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1H, 1'H-3,3'-Biindazol Maddesinin Ratlarda Bazı Biyokimyasal Parametrelere Etkisinin Araştırılması

Yıl 2022, Cilt: 9 Sayı: 1, 152 - 159, 30.06.2022
https://doi.org/10.35193/bseufbd.999490

Öz

İndazoller kimya ve farmakoloji’de önemli bileşiklerdir. Bu çalışmada, ratlara belirli sürelerde enjekte edilen 1H,1'H-3,3'-biindazol maddesinin, ratların kan serumu, karaciğer ve böbrekteki antioksidan vitaminler (A, E, C), Se, MDA miktarları ile GSH-Px enzim aktiviteleri üzerine etkilerinin araştırılması amaçlanmıştır. Serum, karaciğer ve böbrek numunelerindeki selenyum miktarları florimetrik metotla, A, E, C ve MDA seviyeleri ise yüksek performanslı sıvı kromatografisi (HPLC) ile belirlenmiştir. Eritrositlerin GSH-Px enzim aktivite miktarları spektrofotometrik metotla ölçülmüştür. Deneysel sonuçlarımız, A, E, C vitaminleri ve Se düzeylerinin genel olarak kontrol grubuna göre daha düşük olduğu, 3. enjeksiyon periyodunda GSH-Px enzim aktivite miktarının maksimum arttığı ve diğer enjeksiyon periyodlarındaki aktivitelerin kontrol grubuna göre daha yüksek olduğu gözlenmiştir. 1H,1'H-3,3'-biindazolmaddesi uygulamasından sonra ratların A, E, C vitaminleri ve Se düzeyleri azalırken, MDA seviyeleri ve GSH-Px enzim aktivite miktarlarının arttığı tespit edilmiştir. Pek çok hastalığın tedavisinde kullanılan bu tıbbi maddelerin hayati önem taşıdığı ancak metabolizmada oksidatif strese yol açtığı belirlenmiştir. Bu maddeleri içeren ilaçların kullanımlarında antioksidan vitaminlerin ve selenium desteğinin faydalı olabileceği kanaatine varılmıştır.

Kaynakça

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Investigation of the Effect of 1H, 1'H-3,3'-Biindazole on Some Biochemical Parameters in Rats

Yıl 2022, Cilt: 9 Sayı: 1, 152 - 159, 30.06.2022
https://doi.org/10.35193/bseufbd.999490

Öz

Indazoles are important compounds for chemistry and pharmacology. This study aimed to investigate the amount of antioxidant vitamins (A, E, C), Se, MDA and GSH-Px enzyme activities in the blood serum liver and kidneys of rats the 1H,1'H-3,3'-biindazole injected into rats for certain periods. Amounts of selenium in serum, liver and kidney samples were determined by fluorimetric method, A, E, C, and MDA levels were determined by high performance liquid chromatography (HPLC). GSH-Px enzyme activity amounts of erythrocytes were measured by spectrophotometric method. In our experimental results, it was observed that the levels of vitamins A, E, C, and Se were generally lower than the control group, maximum increase in the amount of GSH-Px enzyme activity in the 3rd injection period and the activities in the other injection periods were higher than the control group. It was determined that levels of decreased vitamin A, E, C, and Se while increased of levels MDA and GSH-Px enzyme activity. It has been determined that these medicinal substances used in the treatment of many diseases are vital; however, it causes oxidative stress in metabolism. It has been concluded that it may be useful beneficial of supplements antioxidant vitamins and selenium in the use of drugs containing these substances.

