-one (3b)

m.p. 118°C–120°C; 1H NMR (DMSO-d6, 400 MHz) δ: 2.38 (3H, s), 2.54 (3H, s), 2.69 (3H, s), 6.97 (1H, s), 7.42 (1H, t, J = 7.1 Hz), 7.54–7.61 (5H, m) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 164.5, 161.9, 159.5, 147.7, 147.0, 138.3, 129.8, 127.5, 123.6, 115.3, 97.7, 17.5, 14.7, 14.7ppm; IR (KBr) ν: 3442, 3296, 1653, 1617, 1548, 1397, 1237, 656cm−1. Anal. Calcd. for C16H16N4OS: C 61.52, H 5.16, N 17.94, S 10.26; found: C 61.49, H 5.18, N 17.93, S 10.29.

Ethyl2 -(5 -amino-3-methyl-1-phenyl-1H-pyrazol-4-yl) -4 -methylthiazole-5-carboxylate (3c)

m.p. 144°C–146°C; 1H NMR (DMSO-d6, 400 MHz) δ: 1.31 (3H, t, J = 7.1 Hz), 2.38 (3H, s), 2.67 (3H, s), 4.28 (2H, q, J = 7.1 Hz), 6.93 (1H, d, J = 7.3 Hz), 7.42 (1H, t, J = 7.1 Hz), 7.54–7.61 (5H, m) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 192.2, 183.8, 171.4, 150.1, 149.7, 137.5, 130.0, 128.2, 124.1, 123.2, 99.4, 64.5, 18.8, 15.1, 14.3ppm; IR (KBr) ν: 3378, 3287, 1670, 1619, 1545, 1396, 1263, 649cm−1. Anal. Calcd. for C17H18N4O2S: C 59.63, H 5.30, N 16.36, S 9.36; found: C 59.65, H 5.28, N 16.38, S 9.37.

Ethyl2 -(5-amino -3 -methyl -1 -phenyl -1H-pyrazol-4-yl) thiazole-4-carboxylate (3d)

m.p. 165°C–167°C; 1H NMR (DMSO-d6, 400 MHz) δ: 1.33 (3H, t, J = 7.1 Hz), 2.40 (3H, s), 4.33 (2H, q, J = 7.1 Hz), 6.85 (1H, d, J = 8.1 Hz,), 7.41 (1H, t, J = 7.2 Hz), 7.55 (3H, t, J = 7.4 Hz), 7.62 (2H, d, J = 7.8 Hz), 8.32 (1H, s) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 162.9, 161.1, 146.9, 146.5, 145.2, 138.5, 129.8, 127.4, 123.4, 123.9, 97.6, 61.2, 14.6ppm; IR (KBr) ν: 3434, 3314, 1729, 1602, 1563, 1394, 1221, 639cm−1. Anal. Calcd. for C16H16N4O2S: C 58.52, H 4.91, N 17.06, S 9.76; found: C 58.54, H 4.88, N 17.09, S 9.75.

2-(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl) thiazol-4 (5H)-one (3e)

m.p. 238°C–240°C; 1H NMR (DMSO-d6, 400 MHz) δ: 2.42 (3H, s), 4.01 (2H, s), 7.46 (1H, m), 7.55 (1H, m), 7.56–760 (5H, m) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 189.8, 165.6, 149.9, 149.7, 137.4, 130.0, 128.3, 124.2, 99.4, 36.3, 15.1ppm; IR (KBr) ν: 3342, 3272, 1732, 1627, 1540, 1402, 1203, 639cm−1. Anal. Calcd. for C13H12N4OS: C 57.34, H 4.44, N 20.57, S 11.77; found: C 57.31, H 4.47, N 20.53, S 11.79.

2-(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)-5-methylthiazol-4(5H)-one (3f)

m.p. 137°C–139°C; 1H NMR (DMSO-d6, 400 MHz) δ: 1.55 (3H, d, J = 7.2 Hz), 2.41 (3H, s), 3.85 (1H, m), 7.46 (1H, m), 7.55–760 (5H, m), 7.63 (1H, m) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 190.1, 164.5, 147.7, 147.1, 138.5, 129.8, 127.5, 123.6, 97.8, 65.1, 30.5, 14.7ppm; IR (KBr) ν: 3329, 3265, 1736, 1629, 1534, 1396, 1194, 659cm−1. Anal. Calcd. for C14H14N4OS: C 58.72, H 4.93, N 19.57, S 11.20; found: C 58.73, H 4.96, N 19.55, S 11.17.

Synthesis of imidazolidines 6a-c and tetrahydropyrimidines 6d-f

A mixture of diaminoalkanes 4a-e (10 mmol) and carbon disulfide (5) (10 mmol, 0.76g) in the presence of MgO NPs (2.5 mmol, 0.1g) and 96% ethanol (20ml) were stirred at room temperature for 2.5–5h to give cyclic thioamides 6a-f [Figure 2].[25]
Figure 2: Steps of the synthesis of imidazolidines and tetrahydropyrimidines derivatives

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Imidazolidine -2 -thione (6a)

m.p. 196°C–197°C; 1H NMR (DMSO-d6, 400 MHz) δ: 3.54 (4H, s), 7.91 (2H, s) ppm; IR (KBr) ν: 3312, 1480, 1075, 760cm−1.

