Design, Synthesis and Biological Evaluation of a Novel Sulfonamide Derivative as antiproliferative agents for Human Breast Cancer Cell line (MCF-7)

Baravordeh, Mohaddeseh; Ghafouri, Hossein; Mohammadi, Asadollah; Zarei, Sevda

Design, Synthesis and Biological Evaluation of a Novel Sulfonamide Derivative as antiproliferative agents for Human Breast Cancer Cell line (MCF-7)

Document Type : Original Research

Authors

Mohaddeseh Baravordeh ¹

Hossein Ghafouri ²

Asadollah Mohammadi ³

Sevda Zarei ⁴

¹ masters student, university of guilan

² Associate Professor in Biochemistry, Faculty of Sciences, University of Guilan

³ Associate Professor in Chemistry, Faculty of Sciences, University of Guilan

⁴ Ph.D. student, University of Guilan

Abstract

Aim: During the uncontrolled development of cells in the body, a subset of neoplasms or tumors is formed, the abnormal proliferation of these cells leads to the formation of a mass and eventually cancer. This mass can spread throughout the body. Thus, inhibiting the abnormal growth of cancer cells will have a significant effect on preventing the spread of cancerous tumors and improving the disease. Therefore, in the present study, a new sulfonamide derivative was designed and synthesized (HB20) and its anti-cancer effects on human breast cancer cell line (MCF-7) were investigated.

Materials and Methods: For the synthesis of a sulfonamide derivative (HB20), dcriptiazonium salt was first made using a sulfamethoxazole base compound and then combined with a pyrimidine coupling agent. Concentrations of a new synthetic compound (HB20) against Cells (MCF-7) were used. MTT assay was also performed to measure survival and cell proliferation.

Results: The synthesized compound structure was confirmed by spectral analysis, such as FT- IR, and NMR. Also, Survival in MCF-7 cells treated with a synthetic compound (HB20) was significantly reduced compared to the control group (untreated). HB20 inhibits the proliferation of MCF-7 cancer cells with an IC₅₀ value of 75/23 μg/ml.

Conclusion: The new sulfonamide derivative (HB20) has the potential to inhibit proliferation and anti-cancer properties in the cell line (MCF-7).