Kaynakça

  • Schmidt, A., Beutler, B., & Snovydovych, B. (2008). Recent advances in the chemistry of indazoles. European Journal of Organic Chemistry, 4073-4095. Denya, I., Malan, S.F., & Joubert, J. (2018). Indazole derivatives and their therapeutic applications: a patent review (2013–2017). Expert Opinion on Therapeutic Patents, 28, 441–53.
  • Schmidt, A., Beutler, B., & Snovydovych, B. (2008). Recent advances in the chemistry of indazoles. European Journal of Organic Chemistry, 4073-4095. Denya, I., Malan, S.F., & Joubert, J. (2018). Indazole derivatives and their therapeutic applications: a patent review (2013–2017). Expert Opinion on Therapeutic Patents, 28, 441–53.
  • Dong, J., Zhang, Q., Wang, Z., Huang, G., & Li, S. (2018). Recent advances in the development of indazole based anticancer agents. Chem Med Chem, 13, 1490–507.
  • Dong, J., Zhang, Q., Wang, Z., Huang, G., & Li, S. (2018). Recent advances in the development of indazole based anticancer agents. Chem Med Chem, 13, 1490–507.
  • Elguero, J., Fruchier, A., Tjiou, E.M., & Trofimenko, S. (1995). 13C NMR of indazoles. Chemistry of Heterocyclic Compounds, 31, 1006-1026.
  • Elguero, J., Fruchier, A., Tjiou, E.M., & Trofimenko, S. (1995). 13C NMR of indazoles. Chemistry of Heterocyclic Compounds, 31, 1006-1026.
  • Mosti, L., Menozzi, G., Fossa, P., Filippelli, W., Gessi, S., Rinaldi, B., & Falcone, G. (2000). Synthesis and preliminary biological evaluation of novel N-substituted 1-amino-3-[1- methyl (phenyl)-1H indazol 4-yloxy]-propan-2-ols interesting as potential antiarrhythmic, local anesthetic and analgesic agents. Arzneimittelforschung, 50, 963- 972.
  • Mosti, L., Menozzi, G., Fossa, P., Filippelli, W., Gessi, S., Rinaldi, B., & Falcone, G. (2000). Synthesis and preliminary biological evaluation of novel N-substituted 1-amino-3-[1- methyl (phenyl)-1H indazol 4-yloxy]-propan-2-ols interesting as potential antiarrhythmic, local anesthetic and analgesic agents. Arzneimittelforschung, 50, 963- 972.
  • Ali, N.A., Dar, B.A., Pradhan, V., & Farooqui, M. (2013). Chemistry and biology of indoles and indazoles: amini-review. Mini- Reviews in Medicinal Chemistry, 13(12), 1792-800.
  • Ali, N.A., Dar, B.A., Pradhan, V., & Farooqui, M. (2013). Chemistry and biology of indoles and indazoles: amini-review. Mini- Reviews in Medicinal Chemistry, 13(12), 1792-800.
  • Wang, Y., Yan, M., Ma, R., & Ma, S. (2015). Synthesis and Antibacterial Activity of Novel 4 Bromo-1H Indazole Derivatives as FtsZ Inhibitors. Arch. Pharm Chemistry in Life Sciences, 348, 266-274.
  • Wang, Y., Yan, M., Ma, R., & Ma, S. (2015). Synthesis and Antibacterial Activity of Novel 4 Bromo-1H Indazole Derivatives as FtsZ Inhibitors. Arch. Pharm Chemistry in Life Sciences, 348, 266-274.
  • Gopalakrishnan, M., Sureshkumar, P., Thanusu, J., & Kanagarajan, V. (2008). Synthesis, spectral analysis, antibacterial and antifungal activities of some 4,6-diaryl-4,5-dihydro-3-hydroxy-2[H]-indazole- a novel fused indazole derivative. Journal of Enzyme Inhibition and Medicinal Chemistry, 23, 974-979.
  • Gopalakrishnan, M., Sureshkumar, P., Thanusu, J., & Kanagarajan, V. (2008). Synthesis, spectral analysis, antibacterial and antifungal activities of some 4,6-diaryl-4,5-dihydro-3-hydroxy-2[H]-indazole- a novel fused indazole derivative. Journal of Enzyme Inhibition and Medicinal Chemistry, 23, 974-979.
