The determination of the effect of some 1,3,4 thiadiazole derivatives on biochemical content (Fatty Acids, Sterols, Lipophilic Vitamins) in rat liver

Akif E. Parlak; Yusuf Karagozoglu; Naci í–. Alayunt; Semra Turkoglu; Mustafa Karatepe; Metin Koparir

doi:10.14715/cmb/2018.64.3.6

Issue

Vol. 64 No. 3: Issue 3

Issue Published : March 3, 2018

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The determination of the effect of some 1,3,4 thiadiazole derivatives on biochemical content (Fatty Acids, Sterols, Lipophilic Vitamins) in rat liver

https://doi.org/10.14715/cmb/2018.64.3.6

Akif E. Parlak

Keban Vocational School of Higher Education, Firat University, Elazig, Turkey

Yusuf Karagozoglu

Department of Chemistry, Faculty of Science and Arts, Bingol University, Bingol, Turkey

Naci í–. Alayunt

Banaz Vocational School, Usak University, Usak, Turkey

Semra Turkoglu

Department of Nutrition and Dietetics, Faculty of Health Sciences, Firat University, Elazig, Turkey

Mustafa Karatepe

Department of Chemistry, Faculty of Science and Arts, Firat University, Elazig, Turkey

Metin Koparir

Department of Chemistry, Faculty of Science and Arts, Firat University, Elazig, Turkey

Corresponding Author(s) : Semra Turkoglu

smrturkoglu@hotmail.com

Cellular and Molecular Biology, Vol. 64 No. 3: Issue 3
Article Published : February 28, 2018

Abstract

Thiadiazole derivatives and its metal compounds have antibacterial, antifungal, antitumoral, antiproliferative and antioxidant properties. In the study, the effects caused by thiadiazole ligand and its metal complexes upon the fatty acids and lipophilic vitamins in livers of rats were examined. The fatty acids in liver were specified by GC while the lipophilic vitamins were specified by HPLC. It was observed that the amounts of oleic acids (18:1, n-9) and monounsaturated fatty acids (MUFA) notably increased in the Mn complex group while the amounts of arachidonic acid (20:4, n-6) notably increased in the ligand group, compared to control group. The amounts of vitamin K2, vitamin D3 and Î±-tocopherol considerably increased in all groups compared to control group. It was noted that the amounts of Î±-tocopherol were elevated in both the Mn and Cr complex groups compared to control group. However, this elevation was matching with the amount in the same groups. Nevertheless, the amount of retinol was determined to be lower in the Mn complex group compared to other groups. Accordingly, it can be considered that thanks to the utilization of toxic metals such as manganese, cadmium and chrome, unsaturated fatty acids influenced the activities of the enzymes in liver tissue, which are in charge of fatty acid chain elongation.

Keywords

Hydroxyurea Derivative 1 3 4-thiadiazole Fatty acid Lipophilic vitamin Liver Rat.

Parlak, A. E., Karagozoglu, Y., Alayunt, N. í–., Turkoglu, S., Karatepe, M., & Koparir, M. (2018). The determination of the effect of some 1,3,4 thiadiazole derivatives on biochemical content (Fatty Acids, Sterols, Lipophilic Vitamins) in rat liver. Cellular and Molecular Biology, 64(3), 35–39. https://doi.org/10.14715/cmb/2018.64.3.6

