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HeLa ve Beas-2B Hücre Hatlarına Karşı Benzimidazolyum Tuzlarının İn Vitro Sitotoksik Aktivite Çalışmaları

Year 2020, Volume: 10 Issue: 2, 505 - 513, 15.04.2020
https://doi.org/10.17714/gumusfenbil.613631

Abstract

1H-benzo[d]imidazol çekirdeği içeren altı farklı heterosiklik bileşik (S1-S6) iki basamakta hazırlandı ve
yapıları farklı spektroskopik yöntemler kullanılarak karakterize edildi. Sentezlenen
heterosiklik bileşikler insan serviks adenokarsinom (HeLa) ve insan sağlıklı
akciğer (Beas-2B) hücre hatlarına karşı test edildi. Pozitif kontrol ilaç
olarak cisplatin aynı şartlar altında serviks hücre hattına karşı denendi.
Bileşik S4'ün HeLa hücre hattına karşı yüksek sitotoksik aktivite gösterdiği (IC50:
3.72 ± 0.14 µM) bulundu.
Çalışmanın son basamağında, ilaç adayları ile etkileştirilen hücrelerin renkli
görüntüleri konfokal mikroskobu kullanılarak alındı. 

References

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  • Akkoç, S., 2019a. Derivatives of 1-(2-(Piperidin-1-yl)ethyl)-1H-benzo[d]imidazole: Synthesis, Characterization, Determining of Electronic Properties and Cytotoxicity Studies. ChemistrySelect, 4, 4938-4943.
  • Akkoç, S., 2019b. Antiproliferative Activities of 2-Hydroxyethyl Substituted Benzimidazolium Salts and Their Palladium Complexes Against Human Cancerous Cell Lines. Synthetic Communications, 49, 2903-2914.
  • Akkoç, S., Kayser, V. ve İlhan, İ.Ö., 2019. Synthesis and In Vitro Anticancer Evaluation of Some Benzimidazolium Salts. Journal of Heterocyclic Chemistry, 56, 2934-2944.
  • Akkoç, S., Kayser, V., İlhan, İ.Ö., Hibbs, D.E., Gök, Y., Williams, P.A., Hawkins, B. ve Lai, F., 2017. New Compounds Based on a Benzimidazole Nucleus: Synthesis, Characterization and Cytotoxic Activity Against Breast and Colon Cancer Cell Lines. Journal of Organometallic Chemistry, 839, 98-107.
  • Akkoç, S., Özer İlhan, İ., Gök, Y., Upadhyay, P.J. ve Kayser, V., 2016. In Vitro Cytotoxic Activities of New Silver and PEPPSI Palladium N-heterocyclic Carbene Complexes Derived from Benzimidazolium Salts. Inorganica Chimica Acta, 449, 75-81.
  • Aslan, H.G., Akkoç, S. ve Kökbudak, Z., 2020. Anticancer Activities of Various New Metal Complexes Prepared from a Schiff Base on A549 Cell Line. Inorganic Chemistry Communications, 111, 107645.
  • Bansal, Y. ve Silakari, O., 2012. The Therapeutic Journey of Benzimidazoles: A Review. Bioorganic Medicinal Chemistry, 20, 6208-6236.
  • Busschots, S., O’Toole, S., O’Leary, J.J. ve Stordal, B., 2015. Carboplatin and Taxol Resistance Develops More Rapidly in Functional BRCA1 Compared to Dysfunctional BRCA1 Ovarian Cancer Cells. Experimental Cell Research, 336, 1-14.
  • Cheng, J., Xie, J. ve Luo, X., 2005. Synthesis and Antiviral Activity Against Coxsackie Virus B3 of Some Novel Benzimidazole Derivatives. Bioorganic and Medicinal Chemistry Letters, 15, 267-269.
  • Farahat, A.A., Ismail, M.A., Kumar, A., Wenzler, T., Brun, R., Paul, A., Wilson, W.D. ve Boykin, D.W., 2018. Indole and Benzimidazole Bichalcophenes: Synthesis, DNA Binding and Antiparasitic Activity. European Journal of Medicinal Chemistry, 143, 1590-1596.
