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Year 2024, Volume: 17 Issue: 1, 230 - 240, 28.03.2024

Aydan Arı Salih Günnaz Sevil İrişli

https://doi.org/10.18185/erzifbed.1407972

Abstract

Project Number

FYL -2019 21012

References

  • [1] Zhong, H., Bowen J.P. (2006) Antiangiogenesis drug design: multiple pathways targeting tumor vasculature, Curr. Med. Chem., 13, 849-862.
  • [2] Han, J., Gao X., Liu R., Yang J., Zhang M., Mi Y., Shi Y., Gao Q. (2016) Design, Synthesis of Novel Platinum(II) Glycoconjugates, and Evaluation of Their Antitumor Effects, Chem. Biol. Drug. Des., 87, 867-877.
  • [3] Wang, D., Lippard S. J. (2005) Cellular Processıng of Platınum Antıcancer Drugs, Nat. Rev. Drug. Discov., 4, 307-20.
  • [4] Ören, I., Temiz, Ö., Yalçin, I., Sener, E., Altanlar, N. (1999) Synthesis and antimicrobial activity of some novel 2,5- and/or 6-substituted benzoxazole and benzimidazole derivatives, Eur. J. Pharm. Sci., 7, 153-60.
  • [5] Townsend, L. B., Revankar, G. R. (1970) Benzimidazole nucleosides, nucleotides, and related derivatives, Chem. Rev., 70, 389-438.
  • [6] Tebbe, M. J., Spitzer, W. A., Victor, F., Miller, S. C., Lee, C. C., Sattelberg, T. R., Mckinney, E., Tang, C. J. (1997) Antirhino/Enteroviral Vinylacetylene Benzimidazoles:  A Study of Their Activity and Oral Plasma Levels in Mice , J. Med. Chem., 40, 3937-3946.
  • [7] Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I., Anisimova, V. A. (1999) Benzimidazole derivatives: Spectrum of pharmacological activity and toxicological properties, Khim.-Farm. Zhurn., 33, 6-17.
  • [8] Labanauskas, L.K., Brukstus, A.B., Gaidelis, P.G., Buchinskaite, V.A., Udrenaite E.B., Dauksas, V. K. (2000) Synthesis and antiinflammatory activity of some new 1-acyl derivatives of 2-methylthio-5,6- diethoxybenzimidazole, Pharm. Chem. J., 34, 353-355.
  • [9] Graßmann, S., Sadek, B., Ligneau, X., Elz, S., Ganellin, C.R., Arrang, J.M., Schwartz, J.C., Stark, H., Schunack, W. (2002) Progress in the proxifan class: heterocyclic congeners as novel potent and selective histamine H3-receptor antagonists, Eur. J. Pharm. Sci., 15, 367-378.
  • [10] Can-Eke, B., Puskullu, M. O., Buyukbingol, E., Iscan, M. (1998) A study on the antioxidant capacities of some benzimidazoles in rat tissues, Chem. Biol. Interact., 113, 65-77.
  • [11] Sevak, R., Paul, A., Goswami S., Santini, D. (2002) Gastroprotective effect of beta3 adrenoreceptor agonists ZD 7114 and CGP 12177A in rats, Pharmacol. Res., 46, 351-356.
  • [12] Ozden, S., Atabey, D., Yildiz, S., Goker, H. (2005), Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1-H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups, Bioorg. Med. Chem., 13(5), 1587-1597.
  • [13] Valdez, J., Cedillo, R., Hernandez-Campos, A., Yepez, L., Hernandez- Luis, F., Navarrete-Vazquez, G., Tapia, A., Cortes, R., Hernandez, M., Castillo, R. (2002) Synthesis and antiparasitic activity of 1-H-benzimidazole derivatives. Bioorg. Med. Chem. Lett., 12, 2221-2224.
  • [14] Mock, C., Puscasu, I., Rauterkus, M.J., Tallen, G., Wolff, J.E.A., Krebs B. (2001) Novel Pt(II) anticancer agents and their Pd(II) analogues: syntheses, crystal structures, reactions with nucleobases and cytotoxicities, Inorganica Chimica Acta, 319, 109-116.
