SINTESIS SENYAWA TURUNAN 4’-BROMOCALKON DAN UJI AKTIVITAS ANTIKANKER TERHADAP SEL KANKER HTB-183 DAN WiDr
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(2) IR - PERPUSTAKAAN UNIVERSITAS AIRLANGGA. 4.4.1.4 Sintesis senyawa turunan 4’-bromocalkon dari 2,5-dimetoksi benzaldehida .................................................. 4.4.1.5 Sintesis senyawa turunan 4’-bromocalkon dari N,N-dimetil-4-amino benzaldehida ...................................... 4.4.2 Uji kemurnian dan karakterisasi senyawa target .......................... 4.4.3 Uji aktivitas antikanker dengan MTT assay ................................. BAB V HASIL DAN PEMBAHASAN 5.1 Sintesis Senyawa Turunan 4’-Bromocalkon .......................................... 5.2 Karakterisasi Senyawa Produk ............................................................... 5.2.1 Karakterisasi menggunakan FT-IR ............................................... 5.2.2 Karakterisasi menggunakan NMR ................................................ 5.2.3 Penentuan Aktivitas Antikanker Metode MTT Assay .................... 18 18 19 19 21 29 29 31 41. BAB VI KESIMPULAN DAN SARAN 6.1 Kesimpulan ............................................................................................ 46 6.2 Saran ....................................................................................................... 46 DAFTAR PUSTAKA ....................................................................................... 47 LAMPIRAN ...................................................................................................... 52. xi TESIS. SINTESIS SENYAWA TURUNAN .... YUZKIYA A..
(3) IR - PERPUSTAKAAN UNIVERSITAS AIRLANGGA. DAFTAR PUSTAKA Adesanwo, J.K., Shode, F.O., Aiyelaagbe, O., Oyede, R.T. and Baijnath, H., 2009, Isolation and Characterization of a New Chalcone from the Leaves of Heteropyxis natalensis, International Journal of Medicine and Medical Sciences, 1, 28-32. Albert, B., 1994, Molecular Biology of the Cell, 3th ed., New York and London : Garland Publisher. Inc. American Type Culture Collection, 2017, NCI-H661: ATCC HTB-183. Andersen, Ø.M. and Markham, K.R., 2006, Flavonoids: Chemistry, Biochemistry, and Applications, Boca Raton : CRC Press. Anto,. R.S., 2018, Sintesis 4-fluoro-2’-hidroksicalkon dan 4-kloro-2’hidroksicalkon serta uji in silico terhadap protein P53 dan MDM2, Skripsi, Fakultas Sains dan Teknologi, Universitas Airlangga, Surabaya.. Arianingrum, R. and Arty, I.S., 2018, The Effect of Bromo Chalcone [1-(4’bromophenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propene-1-on] on T47D Breast Cancer Cells, in 2nd International Conference on Chemistry, Chemical Process and Engineering (IC3P), AIP Conf. Proc. 2026, 0200711–020071-7. Balasubramanian, R., Iqbal, H., Gopal, R.V., Baby, C., 2013, Synthesis and preliminary evaluation of a focused chalcone library for anti-inflammatory activity, Pharmaceutical Research: Indian Journal of Pharmaceutical Education and Research, 47(4). Breitmaier, E., 2002, Structure Elusidation by NMR in Organic Chemistry, John Wiley & Sons, LTD, England. Cancer Cemoprevention Research Centre (CCRC), 2018, Fakultas Farmasi, Universitas Gadjah Mada, Yogyakarta, Sel Widr. Cooper, G.M., 2000, The Cell: A Molecular Approach (2nd ed.), Sunderland (MA), Sinauer Associates. Chen, T.R., Drabkowski, D., Hay, R.J., Macy, M., Peterson, W.Jr., 1987, WiDr is a Derivative of Another Colon Adenocarcinoma Cell Line, HT-29, Cancer Genet Cytogenet., 27(1):125-34. Doyle, A. and Griffiths, J.B., 2000, Cell and Tissue Culture for Medical Research, New York : John Willey and Sons Ltd.. 47 TESIS. SINTESIS SENYAWA TURUNAN .... YUZKIYA A..
