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Mustofa Mustofa

Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta 55281

Author-ID : 3957616

Chemical Engineering, Chemistry & Bioengineering Chemistry

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Synthesis and Heme Polymerization Inhibitory Activity (HPIA) Assay of Antiplasmodium of (1)-N-(3,4-Dimethoxybenzyl)-1,10-Phenanthrolinium Bromide from Vanillin Dhina Fitriastuti; Muhammad Idham Darussalam Mardjan; Jumina Jumina; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 14, No 1 (2014)
Publisher : Universitas Gadjah Mada

The synthesis of (1)-N-(3,4-dimethoxy-benzyl)-1,10-phenanthrolinium bromide had been conducted from vanillin. Heme polymerization inhibitory activity assay of the synthesized antiplasmodium has also been carried out. The first step of reaction was methylation of vanillin using dimethylsulfate and NaOH. The mixture was refluxed for 2 h to yield veratraldehyde in the form of light yellow solid (79% yield). Methylation product was reduced using sodium borohydride (NaBH4) with grinding method and yielded veratryl alcohol in the form of yellow liquid (98% yield). Veratryl alcohol was brominated using PBr3 to yield yellowish black liquid (85% yield). The final step was benzylation of 1,10-phenanthroline monohydrate with the synthesized veratryl bromide under reflux condition in acetone for 14 h to afford (1)-N-(3,4-dimethoxy-benzyl)-1,10-phenanthrolinium bromide (84%) as yellow solid with melting point of 166-177 °C. The structures of products were characterized by FT-IR, GC-MS and 1H-NMR spectrometers. The results of heme polymerization inhibitory activity assay of (1)-N-(3,4-dimethoxybenzyl)-1,10-phenanthrolinium bromide showed that it had IC50 HPIA of 3.63 mM, while chloroquine had IC50 of4.37 mM. These results indicated that (1)-N-(3,4-dimethoxybenzyl)-1,10-phenanthrolinium bromide was more potential antiplasmodium than chloroquine.

SYNTHESIS OF TETRAKIS-N,N,N-TRIMETHYLAMMONIUMMETHYL-C-3,4-DIMETHOXYPHENYLCALIX[4]RESORCINARENE IODIDE BASED VANILLIN AND ITS ANTIDOTE ACTIVITY FOR CHROMIUM(VI) INTOXICATION Suryadi Budi Utomo; Jumina Jumina; Dwi Siswanta; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 13, No 2 (2013)
Publisher : Universitas Gadjah Mada

A research has been conducted to synthesize tetrakis-N,N,N-trimethylammoniummethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene iodide from vanillin and investigate its antidote capability for Cr(VI) intoxication. The synthesis was carried out in four steps i.e. (1) O-alkylation of 4-hydroxy-3-methoxybenzaldehyde, (2) HCl-catalyzed condensation of 3,4-dimethoxybenzaldehyde with resorcinol, (3) Mannich reaction of C-3,4-dimethoxyphenylcalix[4]resorcinarene with formaldehyde and dimethylamine in the presence of HCl to yield tetrakis-N,N-dimethylaminomethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene, and (4) treatment the Mannich base with methyl iodide to produce the quaternary ammonium salt of tetrakis-N,N,N-trimethylammoniummethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene iodide. According to the analysis of 1H-NMR spectrometer, the targeted compounds tend to exist in the chair (C2h) conformation. The capability of resorcinarene for Cr(VI) antidote was examined by orally injection method on mice groups. Based on LD50 determination, the resorcinarene was classified as non toxic compound according to Loomis criteria. Therapeutic using quaternary ammonium-modified resorcinarene was able to reduce metal concentrations of Cr(VI) in liver, kidney, and serum in the magnitude of 78.30; 85.72, and 88.79%, respectively. The higher dose of drug administered the greater decrease in the level of heavy metal. Judging from the amount of milligrams of reduced chromium per gram of organ, kidney is the organ having highest decreasing metal concentrations.

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

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.

STUDY ON THE ADSORPTION PROPERTIES OF NOVEL CALIX[6]ARENE POLYMERS FOR HEAVY METAL CATIONS Susy Yunita Prabawati; Jumina Jumina; Sri Juari Santosa; Mustofa Mustofa; Keisuke Ohto
Indonesian Journal of Chemistry Vol 12, No 1 (2012)
Publisher : Universitas Gadjah Mada

A research has been conducted to investigate the capability of a series of novel calix[6]arenes-based polymers: poly-monoallyloxycalix[6]arene (2a), poly-monoallyloxypenta-estercalix[6]arene (2b) and poly-monoallyloxypenta-acidcalix[6]arene (2c) for trapping of heavy metal cations such as Cd(II), Cu(II) and Cr(III). The existence of active hydroxy group (-OH) and with a tunnel-like structure of the polymers, caused the polymers can be used as adsorbents for heavy metals. The adsorption process was carried out in batch method in the variation of acidity (pH), contact time and initial concentration of metal ions. The results showed that the amount of adsorbed metal increased with the increasing of the pH of metal solution. For these three polymers, the amount of metal ions Cd(II), Cu(II) and Cr(III) adsorbed was optimum at pH 7, 6 and 5 respectively. The optimum contact time for Cd(II) and Cu(II) was 120 min, while that for Cr(III) was 60 min. Study of the adsorption kinetics showed that the adsorption of Cd(II), Cu(II) and Cr(III) using polymer 2a followed kinetics model of Ho. For adsorbent 2b and 2c, the adsorption kinetics of Cd(II) and Cr(III) also followed kinetics model of Ho while for the Cu(II) followed Lagergren kinetic models. Isothermal studies showed that the adsorption of metal ions on all adsorbents tend to follow the Langmuir isotherm. The adsorption energies of the three adsorbents were higher than 23 kJ/mole and polymer 2c has the largest adsorption capacity for Cr(III).

KINETICS AND EQUILIBRIUM MODEL OF Pb(II) AND Cd(II) ADSORPTION ONTO TETRAKIS-THIOMETHYL-C-4-METHOXYPHENYLCALIX[4]RESORCINARENE Suryadi Budi Utomo; Jumina Jumina; Dwi Siswanta; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 12, No 1 (2012)
Publisher : Universitas Gadjah Mada

The ability of tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene for trapping Pb(II) and Cd(II) from aqueous solution at different pH, contact times, and initial metal concentration was investigated. Concentration of metal ions before and after interaction was analyzed by Atomic Absorption Spectrophotometer (AAS). The result indicated that tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene is a good host for metal ions, where Cd(II) sorption capacity was higher than that of Pb(II). Effect of pH on batch experiments for the mentioned ions indicated that the optimum pH for metal binding were 5 for both of lead(II) and cadmium(II). In order to investigate the mechanism of adsorption, the 1st-order, pseudo 1st-order, and pseudo 2nd-order kinetic models were used. The adsorption model of metal ions on the resorcinarene followed pseudo second order of Ho & McKay expression. The equilibrium adsorption isotherm has been analyzed by Langmuir and Freundlich equations. Langmuir model had the higher correlation coefficient than that of Freundlich model.

Co-Authors Dhina Fitriastuti Dwi Siswanta Dwi Siswanta Eti Nurwening Sholikhah Jumina Jumina Jumina Jumina Keisuke Ohto Mahardika Agus Wijayanti Muhammad Idham Darussalam Mardjan Ruslin Hadanu Sabirin Mastjeh Sri Juari Santosa Suryadi Budi Utomo Susy Yunita Prabawati

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