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References

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Kritsanida M, Mouroutsou A, Marakos P, Pouli N, Papakonstantinou-Garoufalias S, Pannecouque C, Witvrouw M, De Clercq E. Antiviral Synthesis and antiviral activity evaluation of some new 6-substituted 3-(1-adamantyl)-1,2,4-triazolo [3,4-b] [1,3,4] thiadiazoles. II Farmaco 2002; 57:253-257.
Amorim ELC, Brandao SSF, Cavalcanti COM. Synthesis and structure of substituted bromo and nitrobenzyl benzylidene imidazolidinediones and thiazolidinediones. Ann Pharm Fr 1992; 50:103-111.
De Lima JG, Perrissin M, Chantegrel J, Luu-Duc C, Rousseau A, Narcisse G. Synthesis and pharmacological evaluation of some 3-phenacyl-5-benzylidene-thiazolidine-2,4-diones. Arzneimittelforschung 1994; 44:831-834.
Kadi AA, El-Brollosy NR, Al-Deeb OA, Habib EE, Ibrahim TM, El-Emam AA. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur J Med Chem 2007; 42:235-242.
Jackson T, Woo LW, Trusselle MN, Chander SK, Purohit A, Reed MJ, Potter BV. Dual aromatase-sulfatase inhibitors based on the anastrozole template: synthesis, in vitro SAR, molecular modelling and in vivo activity. Org Biomol Chem 2007; 5:2940-2952.
Matsumoto T, Ootsu K, Okada Y. Effects of 2,2-(Methylenediimino)bis-l,3,4-thiadiazole (NSC-143019) on tumor growth and ımmune responses in mice. Cancer Chemother Rep 1974; 58:331-334.
Stewart JA, Ackerly CC, Myers CF, Newman RA, Krakoff IH. Clinical and clinical pharmacologic studies of 2-amino-1,3,4-thiadiazole. Cancer Chemother Pharmaco 1986; 16:287-291.
Borras J, Casanova J, Cristea T, Gheorghe A, Scozzafava A, Supuran CT, Tudor V. Complexes with biologically active ligands. part 6 Ni(II) coordination compounds of hydrazine and heterocyclic sulfonamides as inhibitors of the zinc enzyme carbonic anhydrase. Met Based Drugs 1996; 3:143-148.
Devasagayam TPA, Pushpendran CK, Eapen J. Differences in lipid peroxidation of rat liver rough and smooth microsomes. Biochim Biophys Acta 1983; 750:91-97.
Yoshikawa T, Toyokuni S, Yamamoto Y, Naito Y (Eds.). Free radicals in chemistry, biology and medicine. OICA International, London 2000, pp. 580.
Oner H, Karatepe M, Karatas F, Oner J, Yilmaz I, Cukurovali A. Effects on the rat testes of thiosemicarbazone derivative schiff base (4-(1-phenyl- methylcyclobutane-3-yl)-2-(2-ydroxybenzylidenehydrazino)thiazole) and its cadmium (II) complex. Cell Biochem Funct 2005; 23:427-433.
Karatepe M, Karatas F. Antioxidant, pro-oxidant effect of the thiosemicarbazone derivative schiff base (4-(1-phenylmethylcyclobutane-3-yl)-2-(2hydroxybenzylidene hydrazino) thiazole) and its metal complexes on rats. Cell Biochem Funct 2006; 24:547-554.
Varvaresou A, Tsantili-Kakoulidou A, Siatra-Papastaikoudi T, Tiligada E. Synthesis and biological evaluation of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole and 1,3,4-thiadiazole analogs. Arzneimittelforschung 2000; 50:48-54.
Cesur N, Birteksöz S, í–tük G. Synthesis and Biological Evaluation of some new thiosemicarbazide, 4-thiazolidinone, 1,3,4-oxadiazole and l,2,4-triazole-3-thione derivatives bearing imidazo[l,2-a]pyridine moiety. Acta Pharmaceutica Turcica 2002; 44:23-41.
í‡etin A., Cansız A., Koparır M. Organic Chem., An Indian J 2006; 2:140.
Hara A, and Radin NS. Lipid extraction of tissues with a low-toxicity solvent. Anal Biochem 1978; 90:420-426.
Christie WW. Gas chromatography and lipids. The Oil Pres, Glaskow 1992.
Tvrzicka E, Vecka M, Stankova B. and Zak A. Analysis of fatty acids in plasma lipoproteins by gas chromatography flame ionisation detection Quantative aspects. Anal Chimica Acta 2002; 465:337-350.
Katsanidis E, Addis PB. Novel HPLC analysis of tocopherols and cholesterol in tissue. Free Radic Biol Med 1999; 27:1137-1140.
Lu GF, Flipovi M, Heinemann FW, Ivanovi-Burmazovi I. Seven-coordinate iron and manganese complexes with acyclic and rigid pentadentate chelates and their superoxide dismutase activity. Inorg Chem 2007; 46:8825–8830.
Turan N, et. al. Pro-oxidant and antiproliferative effects of the 1,3,4-thiadiazole–based Schiff base and its metal complexes, Drug and Chemical Toxicology, 34:4, 369-378
Kudo N, Waku K. Cadmium suppresses delta 9 desaturase activity in rat hepatocytes. Toxicol 1996; 114:101-111.
Dayangac A, Yılmaz M, Konar V, Yilmaz O. The effects of cadmium on fatty acid composition in some tissues of rats. Journal of Research of Eastern Anatolia Region 2006; 4:89-92.
Grawe KP, Pickova J, Dutta PC, Oskarsson A. Fatty acid alterations in liver and milk of cadmium exposed rats and in brain of their suckling offspring. Toxicol Let 2004; 148:73-82.
Sarı A, í‡ukurovalı A. Investigation of the effects of thiosemicarbazone derivative schiff bases containing cyclobutano ring on fatty acids in liver of rabbits. Journal of Research of Eastern Anatolia Region 2008; 7:183-186.
Antueno RJ, Kinckle LC, Smith H, Eliot ML, Allen SJ, Nwaka S, Winther MD. Activity of human âˆ†5 and âˆ†6 desaturases on multiple n-3 and n-6 polyunsaturated fatty acids. FEBS Let 2001; 509:77-80.

