J. Serb. Chem. Soc. 75 (9) 1167–1179 (2010)
UDC 547.461.5:576.385.5:616–006.04; JSCS–4040; doi: 10.2298/JSC091202076P; Original scientific paper

Antiproliferative activity of NCI-DTP glutarimide derivatives. An alignment independent 3D QSAR study
JELENA B. POPOVIĆ-DJORDJEVIĆ, LJILJANA I. DOŠEN-MIĆOVIĆ*, IVAN O. JURANIĆ* and BRANKO J. DRAKULIĆ**

Faculty of Agriculture, University of Belgrade, Nemanjina 6, 11080 Belgrad, Serbia

*Faculty of Chemistry, University of Belgrade, Studentski trg 12–16, 11000 Belgrade, Serbia

**ICTM – Department of Chemistry, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia

(Received 2 December 2009, revised 25 January 2010)

Alignment-free, three dimensional structure–activity relationships (3D QSAR) of the antiproliferative potency of twenty-two glutarimide-containing compounds, taken from National Cancer Institute Developmental therapeutics ProgrAM database, toward eight representative human tumour cell lines are reported. The descriptors used in the QSAR study were derived from GRID molecular interaction fields. The obtained models readily detect structural motifs positively or negatively correlated with the potency of the studied compounds toward each cell line. In this way, the pharmacophoric pattern required for high potency of compounds is reported. This pattern can serve as guidance for the design and syntheses of novel congeners, planned to be tested toward human tumour cell lines.

Keywords: glutarimides; antiproliferative agents; alignment-independent 3D QSAR; GRIND descriptors.

J. Serb. Chem. Soc. 75 (9) 1181–1189 (2010)
UDC 547.292+547.586.2+547.53.024:54–732+537.5; JSCS–4041; doi: 10.2298/JSC090901096A; Original scientific paper

Acetic acid-promoted condensation of o-phenylenediAMine with aldehydes into 2-aryl-1-(arylmethyl)-1H-benzimidazoles

under microwave irradiation

DAVOOD AZARIFAR, MOJGAN PIRHAYATI, BEHROOZ MALEKI*, MEHRANGIZ SANGINABADI and RAZIEH NEJAT YAMI

Faculty of Chemistry, Bu-Ali Sina University, HAMadan-65178, Iran

*Department of Chemistry, Sabzevar Tarbiat Moallem University, Sabzevar-397, Iran

(Received 1 September 2009, revised 30 April 2010)

An efficient and simple procedure was developed for the green synthesis of various 2-aryl-1-(arylmethyl)-1H-benzimidazoles in high yields by acetic acid-promoted condensation of o-phenylenediAMine with aldehydes in air under microwave irradiation and transition metal catalyst-free conditions.

Keywords: 2-aryl-1-(arylmethyl)-1H-benzimidazoles; o-phenylenediAMine; aldehydes; microwave irradiation, acetic acid.

J. Serb. Chem. Soc. 75 (9) 1191–1201 (2010)
UDC 542.9+547.571.+547.551:577.113:577.112.387:547.576; JSCS–4042; doi: 10.2298/JSC100128107Z; Original scientific paper

Interaction between tryptophan-vanillin Schiff base and herring sperm DNA
YAN ZHANG, XINGMING WANG and LISHENG DING*

Department of Chemistry, School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, P. R. China

*Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P. R. China

(Received 28 January, revised 31 March 2010)

The interaction of the Schiff base (K[HL]) with herring sperm DNA was studied by UV–Vis absorption, fluorescence and viscosity methods in a physiological pH environment (pH 7.40), where the Schiff base was derived from vanillin and L-tryptophan. A binding ratio of nK[HL]:nDNA = 5:1 and an apparent molar absorption coefficient of e(K[HL]–DNA) = 4.98×105 L mol^-1 cm^-1 were confirmed by the mole ratio method. The binding constants of KB (301 K) =1.94 ×105 L mol-1 and K_B^Ө (310 K) = 1.09×105 L mol^-1 were obtained by the double reciprocal method. ThermodynAMic parAMeters suggest that the interaction between K[HL] and DNA is driven mainly by enthalpy. Combined with Scatchard methods and viscosity methods, the results indicate the presence of intercalation and groove binding between K[HL] and DNA.

Keywords: vanillin; L-tryptophan; Schiff base; herring sperm DNA; interaction.

