Evaluation of the results of chromen drug derivatives and their effect on colon cancer

Document Type : Original Article

Authors

1 Department of Biology, Faculty of Science, Hakim Sabzevari University, Sabzevar, Iran

2 Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran

Abstract

Cancer is a huge phenomenon in human society that it observe in developing countries and even more developed countries in terms of economic as well. Colon cancer is created by increasing cancer cells that its main reason is the uncontrollable growth of cells in Colon. In this research, two groups of stable chromene compounds which was calculated in the previous study using bioinformatics software selected and their toxicity effect and the kind of cell death that they cause investigated on HT-29 cancer cell line, which is related to colon cancer. Also, toxicity of 2-amino-4-(4-chlorophenyl)-5-oxo-4H,5H-pyrano [2,3-c] chromene -2-carbonitrile (S1), 2-amino-4-(4-bromophenyl)-5-oxo-4H,5H-pyrano [2,3-c] chromene -2-carbonitrile (S2) which had an appropriate stable determined. At concentrations of 1, 2, 3, 5, 10 and 20 μg / ml, a control group was performed on HT-29 cancer cell lines in comparison with the chemotherapeutic drug Campusar with similar concentrations of the chemotherapy drug using MTT assay. Analysis of data was done by statistical software Graphpad Prism 8 and ANOVA test and ultimately, the type of cell death which created by Flow cytometry technique was examined. The results showed that chromium derivatives by causing apoptosis in HT-29 cancer cells could be further studied as a suitable candidate for the effect on colon cancer.

Keywords

Main Subjects


This is an open access article under the CC-BY-SA 4.0 license.( https://creativecommons.org/licenses/by-sa/4.0/)

