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All Journal Journal of Food and Pharmaceutical Science Pharmaciana: Jurnal Kefarmasian Indonesian Journal of Mathematics and Natural Sciences Teknosains: Media Informasi Sains dan Teknologi Alchemy Jurnal Penelitian Kimia Indonesian Journal of Chemistry Journal of Multidisciplinary Applied Natural Science Makara Journal of Science Molekul: Jurnal Ilmiah Kimia Journal of Food and Pharmaceutical Sciences Indonesian Journal of Pharmacology and Therapy
Jumina Jumina
Department of Chemistry, Faculty of Mathematics and Natural Sciences Universitas Gadjah Mada Yogyakarta
Agriculture, Biological Sciences & Forestry Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Civil Engineering, Building, Construction & Architecture Computer Science & IT Control & Systems Engineering Energy Environmental Science Immunology & microbiology Materials Science & Nanotechnology Mathematics Medicine & Pharmacology Neuroscience Physics

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Journal : Makara Journal of Science

 1 
Synthesis of 1-(4-Ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium Bromide and Its Evaluation as Antiplasmodium through Heme Polymerization Inhibitory Activity (HPIA) Assay Fitriastuti, Dhina; Alfiyah, Viny; Mustofa, Mustofa; Jumina, Jumina; Mardjan, Muhammad Idham Darussalam
Makara Journal of Science Vol. 25, No. 1
Publisher : UI Scholars Hub

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This study describes the development of N-benzyl-1,10-phenantrolinium salt as an antiplasmodium agent. The salt, that is, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide, was prepared using vanillin as the starting material in four simple synthetic steps. First, the alkylation of vanillin using diethyl sulfate produced 4-ethoxy-3-methoxybenzaldehyde in 79% yield. Second, the reduction of the protected vanillin by NaBH4 through the grinding method allowed us to obtain 4-ethoxy-3-methoxybenzyl alcohol in 96% yield. Next, the bromination of the benzyl alcohol under solvent-free condition led to the formation of the corresponding benzyl bromide, which in turn underwent bimolecular nucleophilic substitution with 1,10-phenanthroline to produce the desired product, that is, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide, in 58% yield. The evaluation of N-benzyl-1,10-phenantrolinium salt as an antiplasmodium agent was conducted through heme polymerization inhibitory activity (HPIA) assay. The results showed that the phenantroline salt and chloroquine displayed the HPIA half maximal inhibitory concentrations of 3.63 and 4.37 mM, respectively. Therefore, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide displays desirable HPIA and has a great potential to be further developed as an antiplasmodium.
Synthesis, Biological Activity, and Molecular Docking Study of Xanthenol and Its Disproportionation Products as Anticancer and Antimalarial Agents Pratama, Ardhya Ayu; Jumina, Jumina; Anwar, Chairil
Makara Journal of Science Vol. 28, No. 2
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Xanthone and its derivatives are well known for their broad biological activities. This research aims to investigate the anticancer and antimalarial activities of synthesized xanthenol and xanthene compounds and to elucidate their mechanisms of action through molecular docking. The xanthenol compound was obtained through xanthone reduction with sodium triacetoxyborohydride, and xanthene synthesis was studied through three different reaction conditions: uncatalyzed and catalyzed by Lewis acid or Bronsted acid. The reduction reaction produced xanthenol in 30.50% yield, whereas the three reaction conditions produced xanthene and xanthone in 39.35–75.48% yield. An anticancer assay for Vero, WiDr, HeLa, and T47D cell lines was evaluated with a microculture tetrazolium assay, and an antimalarial activity test was examined using the heme polymerization inhibition method. The xanthene compound showed the lowest IC50 value (44 µg/mL) among the products in the T47D cell line. Meanwhile, the antimalarial assay showed that the xanthone compound could inhibit heme polymerization, with an IC50 value of 114 µg/mL. The molecular docking study revealed that the anticancer activity of xanthene occurred through the inhibition of the cyclooxygenase-2 (COX-2) enzyme, and the antimalarial activity of xanthone occurred through the inhibition of the Plasmodium falciparum lactate dehydrogenase enzyme. These results showed that xanthene and xanthone compounds are potential anticancer and antimalarial drugs, respectively.
Design and In Silico Modeling of Heterocyclic-based Xanthone Derivatives as Potential Anticancer Agents Through Tyrosine Kinase Inhibition Kurniawan, Yehezkiel Steven; Yudha, Ervan; Fatmasari, Nela; Yogaswara, Radite; Pranowo, Harno Dwi; Sholikhah, Eti Nurwening; Jumina, Jumina
Makara Journal of Science Vol. 30, No. 1
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Cancer is one of the deadliest diseases nowadays, and tyrosine kinase receptors play crucial roles in cancer cell survival, differentiation, proliferation, and migration. This study designed and developed a new inhibitor from heterocyclic-based xanthone derivatives to target two tyrosine kinase receptors, epidermal growth factor receptor (EGFR) and platelet-derived growth factor receptor (PDGFR), through in silico screening. Eighteen heterocyclic-based xanthones were evaluated through molecular docking for both receptors. All heterocyclic-based xanthones gave the root mean square deviation (RMSD) value lower than 2.00 Å. Xanthone with isobenzothiazole substituent (iBzThio) was found as the most potent inhibitor with binding energies of -10.60 and -12.90 kcal/mol against EGFR and PDGFR, respectively. Further investigation has been performed through molecular dynamics (MD) simulation for 100 ns. From the results of MD simulations, i.e., RMSD, root mean square fluctuation, radius of gyration, solvent accessible surface area, hydrogen bonds, and binding energy parameters, as well as secondary structure fraction, dictionary of protein secondary structure, and Ramachandran plot, iBzThio demonstrated good stability to interact with the active site of both receptors. The binding energies of IBzThio against EGFR and PDGFR receptors were -12.58 and -12.61 kcal/mol after the MD simulations, indicating its potential application as an effective tyrosine kinase inhibitor.
Co-Authors Abdul Karim Zulkarnain ADITYA NUGRAHA Agus Dwi Ananto, Agus Alfiyah, Viny Anggraeni, Putri Dian Anita Dwi Puspitasari Chairil Anwar Desi Suci Handayani Dhina Fitriastuti Dwi Aris Agung Nugrahaningsih Dwi Siswanta Eti Nurwening Sholikhah Faris Hermawan, Faris Fatimi, Hana Anisa Fatmasari, Nela Fitria, Anggit Harizal Harizal Harno Dwi Pranowo Hidetaka Kawakita Iin Narwanti Ikhsan Nur Salim Jeffry Julianus Kasta Gurning Keisuke Ohto Kurniawan, Yehezkiel Steven Laela Hayu Nurani Lathifah Puji Hastuti Marlina, Lala Adetia Maulidan Firdaus Maywan Hariono Mia Munawaroh Yuniyanti Muhammad Idham Darussalam Mardjan Muhammad Yusron Maulana El-Yunusi Mustofa . Mustofa Mustofa Nico Frederick Nisa, Siti Astika Nursofia, Baiq Ike Phebe Hendra Pratama, Ardhya Ayu Priastomo, Yoga Priyangga, Krisfian Tata Aneka Putra, Nicky Rahmana RATNA SARI Reinner Ishaq Lerrick Rul Afiyah Syarif S Matsjeh S Mursiti Sabirin Matsjeh Satrio Ardyantoro Sri Juari Santosa Susy Yunita Prabawati Triana Kusumaningsih Wahyu Widyaningsih Wibowo, Susalit Setya Yogaswara, Radite Yudha, Ervan