References

Diurno MV, Mazzoni O, Piscopo E. On antimicrobial activity of 3-phenylspiro [3H-indole-3,2-thiazolidine]-2,4(1H)-diones. Farmaco 1993; 48:435-441.

Kritsanida M, Mouroutsou A, Marakos P, Pouli N, Papakonstantinou-Garoufalias S, Pannecouque C, Witvrouw M, De Clercq E. Antiviral Synthesis and antiviral activity evaluation of some new 6-substituted 3-(1-adamantyl)-1,2,4-triazolo [3,4-b] [1,3,4] thiadiazoles. II Farmaco 2002; 57:253-257.

Amorim ELC, Brandao SSF, Cavalcanti COM. Synthesis and structure of substituted bromo and nitrobenzyl benzylidene imidazolidinediones and thiazolidinediones. Ann Pharm Fr 1992; 50:103-111.

De Lima JG, Perrissin M, Chantegrel J, Luu-Duc C, Rousseau A, Narcisse G. Synthesis and pharmacological evaluation of some 3-phenacyl-5-benzylidene-thiazolidine-2,4-diones. Arzneimittelforschung 1994; 44:831-834.

Kadi AA, El-Brollosy NR, Al-Deeb OA, Habib EE, Ibrahim TM, El-Emam AA. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur J Med Chem 2007; 42:235-242.

Jackson T, Woo LW, Trusselle MN, Chander SK, Purohit A, Reed MJ, Potter BV. Dual aromatase-sulfatase inhibitors based on the anastrozole template: synthesis, in vitro SAR, molecular modelling and in vivo activity. Org Biomol Chem 2007; 5:2940-2952.

Matsumoto T, Ootsu K, Okada Y. Effects of 2,2-(Methylenediimino)bis-l,3,4-thiadiazole (NSC-143019) on tumor growth and ımmune responses in mice. Cancer Chemother Rep 1974; 58:331-334.

Stewart JA, Ackerly CC, Myers CF, Newman RA, Krakoff IH. Clinical and clinical pharmacologic studies of 2-amino-1,3,4-thiadiazole. Cancer Chemother Pharmaco 1986; 16:287-291.

Borras J, Casanova J, Cristea T, Gheorghe A, Scozzafava A, Supuran CT, Tudor V. Complexes with biologically active ligands. part 6 Ni(II) coordination compounds of hydrazine and heterocyclic sulfonamides as inhibitors of the zinc enzyme carbonic anhydrase. Met Based Drugs 1996; 3:143-148.

