Antioxidant and prooxidant activity of new 1,2-diols and thiadiazoles derivatives in Saccharomyces cerevisiae yeast cells

Arzu Karatepe; Ahmet Çetin

doi:10.17776/csj.764614

EN

Antioxidant and prooxidant activity of new 1,2-diols and thiadiazoles derivatives in Saccharomyces cerevisiae yeast cells

Abstract

The present research was undertaken to determine the effect of substituted 2,2'-[(2R,3R)-2,3-dihydroxy-1,4-dioxobutane-1,4-diyl]bis(N-R-hydrazine-1-carbothioamide and (1R,2R)-1,2-bis[5-(R-amino)-1,3,4-thiadiazole-2-yl]ethane-1,2-diols on the antioxidant status of the yeast Saccharomyces cerevisiae cells. This cell serves a good eukaryotic model system for the study of molecular mechanisms of oxidative stress. The Saccharomyces cerevisiae yeast cells were treated a series of 1,2-diols and thiadiazoles compounds and the malondialdehyde (MDA) and antioxidant vitamins (A, E, C) levels in the medium were measured by HPLC-UV. In the comparison done among groups, the MDA which is an indicator of lipid peroxidation and Vitamin E concentrations were showed statistically changed in the samples. Exposure of yeaset cells to L9 showed an increase in MDA and decrease in vitamin E levels but L2 and L8 showed decrease in MDA and increase in vitamin E levels. The results showed that compounds L9 caused a considerable oxidative stress and L2 and L8 have antioxidant activity.

Keywords

1,2-diols, thiadiazoles, MDA, vitamin, saccharomyces cerevisiae, antioxidant

References

Yang D., An B., Wei W., Tian L., Huang B., Wang H. Coppercatalyzed domino synthesis of nitrogen heterocycle-fused benzoimidazole and 1,2,4- benzothiadiazine 1,1-dioxide derivatives, A C S Comb Sci., 17 (2015) 113–119.
Iizawa, Y., et al. Therapeutic effect of cefozopran (SCE-2787), a new parenteral cephalosporin, against experimental infections in mice. Antimicrobial Agents and Chemotherapy 37 (1993) 100-105.
Oruc, E.E., et al. 1,3,4-thiadiazole derivatives. Synthesis, structure elucidation, and structure-antituberculosis activity relation- ship investigation. Journal of Medicinal Chemistry. 47 (2004) 6760-6767.
Foroumadi, A., et al. Antituberculosis agents VIII. Synthesis and in vitro antimycobacterial activity of alkyl alpha-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetates. Farmaco. 58 (2003) 1073-1076.
Kamal M.D., et al. Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorganic and Medicinal Chemistry. 14 (2006) 3672–3680.
Mullick P., et al. Thiadiazole derivatives as potential anticonvulsant agents. Bulletin of the Korean Chemical Society. 32 (2011) 1011-1016.
Clerici, F., et al. Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxi-olytic activity. Journal of Medicinal Chemistry. 44 (2001) 931-936.
Hasui,T., et al. Identification of benzoxazin-3-one derivatives as novel, potent, and selective nonsteroidal mineralocorticoid receptor antagonists. Journal of Medicinal Chemistry 54 (2011) 8616-8631.
Zheng, K. B., et al. Synthesis and antitumor activity of N1-acetylamino-(5-alkyl/aryl- 1,3,4-thiadiazole-2-yl)-5-fluorouracil deriva- tives. Chinese Chemical Letters. 19 (2008) 1281-1284.
[Chen, C.J., et al. Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2sulfonyl-1,3,4-thiadiazole and 5-(3,4,5- trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives. Bioorganic& Medicinal Chemistry. 15 (2007) 3981-3989.

