AKTIVITAS ANTIKANKER BEBERAPA SENYAWA HASIL SINTESIS TURUNAN KLOROCALKON PADA SEL HTB-183 DAN WiDr
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(2) IR-PERPUSTAKAAN UNIVERSITAS AIRLANGGA. Susetyo, Ellyca, 2019, Anticancer Activity of Some Chlorocalkon Derivative Compounds of HTB-183 and WiDr cells, The thesis was under guidance of Dr. Hery Suwito, M.Si, and Dr. Alfinda Novi Kristanti, DEA, Department of Chemistry, Faculty of Science and Technology, Airlangga University.. ABSTRACT. Cancer is a deadly disease with number of patients continue to increase year by year. Currently cancer treatment method is less efficient, so researchers continue to develop anticancer drugs. One of the potential compounds as anticancer is chlorochalcone derivatives. In this study, four chlorochalcone derivatives and two cycloheksanol pentasubstitution were successfully synthesized by reacting 4'-chloroasetofenon with some benzaldehyde derivatives and NaOH as catalyst through the Claisen-Schimdt reaction. Benzaldehyde derivatives with electron withdrawing group had faster reaction than benzaldehyde derivatives with electron donating group. Structure characterization was done using using FTIR and NMR. Anticancer activity was determined using in vitro MTT assay against HTB-183 cells and WiDr cells. The results of the anticancer activity test showed that the MTKC-4 compound had the lowest IC50 value compared to other test compounds. IC50 value of HTB-183 cell was 20,56 µg/mL and IC50 values of WiDr cells was 11,23 µg/mL. IC50 values of doxorubicin as a positive control was 0.95 µg/mL for HTB-183 and 17,88 µg/mL for WiDr cells. Keywords: Claisent-Schmidt condensation, chlorocalone derivative, anticancer, HTB-183, WiDr. TESIS. vii AKTIVITAS ANTIKANKER BEBERAPA. ELLYCA S.
(3) IR-PERPUSTAKAAN UNIVERSITAS AIRLANGGA. DAFTAR ISI. SAMPUL DALAM ................................................................................................. i HALAMAN PRASYARAT GELAR ................................................................... ii HALAMAN PENGESAHAN .............................................................................. iii UCAPAN TERIMA KASIH................................................................................ iv ABSTRAK ............................................................................................................ vi ABSTRACK ......................................................................................................... vii LEMBAR PERNYATAAN ORISINALITAS ................................................. viii DAFTAR ISI ......................................................................................................... ix DAFTAR GAMBAR ........................................................................................... xi DAFTAR TABEL................................................................................................ xii DAFTAR LAMPIRAN ...................................................................................... xiii BAB I PENDAHULUAN ...................................................................................... 1 1.1 Latar Belakang ............. ......................................................................………...1 1.2 Rumusan Masalah ............................................................................................. 5 1.3 Tujuan Penelitian............................................................................................... 5 1.4 Manfaat Penelitian............................................................................................. 5 BAB II TINJAUAN PUSTAKA ........................................................................... 6 2.1 Calkon .............................................................................................................. 6 2.2 Kondensasi Aldol .............................................................................................. 7 2.3 Adisi Michael .................................................................................................... 9 2.4 Uji Aktivitas Antikanker ................................................................................... 9 BAB III KERANGKA KONSEPTUAL DAN HIPOTESIS............................ 11 3.1 Kerangka Konseptual ...................................................................................... 11 3.2 Hipotesis Penelitian ......................................................................................... 12 BAB IV METODE PENELITIAN .................................................................... 13 4.1 Waktu dan Tempat Penelitian ......................................................................... 13 4.2 Alat dan Bahan ................................................................................................ 13 4.2.1 Alat …… ............................................................................................... 13 4.2.2 Bahan .................................................................................................... 13 4.3 Diagram Alir ................................................................................................... 14 4.4 Cara Kerja ....................................................................................................... 14 4.4.1 Sintesis senyawa turunan calkon........................................................... 14 4.4.2 Penentuan aktivitas antikanker senyawa turunan calkon ...................... 15 BAB V HASIL DAN PEMBAHASAN .............................................................. 17 5.1 Sintesisn Senyawa Target ............................................................................... 17 5.2 Karakterisasi senyawa hasil sintesis ............................................................... 27 5.2.1 Karakterisasi Umum Spektra Fourier Transform Infrared (FTIR) ….…27 5.2.2 Analisis Umum Spektra NMR ………………………………………....27 5.6 Uji Aktivitas Antikanker …………………………………………………......38. TESIS. ix AKTIVITAS ANTIKANKER BEBERAPA. ELLYCA S.