  • [15] Eren, G., Emerce E., Acik, L., Aydin, B., Gumus, F. (2019) A novel Trans-Pt(II) complex bearing 2-acetoxymethylbenzimidazole as a non-leaving ligand (trans-[Pt(AMBi)2Cl2]): Synthesis, antiproliferative activity, DNA interaction and molecular docking studies compared with its cis isomer (cis-[Pt(AMBi)2Cl2]), Journal of Molecular Structure, 1184, 512-518.
  • [16] Garnuszek, P., Liciánska, I., Skierski, J. S., Koronkiewicz, M., Mirowski, M., Wiercioch, R., Mazurek, A. P. (2002) Biological investigation of the platinum(II)-[∗I]iodohistamine complexes of potential synergistic anti-cancer activity, Nuclear Medicine and Biology, 29 (2), 169-175.
  • [17] Tarı, Ö., Gümüs, F., Açık, L., Aydın, B. (2017) Synthesis, characterization and DNA binding studies of platinum(II) complexes with benzimidazole derivative ligands, Bioorganic Chemistry, 74, 272-283.
  • [18] Mitra, I., Mukherjee, S., Venkata P. Reddy B., Dasgupta, S., Bose K, J. C., Mukherjee, S., Linertd, W. and Ch. Moi, S. (2016) Benzimidazole based Pt(II) complexes with better normal cell viability than cisplatin: synthesis, substitution behavior, cytotoxicity, DNA binding and DFT study, RSC Adv., 6, 76600-76613.
  • [19] Nicasio-Collazo, J., Ramirez-Garcia, G., Flores-´ Alamo, M., Gutierrez-Granados, S. Peralt a-Hernandez, J. M., Luis Maldonado, J., J., Jimenez-Halla, O. C. and Serrano, O. (2019) A novel coordination mode of k1-N-Br pyridylbenz-(imida, oxa or othia)-zole to Pt(II): synthesis, characterization, electrochemical and structural analysis, RSC Adv., 9, 14033-14039.
  • [20] Gerth, H.U.V., Rompel, A., Krebs, B., Boos, J., Lanvers-Kaminsky, C. (2005) Cytotoxic effects of novel polyoxotungstates and a platinum compound on human cancer cell lines, Anti-Cancer Drugs, 16, 101-106.
  • [21] Tundo, G.R., Sbardella, D., De Pascali, S.A., Ciaccio, C., Coletta, M., Fanizzi, F.P., Marini, S. (2015) Effect of Cisplatin on Proteasome Activity, J. Biol. Inorg. Chem., 20,101-108.
  • [22] Doğan, U., Özcan, Ö., Alaca, G., Arı, A., Günnaz, S., Yalçın, H. T. Şahin, O., İrişli, S. (2021) Novel Benzimidazole- Platinum(II) Complexes: Synthesis, Characterization, Antimicrobial and Anticancer Activity, Journal of Molecular Structure, 1229, 129785.
  • [23] Price, J.H., Williamson, A.N., Schramm, R.F., Wayland, B.B. (1972) Palladium(II) and platinum(II) alkyl sulfoxide complexes. Examples of sulfur-bonded, mixed sulfur- and oxygen-bonded, and totally oxygen-bonded complexes, Inorg. Chem., 11 (6), 1280-1284.
  • [24] Al-Allaf, T. A. K, Sheet, A. Z. M. (1995) Platinum Group Metal Schiff Base Complexes, Polyhedron, 14, (2), 239-248.
  • [25] Wang, Q., Wang, Z., Chu, L., LI, X., Kan, P., Xin, X., Zhu, Y., Yang, P. (2015) The Effects and Molecular Mechanisms of MiR-106a in Multidrug Resistance Reversal in Human Glioma U87/DDP and U251/G Cell Lines, PLoS One, 10 (5), e0125473.
  • [26] Gao, J., Wang, W. Chem. (2019) Knockdown of galectin-1 facilitated cisplatin sensitivity by inhibiting autophagy in neuroblastoma cells, Biol. Interac., 297, 50-56.
  • [27] Cabrera, A.R., Espinosa-Bustos, C., Faundez, M., Melendez, J., Jaque, P., Danil- iuc, C.G., Aguirre, A., Rojas, R.S., Salas, C.O. (2017) New imidoyl-indazole platinum (II) complexes as potential anticancer agents: Synthesis, evaluation of cytotoxicity, cell death and experimental-theoretical DNA interaction studies, J. Inorg. Biochem., 174, 90-101.