4,4 -Dimethylimidazolidine -2 -thione (6b)

m.p. 105°C–107°C; 1H NMR (DMSO-d6, 400 MHz) δ: 1.17 (6H, q, J = 5.7 Hz), 3.09 (2H, t, J = 5.7 Hz), 7.83 (2H, s) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 175.5, 39.7, 39.6, 19.1ppm; IR (KBr) ν: 3316, 1491, 1075, 763cm−1; Anal. Calcd. for C5H10N2S: C 46.12, H 7.74, N 21.51, S 24.63; found: C 46.07, H 7.77, N 21.49, S 24.67.

Octahydro -2H -benzo[d]imidazole -2-thione (6c)

m.p. 153°C–155°C; 1H NMR (DMSO-d6, 400 MHz) δ: 1.30 (2H, m), 1.47 (2H, m), 1.81 (2H, m), 2.04 (2H, m), 3.29 (2H, m), 7.47 (2H, br) ppm; IR (KBr) ν: 3312, 1480, 1075, 760cm−1.

Tetrahydropyrimidine-2(1H)-thione (6d)

m.p. 210°C–212°C; 1H NMR (DMSO-d6, 400 MHz) δ: 1.90 (2H, m), 3.27 (2H, t, J = 6.1 Hz) 3.33 (2H, d, J = 2.7 Hz), 7.59 (2H, br) ppm; IR (KBr) ν: 3307, 1510, 1022, 786cm−1.

5,5-Dimethyltetrahydropyrimidine-2(1H)-thione (6e)

m.p. 228°C–230°C; 1H NMR (DMSO-d6, 400 MHz) δ: 0.91 (6H, s), 3.31 (4H, s), 7.88 (2H, br) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 175.1, 51.2, 25.6, 23.7ppm; IR (KBr) ν: 3316, 1491, 1075, 763cm−1; Anal. Calcd. for C6H12N2S: C 49.96, H 8.39, N 19.42, S 22.23; found: C 49.93, H 8.44, N 19.46, S 22.17.

4-Ethyltetrahydropyrimidine-2(1H)-thione (6f)

m.p. 139°C–140°C; 1H NMR (DMSO-d6, 400 MHz) δ: 0.84 (3H, t, J = 7.4 Hz), 1.39–1.48 (2H, m), 1.77–1.84 (2H, m), 3.07–3.17 (3H, m), 7.82 (1H, br), 7.89 (1H, br) ppm; 13C NMR (DMSO-d6, 100 MHz) δ: 175.3, 51.5, 38.3, 27.3, 23.7, 9.4ppm; IR (KBr) ν: 3316, 1491, 1075, 763cm−1; Anal. Calcd. for C4H8N2OS: C 36.35, H 6.10, N 21.19, S 24.25; found: C 36.41, H 6.15, N 21.16, S 24.23.

Synthesis of MgO nanoparticles

MgO NPs were synthesized in size 23.7–25.7nm through sol–gel method.[25] 25ml of 0.008 M NaOH was gradually added to a stirring mixture of MgNO3 (12.83g) and starch (0.1g). Mixture was stored for 24h at room temperature. Precipitates were collected and heated at 300°C for 4h to produce MgO NPs. NPs were characterized using X-ray diffractometer and scanning electron microscopy (SEM) techniques [Figure 3] and [Figure 4].
Figure 3: X-ray diffractometer spectrum of MgO nanoparticles

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Figure 4: Scanning electron microscopy image of MgO nanoparticles

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Preparation of glycine solution

Glycine purchased from Sigma-Aldrich was sterilized by filter 0.22 μm.[23]

Preparation of bacterial suspension

V. fluvialis (IBRC-M 10800) was purchased as lyophilized form from the Iranian Biological Resource Center, Tehran, Iran. Bacterium was cultured in Mueller–Hinton broth at 30°C for 24h. The 0.5 McFarland turbidity (1.5 × 108 CFU/ml) of bacterium was spectrophotometrically prepared, which was considered as stored source.[26]

Determination of the minimum inhibitory concentration

All antimicrobial susceptibility tests were done through broth microdilution and disk diffusion methods according to the CLSI guidelines and repeated three times.[26] The results were reported as the mean of these experiments. The antibiotic ciprofloxacin was applied as positive control. In minimum inhibitory concentration (MIC) experiment, initial bacterial suspension was diluted 150 times to achieve a concentration of 1 × 106 CFU/ml. 10 μl of diluted bacterial suspension and 170 μl of Mueller–Hinton broth were added to each well in a 96 well microplate. 20 μl of different concentrations of derivatives was added to wells to achieve the final concentrations in the range of 8192–4μg/ml. Microplates were placed in a shaking incubator at 30°C for 24h. MIC values were determined as the lowest concentration in which the turbidity of bacterial growth was not observed.

