BAB IV. PEMBAHASAN
B. Saran
1. Perlu dilakukan rekristalisasi kembali dengan metanol dan uji KLT double spotting untuk memeriksa kemurnian senyawa hasil sintesis baik sebelum dan setelah rekristalisasi.
2. Perlu dilakukan pemanasan dengan refluks untuk meningkatkan jumlah rendemen yang dihasilkan.
3. Perlu dilakukan uji aktivitas senyawa 4-[(4ˈ-hidroksi-3ˈ -metoksibenzilidena)-amino]-benzensulfonamida sebagai agen antimitosis untuk terapi penyakit kanker secara in vitro.
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DAFTAR PUSTAKA
Ahluwalia, V.K., and Dhingra, S., 2004, Comprehensive Practical Organic Chemistry, Universities Press, UK, pp. 12.
Alberts, B., 2008, Molecular of the Cell, 5th Edition, Garland Science, USA, pp. 965-1111.
American Cancer Society, 2014, Cancer Facts & Figures 2014, American Cancer Society, UK.
Bolsover, S.R., Hyams, J.S., Shephard, E.A., White, H.A., Wiedemann, C.G., 2004, Biology Cell, 2nd Edition, John Willey & Sons, New Jersey, pp. 385. Brown, W.H., Foote, C.S., Iverson, B.L., Anslyn, E.V., 2012, Organic Chemistry,
6th Edition, Brooks/Cole, Belmont, pp. 956.
Bruice, P.Y., 2004, Organic Chemistry: Study Guide and Solution Manual, 4th Edition, Pearson Prentice Hall, USA, pp. 282-285.
Burns, R.G., 1991, -, -, and -Tubulin: Sequence Comparisons and Structural Constraints, Cell Motility and the Cytoskeleton, (20), 181-189.
Campbell, A., Reece, J.B., Mitchell, L.G., 1999, Biologi, Edisi 5, diterjemahkan oleh Rahayu Lestari, Ellyzar I.M. Adil, dan Nova Anita, Erlangga, Jakarta Pusat, hal. 130.
Chan, K.S., Koh, C.G., Li, H.Y., 2012, Mitosis-targed Anti-cancer Therapies: Where They Stand, Cell Death and Disease, (411), 1-11.
Chang, R., 2003, Kimia Dasar: Konsep – Konsep Inti, diterjemahkan oleh Suminar Setiadi Achmadi, Erlangga, Jakarta, hal. 54.
Chohan, Z.H., 2008, Metal-based Sulfonamides: Their Preparation, Characterization and in-vitro Antibacterial, Antifungal & Cytotoxic Properties. X-ray Structure of 4-[(2-hydroxybenzylidene) amino] benzenesulfonamide, Journal of Enzyme Inhibitor and Medicinal Chemistry, (23), 120-130.
Conde, C., and Cáceres, A., 2009, Microtubule assembly, organization and Dynamics in Axons and Dendrites, Neuroscience, (10), 319-332.
Desai, A., and Mitchison, T.J., 1997, Microtubule Polymerization Dynamics,
Annual Review of Cell and Developmental Biology, (13), 83-117.
Dirjen POM RI, 1979, Farmakope Indonesia, Edisi III, Departemen Kesehatan Republik Indonesia, Jakarta, hal. 587.
Dirjen POM RI, 1995, Farmakope Indonesia, Edisi IV, Departemen Kesehatan Republik Indonesia, Jakarta, hal. 48, 52, 1012-1013.
Downard, K., 2004, Mass Spectrometry: A Foundarion Course, Royal Society of Chemistry, UK, pp. 12.
Fessenden, R.J., dan Fessenden, J.S., 1986a, Kimia Organik, Jilid 1, Edisi III, diterjemahkan oleh Aloysius Hadyana Pudjaatmaka, Erlangga, Jakarta, hal. 11-12, 15.
