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SYNTHESIS AND ANTIPLASMODIAL ACTIVITY TESTING OF (1)-N-ALKYL- AND (1)-N-BENZYL-6-NITRO-1,10-PHENANTHROLINIUM SALTS AS NEW POTENTIAL ANTIMALARIAL AGENTS Ruslin Hadanu; Sabirin Mastjeh; Jumina Jumina; Mustofa Mustofa; Eti Nurwening Sholikhah; Mahardika Agus Wijayanti
Indonesian Journal of Chemistry Vol 12, No 2 (2012)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (799.561 KB) | DOI: 10.22146/ijc.21356

Abstract

The synthesis of 5-nitro-1,10-phenanthroline hydrate 2 derivatives from 1,10-phenanthroline monohydrate as starting material has been carried out. The 5-nitro-1,10-phenanthroline hydrate 2 was obtained through nitration reaction using H2SO4 and HNO3 as catalyst and reagent, respectively. Synthesis of (1)-N-alkyl-6-nitro- and (1)-N-benzyl-6-nitro-1,10-phenanthrolinium have been prepared using dimethyl sulphate (DMS), diethyl sulphate (DES), benzyl chloride, benzyl bromine, and benzyl iodide. The reagents of benzyl bromine, and benzyl iodide were synthesized from benzyl chloride using NaBr in ethanol absolute and NaI in acetone, respectively. The five compounds of 5-nitro-1,10-phenanthroline hydrate 2 derivatives were conducted to evaluate the in vitro antiplasmodial activity. The in vitro antiplasmodial was evaluated on strains of Plasmodium falciparum FCR-3 resistant chloroquine and D10 sensitive chloroquine. The 50% inhibition concentration (IC50) of the five compounds ranged from 2.41±1.41 to 0.07±0.01 μM. The results showed that the (1)-N-benzyl-6-nitro-1,10-phenanthrolinium iodide had highest antiplasmodial activity.
SYNTHESIS 7-HYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL Andi Hairil Alimuddin; Muhammad Idham Darussalam Mardjan; Sabirin Matsjeh; Chairil Anwar; Mustofa Mustofa; Eti Nurwening Sholikhah
Indonesian Journal of Chemistry Vol 11, No 2 (2011)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (233.66 KB) | DOI: 10.22146/ijc.21404

Abstract

Eugenol from the isolation of clove leaves oil had been utilized in the synthesis of 7-hydroxy-3',4'-dimethoxy-isoflavone based on deoxybenzoin intermediate. The raw material was firstly converted into methyleugenol using DMS (89.87%). Secondly, methyl eugenol was oxidized using KMnO4 to produce 3,4-dimethoxybenzyl carboxylic acid (21%). Friedel-Craft acylation of it with recorcinol produced 3,4-dimethoxybenzyl-2',4'-dihydroxyphenyl ketone (deoxybenzoin intermediate) in 78% yield. Eventually, cyclization of the intermediate with reagents of BF3.OEt2/DMF/POCl3 yielded 7-hydroxy-3',4'-isoflavone in 85% yield.
SYNTHESIS AND ANTIPLASMODIAL ACTIVITY TESTING OF (1)-N-(4-METHOXYBENZYL)-1,10-PHENANTHROLINIUM BROMIDE Ruslin Hadanu; Sabirin Mastjeh; Jumina Jumina; Mustofa Mustofa; Mahardika Agus Widjayanti; Eti Nurwening Sholikhah
Indonesian Journal of Chemistry Vol 7, No 2 (2007)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (118.7 KB) | DOI: 10.22146/ijc.21698