J. Serb. Chem. Soc. 75 (9) 1203–1208 (2010)
UDC 547.233’447+541.64+678.684:615.281–188; JSCS–4043; doi: 10.2298/JSC100201104A; Short communication

SHORT COMMUNICATION

Molecular weight dependent antistaphylococcal activities of oligomers/polymers synthesized from 3-AMinopyridine
CAHIT AKGUL and MEHMET YILDIRIM

Department of Chemistry, Faculty of Sciences and Arts, Canakkale Onsekiz Mart University, Terzioglu CAMpus, Canakkale, Turkey

(Received 1 February, revised 23 March 2010)

The main aim of this study was to investigate the relationship between molecular weight and the antistaphylococcal activity of oligomers/polymers synthesized from 3-AMinopyridine. Different oligomers/polymers were synthesized from 3-AMinopyridine by changing the oxidative polycondensation reaction conditions. They were characterized by size exclusion chromatography and their antibacterial activities were compared by employing standardized susceptibility assays. The obtained experimental results demonstrated that 3-AMinopyridine had no antistaphylococcal activity. However, as a result of polymerization, strong antistaphylococcal activity was obtained. Oligomers/polymers synthesized from 3-AMinopyridine had varying degrees of antistaphylococcal activity and the maximum activity was obtained from relatively very short oligomers. It was therefore concluded that polymerization of 3-AMinopyridine is required for antistaphylococcal activity and strength of this activity depends on the molecular weights of the synthesized molecules.

Keywords: antibacterial; 3-AMinopyridine; oligomer; Staphylococcus aureus.

J. Serb. Chem. Soc. 75 (9) 1209–1218 (2010)

J. Serb. Chem. Soc. 75 (9) 1219–1230 (2010)

UDC 542.913:547.466+546.742:548.7:541.121:536.7:535.33; JSCS–4045; doi: 10.2298/JSC091028101Z; Original scientific paper

J. Serb. Chem. Soc. 75 (9) 1231–1239 (2010)

UDC 547.235.2’211+547.288.4+546.3–386:542.913:615.281; JSCS–4046; doi: 10.2298/JSC091118102K; Original scientific paper

J. Serb. Chem. Soc. 75 (9) 1241–1249 (2010)

UDC 547.686.004.12:548.12:519.6; JSCS–4047; doi: 10.2298/JSC100419080M; Original scientific paper

Diradical character of some fluoranthenes

SVETLANA MARKOVIĆ, JELENA ĐURĐEVIĆ, SVETLANA JEREMIĆ and IVAN GUTMAN

Faculty of Science, University of Kragujevac, 12 Radoja Domanovića, 34000 Kragujevac, Serbia

(Received 19 April, revised 18 May 2010)

It is shown that some Kekuléan fluoranthenes are diradicals and that their ground state is a triplet. In the energetically less favorable singlet state, these hydrocarbons also exhibit pronounced diradical character. The diradical character y of the compounds under investigation was estimated using the unrestricted symmetry-broken (yPUHF) and complete active space (yNOON) methods. It was found that the yPUHF values better reproduce the diradical character of the investigated hydrocarbons. It was shown that singly occupied molecular orbital (SOMO) and SOMO-1 of a diradical structure occupy different parts of space with a small shared region, resulting in a spin density distribution over the entire molecule. The spatial diradical distribution in the singlet diradical structures was exAMined by inspecting the HOMOs and LUMOs for a and b spin electrons. It was shown that the a-HOMO and the b-LUMO (as well as the b-HOMO and the a-LUMO) occupy practically the sAMe part of space. In this way, there are no unpaired electrons in a singlet diradical structure, yet two of them occupy different parts of space, thus allowing the p-electrons to delocalize.

Keywords: fluoranthenes; diradical; singlet diradical; triplet diradical; unrestricted symmetry-broken method; complete active space calculation.