Fessenden, R.J., dan Fessenden, J.S., 1986b, Kimia Organik, Jilid 2, Edisi III, diterjemahkan oleh Aloysius Hadyana Pudjaatmaka, Erlangga, Jakarta. Fieser, L.F., and Williamson, K.L., 1992, Organic Experiments, 7th Edition, D.C.
Health and Company, USA, pp. 27-43.
Geis-Asteggiante, L., Nuñez, A., Lehotay, S.J., Lightfield, A.R., 2014, Structural Characterization of Product Ions by Electrospray Ionization and Quadrupole Time-of-Flight Mass Spectrometry to Support Regulatory Analysis of Veterinary Drug Residues in Foods, Rapid Communications in Mass Spectrometry, (28), 1-21.
Gross, J.H., 2011, Mass Spectrometry, 2nd second, Springer, New York, pp. 9-11. Ilango, K., and Arunkumar, S., 2011, Synthesis, Antimicrobial and Antitubercular
Activities of Some Novel Trihydroxy Benzamido Azetidin-2-one Derivates, Tropical Journal of Pharmaceutical Research, (2), 219-229. Jordan, M.A., 2002, Mechanism of Action Antitumor Drugs that Interact with
Microtubules and Tubulin, Current Medical Chemistry Anticancer Agents, (2), 1-17.
Kalsi, P.S., 2004, Spectroscopy of Organic Compounds, 6th Edition, New Age International, New Delhi, pp. 66, 67.
Karp, G., 2009, Cell and Molecular Biology: Concepts and Experiments, 6th Edition, John Willey & Sons, pp. 650.
Kumar, K.S., Ganguly, S., Veerasamy, R., Clercq, E.D., 2010, Synthesis, Antiviral Activity and Cytotoxicity Evaluation of Schiff Bases of Some 2-phenyl quinazoline-4(3)H-ones, European Journal of Medicinal Chemistry, (45), 5474-5479.
Kumar, S., Niranjan, M.S., Chaluvaraju, K.C., Jamakhandi, C.M., Kadadevar, D., 2010, Synthesis and Antimicrobial Study of Some Schiff Bases of Sulfonamides, Journal of Current Pharmaceutical Research, (1), 39-42. Lemke, T.L., Williams, D.A., Rochie, V.F., and Zito, S.W., 2008, Foye’s
Principles of Medicinal Chemistry, 6th Edition, Lippincott Williams & Wilkins, USA, p. 1036.
Li, Y., Yang, Z.S., Zhang, H., Cao, B.J., Wang, F.D., 2003, Artemisinin Derivatives Bearing Mannich Base Group: Synthesis and Antimalarial Activity. Bioorganic and Medicinal Chemistry, (11), 4363-4368.
Lodish, H., Berk, A., Matsudaira, P., Kaiser, C.A., Krieger, M., Scott, M.P., Zipursky, L., Darnell, J., 2004, Molecular Cell Biology, 5th Edition, WHFreeman, pp. 819.
MacKenzie, 1967, Experimental Organic Chemistry, 3rd Edition, Prentice-Hall, Inc., Englewood Cliffs, New Jersey.
McIntosh, J.R., Grishchuk, E.L., West, R.R., 2002, Chromosome-Microtubule Interactions During Mitosis, Annual Review of Cell and Developmental Biology, (18), 193-219.
McMurry, J., 2011, Organic Chemistry with Biological Applications 2e, Brooks/Cole, USA. pp. 579.
Mehta, B., and Mehta, M., 2005, Organic Chemistry, New Delhi Prentice Hall of India, India, pp. 550.
Mohamed, S.S., Tamer, A.R., Bensaber, S.M., Jaeda, M.I., Ermeli, N.B., Allafi, A.A., Mrema, I.A., Erhuma, M., Hermann, A., Gbaj, A.M., 2013, Design, Synthsis, Molecular Modeling, and Biological Evaluation of Sulfonamide-imines Derivatives as Potential Anticancer Agents,
Naunyn-Schmiedeberg’s Archives of Pharmacology, (386), 813-822.
