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28
UDC 541.49
ANTIMICROBIAL, TOXICOLOGICAL AND PHYSIOLOGICAL EFFECTS OF THE COMPLEX CO(II) WITH THIOSEMICARBAZONE OF GLYOXYLIC ACID
M.T.Huseynova
A.Guliyev Institute of Chemistry of Additives, NAS of Azerbaijan [email protected] Received 25.02.2019
The complex Co(II) with thiosemicarbazone of glyoxylic acid Co(HGAT)-2H2O was synthesized, and added into the hemolymph tissue of model larvae of Galleria mellonella L and some biochemical parameters and changes of metabolic enzymes activity were studied. For a research used the enzymes Aspartate aminotransferase, Alanine Aminotransferase, Lactate dehydrogenase, Creatine Kinase and Gamma-glutamyltransferase. The first three of them on results of experiments present the greatest interest, so they are chosen for research.. Measurements were taken through 2, 4, 6 and 8. It was revealed that the introduction of the complex synthesized by us to into the first two enzymes increases their bioindicator activity. Introduction of the complex to Lactate dehydrogenase increases activity of the last with 30 ± 2.76 to 131.25 ± 3.10 in 8 hours. The effective results we obtained convinces us of the need to use them to study metal complexes of various structures and mechanisms of influence on the organism and also for fight with wreckers insects at the minimum damage to the environment. Also results of antibacterial and antifungal properties both a ligand, and complex are described.
Keywords: Galleria mellonella, Transaminase enzymes, Co(II) complex, biochemical damage, antimicrobial activity.
https://doi.org/10.32737/0005-2531-2019-2-22-28 Introduction
Metallic complexes of thiosemicarba-zones have a wide spectrum of biological activity, and their pharmacological applications have been extensively studied. There are a number of reviews on many aspects of the chemistry of these compounds, such as preparative methods, stereochemistry, bond types in metal complexes, spectral characteristics, and crystal structures [1-5]. Many papers mention their pharmacological properties of these versatile compounds [6-8]. To our knowledge, this is probably the first review entirely dedicated to their broad range of biological and therapeutic applications. The biological properties of thiosemi-carbazones are often associated with their coordination of metal ions. It is changed in first by lipophilicity, which controls the rate of penetration into the cell [9]. Some side effects may decrease with complexation because the metal complex may be more active than the free li-gand. Also, the free ligand does not show biological activity which the complex can exhibit. The mechanism of action may involve binding to the metal in vivo, or the metal complex may be a carrier for activating the ligand as a cytotoxic agent. Moreover, coordination can lead to a
significant decrease in drug resistance [4]. The metal complexes with thiosemicarbazone derivatives of aldehyde- and keto-acids are of interest due to their biological activity, and structural and magnetic properties. Thiosemicarbazone aldehydes and keto-acids possess antimicrobial, antiviral and anticancer activity and are inhibitors of the synthesis of DNA [10-18].
Structures having O, N, and S atoms lead to active coordination chemistry in the presence of thiosemicarbazone molecules. Metal complexes with these ligands may have a mononuclear, binuclear and polymeric structure [19]. The agricultural pests cause economic losses. We have directed our work to combat insect pests. Carbox-ylic acids are known to form coordination complexes with transition metal carboxylates, and these complexes are widely used in agriculture, biology, medicine, and other fields [10]. It is known that metal complexes of carboxylic acids have antioxidant, antibacterial, antifungal, cyto-toxic, fungicide, insecticide activity and are effective against rot [20-22].
In this study, we examined some biochemical parameters of insects and changes in the activity of metabolic enzymes complex of Co(II), which were previously synthesized Co(C3H4N3O2S)2-2H2O (I) [12] and studied by
X-ray, spectroscopic properties, also examined the biochemical parameters of insects. Model insect Galleria mellonella L. larvae of metabolic enzymes in the hemolymph tissue alanine aminotransferase (AST), aspartate aminotransferase (ALT) creatine kinase (CK), lactate a dehydrogenase (LDH) gamma-glutamyltrans-ferase (GGT) and biochemical parameters of total bilirubin (BILT), direct bilirubin (BILD), total protein (TP), urea (UREA) and uric acid (UA) It is aimed to determine the effects on the amount. This article explores the possibilities of using metal complexes with various chemical structures and mechanisms of action in the fight against harmful insects with minimal damage to non-target organisms and the environment.