J. Serb. Chem. Soc. 75 (9) 1251–1257 (2010)

UDC 546.72’46–36:666.122.3+544.354–128.2:544.478:665.652.7; JSCS–4048, doi: 10.2298/JSC100115092H; Original scientific paper

A study of thermally activated Mg–Fe layered double hydroxides as potential environmental catalysts

MILICA S. HADNAĐEV-KOSTIĆ, TATJANA J. VULIĆ and RADMILA P. MARINKOVIĆ-NEDUČIN

Faculty of Technology, University of Novi Sad, Bul. cara Lazara 1, Novi Sad, Serbia

(Received 15 January, revised 25 February 2010)

Layered double hydroxides (LDHs) and mixed oxides derived after thermal decomposition of LDHs with different Mg–Fe contents were investigated. These materials were chosen because of the possibility to tailor their various properties, such as ion-exchange capability, redox and acid–base and surface area. Layered double hydroxides, [Mg_1-xFe_x(OH)₂](CO₃)_x/2×mH₂O (where x presents the content of trivalent ions, x = M(III)/(M(II) + M(III)) were synthesized using the low supersaturation precipitation method. The influence of different Mg/Fe ratios on the structure and surface properties of the LDH and derived mixed oxides was investigated in correlation to their catalytic properties in the chosen test reaction (Fischer–Tropsch synthesis). It was determined that the presence of active sites in the mixed oxides is influenced by the structural properties of the initial LDH and by the presence of additional Fe phases. Furthermore, a synthesis outside the optimal range for the synthesis of single phase LDHs leads to the formation of metastable, multiphase systems with specific characteristics and active sites.

Keywords: Mg–Fe–LDHs; hydrotalcite; anionic clays; Mg–Fe mixed oxides; Fischer–Tropsch reaction.

J. Serb. Chem. Soc. 75 (9) 1259–1269 (2010)

UDC 621.352:546.34’72’185.001: 544.6.004.12; JSCS–4049; doi: 10.2298/JSC091028101Z; Original scientific paper

Effects of the LiFePO₄ content and the preparation method on the properties of (LiFePO₄+AC)/Li₄Ti₅O₁₂ hybrid battery–capacitors

XUE BU HU, ZI JI LIN*, LI LIU*, YONG JIAN HUAI* and ZHENG HUA DENG*

Department of Chemistry and Materials, Sichuan Normal University, Chengdu, Sichuan 610068, P. R. China

*Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, P. R. China

(Received 28 December 2009, revised 17 March 2010)

Two composite cathode materials containing LiFePO₄ and activated carbon (AC) were synthesized by an in-situ method and a direct mixing technique, which are abbreviated as LAC and DMLAC, respectively. Hybrid battery–capacitors LAC/Li₄Ti₅O₁₂ and DMLAC/Li₄Ti₅O₁₂ were then assembled. The effects of the content of LiFePO₄ and the preparation method on the cyclic voltAMmogrAMs, the rate of charge–discharge and the cycle performance of the hybrid battery–capacitors were investigated. The results showed the overall electrochemical performance of the hybrid battery–capacitors was the best when the content of LiFePO₄ in the composite cathode materials was in the range from 11.8 to 28.5 wt. %, while the preparation method had almost no impact on the electrochemical performance of the composite cathodes and hybrid battery–capacitors. Moreover, the hybrid battery–capacitor devices had a good cycle life performance at high rates. After 1000 cycles, the capacity loss of the DMLAC/Li₄Ti₅O₁₂ hybrid battery–capacitor device at 4C was no more than 4.8 %. Moreover, the capacity loss would be no more than 9.6 % after 2000 cycles at 8C.

Keywords: hybrid battery–capacitor; LiFePO₄ content; preparation method; long cycle life; high rate; electrochemical performance.

J. Serb. Chem. Soc. 75 (9) 1271–1277 (2010)

UDC 546.657’72’27:66.017+537.622:621.318.12; JSCS–4050; doi: 10.2298/JSC100217058Z; Original scientific paper

An overstoichiometric Nd–Fe–B hard magnetic material

TOMÁŠ ŽÁK, NADEŽDA M. TALIJAN*, VLADAN R. ĆOSOVIĆ*, JASNA T. STAJIĆ-TROŠIĆ* and ALEKSANDAR S. GRUJIĆ*

Institute of Physics of Materials, Academy of Sciences of the Czech Republic, v.v.i., Žižkova 22, 616 62 Brno, Czech Republic

*Institute of Chemistry, Technology and Metallurgy, Department of Materials and Metallurgy, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia

(Received 17 February, revised 16 April 2010)