(4) IR-PERPUSTAKAAN UNIVERSITAS AIRLANGGA. BAB VI KESIMPULAN DAN SARAN …………………………………...….. 43 6.1 Kesimpulan …………………………………………………………………. 43 6.2 Saran …………………………………………………………………………43 DAFTAR PUSTAKA .......................................................................................... 44 LAMPIRAN ......................................................................................................... 47. TESIS. x AKTIVITAS ANTIKANKER BEBERAPA. ELLYCA S.
(5) IR-PERPUSTAKAAN UNIVERSITAS AIRLANGGA. DAFTAR PUSTAKA. American Cancer Society. 2016. What we’ll be talking about. Anto, Riski Septi. 2018. Sintesis 4-Fluoro-2’-Hidroksicalkon Dan 4-Kloro-2’Hidroksicalkon Serta Uji in Silico Terhadap Protein P53 Dan MDM2. Skripsi. Universitas Airlangga Aponte, C., Vera, M., Ma, E., Zimic, M., Quiliano, M., Vaisberg, A.J., Gilman, R.H., Hammond, G.B., 2008. Synthesis, Cytotoxicity, and AntiTrypanosoma cruzi Activity of New Chalcones 6230–6234. Karthikeyan, C., Narayana, N.S.H., Ramasamy, S., 2015. Advances in Chalcones with Anticancer Activities. Kristanti, A. N., Aminah, N. S., Tanjung, M., Kurniadi, B., 2008, Buku Ajar Fitokimia, Airlangga University Press, Surabaya. Lawrence, N. J.; McGown, A. T.; Ducki, S.; Hadfield, J. A. 2000. The interaction of chalcones with tubulin. Anti-Cancer Drug. Vol: 15, 135−141 Lipinski, C., Lombardo, F., Dominy, B.W., Feeney, P.J. 1997. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23:3-25. Matias, M., Campos, G., Santos, A. O., Falcao, A., Silvestre, S., Alves, G., 2017, Synthesis, in vitro evaluation and QSAR modelling of potential antitumoral 3,4dihydropyrimidin-2-(1H)-tion, Arab. J. of Chem., 1– 17. Mahapatra, D.K., Bharti, S.K., Asati, V., 2015. European Journal of Medicinal Chemistry Anti-cancer chalcones : Structural and molecular target perspectives. Eur. J. Med. Chem. (98): 69–114. Mosmann, T., 1983, Rapid colorimetric assay for cellular growth and survival : application to proliferation and cytotoxicity assays, J. of Immuno. Met., 65, 5965. Nakano T, Ohno T, Ishikawa H, Suzuki Y, Takashi T. Current advancement in radiation therapy for utarine cervical cancer. J Radial Res 2010;51 (1):1-8. TESIS. 44 AKTIVITAS ANTIKANKER BEBERAPA. ELLYCA S.