Oxtoby, D.W., Gilis, H.P., Nachtrieb, N.H., 2001, Prinsip-Prinsip Kimia Modern, diterjemahkan oleh Achmadi, S.S., Jilid 1, Edisi 4, Erlangga, Jakarta, hal. 344.
Patrick, G., 2004, Organic Chemistry, 2nd Edition, BIOS Scientific Publishers, London, pp. 184-185.
Pavia, D.L., Lampman, G.M, Kriz, G.S., and Engel, R.G, 2011, A Small Scale Approach to Organic Laboratory Technique, 3th Edition, Brooks/Cole, USA, pp. 453.
Pavia, D.L., Lampman, G.M, Kriz, G.S., and Vyvyan, J.R., 2009, Introduction Spectroscopy, 4th Edition, Brooks/Cole, Belmont, pp.105.
Pavia, D.L., Lampman, G.M., Kriz, G.S., 2001, Introduction to Spectroscopy, 3rd Edition, Thomson Brooks/Cole, UK.
Priya, G.R.M., Panneerselvan, P., Karikalan, M., 2011, Synthesis, Characterization and Antibacterial, Antifungal Activities of Schiff Bases of 4-(2-aminphenyl)Morpholines, International Journal of Pharma and Bio Sciences, (2), 267-272.
Reger, D.L, Goode, S.R., Ball, D.W., 2010, Chemistry: Principle and Practice, 3rd Edition, Brooks/Cole, USA, pp. 475.
Sarker, S.D., and Nahar, L., 2007, Chemistry for Pharmacy Students, John Wiley & Sons, UK.
Sastohamidjojo, H., 2001, Spektroskopi, edisi kedua, Liberty, Yogyakarta, hal. 176-181.
Silverstein, R.M., Webster, F.X., Kiemle, D.J., 2005, Spectrometric Indentification of Organic Compounds, 7th Edition, John Willey & Sons, USA, pp. 13-35.
Sitorus, M., 2009, Spektroskopi Elusidasi Struktur Molekul Organik, Graha Ilmu, Yogyakarta, hal. 56, 69.
Smart, L., 2002, Separation, Purification and Identification, Royal Society of Chemistry, United Kingdom, pp. 50.
Solomons, T.W.G., and Fryhle, C.B., 2011, Organic Chemistry, 10th Edition, John Willey & Sons, New Jersey.
Stuart, B.H., 2004, Infrared Spectroscopy: Fundamentals and Applications, Wiley, UK.
Sumardi dan Marianti, M., 2007, Biologi Sel, Graha Ilmu, Yogyakarta, hal.161-176, 187-202.
Supuran, C.T., Nicolae, A., Popescu, A., 1996, Synthesis of Schiff bases derived from sulfanilamide and aromatic aldehydes: the first inhibitors with equally high affinity towards cytocolic and membrane-bound isozymes,
Europe Journal Medicine Chemistry, (31), 431-438.
Uppuluri, S., Knipling, L., Sackett, D.L., Wolff, J., 1993, Localization of the colchicine-binding site of tubulin, Proceedings of the National Academy of Sciences of the United States of America, (24), 11598-11602.
Villar, R., Encio, I., Migliaccio, M., Gil, M.G., Martinez-Merino, V., 2004, Synthesis and cytotoxic activity of lipophilic sulphanamide derivatives of the benzo[b] thiophene 1,1-dioxode, Bioorganic and Medicinal Chemistry, (12), 963-968.
Wade, L.G., 2013, Organic Chemistry, 8th Edition, Pearson Education, USA, pp. 437, 563-596.
WHO, 2013, Cancer, http://www.who.int/mediacentre/factsheets/fs297/en/index. html diakses tanggal 31 Oktober 2013.
Zhou, J., and Giannakakou, P., 2005, Targeting Microtubules for Cancer Chemotherapy, Current medical Chemistry, (5), 65-71.