A commercial Nd-rich Nd–Fe–B-based hard magnetic material was studied. The obtained results were compared before and after recording of the thermomagnetic curve up to 800 °C. The curve itself showed clearly besides Curie points of the Nd₂Fe₁₄B phase and α-Fe also another critical temperature. Mössbauer spectroscopic (MS) phase analysis and X-ray diffraction analysis (XRD) showed in addition to the commonly known phases Nd₂Fe₁₄B and NdFe4B4 also some parAMagnetic and ferromagnetic iron atoms (MS) and Fe₁₇Nd₂ intermetallics (XRD). During the exerted thermal treatment, the content of the Nd₂Fe₁₄B and NdFe₄B₄ phases remained almost unchanged, while iron atoms from remnant minor phases built a separate α-Fe phase. The XRD pattern also showed the presence of some minor Nd phase. The results of Squid magnetic measurements suggest a nanocrystalline decoupled structure of the Nd-rich alloy in the optimized magnetic state. Measurement of the magnetization loop showed, in spite of small changes in the phase composition, that magnetic properties of the quality material deteriorated during the thermal treatment.

Keywords: rapid quenched Nd–Fe–B; overstoichiometric Nd content; Mössbauer phase analysis; XRD; magnetic properties.

J. Serb. Chem. Soc. 75 (9) 1279–1289 (2010)

UDC 544.142+633.844:546.56: 66.061:504.53.054; JSCS–4051; doi: 10.2298/JSC091207086Z; Original scientific paper

Chelate-assisted phytoextraction: effect of EDTA and EDDS on copper uptake by Brassica napus L.

TIJANA M. ZEREMSKI-ŠKORIĆ, PETAR Đ. SEKULIĆ, IVANA V. MAKSIMOVIĆ*, SRĐAN I. ŠEREMEŠIĆ*, JORDANA M. NINKOV, STANKO B. MILIĆ and JOVICA R. VASIN

Institute of Field and Vegetable Crops, Maksima Gorkog 30, Novi Sad, Serbia

*Faculty of Agriculture, University of Novi Sad, Trg Dositeja Obradovića 8, Novi Sad, Serbia

(Received 7 December 2009, revised 12 January 2010)

Chelate-assisted phytoextraction is proposed as an effective approach for the removal of heavy metals from contAMinated soil through the use of high biomass plants. The aim of the present study was to compare the efficiency of the two chelators: EDTA and biodegradable EDDS in enhancing Cu uptake and translocation by Brassica napus L. grown on moderately contAMinated soil and treated with increasing concentrations of EDTA or EDDS. Increasing AMounts of EDDS caused serious growth suppression of B. napus and an increase in shoot metal concentrations. Growth suppression limited the actual AMount of phytoextracted Cu at high concentrations of EDDS. The maximum AMount of extracted Cu was achieved by the application of 8.0 and 4.0+4.0 mmol kg^-1 EDDS. The shoot Cu concentrations after EDTA application were much lower than with EDDS at the sAMe doses. According to these experiments, EDTA does not appear to be an efficient AMendment if Cu phytoextraction with B. napus is considered but EDDS is.

Keywords: phytoextraction; copper; EDTA; EDDS; Brassica napus L.

J. Serb. Chem. Soc. 75 (9) 1291–1302 (2010)

UDC 547.551.1:615.9:626.812:579.81/.85; JSCS–4052; doi: 10.2298/JSC091219103S; Original scientific paper

Toxicity of five anilines to crustaceans, protozoa and bacteria

MARILIIS SIHTMÄE, MONIKA MORTIMER, ANNE KAHRU and IRINA BLINOVA

Laboratory of Molecular Genetics, National Institute of Chemical Physics and Biophysics, Akadeemia tee 23, Tallinn 12618, Estonia

(Received 19 December 2009, revised 18 February 2010)