(6) 45 IR-PERPUSTAKAAN UNIVERSITAS AIRLANGGA. Nielsen, A. T.; Houlihan, W. J. 2011. The Aldol Condensation. Org. React., 16: 1−438. Prabhakar, V., Balasubramanian, R., Sathe, P., 2014. In Vitro Anticancer Activity of Monosubstituted Chalcone Derivatives 3: 1–9. Romero, Granados J.J., Valderrama-treviño, A.I., Contreras-flores, E.H., Barreramera, B., Enríquez, M.H., 2017. Colorectal cancer : Int J Res Med Sci. 2017 Nov;5(11):4667-4676 Riss, T.L., Moravec, R.A., Niles, A.L., Benink, H.A., Worzella, T.J., Minor, L., 2013, Cell Viability Assay, in Sittampalam GS, Coussens NP, Brimacombe K, et al. (Editor), Assay Guidance Manual, Eli Lilly & Company and the National Center for Advancing Translational Sciences, Bethesda. Sliwka, L., Wiktorska, K., Suchocki, P., Milczarek, M., Mielczarek, S., Lubelska, K., Cierpiał, T., Lyżwa, P., Kiełbasiński, P., Jaromin, A., Flis, A., Chilmonczyk, Z., 2016. The Comparison of MTT and CVS Assays for the Assessment of Anticancer Agent Interactions, PLoS One, 11 (5), 1–17. Suffness, M, Pezzuto, JM, 1990, Assays Related to Cancer Drug Discovery. In Methods in Plant Biochemistry: Assays for Bioactivity; Hostettmann, K, Ed.; Academic Press: London, UK, 6, 71–133. Suwito, H, Jumina, Mustofa, Ni’matuzahroh, Puspaningsih, N.N.T., 2015. Anticancer and antimicrobial activity of methoxy amino chalcone derivatives. Der Pharm. Chem. 7 (3): 89-94 Song, Z.; Kwok, R. T.; Zhao, E.; He, Z.; Hong, Y.; Lam, J. W.; Liu, B.; Tang, B. Z. A ratiometric fluorescent probe based on ESIPT and AIE processes for alkaline phosphatase activity assay and visualization in living cells. ACS Appl. Mater. Interfaces 2014, 6, 17245−17254. Starkey, L. S. 2012. Introduction to Strategies For Organis Synthesis. United States of America: John Wiley And Sons. Inc. Van Meerloo J., Kaspers G.J.L., Cloos J., 2011, Cell Sensitivity Assays: The MTT Assay, In: Cree, I. (Editor), Cancer Cell Culture. Methods in Molecular Biology (Methods and Protocols), volume 731, Humana Press, New York. Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C., Miao, Z., 2017. Chalcone : A Privileged Structure in Medicinal Chemistry. pubs.acs.org.. TESIS. AKTIVITAS ANTIKANKER BEBERAPA. ELLYCA S.
(7) 64 IR-PERPUSTAKAAN UNIVERSITAS AIRLANGGA. MTKC-3. MTKC-4. DOX. TESIS. 3.125 1.5625 100 50 25 12.5 6.25 3.125 1.5625 100 50 25 12.5 6.25 3.125 1.5625 50 25 12.5 6.25 3.125 1.5625 0.78125. 1.2 1.23 0.37 0.38 0.39 0.51 0.54 0.56 0.61 0.36 0.38 0.39 0.41 0.42 0.56 0.61 0.25 0.24 0.26 0.3 0.32 0.31 0.4. 1.24 1.24 0.36 0.38 0.38 0.5 0.55 0.57 0.63 0.37 0.37 0.38 0.39 0.46 0.53 0.61 0.26 0.24 0.26 0.29 0.31 0.4 0.4. 1.1 1.1 0.4 0.4 0.4 0.5 0.6 0.6 0.6 0.4 0.4 0.4 0.4 0.4 0.5 0.6 0.2 0.3 0.3 0.3 0.3 0.4 0.4. 115 120 30.7 31.6 35.5 64.4 72 75.1 88.8 29 33.3 35.2 39.5 42.4 75.1 86.6 40.5 37.1 43.6 51.4 56.5 55.8 76.5. 123 122 28.3 33.3 32.1 61.5 73.9 77.3 91.9 30 30 33.3 34 52.7 68.9 87.3 42.4 36.6 41.7 50.7 54.6 76 77.5. 97.9 102 28.8 33.5 40.5 64.4 78.7 76.1 87.3 28.3 34.5 35.5 33.5 45.3 67.7 93.1 25.1 46.3 48.3 52.6 56.8 76 76. AKTIVITAS ANTIKANKER BEBERAPA... 112.01 ± 12.8 114.69 ± 10.9 29.243 ± 1.26 32.829 ± 1.04 36.016 ± 4.21 63.426 ± 1.66 74.9 ± 3.45 76.175 ± 1.08 89.323 ± 2.32 29.084 ± 0.84 32.59 ± 2.35 34.661 ± 1.18 35.697 ± 3.32 46.773 ± 5.3 70.598 ± 3.98 89.004 ± 3.54 35.998 ± 9.47 39.976 ± 5.49 44.521 ± 3.38 51.583 ± 0.98 55.966 ± 1.2 69.278 ± 11.7 76.664 ± 0.74. ELLYCA S.. 20,7. 11,23. 17,88.
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