Suzuki, F., Kawakami, I., Yamamoto, S., Kosai, Y. Japan Kokai, 7776432 1977; Chem. Abstr., 88, (1978) 100351.
Abdel-Ramhan A. E., Mahmoud A. M., El-Sherief H.A., Gahatta A.G. Chem. Abstr. 98 (1983) 72012b.
Foerster H., Mues V., Baasner B., Hagemann H., Eue I., Schmidt R. EuropeanPatent,60426 1981; Chem. Abstr. (1983) 72107m.
Tiwari N., Chaturvedi B., Nizamuddin A. ynthesis and fungicidal activities of some 2-aryloxymethyl-1,3,4-thiadiazolo[2,3,-b]-quinazolin-4-one and 2-aryloxymethyl-5-substituted-1,3,4-thiadiazolo[3,2,-a]-1,3,5-triazine-7-thiones. Indian J. Chem., 28 (1989) 200-202.
Singh H., Yadav L.D.S., Agri. Biol. Chem., 40 (1976) 759-764; (b) Chaaban I., Oji O.O.J. Indian Chem Soc., 61 (1984) 523-525; (c) Mohsen A., Omer M.E., Aboulwafa O.M.J. Heterocycl. Chem., 21 (1984) 1415-1418; (d) Hiremath S.P., Birador J.S., Kudari S.M.J. Indian Chem. Soc., 61 (1984) 74-76.
Rao A. V. R., Bose D.S., Gurjar M.K., Ravindranatran T. Tetrahedron, 45 (1989) 70317040; (b) Seydenpenn J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley: New York, (1995); (c) Wright A.E., Schafer M., Midland S., Munnecke D.E., Sims J.J. Tetrahedron Lett., 30 (1989) 5699-5702.
Kolb H.C., Sharpless K.B., A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides. Tetrahedron, 48 (1992) 10515-10530.
Lohray B.B., Ahuja J.R., J. Chem. Soc. (1991) 95-97; (b) Nicolaou K.C., Huang X., Snyder S.A., Rao P.B., Bela M., Reddy M.V. Angew. Chem. Int. 41 (2002) 834.
Parida S., Dordick J.S.J. Am. Chem. Soc., 113 (1991) 2253-2259; (b) Nelson W.L., Wennerstrom J.E., Sankar S.R.J. Org. Chem., 42 (1977) 1006-1012; (c) Bian chi D., Bosetti A., Cesti P., Golini P. Tetrahedron Lett., 33 (1992) 3231-3234.
Kurina-Sanz M., Bisogno F.R., Lavandera I., Orden A.A., Gotor V., Promiscuous substrate binding explains the enzymatic stereo- and regiocontrolled synthesis of enantiopure hydroxy ketones and diols. Adv. Synth. Catal., 351 (2009) 1842– 1848.
Supuran C.T., Scozzafava A., Carbonic anhydrase inhibitors. Curr Med Chem Immunol Endocrinol Metab Agents. 1 (2001) 61–97.
Singh, N., Rajini, P. S., Free radical scavenging activity of an aqueous extract of potato peel. Food Chem. 85 (2004) 611.
Prior, R. L., Wu, X., Schaich, K., Standardized Methods for the Determination of Antioxidant Capacity and Phenolics in Foods and Dietary Supplements. J. Agric. Food Chem. 53 (2005) 4290.
Uchida, K., Role of Reactive Aldehyde in Cardiovascular Diseases. Free Radical Biol. Med. 28 (2000) 1685.
[25] Cadenas, E., Davies, K. J. A., Mitochondrial Free Radical Generation, Oxidative Stress, and Aging. Free Radical Biol. Med. 29 (2000) 222. Offeing, B.M., Martelli, S.,. Steochemistry and Antitumour Activity of Platinium Metal Complexes of 2- Acetypyridine Thiosemicarbazones. Transition Metal Chemistry., 22 (1997) 263-269.
Karatepe A., (1r, 2r)-etan-1,2 diol tiyadiyazol türevlerinin sentezi, karekterizasyonu ve biyolojik özellikleri. Doktora tezi, Bingöl, 2020.
Karatepe, M., Simultaneous Determination of Ascorbic Acid and Free Malondialdehyde in Human Serum by HPLC/UV. LC-GC North America. 22 (2004) 362-5.
Catignani, G.L., Simultancous Determination of Retinol and α-Tocopherol in Serum of Plazma by Liquid Chromatography, Clin. Chem., 2914 (1983) 708-712.
Almeida, G.M., Thomazellab, D.P.T., Pereira, G.A.G., Monteiro G., Heterologous expression of an alternative oxidase from Moniliophthora perniciosa in Saccharomyces cerevisiae: Antioxidant function and in vivo platform for the study of new drugs against witches’ broom disease. Fungal Genetics and Biology, 126 (2019) 50–55.
Yildirim A., Mavi A., Kara A.A., Determination of antioxidant and antimicrobial activities of Rumexcrispus L. extracts,J. Agri. Food. Chem. 49 (2001) 4083.
Nordberg, J., Arner, E.S.J., , Reactive Oxygen Species, Antioxidants and The Mammalian Thioredoxin System, Free Rad. Biol. and Med., 31(11) (2001) 1287-1317.
Maccarrone, M (Maccarrone, M); Catani, MV (Catani, MV); Iraci, S (Iraci, S); Melino, G (Melino, G); Agro, AF (Agro, AF) A survey of reactive oxygen species and their role in dermatology. J. of the Eu. Academy of Der. and Ven. 8 (1997) 185-202.
Morrow J.D., The isoprostanes: their quantification as an index of oxidant stress status in vivo. Drug Metab Rev. 32 (2000) 377-85.
Vaca, C.E., Wilhelm J., Ringdahl M. H., Interaction of lipid peroxidation products with DNA. A review. Mutation Res., 195 (1988) 137-149.
EnnamanyaJ.P., LavergnebJ.P., Reboudb G., Mode of action of bolesatine, a cytotoxic glycoprotein from Boletus satanas Lenz. Mechanistic approachesToxicolog, 100 (1995) 51-55.
Bird, R.P., Draper, H.H., Comperative Studieson Differant Methods of Malondialdehyde Determination. Methods in Enzymology., 105 (1984) 299-305.
Tomita M., Okuyama T., Kawai S.J., Determination of malonaldehyde in oxidized biological materials by high-performance liquid chromatography. Chromatogr. 31 (1990) 391-7.
Kus C., Kilcigil G.A., Ozbey S., Kaynak F.B., Kaya M., Coban T., Eke B.,C., Synthesis and Antioxidant Properties of Novel N-Methyl-1,3,4-Thiadiazol-2-Amine and 4-Methyl-2H-1,2,4-Triazole-3(4H)-Thione Derivatives of Benzimidazole Class Bioorg. Med. Chem., 16 (2008) 4294-4303.
Dhanya S., Arun M.I., Prakash S., et al. 6-[3-(4-Fluorophenyl)-1H-pyrazol-4-yl]-3-[(2-naphthyloxy)methyl][1,2,4]triazolo[3,4-b][1,3,4]thiadiazole as a potent antioxidant and an anticancer agent induces growth inhibition followed by apoptosis in HepG2 cells. Arabian Journal of Chemistry, 3 (2010) 211-217.
Cressier D., Prouillac C., Hernandez P., et al., Synthesis, Antioxidant Properties and Radioprotective Effects of New Benzothiazoles and Thiadiazoles. Bioorg. Med. Chem., 17 (2009) 5275-5284.
Prouillac C., Vicendo P., Garrigues J.C., Poteau R., Rima G., Evaluation of new thiadiazoles and benzothiazoles as potential radioprotectors: free radical scavenging activity in vitro and theoretical studies (QSAR, DFT). Free Rad Biol Med., , 46 (2009) 1139-1148.