Materials and methods
Collection of hemolymphs. At 2, 4, 6 and
8 hours after injection, the 7 stage larvae were incubated on ice for 5 min. The surface of the larvae was then disinfected with 95% ethyl alcohol. Using the Hamilton needle, hemolymphs from the abdomen of the insect were plucked into the Eppendorf. Some PTU crystals were placed in the Eppendorf to prevent melanisation. Samples were stored at -800C until analysis. The cryotubes were kept at room temperature until the tissue began to thaw before using.
Statistical analysis. One-way analysis of variance [23] (ANOVA) (SPSS 1997) test was used for the evaluation of enzyme activity and biochemical parameters.
"LSD Test" significance [23] (SPSS 1997) was used to determine the importance of the difference between means. A 0.05 probabili-
ty level was used to check the significance of the difference between means.
Practical part
The antimicrobial efficacy of the samples was determined by the method of zonal diffusion according to GOST 9.085-78 using the following microorganisms: bacteria - Pseudomonas aeruginosa, Mycobacterium phlei; mushrooms : Aspergillus niger, Penicillium Chryso-genum, Penicillium chrysogenum, Cladosporium resinae.
For a preliminary assessment of the effectiveness of antimicrobial properties, the test compounds were tested in a solvent (DMF for complex compounds) and ethyl alcohol (for the ligand).
Results
Effect of Co(II) complex on metabolic enzyme activity. The study showed that after 8 hours, statistically increased transaminase activity was observed. It was established that the activity of the AST enzyme increased from 102±4.51 U/L to 4765.5±19.42 U/L after 8 h. It was found that the activity of the ALT enzyme also increases at the end of 8 hours compared with the control group. The activity of the GGT enzyme increased from 2.8±0.23 U/L to 8.42±0.26 U/L after 8 hours. It was observed that the activity of metabolic enzymes was caused by melanization within 6 hours. CK enzyme activity of metabolic enzymes increased from 189.75±2.60 units/L to 739.5±8.58 units/L in 8 h. The activity of the LDH enzyme increased from 30±2.76 U/L to 131.25±3.10 U/L (Table 1, Scheme).
Table 1. Effect of Co(II) complex on the enzyme activity of Galleria mellonella hemolymph
Parameters AST(Aspartate Aminotransferase), U/L) (Avg.*±S.E)t ALT(Alanine Aminotransferase) (U/L) (Avg.*±S.E)t CK(Creatine Kinase) (U/L) (Avg.*±S.E)t LDH(Lactate Dehydrogenase) (U/L) (Avg.*±S.E)t GGT(Gamma Glu-tamylTransferase) (U/L) (Avg.*±S.E)t
control 102 ± 4.51 a 42.5±2.07a 189.75±2.60a 30±2.76a 2.8± 0.23a
2 hours 1161.25±4.62b 172.5±2.21b 732.5±6.75b 96.5±2.08£ 2.50±0.32a
4 hours 2116.25±10.12c 335.25±3.76c 1025.75±4.21c 142.5±9.04c 5.98±0.16b
6 hours 735±6.75d 76.5±3.6d 102±4.01d 18.75±2.86a 1.02±0.34c
8 hours 4765.5± 19.42e 985.5±7.75 e 739.5±8.58e 131.25±3.1c 8.42±0.26d
T Average of four replicates
"Values with the same letter in the same column are not different from each other, P> 0.05 (LSD Test).
The effect of Co(II) complex on biochemical parameters. According to the analysis, it was found that BILT increased statistically 8 h compared with the control group. There were no statistical changes in BILD in 8 h. The number of UREA was increased after 8 h and it was found that the number of UA was statistically reduced at the end of 8 h compared with the control group. The amount of TP decreased from 1.17 ± 0.005 g/dl to 0.72 ± 0.01 g/dl after 8 h (Table 2, Scheme).