  • Gök, Y., Akkoç, S., Çelikal, Ö.Ö., Özdemir, İ. ve Günal, S., 2019. In Vitro Antimicrobial Studies of Naphthalen-1-ylmethyl Substituted Silver N-heterocyclic Carbene Complexes. Arabian Journal of Chemistry, 12, 2513-2518.
  • Gök, Y., Akkoç, S., Çelikal, Ö.Ö., Özdemir, İ., Günal, S. ve Sayin, E., 2013. N-Functionalized Benzimidazol-2-ylidene Silver Complexes: Synthesis, Characterization and Antimicrobial Studies. Turkish Journal of Chemistry, 37 (6) 1007-1013.
  • Özil, M., Parlak, C. ve Baltaş, N., 2018. A Simple and Efficient Synthesis of Benzimidazoles Containing Piperazine or Morpholine Skeleton at C-6 Position as Glucosidase Inhibitors with Antioxidant Activity. Bioorganic Chemistry, 76, 468-477.
  • Rojas-Aguirre, Y., Castillo, I., Hernández, D.J., Nogueda-Torres, B., Márquez-Navarro, A., Villalobos, J.C., Sánchez-Bartéz, F., Sánchez-Torres, L., Gracia-Mora, I., Castillo, R. ve Hernández-Luis, F., 2012. Diversity in the Supramolecular Interactions of 5,6-Dichloro-2-(trifluoromethyl)-1H-benzimidazole with Modified Cyclodextrins: Implications for Physicochemical Properties and Antiparasitic Activity. Carbohydrate Polymers, 87, 471-479.
  • Rosenberg, B., Vancamp, L., Trosko, J.E. ve Mansour, V.H. 1969. Platinum Compounds: a New Class of Potent Antitumour Agents. Nature, 222, 385-386.
  • Sharma, R., Bali, A. ve Chaudhari, B.B., 2017. Synthesis of Methanesulphonamido-Benzimidazole Derivatives as Gastro-sparing Antiinflammatory Agents with Antioxidant Effect. Bioorganic and Medicinal Chemistry Letters, 27, 3007-3013.
  • Shingalapur, R.V., Hosamani, K.M., Keri, R.S. ve Hugar, M.H., 2010. Derivatives of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic and DNA Cleavage Studies. European Journal of Medicinal Chemistry, 45, 1753-1759.
  • Taha, M., Mosaddik, A., Rahim, F., Ali, S., Ibrahim, M. ve Almandil, N.B., 2018. Synthesis, Antiglycation and Antioxidant Potentials of Benzimidazole Derivatives. Journal of King Saud University - Science, 32, 191-194.
  • To, K.K.W., Poon, D.C., Wei, Y., Wang, F., Lin, G. ve Fu, L.W., 2016. Data Showing the Circumvention of Oxaliplatin Resistance by Vatalanib in Colon Cancer. Data in Brief, 7, 437-444.
  • Tonelli, M., Novelli, F., Tasso, B., Vazzana, I., Sparatore, A., Boido, V., Sparatore, F., La Colla, P., Sanna, G., Giliberti, G., Busonera, B., Farci, P., Ibba, C. ve Loddo, R., 2014. Antiviral Activity of Benzimidazole Derivatives. III. Novel Anti-CVB-5, Anti-RSV and Anti-Sb-1 Agents. Bioorganic Medicinal Chemistry, 22, 4893-4909.
  • Yang, Y., Guo, L., Ge, X., Shi, S., Gong, Y., Xu, Z., Zheng, X. ve Liu, Z., 2019. Structure-Activity Relationships for Highy Potent Half-Sandwich Organoiridium (III) Anticancer Complexes with CˆN-Chelated Ligands. Journal of Inorganic Biochemistry, 191, 1-7.
  • Wheate, N.J., Walker, S., Craig, G.E. ve Oun, R., 2010. The Status of Platinum Anticancer Drugs in the Clinic and in Clinical Trials. Dalton Transactions, 39, 8113-8127.
  • World Health Organization, 2018. Cancer, http://www.who.int/news-room/fact-sheets/detail/cancer. 07 Kasım 2019.