Aromatic AMines (anilines and related derivates) are an important class of environmental pollutants that can be released to the aquatic environment as industrial effluents or as breakdown products of pesticides and dyes. The toxicity of aniline, 2-chloroaniline, 3-chloroaniline, 4-chloroaniline and 3,5-dichloroaniline towards a multitrophic test battery comprised of bacteria Aliivibrio fischeri (formerly Vibrio fischeri), a ciliated protozoan Tetrahymena thermophila and two crustaceans (Daphnia magna and ThAMnocephalus platyurus) were investigated. Under the applied test conditions, the toxicity of the anilines notably varied AMong the test species. The bacteria and protozoa were much less sensitive towards the anilines than the crustaceans: EC₅₀ values 13–403 mg L^-1 versus 0.13–15.2 mg L^-1. No general tendency between toxicity and the chemical structure of the anilines (the degree of chloro-substitution and the position of the chloro-substituents) was found in the case of all the tested aquatic species. The replacement of the artificial test medium (ATM) by the river water remarkably decreased the toxicity of anilines to crustaceans but not to protozoa. This research is part of the EU 6^th FrAMework Integrated Project OSIRIS, in which ecotoxicogenomic studies of anilines (e.g., for Daphnia magna) will also be performed that may help to clarify the mechanisms of toxicity of different anilines.

Keywords: ecotoxicity; anilines; test battery; river water; ECOSAR.

J. Serb. Chem. Soc. 75 (9) 1303–1312 (2010)

UDC 628.132:582.26/.27:615.9:577.112.386; JSCS–4053; doi: 10.2298/JSC100113106B; Original scientific paper

Temporal and spatial variability of cyanobacterial toxins microcystins in three interconnected freshwater reservoirs

LUDĚK BLÁHA, LUCIE BLÁHOVÁ, JIŘÍ KOHOUTEK, ONDŘEJ ADAMOVSKÝ, PAVEL BABICA and BLAHOSLAV MARŠÁLEK

Masaryk University, Faculty of Science, Research Centre for Toxic Compounds in the Environment – RECETOX, KAMenice 3, CZ62500 Brno and Institute of Botany, Academy of Sciences of the Czech Republic, Lidická 25/27, 657 20 Brno, Czech Republic

(Received 13 January, revised 18 February 2010)

In spite of substantial research on health and the ecological risks associated with cyanobacterial toxins in the past decades, the understanding of the natural dynAMics and variability of toxic cyanobacterial blooms is still limited. Herein, the results of long term monitoring 1998–1999/2001–2008 of three reservoirs (Vír, Brno and Nové Mlýny, Chech Republic), where toxic blooms develop annually, are reported. These three reservoirs provide a unique model because they are interconnected by the Svratka River, which allows possible transfer of phytoplankton as well as toxins from one reservoir to another. The frequency of the occurrence and dominance of the major cyanobacterial taxa Microcystis aeruginosa did not change during the investigated period but substantial variability was observed in the composition of other phytoplankton. Although absolute concentrations of the studied toxins (microcystins) differed AMong the reservoirs, there were apparent parallel trends. For exAMple, during certain years, the microcystin concentrations were systematically elevated in all three studied reservoirs. Furthermore, the concentration profiles in the three sites were also correlated (parallel trends) within individual seasons based on monthly sAMpling. Microcystin-LR, a variant for which the World Health Organization has recommended a guideline value, formed only about 30–50 % of the total microcystins. This is of importance, especially in the Vír reservoir that serves as a drinking water supply. The maxima in the cell-bound microcystins (intracellular; expressed per dry weight biomass) generally preceded the maxima of total microcystins (expressed per volume of water sAMple). Overall, the maximum concentration in the biomass (all three reservoirs, period 1993–2005) was 6.1 mg g^-1 dry weight and the median values were in the range 0.065–2.3 mg g^-1 dry weight. These are generally high concentrations in comparison with both Czech Republic and worldwide reported data. The present data revealed substantial variability of both toxic cyanobacteria and their peptide toxins that should be reflected by detailed monitoring progrAMs.

Keywords: microcystin; monitoring; trends; HPLC; ELISA.

J. Serb. Chem. Soc. J. Serb. Chem. Soc. 75 (9) 1313 (2010)

Errata (printed version only)

Issue No. 8 (2010), Vol. 75:

– Page 1053: one of the authors (paper JSCS-4030), Milena R. Spasić, is the member of the Serbian Chemical Society.

– Page 1060 (paper JSCS-4030), Acknowledgements should read: The authors wish to thank Filip Stojanović and Gordana Kukić for their excellent technical assistance. This research was supported by Ministry of Science and Technological Development of the Republic of Serbia, Grant No. 145035.

– Page 1161: paper JSCS-4039 should be denoted as Extended Abstract of the Section Lecture at the Meeting of the Chemical Engineering Section of the Serbian Chemical Society, held 5 February, 2010.

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