The effect of Co(II) complex on antimicrobial activity. For a preliminary assessment of the effectiveness of the antimicrobial properties of the tested compounds were examined in various solvents (DMF for complex compounds) and ethyl alcohol (for ligand). DMF solvent and ethyl alcohol were used as controls. Pyridine was also tested as a solvent, but it turned out that it has high antimicrobial activity and completely inhibits the growth of
microorganisms. Therefore, it is impractical to use this solvent as a control. Meat-peptone agar (MPA) was used to grow bacterial cultures, and mash agar (CA) was used for fungi. Test compounds were added to the solvent and alcohol in a mass percentage of 1.0, 0.5, and 0.25. The tests were carried out as follows: in a Petri dish poured the nutrient medium in an amount of 20-25 ml and allow it to cool. Sowing of microorganisms was performed on the surface of the nutrient medium. Then, wells of 4-5 mm in depth were made on the surface of the medium using a sterile drill with a diameter of 10 mm, to which 0.3-0.5 ml of the tested samples with the indicated compounds were added. Next, Petri dishes were placed in a thermostat and kept for 2 days using bacteria and 3-4 days for fungi at 29 ± 20C. It is more, the more effective antimicrobial action. These antimicrobial screening are presented in Table 3.
Parameters TP(Total Protein) (g/dL) (Avg*±S.E)t BILT (Bilirubin Total) (mg/dL) (Avg*±S.E)t BILD (Bilirubin Direct) (mg/dL) (Avg*±S.E)t UREA (Urea) (mg/dL) (Avg*±S.E)t UA(Uric Acid) (mg / dL) (Avg*±S.E)t
control 1.17 ± 0.005a 0.02±0.005a 0.04±0.005a 3.20 ±0.16a 0.36±0.02a
2 h 0.82±0.04b 0.12±0.03b 0.08±0.005a 3.44±0.20a 0.05±0.005b
4 h 1.24±0.05a 0.18±0.03c 0.18±0.012a 8.92±0.44b 0.16±0.016c
6 h 0.32±0.02c 0.08±0.004b 0.09±0.004a 3.96±0.20a 0.08±0.004b
8 h 0.72 ± 0.01b 0.17±0.01c 0.07±0.012a 9.02±0.64b 0.18±0.016c
--
Average of four replicates
t Values with the same letter in the same column are not different from each other, P> 0.05 (LSD Test).
Table 2. Effect of Co(II) complex on some biochemical parameters of Galleria mellonella hemolymph tissue
Table 3. Antimicrobial screening data
DMF solvent
Compound microbial extermination zone
Biocide bacterium mushrooms
concentration (Pseudomonas aeruginosa, Mycobacterium phlei) (Aspergillus niger, Penicillum Chrysogenium)
Thiosemicarbazide of gly-oxylic acid (H2GAT) 1 2.8-3.4 3.2-3.5
0.5 2.5-2.7 3.0-3.2
0.25 2.5-2.5 2.5-2.5
1 3.2-3.5 3.5-4.0
Co(HGAT)-2H2O 0.5 2.8-2.6 1.8-2.0
0.25 2.4-2.6 1.8-2.0
DMF test sample - 2.4-2.6 2.2-2.4
Discussion
Some biomolecules, such as protein, lipid and carbohydrate, are essential for the vital activities of insects. These biomolecules are affected by biological (diapoz, nutrient quality, sex, etc.) and chemical (insecticide applications) factors. There is oxidative stress in insects against insecticides [24-26]. Against this stress, free radicals are formed in insects. These reactive molecules negatively affect many biological systems such as proteins, lipids, nucleic acids and enzymes in insects [27, 28]. Insects; they produce antioxi-dant enzymes against oxidative damage and try to eliminate the damage. If the antioxidant defense system is inadequate, increased damage causes cellular ageing, cancer formation or cell death. Co(II) complex has been shown to increase metabolic enzyme activity of Galleria mellonella hemolymph. Chemical and biological agents cause tissue damage in organisms, resulting in the release of cellular enzymes, which leads to an increase in enzyme concentration. Galleria melloenlla larvae of an antihelmintic antibiotic, oxfendazole, have been found to increase metabolic enzyme activity statistically in the hemolymph tissue. The activities of transaminase enzymes are used as a clinical diagnosis in order to test organ dysfunctions in mammals and to detect functional damage if any [29]. However, these tests have been used by researchers who study the effects of chemicals with high environmental biology and toxic effects on insects. The Co(II) complex increased the activity of Galleria mellonella transferase by 8 h. Especially the increase in the amount of AST and ALT is