Devasagayam TPA, Pushpendran CK, Eapen J. Differences in lipid peroxidation of rat liver rough and smooth microsomes. Biochim Biophys Acta 1983; 750:91-97.

Yoshikawa T, Toyokuni S, Yamamoto Y, Naito Y (Eds.). Free radicals in chemistry, biology and medicine. OICA International, London 2000, pp. 580.

Oner H, Karatepe M, Karatas F, Oner J, Yilmaz I, Cukurovali A. Effects on the rat testes of thiosemicarbazone derivative schiff base (4-(1-phenyl- methylcyclobutane-3-yl)-2-(2-ydroxybenzylidenehydrazino)thiazole) and its cadmium (II) complex. Cell Biochem Funct 2005; 23:427-433.

Karatepe M, Karatas F. Antioxidant, pro-oxidant effect of the thiosemicarbazone derivative schiff base (4-(1-phenylmethylcyclobutane-3-yl)-2-(2hydroxybenzylidene hydrazino) thiazole) and its metal complexes on rats. Cell Biochem Funct 2006; 24:547-554.

Varvaresou A, Tsantili-Kakoulidou A, Siatra-Papastaikoudi T, Tiligada E. Synthesis and biological evaluation of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole and 1,3,4-thiadiazole analogs. Arzneimittelforschung 2000; 50:48-54.

Cesur N, Birteksöz S, í–tük G. Synthesis and Biological Evaluation of some new thiosemicarbazide, 4-thiazolidinone, 1,3,4-oxadiazole and l,2,4-triazole-3-thione derivatives bearing imidazo[l,2-a]pyridine moiety. Acta Pharmaceutica Turcica 2002; 44:23-41.

í‡etin A., Cansız A., Koparır M. Organic Chem., An Indian J 2006; 2:140.

Hara A, and Radin NS. Lipid extraction of tissues with a low-toxicity solvent. Anal Biochem 1978; 90:420-426.

Christie WW. Gas chromatography and lipids. The Oil Pres, Glaskow 1992.

Tvrzicka E, Vecka M, Stankova B. and Zak A. Analysis of fatty acids in plasma lipoproteins by gas chromatography flame ionisation detection Quantative aspects. Anal Chimica Acta 2002; 465:337-350.

Katsanidis E, Addis PB. Novel HPLC analysis of tocopherols and cholesterol in tissue. Free Radic Biol Med 1999; 27:1137-1140.

Lu GF, Flipovi M, Heinemann FW, Ivanovi-Burmazovi I. Seven-coordinate iron and manganese complexes with acyclic and rigid pentadentate chelates and their superoxide dismutase activity. Inorg Chem 2007; 46:8825–8830.

Turan N, et. al. Pro-oxidant and antiproliferative effects of the 1,3,4-thiadiazole–based Schiff base and its metal complexes, Drug and Chemical Toxicology, 34:4, 369-378

Kudo N, Waku K. Cadmium suppresses delta 9 desaturase activity in rat hepatocytes. Toxicol 1996; 114:101-111.

Dayangac A, Yılmaz M, Konar V, Yilmaz O. The effects of cadmium on fatty acid composition in some tissues of rats. Journal of Research of Eastern Anatolia Region 2006; 4:89-92.

Grawe KP, Pickova J, Dutta PC, Oskarsson A. Fatty acid alterations in liver and milk of cadmium exposed rats and in brain of their suckling offspring. Toxicol Let 2004; 148:73-82.

Sarı A, í‡ukurovalı A. Investigation of the effects of thiosemicarbazone derivative schiff bases containing cyclobutano ring on fatty acids in liver of rabbits. Journal of Research of Eastern Anatolia Region 2008; 7:183-186.

Antueno RJ, Kinckle LC, Smith H, Eliot ML, Allen SJ, Nwaka S, Winther MD. Activity of human âˆ†5 and âˆ†6 desaturases on multiple n-3 and n-6 polyunsaturated fatty acids. FEBS Let 2001; 509:77-80.

Author biographies is not available.