  • Lin, S., Zhang, F., Jiang, G., Qureshi, S. A., Yang, X., Chicchi, G. G., Tota, L., Bansal, A., Brady, E., Trujillo, M., Salituro, G., Miller, C., Tata, J. R., Zhang, B. B., & Parmee, E. R. (2015). A novel series of indazole-/indole based glucagon receptor antagonists. Bioorganic & Medicinal Chemistry Letters, 25, 4143–4147.
  • Lin, S., Zhang, F., Jiang, G., Qureshi, S. A., Yang, X., Chicchi, G. G., Tota, L., Bansal, A., Brady, E., Trujillo, M., Salituro, G., Miller, C., Tata, J. R., Zhang, B. B., & Parmee, E. R. (2015). A novel series of indazole-/indole based glucagon receptor antagonists. Bioorganic & Medicinal Chemistry Letters, 25, 4143–4147.
  • Zhang, H. C., Derian, C. K., Andrade-Gordon, P., Hoekstra, W. J., McComsey, D. F., White, K. B., Poulter, B. L., Addo, M. F., Cheung, W. M., Damiano, B. P., Oksenberg, D., Reynolds, E. E., Pandey, A., Scarborough, R. M., & Maryanoff, B. E. (2001). Discovery and optimization of a novel series of thrombin receptor (PAR-1) antagonists: Potent, selective peptide mimetics based on indole and indazole templates. Journal of Medicinal Chemistry, 44(7), 1021-1024.
  • Zhang, H. C., Derian, C. K., Andrade-Gordon, P., Hoekstra, W. J., McComsey, D. F., White, K. B., Poulter, B. L., Addo, M. F., Cheung, W. M., Damiano, B. P., Oksenberg, D., Reynolds, E. E., Pandey, A., Scarborough, R. M., & Maryanoff, B. E. (2001). Discovery and optimization of a novel series of thrombin receptor (PAR-1) antagonists: Potent, selective peptide mimetics based on indole and indazole templates. Journal of Medicinal Chemistry, 44(7), 1021-1024.
  • Thomas, B., Saravanan, K. S., Kochupurackal, P., & Mohanakumar, K. P. (2008). In vitro and in vivo evidence that antioxidant action contributes to the neuroprotective effects of the neuronal nitric oxide synthase and monoamine oxidase-B inhibitor, 7-nitro indazole. Neurochemistry International, 52, 990-1001.
  • Thomas, B., Saravanan, K. S., Kochupurackal, P., & Mohanakumar, K. P. (2008). In vitro and in vivo evidence that antioxidant action contributes to the neuroprotective effects of the neuronal nitric oxide synthase and monoamine oxidase-B inhibitor, 7-nitro indazole. Neurochemistry International, 52, 990-1001.
  • Shirinzadeh, H., Altanlar, N., Yucel, N., Ozden, S., & Suzen, S. (2011). Antimicrobial evaluation of indole containing hydrazone derivatives. Zeitschrift für Naturforschung C, 66, 340–344.
  • Shirinzadeh, H., Altanlar, N., Yucel, N., Ozden, S., & Suzen, S. (2011). Antimicrobial evaluation of indole containing hydrazone derivatives. Zeitschrift für Naturforschung C, 66, 340–344.
  • Yurttaş, L., Ertaş, M., Cankılıç, M. Y., & Demirayak, Ş. (2017). Synthesis and antimycobacterial activity evaluation of isatin-derived 3-[(4-aryl-2-thiazolyl])hydrazone]-1H-indol-2, 3-diones.Acta Pharmaceutica Sciencia, 55, 51–58.
  • Yurttaş, L., Ertaş, M., Cankılıç, M. Y., & Demirayak, Ş. (2017). Synthesis and antimycobacterial activity evaluation of isatin-derived 3-[(4-aryl-2-thiazolyl])hydrazone]-1H-indol-2, 3-diones.Acta Pharmaceutica Sciencia, 55, 51–58.
  • Servi, S., & Akgün, Z. R., (2002). A Novel and efficient syntesis of 3-aryl and 3-hetero-aryl substituted-1H-indazoles and their mannich derivatives. Synthetic Communication, 32(22), 3399-3405.