an essential biomarker of progressive tissue and cell damage [30]. In this study, it was determined that AST activity and ALT activity increase statistically. This increase indicates that insect cell damage increases over time. A decrease in the activity of the transaminase enzyme in an insect after 6 hours indicates a toxic effect of the Co(C3H4N3O2S)2-2H2O complex, which leads to the inactivation of enzymes and denaturation. It was reported that AST and ALT activity increased significantly in Culexfatigans (Wiedemann) species exposed to various insecticides [31]. In another study, AST and ALT enzyme activities of the Philosamiaricini (Boisduval) larvae fed with tetracycline were doubled [32]. In another study in which the toxic effects of organophosphorus insecticides on Galleria mellonella larvae were investigated, it was observed that AST and ALT activity increased significantly. In another study, it was reported that endoparasitoid Pimplaturionellae poison significantly increased the activity of Galleria mellonella AST and ALT.
LDH is a metabolic enzyme that increases damage to the cells and tissues of organisms. It was established that the Co(II) complex statistically increases at the end of 8 h in the hemolymph tissue of the larvae of G. mellonella. Increased activity of LDH, as well as the activity of AST and ALT contribute to cell damage. Microplusus antiparasitic drug Rhipicephalus (Boophilus) in a study on the oxidative level of fluazuron; with an increase in the time of chemical exposure, hemoglobin activity in hemo-lymph and adipose tissue increased [28]. In
another study, the biological agent Klebsiella oxytoca, injected into the larvae of Galleria mellonella, had a significant increase in the activity of the LDH enzyme in the hemolymph tissue of the insect within 8 hours. The determination of changes in the total protein content of a particular tissue in insects is important in terms of whether substances contained in nutrients are used effectively and whether this affects growth. Since proteins stored in the larval period are used as energy sources, it is known that they play an important role in the development of the insect [33].
The Co(II) complex increased the biochemical parameters (BILT and UREA) of Galleria mellonella after 8 h and it was determined that the amount of UA decreases statistically at the end of 8 h. This complex has no statistical effect on BILD. In a study on the effect of neem tree oil on Xanthogaleruca luteola, it was reported that the amount of urea in high concentrations increased [34]. In a study investigating the biochemical effects of pyriproxyfen on silkworm, it has been shown that the insect increases the amount of urea and uric acid in the hemolymph tissue at high concentrations [27]. Understanding the mechanism of action of the Co(C3H4N3O2S)2-2H2O complex on the model organism Galleria mellonella will allow the development of new chemical methods that are less toxic to non-target organisms and the environment in combating harmful insects.
Conclusion
In this study, we examined some of the biochemical parameters of insects. This study is In this study, we examined the use of metal complexes with various chemical structures and mechanisms of action in the fight against harmful insects with minimal damage, so as not to affect organisms and the environment. Galleria mellonella larvae of Co(C3H4N3O2S)2-2H2O complex decreased the total protein content in hemolymph tissue within 8 hours. This may be because of the toxic effect of the complex Co(C3HN3O2S)2-2H2O adversely affects the development of the insect. Co(II) complex increased the biochemical parameters (BILT and UREA) of Galleria mellonella within 8 hours.