Keywords

sulfonamide derivatives

Breast Cancer

MCF-7 cell line

MTT

Subjects

Pharmaceutical Biotechnology

1. Roy P, Saikia B. Cancer and cure: A critical analysis. Indian journal of cancer. 2016;53(3):441.
2. Sudhakar A. History of cancer, ancient and modern treatment methods. Journal of cancer science & therapy. 2009;1(2):1.
3. Ghobrial IM, Witzig TE, Adjei AA. Targeting apoptosis pathways in cancer therapy. CA: a cancer journal for clinicians. 2005;55(3):178-94.
4. Li Y, Upadhyay S, Bhuiyan M, Sarkar FH. Induction of apoptosis in breast cancer cells MDA-MB-231 by genistein. Oncogene. 1999;18(20):3166-72.
5. Williams F, Jeanetta SC. Lived experiences of breast cancer survivors after diagnosis, treatment and beyond: qualitative study. Health expectations. 2016;19(3):631-42.
6. Oliveira N, Gomig T, Milioli H, Cordeiro F, Costa G, Urban C, et al. Comparative proteomic analysis of ductal and lobular invasive breast carcinoma. Genet Mol Res. 2016;15(2):1-10.
7. Al-Badrashiny M, Bellaachia A. Breast cancer survivability prediction via classifier ensemble. International Journal of Computer and Information Engineering. 2016;10(5):833-7.
8. Simstein R, Burow M, Parker A, Weldon C, Beckman B. Apoptosis, chemoresistance, and breast cancer: insights from the MCF-7 cell model system. Experimental biology and medicine. 2003;228(9):995-1003.
9. Scozzafava A, Mastrolorenzo A, Supuran C. Sulfonamides and sulfonylated derivatives as anticancer agents. Current cancer drug targets. 2002;2(1):55-75.
10. Koyuncu I, Tülüce Y, Slahaddin Qadir H, Durgun M, Supuran CT. Evaluation of the anticancer potential of a sulphonamide carbonic anhydrase IX inhibitor on cervical cancer cells. Journal of enzyme inhibition and medicinal chemistry. 2019;34(1):703-11.
11. Eliopoulos GM, Huovinen P. Resistance to trimethoprim-sulfamethoxazole. Clinical infectious diseases. 2001;32(11):1608-14.
12. Smilack JD, editor Trimethoprim-sulfamethoxazole. Mayo Clinic Proceedings; 1999: Elsevier.
13. El-Sayed NS, El-Bendary ER, El-Ashry SM, El-Kerdawy MM. Synthesis and antitumor activity of new sulfonamide derivatives of thiadiazolo [3, 2-a] pyrimidines. European journal of medicinal chemistry. 2011;46(9):3714-20.
14. Rama I, Selvameena R. Synthesis, structure analysis, anti-bacterial and in vitro anti-cancer activity of new Schiff base and its copper complex derived from sulfamethoxazole. Journal of Chemical Sciences. 2015;127(4):671-8.
15. Zonouz AM, Eskandari I, Khavasi HR. A green and convenient approach for the synthesis of methyl 6-amino-5-cyano-4-aryl-2, 4-dihydropyrano [2, 3-c] pyrazole-3-carboxylates via a one-pot, multi-component reaction in water. Tetrahedron Letters. 2012;53(41):5519-22.
16. Wang C, Dong S, Zhang L, Zhao Y, Huang L, Gong X, et al. Cell surface binding, uptaking and anticancer activity of L-K6, a lysine/leucine-rich peptide, on human breast cancer MCF-7 cells. Scientific reports. 2017;7(1):1-13.
17. Jamalzadeh L, Ghafoori H, Aghamaali M, Sariri R. Induction of Apoptosis in Human Breast Cancer MCF-7 Cells by a Semi-Synthetic Derivative of Artemisinin: A Caspase-Related Mechanism. Iranian journal of biotechnology. 2017;15(3):157.
18. Bouchain G, Leit S, Frechette S, Khalil EA, Lavoie R, Moradei O, et al. Development of potential antitumor agents. Synthesis and biological evaluation of a new set of sulfonamide derivatives as histone deacetylase inhibitors. Journal of Medicinal Chemistry. 2003;46(5):820-30.
19. Ali I, Wani WA, Saleem K, Hsieh M-F. Anticancer metallodrugs of glutamic acid sulphonamides: in silico, DNA binding, hemolysis and anticancer studies. RSC advances. 2014;4(56):29629-41.
20. Mohan R, Banerjee M, Ray A, Manna T, Wilson L, Owa T, et al. Antimitotic sulfonamides inhibit microtubule assembly dynamics and cancer cell proliferation. Biochemistry. 2006;45(17):5440-9.
21. Ghorab MM, Ragab FA, Hamed MM. Design, synthesis and anticancer evaluation of novel tetrahydroquinoline derivatives containing sulfonamide moiety. European journal of medicinal chemistry. 2009;44(10):4211-7.
22. Ghorab MM, Ragab FA, Heiba HI, El-Gazzar MG, Zahran SS. Synthesis, anticancer and radiosensitizing evaluation of some novel sulfonamide derivatives. European journal of medicinal chemistry. 2015;92:682-92.
23. Cumaoglu A, Dayan S, Agkaya AO, Ozkul Z, Ozpozan NK. Synthesis and pro-apoptotic effects of new sulfonamide derivatives via activating p38/ERK phosphorylation in cancer cells. Journal of Enzyme Inhibition and Medicinal Chemistry. 2015;30(3):413-9.
24. Bonakdar APS, Vafaei F, Farokhpour M, Esfahani MHN, Massah AR. Synthesis and anticancer activity assay of novel chalcone-sulfonamide derivatives. Iranian journal of pharmaceutical research: IJPR. 2017;16(2):565.
25. Gupta R, Kazmi I, Afzal M, Khan R, Chauhan M, Al-Abbasi FA, et al. Combination of sulfamethoxazole and selenium in anticancer therapy: a novel approach. Molecular and cellular biochemistry. 2013;384(1-2):279-85.