Abstract

Synthesis of (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide from 1,10-phenanthroline monohydrate and 4-methoxybenzaldehyde as starting material and evaluation of its antiplasmodial activities have been carried out. The 4-methoxybenzyl alcohol was prepared from 4-methoxy-benzaldehyde using sodium borohydride (NaBH4) reagent and ethanol absolute solution. The mixture was refluxed for 3 h. To yield colorless dilution compound with 90.41 % in efficiency. Furthermore, bromination of 4-methoxybenzyl alcohol with phosphorus bromide (PBr3) was conducted by refluxing for 3 h. The product of this reaction was yellow liquid of 4-methoxybenzyl bromide, 79.03% yield and 95.34 % purity. The final step of reaction was benzylation of 1,10-phenanthroline monohydrate with 4-methoxybenzyl bromide reagent. It was conducted by refluxing in aceton for 8 h at 55 oC. The yield of the reaction was (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide (77.63%). It is pink solid form, and its melting point is 192-193 oC. Identification of the product was carried out by means of GC-MS, IR and 1H-NMR spectrometers. The in vitro antiplasmodial activity on chloroquine-resistant Plasmodium falciparum FCR-3 strain and chloroquine sensitive P. falciparum D10 strain for (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide were determined by microscopic method. The result showed that after 72 h incubation, it has IC50 0.93±0.02 µM and 1.21±0.09 µM, respectively.
QUANTITAVE STRUCTURE-ACTIVITY RELATIONSHIP ANALYSIS (QSAR) OF ANTIMALARIAL 1,10-PHENANTHROLINE DERIVATIVES COMPOUNDS Ruslin Hadanu; Sabirin Mastjeh; Mustofa Mustofa; Eti Nurwening Sholikhah; Mahardika Agus Wijayanti; Iqmal Tahir
Indonesian Journal of Chemistry Vol 7, No 1 (2007)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (213.469 KB) | DOI: 10.22146/ijc.21716

Abstract

Quantitative Electronic Structure-Activity Relationship (QSAR) analysis of a series of 1,10-phenanthroline derivatives as antiplasmodial compounds have been conducted using atomic net charges (q), dipole moment (μ) ELUMO, EHOMO, polarizability (α) and log P as the descriptors. The descriptors were obtained from computational chemistry method using semi-empirical PM3. Antiplasmodial activities were taken as the activity of the drugs  against  chloroquine-resistant Plasmodium falciparum FCR3 strain and are presented as the value of ln (1/IC50) where IC50 is an effective concentration inhibiting 50% of the parasite growth. The best model of QSAR model was determine by multiple linear regression method and giving equation of QSAR: ln 1/IC50  =  3.732 + (5.098) qC5 + (7.051) qC7 + (36.696) qC9 + (41.467) qC11 -(135.497) qC12 + (0.332) μ -                    (0.170) α + (0.757) log P.The equation was significant on the 95% level with statistical parameters: n=16; r=0.987; r2= 0.975; SE=0.317;  Fcalc/Ftable = 15.337 and gave the PRESS=0.707. Its means that there were only a relatively few deviations between the experimental and theoretical data of antimalarial activity.
Synthesis of Chalcone Derivatives and Their in vitro Anticancer Test Against Breast (T47D) and Colon (WiDr) Cancer Cell Line Chairil Anwar; Yogo Dwi Prasetyo; Sabirin Matsjeh; Winarto Haryadi; Eti Nurwening Sholikhah; Nendrowati Nendrowati
Indonesian Journal of Chemistry Vol 18, No 1 (2018)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (336.088 KB) | DOI: 10.22146/ijc.26864

Abstract

The synthesis of chalcone derivatives as target compounds and anticancer test against breast (T47D) and colon (WiDr) cell line had been performed. The synthesis was performed by Claisen-Schmidt condensation by using acetophenone and benzaldehyde derivatives. The anticancer activity test of chalcone derivatives was carried out by MTT assay against T47D and WiDr cell lines. The synthesis was started by reacting 4-hydroxyacetophenone and benzaldehyde derivatives such as p-anisaldehyde (chalcone A [(E)-4'-hydroxy-4-methoxychalcone]), veratraldehyde (chalcone B [(E)-4'-hydroxy-3,4-dimethoxychalcone]), 4-chlorobenzaldehyde (chalcone C [(E)-4'-hydroxy-4-chlorochalcone]) and 2,4-dihydroxyacetophenone with 4-chlorobenzaldehyde (chalcone D [(E)-2',4'-dihydroxy-4-chlorochalcone]) in methanol as solvent. The synthesis was carried out in alkaline condition (KOH) by stirring the mixture at room temperature for 48 h. The structures of products were identified by FTIR, GC-MS, 1H- and 13C-NMR spectrometers. The results showed that the chalcone derivatives (A-D) were yielded in 96; 97; 96; and 93%, respectively as yellow solid. The anticancer test indicated that the chalcone D was the most active towards T47D cell line with IC50 of 42.66 μg/mL and the chalcone C was the most active against WiDr cell line with IC50 of 20.42 μg/mL.
Computational Design of Thioxanthone Derivatives as Potential Antimalarial Agents through Plasmodium falciparum Protein Inhibition Faris Hermawan; Jumina Jumina; Harno Dwi Pranowo; Eti Nurwening Sholikhah; Muthia Rahayu Iresha
Indonesian Journal of Chemistry Vol 22, No 1 (2022)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.69448