Benzimidazole-Platinum Complex and Its Cytotoxic activity on U87 Cell Lines

Year 2024, Volume: 17 Issue: 1, 230 - 240, 28.03.2024

Aydan Arı Salih Günnaz Sevil İrişli

https://doi.org/10.18185/erzifbed.1407972

Abstract

Çalışmanın amacı, güçlü sitotoksik aktiviteye ve düşük yan etkilere sahip olabilen yeni bir benzimidazol-platin(II) kompleksinin sentezi, karakterizasyonu ve sitotoksik aktivitelerinin değerlendirilmesidir. Bir benzimidazol ligandı, 2-(3-fenoksifenil)-1-fenil-1H-benzimidazol (L) ve bunun yeni platin kompleksi (Pt-L), sentezlenmiş yapıları farklı spektroskopik yöntemlerle karakterize edilmiştir. Çalışmada, sentezlenen kompleksin öncelikle U87 kanser hattındaki aktivitesi incelenmiş, daha sonra sağlıklı Vero hatları üzerinde çalışılmıştır.

Keywords

Benzimidazole Benzimidazole- Platinum complexes glioblastoma cytotoxic activity

Ethical Statement

There are no ethical issues regarding the publication of this study

Supporting Institution

Ege University Scientific Research Project (No: FYL -2019 21012)

Project Number

FYL -2019 21012

Thanks

We also give thanks to MATAL Center, Ege University, for cytotoxicity activities.