In Vitro Cytotoxic Activity Studies of Benzimidazolium Salts against HeLa and Beas-2B Cell Lines

Year 2020, Volume: 10 Issue: 2, 505 - 513, 15.04.2020
https://doi.org/10.17714/gumusfenbil.613631

Abstract

Six different heterocyclic
compounds containing 1H-benzo[d]imidazole nuclei (S1-S6) were prepared in two steps and their structures were characterized
using different spectroscopic methods. The synthesized heterocyclic compounds
were tested against human cervix adenocarcinoma (HeLa) and human healthy lung
(Beas-2B) cell lines
. Cisplatin as a positive control drug was tested against the cervix
cell line under the same conditions. Compound S4 was found to exhibit high cytotoxic activity against HeLa cell
line (IC50: 3.72 ± 0.14 µM). In the last step of the study, color
images of the cells interacted with the drug candidates were taken using confocal
microscope.

References

  • Abdelgawad, M.A., Bakr, R.B., Ahmad, W., Al-Sanea, M.M. ve Elshemy, H.A.H., 2019. New Pyrimidine-Benzoxazole/Benzimidazole Hybrids: Synthesis, Antioxidant, Cytotoxic Activity, In Vitro Cyclooxygenase and Phospholipase A2-V Inhibition. Bioorganic Chemistry, 92, 103218.
  • Akkoç, S., 2019a. Derivatives of 1-(2-(Piperidin-1-yl)ethyl)-1H-benzo[d]imidazole: Synthesis, Characterization, Determining of Electronic Properties and Cytotoxicity Studies. ChemistrySelect, 4, 4938-4943.
  • Akkoç, S., 2019b. Antiproliferative Activities of 2-Hydroxyethyl Substituted Benzimidazolium Salts and Their Palladium Complexes Against Human Cancerous Cell Lines. Synthetic Communications, 49, 2903-2914.
  • Akkoç, S., Kayser, V. ve İlhan, İ.Ö., 2019. Synthesis and In Vitro Anticancer Evaluation of Some Benzimidazolium Salts. Journal of Heterocyclic Chemistry, 56, 2934-2944.
  • Akkoç, S., Kayser, V., İlhan, İ.Ö., Hibbs, D.E., Gök, Y., Williams, P.A., Hawkins, B. ve Lai, F., 2017. New Compounds Based on a Benzimidazole Nucleus: Synthesis, Characterization and Cytotoxic Activity Against Breast and Colon Cancer Cell Lines. Journal of Organometallic Chemistry, 839, 98-107.
  • Akkoç, S., Özer İlhan, İ., Gök, Y., Upadhyay, P.J. ve Kayser, V., 2016. In Vitro Cytotoxic Activities of New Silver and PEPPSI Palladium N-heterocyclic Carbene Complexes Derived from Benzimidazolium Salts. Inorganica Chimica Acta, 449, 75-81.
  • Aslan, H.G., Akkoç, S. ve Kökbudak, Z., 2020. Anticancer Activities of Various New Metal Complexes Prepared from a Schiff Base on A549 Cell Line. Inorganic Chemistry Communications, 111, 107645.
  • Bansal, Y. ve Silakari, O., 2012. The Therapeutic Journey of Benzimidazoles: A Review. Bioorganic Medicinal Chemistry, 20, 6208-6236.
  • Busschots, S., O’Toole, S., O’Leary, J.J. ve Stordal, B., 2015. Carboplatin and Taxol Resistance Develops More Rapidly in Functional BRCA1 Compared to Dysfunctional BRCA1 Ovarian Cancer Cells. Experimental Cell Research, 336, 1-14.
  • Cheng, J., Xie, J. ve Luo, X., 2005. Synthesis and Antiviral Activity Against Coxsackie Virus B3 of Some Novel Benzimidazole Derivatives. Bioorganic and Medicinal Chemistry Letters, 15, 267-269.
  • Farahat, A.A., Ismail, M.A., Kumar, A., Wenzler, T., Brun, R., Paul, A., Wilson, W.D. ve Boykin, D.W., 2018. Indole and Benzimidazole Bichalcophenes: Synthesis, DNA Binding and Antiparasitic Activity. European Journal of Medicinal Chemistry, 143, 1590-1596.
  • Gök, Y., Akkoç, S., Çelikal, Ö.Ö., Özdemir, İ. ve Günal, S., 2019. In Vitro Antimicrobial Studies of Naphthalen-1-ylmethyl Substituted Silver N-heterocyclic Carbene Complexes. Arabian Journal of Chemistry, 12, 2513-2518.