Abstract

Plasmodium falciparum (P. falciparum) is the most fatal among the other Plasmodium parasites that infect humans with the malaria disease. Currently, the resistance of P. falciparum against some antifolate drugs has become a severe problem. On the other hand, xanthone and thioxanthone derivatives have been reported to have remarkable antimalarial activity. However, molecular docking studies have not evaluated thioxanthone derivative compounds as antimalarial agents. Accordingly, this research investigated the binding pose and inhibition mechanism of several thioxanthone derivatives against P. falciparum proteins DHFR (PDB ID: 1J3K) and DHODH (PDB ID: 1TV5) through molecular docking study. The compound structures were geometrically optimized using Gaussian 09 software and docked to the receptors using AutoDock4 software. The results showed that the free binding energy of thioxanthone derivatives ranged between -6.77 to -7.50 and -8.45 to -9.55 kcal mol–1 against pfDHFR and pfDHODH, respectively, with RMSD values of less than 2 Å. Compound F (4-iodo-3,4-dihydroxy-thioxanthone) gave the most substantial free binding energy against both proteins. Furthermore, the hydrogen bond interaction of compound F was the same as the native ligands of pfDHFR and pfDHODH. These results suggested that compound F has a more robust interaction in pfDHFR and pfDHODH. Thus, it is promising to further evaluate the compound as a candidate for a new antimalarial agent.
Synthesis, Cytotoxicity Evaluation and Molecular Docking Studies of Xanthyl-Cinnamate Derivatives as Potential Anticancer Agents Muthia Rahayu Iresha; Jumina Jumina; Harno Dwi Pranowo; Eti Nurwening Sholikhah; Faris Hermawan
Indonesian Journal of Chemistry Vol 22, No 5 (2022)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.76164

Abstract

A new series of xanthyl-cinnamate hybrid compounds (4a-d) have been synthesized and screened through in vitro assay against four human cancer cell lines, i.e., HeLa, T47D, A549, and WiDr. The results revealed that xanthone hybridization with cinnamic acid increases the selectivity of the compounds with SI values of 2.75–209.03 compared to its parent oxygenated-xanthone. Compound 1,3-dihydroxyxanthen-6-yl cinnamate (4c) showed high cytotoxic activity against WiDr cell lines with an IC50 value of 39.57 µM. Molecular docking studies revealed the possible binding modes of all hybrid compounds with EGFR protein. A complex of 3,6-dihydroxyxanthen-1-yl cinnamate (4d)-EGFR, as the best binding model, exhibited higher predicted EGFR inhibitory activity than erlotinib and oxygenated-xanthone with a ΔG and Ki value of -35.02 kJ/mol and 0.74 µM, respectively. Compounds 4c and 4d were chosen as the most potent derivates from the study.
Brominated Flame Retardants: A Literature Review of The Toxicity Mechanisms, Clinical Manifestations, And Current Treatments Prasetyo, Yacobus Christian; Sholikhah, Eti Nurwening
Occupational and Environmental Medicine Journal of Indonesia Vol. 1, No. 2
Publisher : UI Scholars Hub