Determination of the minimum bactericidal concentration

A sample of all wells without turbidity in MIC test was cultured in Mueller-Hinton agar and incubated at 30°C for another 24h.[27] The lowest concentration inhibited the visible growth of bacterial colonies was reported as minimum bactericidal concentration (MBC) values.

Measurement of the inhibition zone diameter

100 μl of initial bacterial suspension was spread on Mueller-Hinton agar. Sterile blank discs were placed on the agar media. 10 μl of compounds at a concentration of 10240μg/ml were poured onto them. Plates were incubated under similar conditions. Visible inhibition zone diameters (IZDs) were measured by caliper.

  Results Top

No inhibitory activity was observed with MgO NPs and glycine [Table 1]. In thiazoles 3a-f, only derivative 3e could block the growth of pathogen with IZD = 7.1mm, MIC = 2048μg/ml, and MBC = 4096μg/ml. Imidazolidine derivatives 6a and b and tetrahydropyrimidine derivatives 6d-f showed antibacterial properties against V. fluvialis with IZDs = 6.7–19.1mm, MICs = 256–2048μg/ml, and MBCs = 1024–4096μg/ml. The best inhibitory activity was recorded with imidazolidine-2-thione (6a).
Table 1: Antibacterial effects of compounds against Vibrio fluvialis

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  Discussion Top

The excessive consumption of antibiotics has led to the spread of resistant bacterial strains. V. fluvialis is an emerging pathogen that its standard and drug-resistant strains are rapidly expanding. In this research project, antimicrobial potentials of glycine, MgO NPs, and synthetic heterocyclic compounds including thiazoles 3a-f, imidazolidines 6a-c, and tetrahydropyrimidines 6d-f were assessed on standard strain of V. fluvialis.

Glycine did not show inhibitory activity against V. fluvialis. It was suggested that this amino acid could block the growth of bacteria, especially Gram-positive strains by inhibiting peptidoglycan synthesis.[28] It was found that chloro and bromoglycine derivatives could more efficiently inhibit the activity of B. subtilis, although they were ineffective on  Salmonella More Details enterica.[29] In addition, no antimicrobial activity has been observed with glycine betaine.[30]

No antimicrobial activity was recorded with MgO NPs. These NPs are effective on bacteria through generation of oxygen-free radicals, alkalization of environment, and destruction of cell wall.[31] Factors such as size, pH, form, and concentration affect antibacterial properties. They were more effective on Gram-positive bacteria than Gram-negative strains.[32] They are ineffective against bacteria of the family Vibrionaceae such as Vibrio harveyi and Vibrio parahaemolyticus.[33]

Derivative 3e was the only effective thiazole on V. fluvialis. It contains a thiazolone ring, unlike derivatives 3a-d, it contains a thiazolone ring. Molecular structure of heterocycle 3f is similar to 3e, except that it contains methyl substituent on the 5-position of the thiazolone ring instead of hydrogen. Inhibition of DNA gyraseB enzyme or HFq protein was recommended for their action mechanism.[8],[34] A variety of antibacterial activities were observed with compounds containing thiazole ring; substituents including phenyl, nitro, chloro, fluoro, bromo, and fused or attached heterocycles have improved their inhibitory effects.[8] Antimicrobial potential of thirty thiazole derivatives were evaluated by Bharti et al. against V. cholera; only two compounds containing bromophenyl and diphenyl substituents were effective on this pathogen.[35] Similar inhibitory activities were observed with some chlorothiazole derivatives on Vibrio parahaemolyticus.[36]

Antibacterial activity was recorded with imidazolidines 6a and b. It seems that antibacterial effects of imidazidines 6a-c had decreased with increasing the molecular volume. Imidazolidine derivatives could inhibit dihydrofolate reductase, which reduces dihydrofolic acid to tetrahydrofolic acid and lipid synthesis.[37] A variety of biological activities such as antitumor, antiviral, and antifungal were observed with N-aryl imidazolidineiminothiones;[38] they were quite successful in inhibiting E. coli, P. aeruginosa, and B. subtilis.

All tetrahydropyrimidines 6d-f were effective on V. fluvialis. Molecular volume has been ineffective on antibacterial activity. Inhibitory activity of tetrahydropyrimidine derivatives was evaluated on pathogenic bacteria such as E. coli, S. aureus, P. aeruginosa, K. pneumoniae, and B. subtilis.[39],[40],[41]

  Conclusion Top

To conclude, some synthetic heterocycles, especially imidazolidine-2-thion (6a) showed inhibitory activity against V. fluvialis, while their effects were not significant in comparison with ciprofloxacin. Introduction of new substituents on these heterocyclic compounds or their utilization as ligand in complexes can improve antibacterial effects; it must be considered in future researches.


The authors would like to thank the Torbat Jam Faculty of Medical Sciences for their facilities and financial support.

Financial support and sponsorship

This work was financial support by Torbat Jam Faculty of Medical Sciences under Grant (number REC.1397.019).

Conflicts of interest

There are no conflicts of interest.

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  [Figure 1], [Figure 2], [Figure 3], [Figure 4]

  [Table 1]


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