(4) IR - PERPUSTAKAAN UNIVERSITAS AIRLANGGA. 48. Eryanti, Y., Zamri, A., Jasril, R., 2010, Sintesis Turunan 2’-hidroksi Kalkon melalui Kondensasi Claisen-Schmidt dan Uji Aktivitasnya sebagai Antimikroba, Jurnal Natur Indonesia, 12, 223-227. Farida, K., 2010, Kanker Payudara dan Masektomi pada Pengidapnya, Jurnal Pembelajaran, 3, 34-38. Field, L.D., Sternhell, S., Kalman, J.R., 2008, Organic Struture from Spectra, 4th ed., John Wiley & Sons, LTD, England. Fitria, D., 2018, blogspot: devifitria16 , Carbonyl Chemistry. Hwang, T., Leu, Y., Kao, S., Tang, M., Chang, H., 2006, Viscolin a new chalcone from Viscum coloratum, inhibits human neutrophil superoxide anion and elastase release via a cAMP-dependent pathway, Free Rad. Bio. Med., 41, 1433-1441. Kurt, B.Z., Kandas, N.O., Dag, A., Sonmez, F., Kucukislamoglu, M., 2017, Synthesis and biological evaluation of novel coumarine-chalcone derivatives containing urea moiety as potential anticancer agents, Arab. J. of Chem., Article in Press. Kristanti, A.N., Aminah, N.S., Tanjung, M., Kurniadi, B., 2008, Buku Ajar Fitokimia, Airlangga University Press, Surabaya. Lahtchev, K.L., Batovska, D.I., Parushev, S.P., Ubiyvovk, V.M., Sibirny, A.A., 2008, Antifungal activity of chalcones: a mechanistic study using various yeast strains, Eur. J. Med. Chem., 43, 2220-2228. Larsen, M., Kromann, H., Kharazmi, A., Nielsen, S.F., 2005, Conformationally restricted anti-plasmodial chalcones, Bioorg. Med. Chem. Lett., 15, 48584861. Liaras, K., Geronikaki, A., Glamoclija, J., Ciric, A., Sokovic, M., 2011, Thiazolebased chalcones as potent antimicrobial agents. synthesis and biological evaluation, Bioorg. Med. Chem., 19, 3135-3140. Lipinski, C., Lombardo, F., Domony, B.W., Feeney, P.J., 1997, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Del. Rev., 23, 3-25. Mahapatra, D.M., Bharti, S.K., Asati, V., 2015, Anti-cancer chalcones: structural and molecular target perspectives, Eur. J. Med. Chem., 98, 69-114. Mai, C.W., Yaeghoobi, M., Abd-Rahman, N., Kang, Y.B., Pichika, M.R., 2014, Chalcones with electron-withdrawing and electron-donating substituents:. TESIS. SINTESIS SENYAWA TURUNAN .... YUZKIYA A..