Show Abstract | Download Original | Original Source | Check in Google Scholar

Abstract

Brominated flame retardants (BFRs) are organohalogen compounds that can inhibit fire formation and delay its spread in manufacturing materials. BFRs are known to be toxic for the environment and humans. BFRs could persist for years prolonging potential exposure and toxicity to living beings. Indonesia had begun to reduce the use, even though some of toxic BFRs are still illegally circulating. This review aims to describe some aspects of BFRs toxicity including the mechanism, its clinical manifestations, and the current possible treatments. Toxicity after BFRs exposure includes endocrine, neurodevelopmental, and genotoxicity. The toxicity is manifested into some clinical conditions such as hypothyroidism, gonadal disturbance, or neurological disorders. Currently no definitive specific treatment is available, so the treatment is focused on primary survey as well as surface decontamination with running water and gastrointestinal decontamination with activated charcoal of some dose if the ingestion is less than 1 hour.
Metabolic Profiling, Antioxidant, and Anti-lipase Activity from Combined Leaves Extracts of Tamarindus indica and Murraya paniculata: A Simplex Lattice Design Approach Sholikhah, Eti Nurwening; Wiyono, Tri; Pratiwi, Woro Rukmi
Science and Technology Indonesia Vol. 9 No. 4 (2024): October
Publisher : Research Center of Inorganic Materials and Coordination Complexes, FMIPA Universitas Sriwijaya

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.26554/sti.2024.9.4.828-839

Abstract

Tamarindus indica leaves are recognized for their potent antioxidant and hypolipidemic properties, whereas Murraya paniculata leaves are known for their abilities to lower lipids and glucose levels. This study aimed to assess the combined extract of both leaves against pancreatic lipase inhibition and analyze their metabolomic profiles as an initial step toward developing a polyherbal treatment for hypertriglyceridemia. The extracts were subjected to Liquid Chromatography-High Resolution Mass Spectrometer (LC-HRMS) untargeted system coupled with Compounds Discoverer software to reveal their metabolomic profile. Subsequently, both individual extracts and their combination were evaluated for anti-lipase activity using pancreatic lipase enzyme with p-nitrophenyl butyrate as the substrate. The combination of the two extracts (0-300 μg/mL, 300 μg/mL in total) was prepared following the Simplex Lattice Experimental Design with 5 different composition variations. Results: The findings indicated that Tamarindus indica leaf extract (TIE) predominantly exhibited lipase inhibitory activity. Interestingly, the addition of Murraya paniculata extract (MPE) diminished this enzyme inhibitory effect. TIE was found to be rich in polyhydroxy flavonoids followed by fatty amides, whereas MPE contained mainly polymethoxy flavonoids, fatty amides, and coumarins. The presence of fatty amides in both extracts was identified as a potential cause for this incompatibility. In summary, Tamarindus indica leaf extract demonstrated strong lipase inhibition; however, its effectiveness was reduced when combined with Murraya paniculata extract, possibly due to primary fatty amides. Further research is necessary to explore strategies for eliminating these compounds and confirming their impact in vivo.
One-Pot Synthesis and In Vitro Studies of Calix[4]-2-methylresorcinarene Derivatives as Antimalarial Agents Against Plasmodium falciparum Chloroquine-Resistant Strain FCR-3 Nursofia, Baiq Ike; Kurniawan, Yehezkiel Steven; Jumina, Jumina; Pranowo, Harno Dwi; Sholikhah, Eti Nurwening; Julianus, Jeffry; Wibowo, Susalit Setya; Fatimi, Hana Anisa; Priastomo, Yoga; Priyangga, Krisfian Tata Aneka
Indonesian Journal of Chemistry Vol 24, No 6 (2024)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.94885

