Synthesis of New Anthraquinone Derivatives and Anticancer Effects on Breast Cancer Cell Lines

Ebru Hacıosmanoglu; Funda Ozkok; Alper Kemal Onsu; Muhammet Bektas; Basak Varol; Sacide Pehlıvan

Research Article

Year 2018, Issue: 4, 271 - 276, 04.12.2018

Ebru Hacıosmanoglu Funda Ozkok Alper Kemal Onsu Muhammet Bektas Basak Varol Sacide Pehlıvan

Abstract

References

Almutairi, M. S., Hegazy, G. H., Haiba, M. E., Ali, H. I., Khalifa, N. M., & Soliman Ael, M. (2014). Synthesis, docking and biological activities of novel hybrids celecoxib and anthraquinone analogs as potent cytotoxic agents. Int J Mol Sci, 15(12), 22580-22603. doi:10.3390/ijms151222580 Errington, R. J., Sadiq, M., Cosentino, L., Wiltshire, M., Sadiq, O., Sini, M., . . . Pors, K. (2018). Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones. Bioorg Med Chem Lett, 28(8), 1274-1277. doi:10.1016/j.bmcl.2018.03.040 Ferrazzi, E., Palumbo, M., Valisena, S., Antonello, C., & Palu, G. (1986). Antitumor activity of new anthraquinone derivatives. Chemioterapia, 5(5), 330-336. Huang, H. S., Chiou, J. F., Chiu, H. F., Hwang, J. M., Lin, P. Y., Tao, C. W., . . . Jeng, W. R. (2002). Synthesis of symmetrical 1,5-bis-thio-substituted anthraquinones for cytotoxicity in cultured tumor cells and lipid peroxidation. Chem Pharm Bull (Tokyo), 50(11), 1491-1494. Iqbal, J., Saeed, A., Raza, R., Matin, A., Hameed, A., Furtmann, N., . . . Bajorath, J. (2013). Identification of sulfonic acids as efficient ecto-5′-nucleotidase inhibitors. European Journal of Medicinal Chemistry, 70, 685-691. doi:https://doi.org/10.1016/j.ejmech.2013.10.053 Locatelli, M., Epifano, F., Genovese, S., Carlucci, G., Koncic, M. Z., Kosalec, I., & Kremer, D. (2011). Anthraquinone profile, antioxidant and antimicrobial properties of bark extracts of Rhamnus catharticus and R. orbiculatus. Nat Prod Commun, 6(9), 1275-1280. Meran, M., Akkus, P. D., Kurkcuoglu, O., Baysak, E., Hizal, G., Haciosmanoglu, E., . . . Guner, F. S. (2018). Noncovalent Pyrene-Polyethylene Glycol Coatings of Carbon Nanotubes Achieve in Vitro Biocompatibility. Langmuir, 34(40), 12071-12082. doi:10.1021/acs.langmuir.8b00971 Nobili, S., Lippi, D., Witort, E., Donnini, M., Bausi, L., Mini, E., & Capaccioli, S. (2009). Natural compounds for cancer treatment and prevention. Pharmacol Res, 59(6), 365-378. doi:10.1016/j.phrs.2009.01.017 Ozkok, F and Şahin, YM. (2016). Biyoaktif Antrakinon Anologlarının Sentezine Yönelik Özgün Metot Geliştirilmesi, TÜRKIYE, Patent, TR 2016/19610 Palumbo, M., Palu, G., Gia, O., Ferrazzi, E., Gastaldi, S., Antonello, C., & Meloni, G. A. (1987). Bis-substituted hydroxy-anthracenediones: DNA binding and biological activity. Anticancer Drug Des, 1(4), 337-346. Pickhardt, M., Gazova, Z., von Bergen, M., Khlistunova, I., Wang, Y., Hascher, A., . . . Mandelkow, E. (2005). Anthraquinones inhibit tau aggregation and dissolve Alzheimer's paired helical filaments in vitro and in cells. J Biol Chem, 280(5), 3628-3635. doi:10.1074/jbc.M410984200 Rassu, M., Ferrazzi, E., Stefanelli, S., Palu, G., Antonello, C., & Palumbo, M. (1991). [Structure-activity relationship of several mitoxantrone analogues]. G Ital Chemioter, 38(1-3), 201-203. Wang, W., Bai, Z., Zhang, F., Wang, C., Yuan, Y., & Shao, J. (2012). Synthesis and biological activity evaluation of emodin quaternary ammonium salt derivatives as potential anticancer agents. Eur J Med Chem, 56, 320-331. doi:10.1016/j.ejmech.2012.07.051

Synthesis of New Anthraquinone Derivatives and Anticancer Effects on Breast Cancer Cell Lines

Year 2018, Issue: 4, 271 - 276, 04.12.2018

Ebru Hacıosmanoglu Funda Ozkok Alper Kemal Onsu Muhammet Bektas Basak Varol Sacide Pehlıvan

