GREEN SYNTHESIS OF HALOGEN SUBSTITUTED CHALCONE AGAINST CERVICAL CANCER (HeLa) CELL LINES

  • Retno Aliyatul Fikroh UIN Sunan Kalijaga Yogyakarta, Indonesia
  • Sabirin Matsjeh Universitas Gadjah Mada, Yogyakarta, Indonesia
  • Chairil Anwar Universitas Gadjah Mada, Yogyakarta, Indonesia
  • Beta Achromi Nurohmah Nara Institute of Science and Technology, Japan
https://doi.org/10.21154/insecta.v4i1.5876
Abstract views: 385 , PDF downloads: 471
Keywords: Chalcone, Green Synthesis, Cervical cancel cell

Abstract

Cervical cancer is the second leading cause of death in women. Many cancer treatments currently provide toxic effects on normal cells. Therefore, alternative treatment using chalcone derivatives has potent anticancer properties that can help reduce cancer side effects. Chalcone derivatives with halogen and methoxy groups in ring B can potentially inhibit cancer cells. This research aimed to synthesize halogen-substituted chalcone by a green chemistry approach and determine activity against cervical cancer (HeLa) cell lines. The Claisen-Schmidt reaction was used to synthesize 2'-hydroxy-2-bromo-4,5-dimethoxychalcone using a grinding technique. The purity of the synthesized compound was determined using thin-layer chromatography and melting range. The compounds' structures were characterized using FTIR, MS 1H, and 13C-NMR. The result showed that the synthesized compound was yielded in 53% as a yellow solid. In vitro cytotoxicity of the synthesized chalcone was evaluated by the MTT assay method. The IC50 of the compound was 67,23 μg/mL as a moderate activity inhibiting cervical cancer (HeLa) cell lines. Based on the IC50 value, this compound can be a candidate for anticancer against Cervical cancer (HeLa) cell lines.

Author Biography

Retno Aliyatul Fikroh, UIN Sunan Kalijaga Yogyakarta, Indonesia
Pendidikan Kimia UIN Sunan Kalijaga Yogyakarta

References

Anwar, C., Prasetyo, Y. D., Matsjeh, S., Haryadi, W., Sholikhah, E. N., & Nendrowati. (2018). Synthesis of chalcone derivatives and their in vitro anticancer test against breast (T47D) and colon (wiDr) cancer cell line. Indonesian Journal of Chemistry, 18(1), 102–107. https://doi.org/10.22146/ijc.26864

Bazzaro, M., Anchoori, R. K., Mudiam, M. K. R., Issaenko, O., Kumar, S., Karanam, B., Lin, Z., Isaksson Vogel, R., Gavioli, R., Destro, F., Ferretti, V., Roden, R. B. S., & Khan, S. R. (2011). α,β-unsaturated carbonyl system of chalcone-based derivatives is responsible for broad inhibition of proteasomal activity and preferential killing of human papilloma virus (HPV) positive cervical cancer cells. Journal of Medicinal Chemistry, 54(2), 449–456. https://doi.org/10.1021/jm100589p

Bray, F., Ferlay, J., Soerjomataram, I., Siegel, R. L., Torre, L. A., & Jemal, A. (2018). Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: A Cancer Journal for Clinicians, 68(6), 394–424. https://doi.org/10.3322/caac.21492

Elkanzi, N. A. A., Hrichi, H., Alolayan, R. A., Derafa, W., Zahou, F. M., & Bakr, R. B. (2022). Synthesis of Chalcones Derivatives and Their Biological Activities: A Review. ACS Omega, 7(32), 27769–27786. https://doi.org/10.1021/acsomega.2c01779

Fikroh, R. A., Matsjeh, S., & Anwar, C. (2020). Synthesis and anticancer activity of (E)-2’-hydroxy-2-bromo-4,5-dimethoxychalcone against breast cancer (MCF-7) cell line. Molekul, 15(1), 34–39. https://doi.org/10.20884/1.jm.2020.15.1.558

Ketabforoosh, S. H. M. E., Kheirollahi, A., Safavi, M., Esmati, N., Ardestani, S. K., Emami, S., Firoozpour, L., Shafiee, A., & Foroumadi, A. (2014). Synthesis and anti-cancer activity evaluation of new dimethoxylated chalcone and flavanone analogs. Archiv Der Pharmazie, 347(11), 853–860. https://doi.org/10.1002/ardp.201400215

Kopustinskiene, D. M., Jakstas, V., Savickas, A., & Bernatoniene, J. (2020). Flavonoids as anticancer agents. Nutrients, 12(2), 1–25. https://doi.org/10.3390/nu12020457

Kristina, S. A., Endarti, D., & Aditama, H. (2022). Prediction of Productivity Costs Related to Cervical Cancer Mortality in Indonesia 2018. Malaysian Journal of Medical Sciences, 29(1), 138–144. https://doi.org/10.21315/mjms2022.29.1.13

Krzywik, J., Mozga, W., Aminpour, M., Janczak, J., Maj, E., Wietrzyk, J., Tuszyński, J. A., & Huczyński, A. (2020). Synthesis, antiproliferative activity and molecular docking studies of novel doubly modified colchicine amides and sulfonamides as anticancer agents. Molecules, 25(8). https://doi.org/10.3390/molecules25081789