  • Servi, S., & Akgün, Z. R., (2002). A Novel and efficient syntesis of 3-aryl and 3-hetero-aryl substituted-1H-indazoles and their mannich derivatives. Synthetic Communication, 32(22), 3399-3405.
  • Miller, K. W., Lorr, N. A., & Yang, C. S. (1984). Simultaneous determination of plasma retinol, α -tocopherol, lycopene, α-carotene, and β-carotene by high performance liquid chromatography. Analytical Biochemistry, 38, 340-345.
  • Miller, K. W., Lorr, N. A., & Yang, C. S. (1984). Simultaneous determination of plasma retinol, α -tocopherol, lycopene, α-carotene, and β-carotene by high performance liquid chromatography. Analytical Biochemistry, 38, 340-345.
  • Çetinkaya, N., & Özcan, H. (1991). Investigation of seasonal variations in cow serum Retinol and -Carotene by high performance liquid chromatographic method comp. Biochem. Physiol, 100(4), 1003-1008.
  • Çetinkaya, N., & Özcan, H. (1991). Investigation of seasonal variations in cow serum Retinol and -Carotene by high performance liquid chromatographic method comp. Biochem. Physiol, 100(4), 1003-1008.
  • Cerhata, D., Bauerova, A., & Ginter, B. (1994). Determination of ascorbic acid in serum using high-performanceliquid chromatography and its correlation with spectrophotometric (colorimetric) determination. Caska Slow Farm, 43, 166-168.
  • Cerhata, D., Bauerova, A., & Ginter, B. (1994). Determination of ascorbic acid in serum using high-performanceliquid chromatography and its correlation with spectrophotometric (colorimetric) determination. Caska Slow Farm, 43, 166-168.
  • Karatas, F., Karatepe, M., & Baysar, A. (2002). Determination of free malondialdehyde in human serum by high-performance liquid chromatography. Analytical Biochemistry, 311, 76-79.
  • Karatas, F., Karatepe, M., & Baysar, A. (2002). Determination of free malondialdehyde in human serum by high-performance liquid chromatography. Analytical Biochemistry, 311, 76-79.
  • Breyer, P. H., & Gilbert, B. P. (1987). Determination of Selenium (IV) differential pulse voltametry of the 3,3’-Diaminobenzidine piazselenol. Analytica Chimica Acta, 201, 23-32.
  • Breyer, P. H., & Gilbert, B. P. (1987). Determination of Selenium (IV) differential pulse voltametry of the 3,3’-Diaminobenzidine piazselenol. Analytica Chimica Acta, 201, 23-32.
  • Arain, M. A., Khuhawar, M. Y., & Bhanger, M. I. (1999). Liquid chromatographic determination of Selenium in vegetables and tea leaves as 2,1,3-Benzoselenadiazole. J. Chem. Soc. Pak, 21(2), 137-140.
  • Arain, M. A., Khuhawar, M. Y., & Bhanger, M. I. (1999). Liquid chromatographic determination of Selenium in vegetables and tea leaves as 2,1,3-Benzoselenadiazole. J. Chem. Soc. Pak, 21(2), 137-140.
  • Paglia, D. E., & Valentine, W. N. (1967). Studies on quantitative and qualitative characteristics of erythrocyte glutathione peroxidase. Journal of Laboratory and Clinical Medicine, 70, 158-169.
  • Paglia, D. E., & Valentine, W. N. (1967). Studies on quantitative and qualitative characteristics of erythrocyte glutathione peroxidase. Journal of Laboratory and Clinical Medicine, 70, 158-169.
  • North, J., & Jackson, M. C. (2018). Indole-based therapeutics. U.S. Patent Application No. 15/669, 289.
  • North, J., & Jackson, M. C. (2018). Indole-based therapeutics. U.S. Patent Application No. 15/669, 289.