Details

Primary Language

English

Subjects

-

Journal Section

Research Article

Authors

Arzu Karatepe ^*
Türkiye

Ahmet Çetin
0000-0003-4662-7370
Türkiye

Publication Date

September 30, 2020

Submission Date

July 6, 2020

Acceptance Date

August 25, 2020

Published in Issue

Year 2020 Volume: 41 Number: 3

DOI

https://doi.org/10.17776/csj.764614

IZ

https://izlik.org/JA26KK82JZ

APA

Karatepe, A., & Çetin, A. (2020). Antioxidant and prooxidant activity of new 1,2-diols and thiadiazoles derivatives in Saccharomyces cerevisiae yeast cells. Cumhuriyet Science Journal, 41(3), 712-719. https://doi.org/10.17776/csj.764614

AMA

1.Karatepe A, Çetin A. Antioxidant and prooxidant activity of new 1,2-diols and thiadiazoles derivatives in Saccharomyces cerevisiae yeast cells. CSJ. 2020;41(3):712-719. doi:10.17776/csj.764614

Chicago

Karatepe, Arzu, and Ahmet Çetin. 2020. “Antioxidant and Prooxidant Activity of New 1,2-Diols and Thiadiazoles Derivatives in Saccharomyces Cerevisiae Yeast Cells”. Cumhuriyet Science Journal 41 (3): 712-19. https://doi.org/10.17776/csj.764614.

EndNote

Karatepe A, Çetin A (September 1, 2020) Antioxidant and prooxidant activity of new 1,2-diols and thiadiazoles derivatives in Saccharomyces cerevisiae yeast cells. Cumhuriyet Science Journal 41 3 712–719.

IEEE

[1]A. Karatepe and A. Çetin, “Antioxidant and prooxidant activity of new 1,2-diols and thiadiazoles derivatives in Saccharomyces cerevisiae yeast cells”, CSJ, vol. 41, no. 3, pp. 712–719, Sept. 2020, doi: 10.17776/csj.764614.

ISNAD

Karatepe, Arzu - Çetin, Ahmet. “Antioxidant and Prooxidant Activity of New 1,2-Diols and Thiadiazoles Derivatives in Saccharomyces Cerevisiae Yeast Cells”. Cumhuriyet Science Journal 41/3 (September 1, 2020): 712-719. https://doi.org/10.17776/csj.764614.

JAMA

1.Karatepe A, Çetin A. Antioxidant and prooxidant activity of new 1,2-diols and thiadiazoles derivatives in Saccharomyces cerevisiae yeast cells. CSJ. 2020;41:712–719.

MLA

Karatepe, Arzu, and Ahmet Çetin. “Antioxidant and Prooxidant Activity of New 1,2-Diols and Thiadiazoles Derivatives in Saccharomyces Cerevisiae Yeast Cells”. Cumhuriyet Science Journal, vol. 41, no. 3, Sept. 2020, pp. 712-9, doi:10.17776/csj.764614.

Vancouver

1.Arzu Karatepe, Ahmet Çetin. Antioxidant and prooxidant activity of new 1,2-diols and thiadiazoles derivatives in Saccharomyces cerevisiae yeast cells. CSJ. 2020 Sep. 1;41(3):712-9. doi:10.17776/csj.764614

Cited By

Design, synthesis, in-silico and biological evaluation of novel 2-Amino-1,3,4-thiadiazole based hydrides as B-cell lymphoma-2 inhibitors with potential anticancer effects

Journal of Molecular Structure

https://doi.org/10.1016/j.molstruc.2022.133673

Synthesis, Characterization and Biological Activities of Novel Chiral Bis 1,2-diolcarbothioamides

Journal of Physical Chemistry and Functional Materials

https://doi.org/10.54565/jphcfum.1539891

As of 2026, Cumhuriyet Science Journal will be published in six issues per year, released in February, April, June, August, October, and December