  • Gök, Y., Akkoç, S., Çelikal, Ö.Ö., Özdemir, İ., Günal, S. ve Sayin, E., 2013. N-Functionalized Benzimidazol-2-ylidene Silver Complexes: Synthesis, Characterization and Antimicrobial Studies. Turkish Journal of Chemistry, 37 (6) 1007-1013.
  • Özil, M., Parlak, C. ve Baltaş, N., 2018. A Simple and Efficient Synthesis of Benzimidazoles Containing Piperazine or Morpholine Skeleton at C-6 Position as Glucosidase Inhibitors with Antioxidant Activity. Bioorganic Chemistry, 76, 468-477.
  • Rojas-Aguirre, Y., Castillo, I., Hernández, D.J., Nogueda-Torres, B., Márquez-Navarro, A., Villalobos, J.C., Sánchez-Bartéz, F., Sánchez-Torres, L., Gracia-Mora, I., Castillo, R. ve Hernández-Luis, F., 2012. Diversity in the Supramolecular Interactions of 5,6-Dichloro-2-(trifluoromethyl)-1H-benzimidazole with Modified Cyclodextrins: Implications for Physicochemical Properties and Antiparasitic Activity. Carbohydrate Polymers, 87, 471-479.
  • Rosenberg, B., Vancamp, L., Trosko, J.E. ve Mansour, V.H. 1969. Platinum Compounds: a New Class of Potent Antitumour Agents. Nature, 222, 385-386.
  • Sharma, R., Bali, A. ve Chaudhari, B.B., 2017. Synthesis of Methanesulphonamido-Benzimidazole Derivatives as Gastro-sparing Antiinflammatory Agents with Antioxidant Effect. Bioorganic and Medicinal Chemistry Letters, 27, 3007-3013.
  • Shingalapur, R.V., Hosamani, K.M., Keri, R.S. ve Hugar, M.H., 2010. Derivatives of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic and DNA Cleavage Studies. European Journal of Medicinal Chemistry, 45, 1753-1759.
  • Taha, M., Mosaddik, A., Rahim, F., Ali, S., Ibrahim, M. ve Almandil, N.B., 2018. Synthesis, Antiglycation and Antioxidant Potentials of Benzimidazole Derivatives. Journal of King Saud University - Science, 32, 191-194.
  • To, K.K.W., Poon, D.C., Wei, Y., Wang, F., Lin, G. ve Fu, L.W., 2016. Data Showing the Circumvention of Oxaliplatin Resistance by Vatalanib in Colon Cancer. Data in Brief, 7, 437-444.
  • Tonelli, M., Novelli, F., Tasso, B., Vazzana, I., Sparatore, A., Boido, V., Sparatore, F., La Colla, P., Sanna, G., Giliberti, G., Busonera, B., Farci, P., Ibba, C. ve Loddo, R., 2014. Antiviral Activity of Benzimidazole Derivatives. III. Novel Anti-CVB-5, Anti-RSV and Anti-Sb-1 Agents. Bioorganic Medicinal Chemistry, 22, 4893-4909.
  • Yang, Y., Guo, L., Ge, X., Shi, S., Gong, Y., Xu, Z., Zheng, X. ve Liu, Z., 2019. Structure-Activity Relationships for Highy Potent Half-Sandwich Organoiridium (III) Anticancer Complexes with CˆN-Chelated Ligands. Journal of Inorganic Biochemistry, 191, 1-7.
  • Wheate, N.J., Walker, S., Craig, G.E. ve Oun, R., 2010. The Status of Platinum Anticancer Drugs in the Clinic and in Clinical Trials. Dalton Transactions, 39, 8113-8127.
  • World Health Organization, 2018. Cancer, http://www.who.int/news-room/fact-sheets/detail/cancer. 07 Kasım 2019.
There are 24 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Senem Akkoc 0000-0002-1260-9425

Publication Date April 15, 2020
Submission Date August 31, 2019
Acceptance Date March 7, 2020
Published in Issue Year 2020 Volume: 10 Issue: 2

Cite

APA Akkoc, S. (2020). HeLa ve Beas-2B Hücre Hatlarına Karşı Benzimidazolyum Tuzlarının İn Vitro Sitotoksik Aktivite Çalışmaları. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 10(2), 505-513. https://doi.org/10.17714/gumusfenbil.613631