Abstract

Antraquinone
and their analogues are among the important compounds investigated to develop
novel bioactive and biocompatible molecules with potential for medical
applications. The most important quinone class as anthraquinones occur widely
in plants such as aloe vera and tipton's weed. Anthraquinone derivatives have
aroused special interest since they have demonstrated potential therapeutic
uses as antibacterial, antiviral, antifungal agents and other biological
activities. Mitoxantrone, an anthraquinone analogue, is known as a synthetic
anticancer analog of anthracycline antibiotics. Mitoxantrone as anticancer drug
is a powerful inhibitor of the enzyme that is in charge with the repair of
damaged DNA. In this study, new anthraquinone derivatives([1-(4-Chlorothiophenyl)-9,10-dioxoanthraquinone],[1-(4-Aminothiophenyl)-9,10
dioxoanthraquinone]) were characterized by spectroscopic methods (1H-NMR,
13C-NMR, FT-IR, UV-Vis analyzes). Breast cancer cell lines (MDA- MB-231 and
MCF-7) and human umbilical vein endothelial cells (HUVECs) were proliferated in standard culture conditions. Cells were incubated
with these derivatives for 24 and 48 h with in different concentrations. Cell
proliferation assays, MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium
Bromide) and CCK-8 (Cell Counting Kit-8), were performed to reveal anticancer
effect of new anthraquinone derivatives. As a result, Cell viability of MDA-
MB-231 and MCF-7 cells were decreased significantly (p<0.05) by new
anthraquinone derivatives treatment whereas cytotoxic effect was not observed
in HUVECs. In this study new synthesized anthraquinone derivatives were tested
and comparable results were observed both in vitro cytotoxicity assay and
statistical analysis. This anthraquinone derivatives are promising for its
further development as an anticancer drug.

Keywords

Anthraquinone derivatives , Thiol , breast cancer , Cell lines

References

Almutairi, M. S., Hegazy, G. H., Haiba, M. E., Ali, H. I., Khalifa, N. M., & Soliman Ael, M. (2014). Synthesis, docking and biological activities of novel hybrids celecoxib and anthraquinone analogs as potent cytotoxic agents. Int J Mol Sci, 15(12), 22580-22603. doi:10.3390/ijms151222580 Errington, R. J., Sadiq, M., Cosentino, L., Wiltshire, M., Sadiq, O., Sini, M., . . . Pors, K. (2018). Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones. Bioorg Med Chem Lett, 28(8), 1274-1277. doi:10.1016/j.bmcl.2018.03.040 Ferrazzi, E., Palumbo, M., Valisena, S., Antonello, C., & Palu, G. (1986). Antitumor activity of new anthraquinone derivatives. Chemioterapia, 5(5), 330-336. Huang, H. S., Chiou, J. F., Chiu, H. F., Hwang, J. M., Lin, P. Y., Tao, C. W., . . . Jeng, W. R. (2002). Synthesis of symmetrical 1,5-bis-thio-substituted anthraquinones for cytotoxicity in cultured tumor cells and lipid peroxidation. Chem Pharm Bull (Tokyo), 50(11), 1491-1494. Iqbal, J., Saeed, A., Raza, R., Matin, A., Hameed, A., Furtmann, N., . . . Bajorath, J. (2013). Identification of sulfonic acids as efficient ecto-5′-nucleotidase inhibitors. European Journal of Medicinal Chemistry, 70, 685-691. doi:https://doi.org/10.1016/j.ejmech.2013.10.053 Locatelli, M., Epifano, F., Genovese, S., Carlucci, G., Koncic, M. Z., Kosalec, I., & Kremer, D. (2011). Anthraquinone profile, antioxidant and antimicrobial properties of bark extracts of Rhamnus catharticus and R. orbiculatus. Nat Prod Commun, 6(9), 1275-1280. Meran, M., Akkus, P. D., Kurkcuoglu, O., Baysak, E., Hizal, G., Haciosmanoglu, E., . . . Guner, F. S. (2018). Noncovalent Pyrene-Polyethylene Glycol Coatings of Carbon Nanotubes Achieve in Vitro Biocompatibility. Langmuir, 34(40), 12071-12082. doi:10.1021/acs.langmuir.8b00971 Nobili, S., Lippi, D., Witort, E., Donnini, M., Bausi, L., Mini, E., & Capaccioli, S. (2009). Natural compounds for cancer treatment and prevention. Pharmacol Res, 59(6), 365-378. doi:10.1016/j.phrs.2009.01.017 Ozkok, F and Şahin, YM. (2016). Biyoaktif Antrakinon Anologlarının Sentezine Yönelik Özgün Metot Geliştirilmesi, TÜRKIYE, Patent, TR 2016/19610 Palumbo, M., Palu, G., Gia, O., Ferrazzi, E., Gastaldi, S., Antonello, C., & Meloni, G. A. (1987). Bis-substituted hydroxy-anthracenediones: DNA binding and biological activity. Anticancer Drug Des, 1(4), 337-346. Pickhardt, M., Gazova, Z., von Bergen, M., Khlistunova, I., Wang, Y., Hascher, A., . . . Mandelkow, E. (2005). Anthraquinones inhibit tau aggregation and dissolve Alzheimer's paired helical filaments in vitro and in cells. J Biol Chem, 280(5), 3628-3635. doi:10.1074/jbc.M410984200 Rassu, M., Ferrazzi, E., Stefanelli, S., Palu, G., Antonello, C., & Palumbo, M. (1991). [Structure-activity relationship of several mitoxantrone analogues]. G Ital Chemioter, 38(1-3), 201-203. Wang, W., Bai, Z., Zhang, F., Wang, C., Yuan, Y., & Shao, J. (2012). Synthesis and biological activity evaluation of emodin quaternary ammonium salt derivatives as potential anticancer agents. Eur J Med Chem, 56, 320-331. doi:10.1016/j.ejmech.2012.07.051

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Details

Primary Language	English
Journal Section	Articles
Authors	Ebru Hacıosmanoglu Funda Ozkok Alper Kemal Onsu Muhammet Bektas Basak Varol Sacide Pehlıvan
Publication Date	December 4, 2018
Published in Issue	Year 2018 Issue: 4

Cite

APA	Hacıosmanoglu, E., Ozkok, F., Onsu, A. K., … Bektas, M. (2018). Synthesis of New Anthraquinone Derivatives and Anticancer Effects on Breast Cancer Cell Lines. The Eurasia Proceedings of Science Technology Engineering and Mathematics(4), 271-276.