(5) IR - PERPUSTAKAAN UNIVERSITAS AIRLANGGA. 49. anticancer activity against TRAIL resistant cancer cells, structure-activity relationship analysis and regulation of apoptotic proteins, Eur. J. Med. Chem., 77, 378-387. Meiyanto, M., Kudo, G., Lee, Y., Yang, T.J., Gelboin, H.V., Gonzalez, F.J., 1999, Targeted disruption of the microsomal epoxide hydrolase gene, The Journal of Biological Chemistry, 274, 23963-23968. Miller, A., Solomon, P.H., 1999, Writing Reaction Mechanism in Organic Chemistry, 2nd ed., Elsevier Science & Technology Books, Oxford. Mobinikhaledi, A., Kalhor, M., Jamalifar, H., 2012, Synthesis, characterization and antimicrobial activities of some novel bischalcones, Med. Chem. Res., 21, 1811-1816. Mosmann, T., 1983, Rapid colorimetric assay for cellular growth and survival : application to proliferation and cytotoxicity assays, J. of Immuno. Met., 65, 59-65. Muti’ah, R., 2014, Pengembangan Fitofarmaka Antikanker, Malang : UIN Maliki Press, 22-24. Okwu, D.W., and Ukanwa, N., 2010, Isolation and Characterization of Flavanoids Chalcones and Anthocynidines from Bridelia ferruginea benth, Pelagia. Res. Lib., 1(2), 21-28. Oldoni, T.L.C., Cabral, I.S.R., d’Arce, M.A.B.R., Rosalen, P.I., Ikegaki, M., Nascimento, A.M., Alencar, S.M., 2011, Isolation and analysis of bioactive isoflavonoid and chalcone from a new type of Brazilian propolis, Separation and Purification Technology, 27, 208-213. Parkway Cancer Center Indonesia, 2018, Kanker kolorektal: Mencegah dan Mengobati, Informasi Kanker. Parkway Cancer Center Indonesia, 2018, Kanker paru-paru: Mencegah dan Mengobati, Informasi Kanker. Patrick, G.L., 2000, Organic Chemistry, BIOS Scientific Publishers Limited. Pavia, D.L., Lampman, G.M., Kriz, G.S., Vyvyan, J.R., 2009, Introduction to Spectroscopy, Fourth Edition, Brooks/Cole, Cengage Learning, BelmontCalifornia, USA. Pinalia, A., 2011, kristalisasi amonium perklorat (AP) dengan sistem pendiginan terkontrol untuk menghasilkan Kristal berbentuk bulat, Majalah Teknologi Dirgantara, 9(2).. TESIS. SINTESIS SENYAWA TURUNAN .... YUZKIYA A..
(6) IR - PERPUSTAKAAN UNIVERSITAS AIRLANGGA. 50. Pingaew, R., Saekee, A., Mandi, P., Nantasenamat, C., Prachayasittikul, S., Ruchirawat, S., Prachayasittikul, V., 2014, Synthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents, Eur. J. Med. Chem., 85, 65-76. Pusat data dan informasi Kementerian Kesehatan RI, 2016, Situasi Penyakit Kanker, Infodatin. Prasad, R.Y., Rao, A.S., Rambabu, 2009, Synthesis of Some 4’-Amino Chalcones and their Antiinflammatory and Antimicrobial Activity, Asian J. of Chem., 21 92) 907-914. Rahman, A.U., Choudhary, M.I., Thomsen, W.J., 2001, Bioassay Techniques for Drug Development, Amsterdam, The Netherlands : Harwood Academic Publishers, 30-31. Rohman, A., dan Gandjar, I.G., 2007, Kimia Farmasi Analisis, Pustaka Pelajar, Yogyakarta. Ruddon, R.W., 2007, Cancer Biology Fourth Eddition, London : Oxford University Press. Solomons, T.W.G & Fryhle, C.B. (2011). Organic Chemistry. (edisi kesepuluh). Amerika Serikat : John Wiley and Sons Inc. Suffness, M, Pezzuto, J.M, 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., 2014, Sintesis senyawa turunan calkon sebagai senyawa antimalaria, antikanker dan antimikroba, Disertasi, Fakultas Matematika dan Ilmu Pengetahuan Alam, Universitas Gadjah Mada, Yogyakarta. 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. 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. Starkey, L.S., 2012, Introduction to Strategies for Organic Synthesis, John Wiley and Sons. INC, Unites State of America.. TESIS. SINTESIS SENYAWA TURUNAN .... YUZKIYA A..
(7) IR - PERPUSTAKAAN UNIVERSITAS AIRLANGGA. 51. Sloane, D., 2009, Cancer epidemiology in the united states : racial, social, and economic factors, Methods Mol. Bio., 471, 65-83. Thanigaimani, K., Arshad, S., Khalib, N.C., Razak, I.A., 2015, A New Chalcone Structure of (E)-1-(4-Bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one: Synthesis, Structural Characterizations, Quantum Chemical Investigations and Biological Evaluations, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 149, 90-102. Wade, L.G., 2006, Organic Chemistry, 6th ed., Pearson Education International, New Jersey. Wu, J.H., Wang, X.H., Yi, Y.H., Lee, K.H., 2003, Anti-AIDS Agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos, Bioorg. Med. Chem. Lett., 13, 1813-1815. Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C., Miao, Z., 2017, Chalcone: A Privileged Structure in Medicinal Chemistry, Chem. Rev... TESIS. SINTESIS SENYAWA TURUNAN .... YUZKIYA A..