[1] Fearon, E. R., & Vogelstein, B. (1990). A genetic model for colorectal tumorigenesis. Cell, 61(5), 759-767.
[2] Engin, O. (2015). Colon polyps and the prevention of colorectal cancer. Springer.
[3] Estrada, R. G. M. D., & Spjut, H. J. M. D. (1980). Hyperplastic polyps of the large bowel. The American journal of surgical pathology, 4(2), 127-133.
[4] Ullah, M. F. (2008). Cancer multidrug resistance (MDR): a major impediment to effective chemotherapy. Asian Pacific Journal of Cancer Prevention, 9(1), 1-6.
[5] Steller, H. (1995). Mechanisms and genes of cellular suicide. Science, 267(5203), 1445-1449.
[6] Dlamini, Z., Mbita, M., & Zungu, M. (2004). Genealogy, expression, and molecular mechanisms in apoptosis. Pharmacology & Therapeutics. 101(1), 1-15.
[7] Proskuryakov, S. Y., Konoplyannikov, A. G., & Gabai, V. L. (2003). Necrosis: a specific form of programmed cell death? Experimental Cell Research, 283(1), 1-16.
[8] Abrams, J. M., & White, M. A. (2004). Coordination of cell death and the cell cycle: linking proliferation to death through private and communal couplers. Current Opinion in Cell Biology, 16(6), 634-638.
[9] Ellis, G. (2009). Chromenes, Chromanones, and Chromones. John Wiley & Sons.
[10] Okasha, R. M., Alblewi, F. F., H. Afifi, T. H., Fouda, A. M., Al-Dies, A. M., & El-Agrody, A. M. (2017). Design of new benzo[h]chromene derivatives: antitumor activities and structure-activity relationships of the 2,3-positions and fused rings at the 2,3-positions. Molecules, 22(3), 479-496.
[11] Lee, J. Y., Ahn, S. S., Jeong, Y. J., Choi, J., Ahn, S., Koh, D., Lee, Y. H., Lim, Y., & Shin, S. Y. (2020). A synthetic pan-aurora kinase inhibitor, 5-methoxy-2-(2-methoxynaphthalen-1-yl)-4H-chromen-4-one, triggers reactive oxygen species-mediated apoptosis in HCT116 colon cancer cells. Journal of Chemistry, Article ID 3025281.
[12] Ahagh, M. H., Dehghan, G., Mehdipour, M., Teimuri-Mofrad, R., Payami, E., Sheibani, N., Ghaffari, M., & Asadi, M. (2019). Synthesis, characterization, anti-proliferative properties and DNA binding of benzochromene derivatives: Increased Bax/Bcl-2 ratio and caspase-dependent apoptosis in colorectal cancer cell line. Bioorganic Chemistry, 93, 103329.
[13] Ahmed, H. E. A., El-Nassag, M. A. A., Hassan, A. H., Okasha, R. M., Ihmaid, S., Fouda, A. H., Afifi, T. H., Aljuhani, A., & El-Agrody, A. M. (2018). Introducing novel potent anticancer agents of 1H-benzo[f]chromene scaffolds, targeting c-Src kinase enzyme with MDA-MB-231 cell line anti-invasion effect. Journal of Enzyme Inhibition and Medical Chemistry, 33(1), 1074-1088.
[14] Hekmati, M., Yousefi, M., Ziyadi, H., Ghasemi, E., Safari Mehr, P., Veisi, H., & Maleki, B. (2021). Catalytic applications of coated nanopalladium particles coated on modified GO by Thymbraspicata extract in Suzuki coupling reactions. Applied Chemistry, 16(58), 233-244. (in persion)
[15] Maleki, B., Ayazi Jannat Abadi, S., Baghayeri, M., Rahnamaye Aliabad, H. A., & Veisi, H. (2018). One-pot and three-component of tetrahydrobenzo [b] pyran derivatives using heterogeneous and recyclable catalysts and its application toward silver nanoparticle synthesis. Applied Chemistry, 13(48), 209-230. (in persion)
[16] Sargazi Karbasaki, S., Bagherzade, G., Maleki, B., & Ghani, M. (2021). Fabrication of sulfamic acid functionalized magnetic nanoparticles with denderimeric linkers and its application for microextraction purposes, one-pot preparation of pyrans pigments and removal of malachite green. Journal of the Taiwan Institute of Chemical Engineers, 118, 342-354.
[17] LaPensee, E. W., Schwemberger, S. J., LaPensee, C. R., Bahassi, E. M., Afton, S. E., & Ben-Jonathan, N. (2009). Prolactin confers resistance against cisplatin in breast cancer cells by activating glutathione- S –transferase. Carcinogenesis, 30(8), 1298-1304.
[18] Martin, S. J., Reutelingsperger, C. P., McGahon, A. J., Rader, J. A., Van Schie, R. C., LaFace, D. M., & Green, D. L. (1995). Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl. Journal of Experimental Medicine, 182 (5): 1545–1556.
[19] Thomas, N., & Zachariah, S. M. (2013). Pharmacological activities of chromene derivatives: an overview. Asian Journal of Pharmaceutical and Clinical Research, 6(2), 11-15.
[20] Naseri, M. H., Hessami, T. S., Mahdavi, M., Moosavi, M., Abasalti, S., & Foroumadi, A. (2013). Induction of differentiation and cell death of the derivative of 4-aryl-4H-Chromenes Family on NB4 human promyelocytic Leukemia cell line. Journal of Cell and Tissue. 2(4), 139-147.
[21] Gourdeau, H., Leblond, L., Hamelin, B., Desputeau, C., Dong, K., Kianicka, I., Custeau, D.,  Boudreau, C., Geerts, L., Cai, S. X., Drewe, J., Labrecque, D., Kasibhatla, S., & Tseng, B. (2004). Antivascular and antitumor evaluation of 2-amino-4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-chromenes, a novel series of anticancer agents. Molecular Cancer Therapeutics, 3 (11): 1375–1384.
[22] Khan, M., Rasul, A., Yi, F., Zhong, L., & Ma, T. (2011). Jaceosidin induces p53-dependent G2/M phase arrest in U87 glioblastoma cells. Asian Pacific Journal of Cancer Prevention, 12(12), 3235-3238.