It was found that the amount of UA decreased statistically at the end of 8 hours. It was determined that this complex has no statistical effect on BILD. The results of antimicrobial activity show that the metal complex exhibits antimicrobial properties, and it is important to note that they exhibit increased inhibitory activity compared to the parent ligand. It was also suggested that concentration plays an important role in increasing the degree of inhibition; as the concentration increases, the activity increases.
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QLÏOKSÏL TURÇUSUNUN TÏOSEMÏKARBAZONUNUN Co(II) KOMPLEKSÏNÏN TOKSiKOLOJi,
FiZiOLOJi VO ANTÏMÏKROB TOSÏRl
M.T.Hüseynova
Qliaksil turçusunun tiosemikarbazonunun Co(II) kompleksi Co(HGAT)-2H2O sintez edilib, Galleria mellonella L. qurd nümunalarinin hemolimfa toxumalarina daxil edilib, bazi biokimyavi parametrlar va metabolik fermentlarin aktiv-liklarinin dayiçmasi öyranilib. Tadqiqat ûçûn Aspartate aminotransferase, Alanine aminotransferase, Lactate dehydrogenase, Сгeatine kinase va Gamma-glutamyltransferasе fermentlarindan istifada edilib. Tacrübalarin naticalarina asasan tadqiqat ûçûn götürülmüij nümunalardan ilk ûçû daha böyük maraq kasb edir. Ôlçmalarin naticalari 2, 4, 6 va 8 saatdan sonra qeyd edilib. Müayyan edilmiçdir ki, sintez edilmiç kompleks ilk iki fermentin bioindikator aktivliyini artinr. Kompleksin Lactate dehydrogenase fermentina daxil edilmasi isa 8 saatdan sonra onun aktivliyini 30±2.7-dan 131.25±3.10-a qadar artirir. Olda etdiyimiz effektiv naticalar demaya imkan verir ki, sintez etdiyimiz kompleks müxtalif quruluçlu metal komplekslarin va orqanizma tasir mexanizmlarinin öyranilmasinda, hamçinin atraf mühita an az zarar vermakla zararli ha çaratlarla mübarizada istifada edila bilar. Hamçinin liqand va kompleksin göbalak aleyhina va antibakterial xassalarinin naticalari da qeyd edilmiçdir.
Açar sözlar: Galleria mellonella, Transaminaz fermentlari, Co(II) kompleksi, biokimyavi zada, antimikrob faaliyyati.
АНТИМИКРОБНЫЕ, ТОКСИКОЛОГИЧЕСКИЕ И ФИЗИОЛОГИЧЕСКИЕ ЭФФЕКТЫ КОМПЛЕКСА Co(II) С ТИОСЕМИКАРБАЗОНОМ ГЛИОКСИЛОВОЙ КИСЛОТЫ
М.Т.Гусейнова
Синтезирован комплекс Co(II) с тиосемикарбазоном глиоксиловой кислоты Co(HGAT)-2H2O, который вводили в ткань гемолимфы модельных личинок насекомых Galleria mellonella L. и изучали некоторые биохимические параметры и изменение активности метаболических ферментов. Для иследования использовали ферменты Aspartate aminotransferase, Alanine aminotransferase, Lactate dehydrogenase, Creatine kinase и Gamma-glutamyltransferase. Наибольший интерес по результатам экспериментов представляли первые три из них, которые были выбраны для ^следования. Измерения проводили через 2, 4, 6 и 8 ч. Было выявлено, что введение синтезированного нами комплекса в первые два фермента повышает их биоиндикаторную активность. Введение комплекса в Lactate dehydrogenase повышает активность последнего с 30±2.76 до 131.25±3.10 через 8 ч. Полученные нами эффективные результаты убеждают в необходимости использования их для изучения комплексов металлов различных структур и механизмов влияния на организм, а также для борьбы с вредными насекомыми при минимальном ущербе окружающей среде. Описаны также результаты антибактериальных и противогрибковых свойств как лиганда, так и всего комплекса.
Ключевые слова: Galleria mellonella, ферменты TpancaMuna3u, комплекс Co(II), биохимическое повреждение, антимикробная активность.