(8) IR - PERPUSTAKAAN UNIVERSITAS AIRLANGGA. MTBC-2. MTBC-3. sp-MTBC-3. 100 50 25 12.5 6.25 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. 0.392 0.415 0.421 0.462 0.518 0.553 0.598 0.624 0.636 0.662 0.695 0.707 0.787 0.895 0.954 1.047 1.071 1.091 1.131 1.131 1.133. 0.399 0.415 0.425 0.487 0.548 0.593 0.616 0.607 0.614 0.605 0.691 0.73 0.79 0.874 1.031 1.078 1.08 1.169 1.179 1.179 1.213. 0.401 0.431 0.428 0.498 0.585 0.603 0.624 0.615 0.632 0.639 0.683 0.661 0.828 0.943 1.046 1.055 1.178 1.099 1.189 1.189 1.201. 64.881 69.877 71.180 80.087 92.252 99.855 109.631 1.762 4.112 9.204 15.666 18.016 33.681 54.830 66.384 84.595 89.295 93.211 101.044 101.044 101.436. 66.401 69.877 72.049 85.518 98.769 108.545 113.541 -1.567 -0.196 -1.958 14.883 22.520 34.269 50.718 81.462 90.666 91.057 108.486 110.444 110.444 117.102. 66.836 73.353 72.701 87.907 106.807 110.717 115.279 0.000 3.329 4.700 13.316 9.008 41.710 64.230 84.399 86.162 110.248 94.778 112.402 112.402 114.752. 66.039 ± 0.005 71.035 ± 0.009 71.977 ± 0.004 84.504 ± 0.018 99.276 ± 0.034 106.372 ± 0.026 112.817 ± 0.013 0.065 ± 0.009 2.415 ± 0.012 3.982 ± 0.029 14.621 ± 0.006 16.514 ± 0.035 36.554 ± 0.023 56.593 ± 0.035 77.415 ± 0.049 87.141 ± 0.016 96.867 ± 0.059 98.825 ± 0.043 107.963 ± 0.031 107.963 ± 0.031 111.097 ± 0.043. > 100. 1,87. > 100. 72 TESIS. SINTESIS SENYAWA TURUNAN .... YUZKIYA A..
(9) IR - PERPUSTAKAAN UNIVERSITAS AIRLANGGA. MTBC-4. MTBC-01. 100 50 25 12.5 6.25 3.125 1.5625 100 50 25 12.5 6.25 3.125 1.5625. 0.291 0.331 0.436 0.447 0.463 0.458 0.461 0.526 0.534 0.533 0.539 0.566 0.666 0.795. 0.283 0.34 0.474 0.445 0.438 0.448 0.469 0.503 0.512 0.522 0.558 0.553 0.66 0.887. 0.293 0.339 0.413 0.455 0.483 0.484 0.466 0.496 0.506 0.508 0.541 0.558 0.654 0.865. 50.203 59.943 85.511 88.190 92.086 90.869 91.599 93.990 95.728 95.510 96.814 102.679 124.403 152.426. 48.255 50.690 62.135 61.891 94.765 79.911 87.703 90.138 85.998 96.956 88.433 97.200 93.547 92.817 88.993 87.473 90.949 89.645 93.121 90.080 100.941 97.248 99.855 100.941 123.099 121.796 172.411 167.632. 49.716 ± 0.005 61.323 ± 0.005 86.729 ± 0.031 88.677 ± 0.005 91.680 ± 0.023 92.167 ± 0.019 92.654 ± 0.004 90.152 ± 0.016 92.107 ± 0.015 92.904 ± 0.013 98.335 ± 0.010 101.159 ± 0.007 123.099 ± 0.006 164.156 ± 0.048. > 100. > 100. 73 TESIS. SINTESIS SENYAWA TURUNAN .... YUZKIYA A..
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