Synthesis and Cytotoxic Evaluation of 2-Pyrazoline Derivative on Leukemia Cancer Cell Line K562

Journal of Chemical Health Risks

مقاله 7، دوره 8، شماره 4، اسفند 2018، صفحه 323-328   

نوع مقاله: Original Article

شناسه دیجیتال (DOI): 10.22034/jchr.2018.545324

نویسندگان

Masoud Shaabanzadeh^{* 1}؛ Maryam Bikhof Torbati²

¹Department of Chemistry, Damghan Branch, Islamic Azad University, Damghan, Iran

²Department of Biology, Yadegar-e-Imam Khomeini (RAH) Shahr-e-Rey Branch, Islamic Azad University, Tehran, Iran

چکیده

The 2-pyrazoline derivatives have a wide range of biological effects, such as anti-viral, anti-bacterial, anti-fungal, anti-depressant and anti-cancer effects. Studies have shown that compounds containing 2-pyrazoline along with another heterocycles may show more effective biological properties. In this study, a 2-pyrazoline derivative with a spiro-indenoquinoxaline ring at C3 position was synthesized by one-pot microwave-assisted method and its chemical structure was confirmed by ¹H NMR spectroscopy. The cytotoxic effects of the compound were evaluated on the K562 cell line and phytohemagglutinin-activated peripheral blood mononuclear cells (PHA+PBMC) by MTT assay. Additionally, the cytotoxic effects of cisplatin on these cells were investigated and compared with those of 2-pyrazoline. The IC50 values ​​obtained from the 2-pyrazoline derivative effects on the K562 cell line and PHA+PBMC cells were 45 and 55 μg/mL respectively, while cisplatin inhibited proliferation of the same cells with IC50 value 1.71 and 7.8 µg/mL respectively. The results of this study showed that the synthesized derivative had a cytotoxic activity on the K562 cancer cell line at higher concentrations than cisplatin.

کلیدواژه‌ها

2-Pyrazoline؛ Indenoquinoxaline؛ anticancer؛ Cytotoxic effect؛ Leukemia؛ K562 cell line؛ PBMC

مراجع

1. Torre L.A., Siegel R.L., Ward E.M., Jemal A., 2016. Global cancer incidence and mortality rates and trends-an update. Cancer Epidemiol Prevent Biomarkers. 25(1), 16-27.

2.Li J.J., 2006 Laughing Gas Viagra and Lipitor: The Human Stories behind the Drugs We Use. Oxford University Press, UK.

3. Takimoto C.H., Calvo E., 2008. Principles of oncologic pharmacotherapy. Cancer management: a multidisciplinary approach. 11, 1-9.

4. Marella A., Ali R., Alam T., Saha R., Tanwar O., Akhter M., Shaquiquzzaman M., Mumtaz Alam M., 2013. Pyrazolines: a biological review. Mini Rev Med Chem. 13(6), 921-931.

5. Bashir R., Ovais, S., Yaseen S., Hamid H., Alam M.S., Samim M., Singh S., Javed K., 2011. Synthesis of some new 1, 3, 5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents. Bioorg. Med Chem Lett. 21(14), 4301-4305.

6. Ciupa A., Paul A., Mahon M.F., Wood P.J., Caggiano L., 2013. Synthesis and antiproliferative activity of some 3-(pyrid-2-yl)-pyrazolines. Med Chem Comm. 4(6), 956-961.

7. Gowramma B., Jubie S., Kalirajan R., Gomathy S., Elango K., 2009. Synthesis, anticancer activity of some 1-(Bis N, N-(Chloroethyl)-amino acetyl)-3, 5-disubstituted 1, 2-pyrazolines. Int J Pharm Tech Res. 1(2), 347-352.

8. Havrylyuk D., Zimenkovsky B., Vasylenko O., Zaprutko L., Gzella A., Lesyk R., 2009. Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity. Eur J Med Chem. 44(4), 1396-1404.

9. Khalil N.A., Ahmed E.M., El-Nassan H.B., 2013. Synthesis, characterization, and biological evaluation of certain 1, 3-thiazolone derivatives bearing pyrazoline moiety as potential anti-breast cancer agents. Med Chem Res. 22(2), 1021-1027.

10. Carta A., Piras S., Loriga G., Paglietti G., 2006. Chemistry, biological properties and SAR analysis of quinoxalinones. Mini Rev Med Chem. 6(11), 1179-1200.

11. Santos Bubniak L.D., Gaspar P.C., de Moraes A.C.R., Bigolin A., de Souza R.K., Buzzi F.C., Corrêa R., Filho V.C., Bretanha L.C., Micke G.A., Nunes R.J., 2016. Effects of 1, 3, 5-triphenyl-4, 5-dihydro-1 H-pyrazole derivatives on cell-cycle and apoptosis in human acute leukemia cell lines. Can J Physiol Pharmacol. 95(5), 548-563.

12. Lee H., Cho S., Namgoong K., Jung J.K., Cho J., Yang, S.I., 2004. Synthesis and in vitro evaluation of 7-dialkylaminomethylbenzo [g] quinoxaline-5, 10-diones. Bioorg Med Chem Lett. 14(5), 1235-1237.

13. Huang X.F., Lu X., Zhang Y., Song G.Q., He Q.L., Li Q.S., Yang X.H., Wei Y., Zhu H.L., 2012. Synthesis, biological evaluation, and molecular docking studies of N-((1, 3-diphenyl-1H-pyrazol-4-yl)methyl) aniline derivatives as novel anticancer agents. Bioorg Med Chem. 20(16), 4895-4900.