References

  • [1] Zhong, H., Bowen J.P. (2006) Antiangiogenesis drug design: multiple pathways targeting tumor vasculature, Curr. Med. Chem., 13, 849-862.
  • [2] Han, J., Gao X., Liu R., Yang J., Zhang M., Mi Y., Shi Y., Gao Q. (2016) Design, Synthesis of Novel Platinum(II) Glycoconjugates, and Evaluation of Their Antitumor Effects, Chem. Biol. Drug. Des., 87, 867-877.
  • [3] Wang, D., Lippard S. J. (2005) Cellular Processıng of Platınum Antıcancer Drugs, Nat. Rev. Drug. Discov., 4, 307-20.
  • [4] Ören, I., Temiz, Ö., Yalçin, I., Sener, E., Altanlar, N. (1999) Synthesis and antimicrobial activity of some novel 2,5- and/or 6-substituted benzoxazole and benzimidazole derivatives, Eur. J. Pharm. Sci., 7, 153-60.
  • [5] Townsend, L. B., Revankar, G. R. (1970) Benzimidazole nucleosides, nucleotides, and related derivatives, Chem. Rev., 70, 389-438.
  • [6] Tebbe, M. J., Spitzer, W. A., Victor, F., Miller, S. C., Lee, C. C., Sattelberg, T. R., Mckinney, E., Tang, C. J. (1997) Antirhino/Enteroviral Vinylacetylene Benzimidazoles:  A Study of Their Activity and Oral Plasma Levels in Mice , J. Med. Chem., 40, 3937-3946.
  • [7] Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I., Anisimova, V. A. (1999) Benzimidazole derivatives: Spectrum of pharmacological activity and toxicological properties, Khim.-Farm. Zhurn., 33, 6-17.
  • [8] Labanauskas, L.K., Brukstus, A.B., Gaidelis, P.G., Buchinskaite, V.A., Udrenaite E.B., Dauksas, V. K. (2000) Synthesis and antiinflammatory activity of some new 1-acyl derivatives of 2-methylthio-5,6- diethoxybenzimidazole, Pharm. Chem. J., 34, 353-355.
  • [9] Graßmann, S., Sadek, B., Ligneau, X., Elz, S., Ganellin, C.R., Arrang, J.M., Schwartz, J.C., Stark, H., Schunack, W. (2002) Progress in the proxifan class: heterocyclic congeners as novel potent and selective histamine H3-receptor antagonists, Eur. J. Pharm. Sci., 15, 367-378.
  • [10] Can-Eke, B., Puskullu, M. O., Buyukbingol, E., Iscan, M. (1998) A study on the antioxidant capacities of some benzimidazoles in rat tissues, Chem. Biol. Interact., 113, 65-77.
  • [11] Sevak, R., Paul, A., Goswami S., Santini, D. (2002) Gastroprotective effect of beta3 adrenoreceptor agonists ZD 7114 and CGP 12177A in rats, Pharmacol. Res., 46, 351-356.
  • [12] Ozden, S., Atabey, D., Yildiz, S., Goker, H. (2005), Synthesis and potent antimicrobial activity of some novel methyl or ethyl 1-H-benzimidazole-5-carboxylates derivatives carrying amide or amidine groups, Bioorg. Med. Chem., 13(5), 1587-1597.
  • [13] Valdez, J., Cedillo, R., Hernandez-Campos, A., Yepez, L., Hernandez- Luis, F., Navarrete-Vazquez, G., Tapia, A., Cortes, R., Hernandez, M., Castillo, R. (2002) Synthesis and antiparasitic activity of 1-H-benzimidazole derivatives. Bioorg. Med. Chem. Lett., 12, 2221-2224.
  • [14] Mock, C., Puscasu, I., Rauterkus, M.J., Tallen, G., Wolff, J.E.A., Krebs B. (2001) Novel Pt(II) anticancer agents and their Pd(II) analogues: syntheses, crystal structures, reactions with nucleobases and cytotoxicities, Inorganica Chimica Acta, 319, 109-116.
  • [15] Eren, G., Emerce E., Acik, L., Aydin, B., Gumus, F. (2019) A novel Trans-Pt(II) complex bearing 2-acetoxymethylbenzimidazole as a non-leaving ligand (trans-[Pt(AMBi)2Cl2]): Synthesis, antiproliferative activity, DNA interaction and molecular docking studies compared with its cis isomer (cis-[Pt(AMBi)2Cl2]), Journal of Molecular Structure, 1184, 512-518.
  • [16] Garnuszek, P., Liciánska, I., Skierski, J. S., Koronkiewicz, M., Mirowski, M., Wiercioch, R., Mazurek, A. P. (2002) Biological investigation of the platinum(II)-[∗I]iodohistamine complexes of potential synergistic anti-cancer activity, Nuclear Medicine and Biology, 29 (2), 169-175.