  • Yaquan, C., Chunying, L., Pu, Y., Pan, L., & Chunli, W. (2021). Indazole scaffold: a generalist formarketed and clinical drugs. Medicinal Chemistry Research, 30, 501-518.
  • Yaquan, C., Chunying, L., Pu, Y., Pan, L., & Chunli, W. (2021). Indazole scaffold: a generalist formarketed and clinical drugs. Medicinal Chemistry Research, 30, 501-518.
  • Ashok, D., Gundu, S., Aamate, V. K., & Devulapally, M. G. (2018). Conventional and microwave-assisted synthesis of new indole-tethered benzimidazole-based 1,2,3-triazoles and evaluation of their antimycobacterial, antioxidant and antimicrobial activities. Molecular Diversity, 22, 769–778.
  • Ashok, D., Gundu, S., Aamate, V. K., & Devulapally, M. G. (2018). Conventional and microwave-assisted synthesis of new indole-tethered benzimidazole-based 1,2,3-triazoles and evaluation of their antimycobacterial, antioxidant and antimicrobial activities. Molecular Diversity, 22, 769–778.
  • Nyantakyi, S. A., Li, M., Gopal, P., Zimmerman, M., Dartois, V., Gengenbacher, M., Dick, T., & Go, M. L. (2018). Indolyl Azaspiroketal Mannich bases are potent anti-mycobacterial agents with selective membrane permeabilizing effects and in vivo activity. Journal of Medicinal Chemistry, 61, 5733–5750.
  • Nyantakyi, S. A., Li, M., Gopal, P., Zimmerman, M., Dartois, V., Gengenbacher, M., Dick, T., & Go, M. L. (2018). Indolyl Azaspiroketal Mannich bases are potent anti-mycobacterial agents with selective membrane permeabilizing effects and in vivo activity. Journal of Medicinal Chemistry, 61, 5733–5750.
  • Shirinzadeh, H., Altanlar, N., Yucel, N., Ozden, S., & Suzen, S. (2011). Antimicrobial evaluation of indole containing hydrazone derivatives. Zeitschrift für Naturforschung C, 66, 340–344.
  • Shirinzadeh, H., Altanlar, N., Yucel, N., Ozden, S., & Suzen, S. (2011). Antimicrobial evaluation of indole containing hydrazone derivatives. Zeitschrift für Naturforschung C, 66, 340–344.
  • Yurttaş, L., Ertaş, M., Cankılıç, M. Y., & Demirayak, Ş. (2017). Synthesis and antimycobacterial activity evaluation of isatin-derived 3-[(4-aryl-2-thiazolyl])hydrazone]-1H-indol-2, 3-diones. Acta Pharmaceutica Sciencia, 55, 51–58.
  • Yurttaş, L., Ertaş, M., Cankılıç, M. Y., & Demirayak, Ş. (2017). Synthesis and antimycobacterial activity evaluation of isatin-derived 3-[(4-aryl-2-thiazolyl])hydrazone]-1H-indol-2, 3-diones. Acta Pharmaceutica Sciencia, 55, 51–58.
  • Servi, S., & Akgun, Z.R. (2002). A novel and efficient synthesis of 3-aryl and 3-heteroaryl substituted 1H-indazoles and their Mannich derivatives. Synthetic Communications, 32(22), 3399–3405.
  • Servi, S., & Akgun, Z.R. (2002). A novel and efficient synthesis of 3-aryl and 3-heteroaryl substituted 1H-indazoles and their Mannich derivatives. Synthetic Communications, 32(22), 3399–3405.
  • Liu, Z.W., Zhang, T., & Yang, Z. (2007). Involvement of nitric oxide in spatial memory deficits in status epilepticus rats. Neurochemical Research, 32, 1875-1883.
  • Liu, Z.W., Zhang, T., & Yang, Z. (2007). Involvement of nitric oxide in spatial memory deficits in status epilepticus rats. Neurochemical Research, 32, 1875-1883.