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LAMPIRAN
Lampiran 1. Data penimbangan starting material dan perhitungan rendemen teoretis
Replikasi I
Sulfanilamida Vanilin
Berat wadah (g) 0,425 0,413
Berat wadah + zat (g) 0,944 0,567
Berat wadah + sisa (g) 0,427 0,414
Berat zat (g) 0,517 0,153 Jumlah (mmol) 3,002 1,003 Persamaan reaksi Mula-mula = 3,002 1,003 - Reaksi = 1,003 1,003 1,003 Sisa = 1,999 - 1,003
Massa rendemen yang diperoleh = nBM
= 1,003 mmol x 306 mg/mmol = 306,918 mg
Replikasi II
Sulfanilamida Vanilin
Berat wadah (g) 0,420 0,417
Berat wadah + zat (g) 0,938 0,571
Berat wadah + sisa (g) 0,422 0,419
Berat zat (g) 0,516 0,152 Jumlah (mmol) 2,996 0,997 Persamaan reaksi Mula-mula = 2,996 0,997 - Reaksi = 0,997 0,997 0,997 Sisa = 1,999 - 0,997
Massa rendemen yang diperoleh = nBM
= 0,997 mmol x 306 mg/mmol = 305,082 mg
Replikasi IIIz
Sulfanilamida Vanilin
Berat wadah (g) 0,248 0,262
Berat wadah + zat (g) 0,766 0,416
Berat wadah + sisa (g) 0,248 0,263
Berat zat (g) 0,518 0,153 Jumlah (mmol) 3,008 1,003 Persamaan reaksi Mula-mula = 3,008 1,003 - Reaksi = 1,003 1,003 1,003 Sisa = 1,005 - 1,003
Massa rendemen yang diperoleh = nBM
= 1,003 mmol x 306 mg/mmol = 306,918 mg
Lampiran 2. Data penimbangan dan perhitungan rendemen crude product
yang didapat
Replikasi I Replikasi II Replikasi III
Berat wadah (g) 0,512 0,544 0,495
Berat wadah + zat (g) 0,576 0,604 0,558
Berat zat (g) 0,064 0,060 0,063 Replikasi I Replikasi II Replikasi III
Massa zat yang dihasilkan (g) 0,064 0,060 0,063
Massa teoritis (g) 0,307 0,305 0,307
% rendemen (b/b) 20,85% 19,67% 20,52%
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BIOGRAFI PENULIS
Penulis lahir di Jakarta pada tanggal 5 September 1993. Penulis memiliki seorang ayah bernama Happy Setya dan seorang ibu bernama Dwi Lukito Siwi, serta seorang kakak dan seorang adik bernama Andika Purwa Setya dan Mia Permata Sari. Tahun 1998, penulis menyelesaikan pendidikan pertama di TK Sahati Jakarta Pusat. Setelah itu, penulis melanjutkan pendidikan di SD Negeri 1 Tambahrejo Kendal pada tahun 1998 sampai dengan 2004, SMP Negeri 1 Sukorejo Kendal pada tahun 2004 hingga 2007, SMA Negeri 1 Sukorejo Kendal pada tahun 2007 hingga 2010. Lulus jenjang SMA, penulis melanjutkan pendidikan di Fakultas Farmasi Sanata Dharma Yogyakarta sampai tahun 2014.
Selama menjadi mahasiswa, penulis terlibat dalam beberapa kegiatan kemahasiswaan dan keorganisasian antara lain, Ekaristi Kaum Muda (EKM), panitia paskah 2010 di tingkat universitas, dan keanggotaan serta kepengurusan UKM Komunitas Jalinan Kasih Mahasiswa Katolik (JKMK) periode 2011-2012. Di samping itu, penulis memiliki pengalaman kerja sebagai asisten dosen praktikum Kimia Organik pada tahun 2011 dan Kimia Analisis pada tahun 2012. Penulis juga berpartisipasi dalam beberapa perlombaan di bidang akademik. Penulis menjadi peserta lomba Olimpiade Farmasi Indonesia V tahun 2013, juara III ON-MIPA 2013 dan juara I ON-MIPA 2014 bidang kimia tingkat Wilayah V Daerah Istimewa Yogyakarta.