Abstract

Malaria is an endemic disease in Indonesia caused by infection from the Plasmodium parasite. Recently, antimalarial resistance significantly contributed to the decline in the cure rate of malaria sufferers. In this work, three calix[4]resorcinarenes have been synthesized from 2-methylresorcinol and different benzaldehyde derivatives, i.e., 4-chlorobenzaldehyde, 4-methoxybenzaldehyde, and 4-dimethylaminobenzaldehyde through the one-pot synthesis procedure. The calix[4]resorcinarenes synthesis was done through a cyclo-condensation reaction by using HCl 37% as the catalyst and ethanol as the solvent in an one-pot reaction. The structures of the synthesized products were confirmed using Fourier transform infrared, proton-nuclear magnetic resonance, and liquid chromatography-mass spectrometry techniques. The antimalarial activity assay was evaluated against the Plasmodium falciparum FCR-3 strain through an in vitro study. Three synthesized compounds, i.e., C-4-chlorophenylcalix[4]-2-methylresorcinarene, C-4-methoxyphenylcalix[4]-2-methylresorcinarene and C-4-dimethylaminophenylcalix[4]-2-methylresorcinarene have been successfully synthesized in up to 97% yield. The C-4-chlorophenylcalix[4]-2-methylresorcinerene exhibited the most potent antimalarial activity with a half-maximal inhibitory concentration (IC50) value of 2.66 µM against P. falciparum FCR-3 while the C-4-methoxyphenylcalix[4]-2-methylresorcinarene and C-4-dimethylaminophenylcalix[4]-2-methylresorcinarene gave the IC50 values of 23.63 and 13.82 µM, respectively. From the results, it could be concluded that the antimalarial activity of calix[4]-2-methylresorcinarenes was influenced by the type of substituent of aromatic rings at the para position.
Co-Authors Achmad Djunaidi Achmad Djunaidi Adisty Ridha Damasuri Adisty Ridha Damasuri Aditya Nugraha ADITYA NUGRAHA Agus Dwi Ananto, Agus Anak Agung Ayu Niti Wedayani Anak Agung Ngurah Nata Baskara Andi Hairil Alimuddin Bayu Putra Chairil Anwar Chairil Anwar Danang Setia Budi Demianus Tafor Demianus Tafor Dian Permata Sari Dwi Aris Agung Nugrahaningsih Ema Damayanti Erna Kristin Erwin Astha Triyono Faris Hermawan Fatimi, Hana Anisa Fitria, Anggit Gandes Retno Rahayu Harizal Harizal Harno Dwi Pranowo Harno Dwi Pranowo Harno Dwi Pranowo Hera Nirwati Iin Narwanti Ikhsan Nur Salim Ikhsan Nur Salim Iqmal Tahir JAKA WIDADA Jeffry Julianus Jumina Jumina Jumina Jumina Jumina Jumina Jumina Jumina Jumina Jumina Jumina Jumina Jumina Kasta Gurning Kurniawan, Yehezkiel Steven Laela Hayu Nurani Mae Sri Hartati Wahyuningsih Mahardika Agus Widjayanti Mahardika Agus Wijayanti Mahardika Agus Wijayanti Mahardika Agus Wijayanti Mahardika Agus Wijayanti Marlinda, Wade Masriani . Maulina Diah Maulina Diah Maya Dian Rakhmawatie Mega Pandu Arfiyanti Mia Munawaroh Yuniyanti Muhammad Idham Darussalam Mardjan Muhammad Kusumawan Herliansyah Muhammad Yusron Maulana El-Yunusi Mujur Mujur Mustafa Mustafa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Mustofa Muthia Rahayu Iresha Muthia Rahayu Iresha Nendrowati Nendrowati Ngatidjan Ngatidjan Nursofia, Baiq Ike Pramana Pananja Putra Pratiwi, Woro Rukmi Pratiwi, Woro Rukmi Priastomo, Yoga Primahana, Gian Priska Ernestina Tenda Priyangga, Krisfian Tata Aneka Pulung, Maria Ludya Ratna Sari RATNA SARI Respati Tri Swasono Rul Afiyah Syarif Ruslin Hadanu Sabirin Mastjeh Sabirin Mastjeh Sabirin Mastjeh Sabirin Mastjeh Sabirin Matsjeh Sabirin Matsjeh Samekto Wibowo Samekto Wibowo Setyo Purwono Sitarina Widyarini Susi Iravati Susi Iravati Tri Joko Raharjo Tri Murini Wahyu Nitari Wahyu Widyaningsih Wibowo, Susalit Setya Widya Wasityastuti Winarto Haryadi Wiyono, Tri Yacobus Christian Prasetyo Yogaswara, Radite Yudha, Ervan Yuniyanti, Mia Munawaroh Zulfa Faiqoh