  • Pawlak, W., Kedziora, J., Zolynski, K., Kedziora-Kornatowska, K., Blaszczyk, J., Witkowski, P., & Zieleniewski, J. (1998). Effect of long term bed rest in men on enzymatic antioxidative defense and lipid peroxidation in erythrocytes. Journal of Gravitational Physiology, 5, 163- 164.
  • Pawlak, W., Kedziora, J., Zolynski, K., Kedziora-Kornatowska, K., Blaszczyk, J., Witkowski, P., & Zieleniewski, J. (1998). Effect of long term bed rest in men on enzymatic antioxidative defense and lipid peroxidation in erythrocytes. Journal of Gravitational Physiology, 5, 163- 164.
  • Karatas, F., Kara, H., Servi, S., Kıran, T.R., & Saydam, S. (2008). Investigation of oxidative status of the 2-furan-2-yl-1H-benzimidazole in rats. Biological Trace Element Research, 126, 214- 221.
  • Karatas, F., Kara, H., Servi, S., Kıran, T.R., & Saydam, S. (2008). Investigation of oxidative status of the 2-furan-2-yl-1H-benzimidazole in rats. Biological Trace Element Research, 126, 214- 221.
  • Karatas, F., Coteli, E., Aydin, S., Servi, S., & Kara, H. (2010). Effect of 3-(1H-Pyrrol-2-yl)-1H-indazole on the antioxidant status of rats. Biological Trace Element Research, 136, 79–86.
  • Karatas, F., Coteli, E., Aydin, S., Servi, S., & Kara, H. (2010). Effect of 3-(1H-Pyrrol-2-yl)-1H-indazole on the antioxidant status of rats. Biological Trace Element Research, 136, 79–86.
  • Halliwell, B. (1994). Free radical antioxidants in human disease. Curiosity cause or consequence.The Lancet, 344, 721-724.
  • Halliwell, B. (1994). Free radical antioxidants in human disease. Curiosity cause or consequence.The Lancet, 344, 721-724.
  • Kaynar, H., Meral, M., Turhan, H., Keles, M., Celik, G., & Akcay, F. (2005). Glutathione peroxidase, glutathione-S-transferase, catalase, xanthine oxidase, Cu-Zn superoxide dismutase activities, total glutathione, nitric oxide and malondialdehyde levels in erythrocytes of patients with small cell and non-small cell lung cancer. Cancer letters, 227(2), 133-139.
  • Kaynar, H., Meral, M., Turhan, H., Keles, M., Celik, G., & Akcay, F. (2005). Glutathione peroxidase, glutathione-S-transferase, catalase, xanthine oxidase, Cu-Zn superoxide dismutase activities, total glutathione, nitric oxide and malondialdehyde levels in erythrocytes of patients with small cell and non-small cell lung cancer. Cancer letters, 227(2), 133-139.
  • Bostancı, H. E. (2014). Deneysel olarak Diyabet oluşturulmuş sıçanlarda vitaminlerin oksidasyona etkisi. Yüksek Lisans Tezi, Pamukkale Üniversitesi, Sağlık Bilimleri Enstitüsü, Tıbbi Biyokimya Anabilim Dalı, Denizli.
  • Bostancı, H. E. (2014). Deneysel olarak Diyabet oluşturulmuş sıçanlarda vitaminlerin oksidasyona etkisi. Yüksek Lisans Tezi, Pamukkale Üniversitesi, Sağlık Bilimleri Enstitüsü, Tıbbi Biyokimya Anabilim Dalı, Denizli.
Toplam 68 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Makaleler
Yazarlar

Ebru Çöteli 0000-0002-9473-0914

Fikret Karataş 0000-0002-0884-027X

Haki Kara 0000-0002-0295-0582

Süleyman Servi 0000-0003-0827-8624

Yayımlanma Tarihi 30 Haziran 2022
Gönderilme Tarihi 22 Eylül 2021
Kabul Tarihi 19 Ocak 2022
Yayımlandığı Sayı Yıl 2022 Cilt: 9 Sayı: 1

Kaynak Göster

APA Çöteli, E., Karataş, F., Kara, H., Servi, S. (2022). 1H, 1’H-3,3’-Biindazol Maddesinin Ratlarda Bazı Biyokimyasal Parametrelere Etkisinin Araştırılması. Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi, 9(1), 152-159. https://doi.org/10.35193/bseufbd.999490