  • [17] Tarı, Ö., Gümüs, F., Açık, L., Aydın, B. (2017) Synthesis, characterization and DNA binding studies of platinum(II) complexes with benzimidazole derivative ligands, Bioorganic Chemistry, 74, 272-283.
  • [18] Mitra, I., Mukherjee, S., Venkata P. Reddy B., Dasgupta, S., Bose K, J. C., Mukherjee, S., Linertd, W. and Ch. Moi, S. (2016) Benzimidazole based Pt(II) complexes with better normal cell viability than cisplatin: synthesis, substitution behavior, cytotoxicity, DNA binding and DFT study, RSC Adv., 6, 76600-76613.
  • [19] Nicasio-Collazo, J., Ramirez-Garcia, G., Flores-´ Alamo, M., Gutierrez-Granados, S. Peralt a-Hernandez, J. M., Luis Maldonado, J., J., Jimenez-Halla, O. C. and Serrano, O. (2019) A novel coordination mode of k1-N-Br pyridylbenz-(imida, oxa or othia)-zole to Pt(II): synthesis, characterization, electrochemical and structural analysis, RSC Adv., 9, 14033-14039.
  • [20] Gerth, H.U.V., Rompel, A., Krebs, B., Boos, J., Lanvers-Kaminsky, C. (2005) Cytotoxic effects of novel polyoxotungstates and a platinum compound on human cancer cell lines, Anti-Cancer Drugs, 16, 101-106.
  • [21] Tundo, G.R., Sbardella, D., De Pascali, S.A., Ciaccio, C., Coletta, M., Fanizzi, F.P., Marini, S. (2015) Effect of Cisplatin on Proteasome Activity, J. Biol. Inorg. Chem., 20,101-108.
  • [22] Doğan, U., Özcan, Ö., Alaca, G., Arı, A., Günnaz, S., Yalçın, H. T. Şahin, O., İrişli, S. (2021) Novel Benzimidazole- Platinum(II) Complexes: Synthesis, Characterization, Antimicrobial and Anticancer Activity, Journal of Molecular Structure, 1229, 129785.
  • [23] Price, J.H., Williamson, A.N., Schramm, R.F., Wayland, B.B. (1972) Palladium(II) and platinum(II) alkyl sulfoxide complexes. Examples of sulfur-bonded, mixed sulfur- and oxygen-bonded, and totally oxygen-bonded complexes, Inorg. Chem., 11 (6), 1280-1284.
  • [24] Al-Allaf, T. A. K, Sheet, A. Z. M. (1995) Platinum Group Metal Schiff Base Complexes, Polyhedron, 14, (2), 239-248.
  • [25] Wang, Q., Wang, Z., Chu, L., LI, X., Kan, P., Xin, X., Zhu, Y., Yang, P. (2015) The Effects and Molecular Mechanisms of MiR-106a in Multidrug Resistance Reversal in Human Glioma U87/DDP and U251/G Cell Lines, PLoS One, 10 (5), e0125473.
  • [26] Gao, J., Wang, W. Chem. (2019) Knockdown of galectin-1 facilitated cisplatin sensitivity by inhibiting autophagy in neuroblastoma cells, Biol. Interac., 297, 50-56.
  • [27] Cabrera, A.R., Espinosa-Bustos, C., Faundez, M., Melendez, J., Jaque, P., Danil- iuc, C.G., Aguirre, A., Rojas, R.S., Salas, C.O. (2017) New imidoyl-indazole platinum (II) complexes as potential anticancer agents: Synthesis, evaluation of cytotoxicity, cell death and experimental-theoretical DNA interaction studies, J. Inorg. Biochem., 174, 90-101.
There are 27 citations in total.

Details

Primary Language English
Subjects Transition Metal Chemistry
Journal Section Makaleler
Authors

Aydan Arı 0009-0004-0768-2232

Salih Günnaz 0000-0002-7422-6593

Sevil İrişli 0000-0002-3727-2216

Project Number FYL -2019 21012
Early Pub Date March 27, 2024
Publication Date March 28, 2024
Submission Date December 21, 2023
Acceptance Date February 12, 2024
Published in Issue Year 2024 Volume: 17 Issue: 1

Cite

APA Arı, A., Günnaz, S., & İrişli, S. (2024). Benzimidazole-Platinum Complex and Its Cytotoxic activity on U87 Cell Lines. Erzincan University Journal of Science and Technology, 17(1), 230-240. https://doi.org/10.18185/erzifbed.1407972
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