Kumar, S., Lamba, M. S., & Makrandi, J. K. (2008). An efficient green procedure for the synthesis of chalcones using C-200 as solid support under grinding conditions. Green Chemistry Letters and Reviews, 1(2), 123–125. https://doi.org/10.1080/17518250802325993

Mao, Z., Zheng, X., Qi, Y., Zhang, M., Huang, Y., Wan, C., & Rao, G. (2016). Synthesis and biological evaluation of novel hybrid compounds between chalcone and piperazine as potential antitumor agents. RSC Advances, 6(10), 7723–7727. https://doi.org/10.1039/c5ra20197g

Oktavia, D., Balatif, N., & Zamri, A. (2018). Sintesis Dan Uji Toksisitas Senyawa Analog Kalkon Dari 4’- Hidroksiasetofenon Dengan Dimetoksibenzaldehid. Photon: Jurnal Sain Dan Kesehatan, 6(01), 45–49. https://doi.org/10.37859/jp.v6i01.462

Prabawati, S. Y., Yuda, K. E., Firdaus, R. C., Sugihati, A., & Departement, C. (2022). Green Synthesis of Several Chalcone Derivatives Using Grinding Technique. Advanced Engineering Science, 54(08), 2449–2456.

Qorina, F., Arsianti, A., Fithrotunnisa, Q., Tejaputri, N. A., Azizah, N. N., & Putrianingsih, R. (2020). Cytotoxicity of soursop leaves (Annona muricata) against cervical HeLa cancer cells. Pharmacognosy Journal, 12(1), 20–24. https://doi.org/10.5530/pj.2020.12.4

Ramalho, S. D., Bernades, A., Demetrius, G., Noda-Perez, C., Vieira, P. C., Dos Santos, C. Y., Da Silva, J. A., De Moraes, M. O., & Mousinho, K. C. (2013). Synthetic chalcone derivatives as inhibitors of cathepsins K and B, and their cytotoxic evaluation. Chemistry and Biodiversity, 10(11), 1999–2006. https://doi.org/10.1002/cbdv.201200344

Ranjit, P. M., Rahaman, S. A., Kumar, K. P., Rajendra Prasad, Y., Santhipriya, T., Manikanta, G. C. V. S., & Sudeepthi, N. R. L. (2013). Synthesis, screening and in vitro anticancer activity of piperazine nucleus containing novel chalcones on different cell lines. International Journal of PharmTech Research, 5(1), 284–293.

Rao, Y. K., Fang, S. H., & Tzeng, Y. M. (2004). Differential effects of synthesized 2′-oxygenated chalcone derivatives: Modulation of human cell cycle phase distribution. Bioorganic and Medicinal Chemistry, 12(10), 2679–2686. https://doi.org/10.1016/j.bmc.2004.03.014

Suryani, N., Matsjeh, S., Mutmainah, Putri, D. E. K., Iskandar, D., & Asyura, S. (2020). Cytotoxicity Assay of 2,4-Dihydroxide- 4’ -Methoxychalcone Against Cervical (HeLa) Cancer Cell by MTT Assay. Biota: Biologi Dan Pendidikan Biologi, 13(1), 12–20.

Susanti Vh, E., & Eko Setyowati, W. A. (2018). A Green Synthesis of Chalcones As an Antioxidant and Anticancer. IOP Conference Series: Materials Science and Engineering, 299(1), 1–6. https://doi.org/10.1088/1757-899X/299/1/012077

Tanamatayarat, P., Limtrakul, P., Chunsakaow, S., & Duangrat, C. (2003). Screening of Some Rubiaceous Plants for Cytotoxic Activity Against Cervix Carcinoma (KB-3-1) Cell Line. Journal of Pharmaceutical Sciences, 27(3–4), 167–172.

Tungmunnithum, D., Thongboonyou, A., Pholboon, A., & Yangsabai, A. (2018). Flavonoids and Other Phenolic Compounds from Medicinal Plants for Pharmaceutical and Medical Aspects: An Overview. Medicines, 5(3), 93. https://doi.org/10.3390/medicines5030093

Venkateswararao, E., Sharma, V. K., Lee, K. C., Sharma, N., Park, S. H., Kim, Y., & Jung, S. H. (2012). A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB. European Journal of Medicinal Chemistry, 54, 379–386. https://doi.org/10.1016/j.ejmech.2012.05.019

Yadav, V. R., Prasad, S., Sung, B., & Aggarwal, B. B. (2011). The role of chalcones in suppression of NF-κB-mediated inflammation and cancer. International Immunopharmacology, 11(3), 295–309. https://doi.org/10.1016/j.intimp.2010.12.006

Zangade, S., & Mokle, S. (2011a). An Efficient and Operationally Simple Synthesis of Some New Chalcones by Using Grinding Technique. Chemical Sciences Journal, 2, 1–6. https://doi.org/10.4172/2150-3494.1000011

Zangade, S., & Mokle, S. (2011b). An Efficient and Operationally Simple Synthesis of Some New Chalcones by Using Grinding Technique. Chemical Sciences Journal, 2, 1–6. https://doi.org/10.4172/2150-3494.1000011

PlumX Metrics

Published
2023-05-31
Issue
Vol. 4 No. 1 (2023)
Section
Articles

Copyright (c) 2023 Retno Aliyatul Fikroh; Sabirin Matsjeh; Chairil Anwar; Beta Achromi Nurohmah

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.