JSCS Vol 77, No. 1

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J. Serb. Chem. Soc. 77 (1) 1–8 (2012)

UDC 547.497.1+547.792+542.913:57–188; JSCS–4243; doi: 10.2298/JSC110212157P; Original scientific paper

 

Synthesis of 1,6-hexanediyl-bis(semicarbazides) and 1,6-hexanediyl-bis(1,2,4-triazol-5-ones) and their antiproliferative and antimicrobial activity

Monika PITUCHA, Jolanta RZYMOWSKA*, Alina OLENDER** and Ludmiła GRZYBOWSKA-SZATKOWSKA***

Department of Organic Chemistry, Medical University, 20-081 Lublin, Poland

*Department of Biology and Genetics, Medical University, 20-081 Lublin, Poland

**Chair and Department of Medical Microbiology, Medical University, 20-093 Lublin, Poland

***Department of Oncology, Medical University, 20-090 Lublin, Poland

 

(Received 12 February, revised 14 August 2011)

A series of 1,6-bis(3-substituted 1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl)hexanes 3a–g were synthesized by the cyclization reaction of 1,6-bis{[(2-substituted hydrazinyl)carbonyl]AMino}hexanes 2a–g in alkaline medium. The new derivatives 3a–c were screened in vitro for their antiproliferative and anti­cancer activity in human tumor cell lines derived from breast and lung car­cinoma cells. Compounds 3a (at a concentration of 0.18 mM), 3b (at concentrations of 0.12 and 0.02 mM) and 3c (at concentrations of 0.23 and 0.11 mM) were found to be the most effective against the lung cell line. Compound 3a had the greatest antiproliferative effect on the breast carcinoma cell line. Representative compounds were established and evaluated as antimicrobial agents. All the tested derivatives showed minimum inhibitory concentrations (MIC) in the range 1.87–7.5 µg mL^-1. Compound 3b was the most effective against Can­dida albicans (MIC 1.87 µg mL^-1).

 

Keywords: synthesis; semicarbazide; 1,2,4–triazole; biological activity.

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J. Serb. Chem. Soc. 77 (1) 9–16 (2012)

UDC 547.78+547.233+547.282.1:615.28–188; JSCS–4244; doi: 10.2298/JSC110123155M; Original scientific paper

 

New oxadiazole derivatives of isonicotinohydrazide in the search for antimicrobial agents: Synthesis and in vitro evaluation

MANAV MALHOTRA, MOHIT SANDUJA*, ABDUL SAMAD** and AAKASH DEEP***

Department of Pharmaceutical Chemistry, Meerut Institute of Engineering and Technology, Bypass Road-Baghpat Crossing, Meerut-250005, Uttar Pradesh, India

*Department of Pharmaceutical Chemistry, ISF College of Pharmacy, Ferozepur Road, Moga-142001, India

**Department of Pharmaceutical Chemistry, College of Pharmacy in Al-Kharj, King Saud University, Riyadh, Saudi Arabia

***Department of PharmaceuticalSciences, Maharshi Dayanand University, Rohtak-124001, India

 

(Received 23 January, revised 24 June 2011)

Structural modifications of the front line antitubercular drug isoniazid provide lipophilic adaptations of the drug in which the hydrazide moiety of iso­niazid is replaced by 1,3,4-oxadiazole heterocycles to eliminate in vivo acetyla­tion by arylAMine N-acetyltransferase, which results in the formation of inac­tive acetylated drug. In the present study, a series of sixteen oxadiazole deriva­tives were synthesized and characterized by IR, ¹H-NMR, ¹³C-NMR and mass spectral studies. All the synthesized compounds were evaluated for their anti­microbial activity by broth dilution method against two GrAM-positive bacterial strains (Bacillus subtilis and Staphylococcus aureus), two GrAM-negative bac­terial strains (Pseudomonas aeruginosa and Escherichia coli) and two fungal strains (Candida albicans and Aspergillus niger). The minimum inhibitory concentrations of the compounds were in the range of 1.56–50 µg ml^-1 against the bacterial and fungal strains. The results revealed that all the synthesized compounds have a significant biological activity against the tested microor­ga­nisms. Among the synthesized derivatives 4g, 4h, 4m and 4p were found to be the most effective antimicrobial compounds.

 

Keywords: 1,3,4-oxadiazoles; antimicrobial activity; isoniazid; Mannich bases; lipophilicity.

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J. Serb. Chem. Soc. 77 (1) 17–26 (2012)

UDC 547.869+547.789+542.913:615.28–188; JSCS–4245; doi: 10.2298/JSC100924152S; Original scientific paper

 

Synthesis and biological activity of 4-thiazolidinone derivatives of phenothiazine

RITU SHARMA, PUSHKAL SAMADHIYA, SAVITRI D. SRIVASTAVA and SANTOSH K. SRIVASTAVA

Synthetic Organic Chemistry Laboratory, Department of Chemistry, Dr. H. S. Gour University (A Central University), Sagar-470003, India

 

(Received 24 September 2010, revised 24 April 2011)

A new series of N-[3-(10H-phenothiazin-10-yl)propyl]-2-(substituted phenyl)-4-oxo-5-(substituted benzylidene)-3-thiazolidinecarboxAMide, 5a–s were synthesized. The reaction of thioglycolic acid with N-[3-(10H-pheno­thia­zin-10-yl)propyl]-N’-[(substituted phenyl)methylidene]urea, 3a–s in the pre­sence of anhydrous ZnCl2 afforded the new heterocyclic com­pounds N-[3-(10H-phenothiazin-10-yl)propyl]-2-(substituted phenyl)-4-oxo-3-thiazolidine­carboxAMide, 4a–s. The latter product on treatment with several selected sub­stituted aromatic aldehydes in the presence of C₂H₅ONa underwent the Knoe­venagel reaction to yield 5a–s. The structure of com­pounds 1, 2, 3a–s, 4a–s and 5a–s were confirmed by IR, ¹H-NMR, ¹³C-NMR and FAB mass spec­tros­copy and by chemical analysis. All the above compounds were screened for their antimicrobial activity against some selected bacteria and fungi and for their antituberculosis activity, the compounds were screened against the bac­terium Mycobacterium tuberculosis.

 

Keywords: synthesis; phenothiazine; 4-oxothiazolidine; antimicrobial; antitu­bercular.

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J. Serb. Chem. Soc. 77 (1) 27–42 (2012)

UDC ^‘Pseudomonas aeruginosa san-ai:577.115.002.2; JSCS–4246; doi: 10.2298/JSC110211156R; Original scientific paper

 

Production and characterization of rhAMnolipids from Pseudomonas aeruginosa san-ai

Milena G. RikaloviĆ*, Gordana Gojgić-Cvijović**, Miroslav M. Vrvić*,** and Ivanka Karadžić***

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

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

***School of Medicine, Department of Chemistry, University of Belgrade, Višegradska 26, Belgrade, Serbia

 

(Received 11 February, revised 3 August 2011)

The production and characteristics of rhAMnolipid biosurfactant ob­tained by the strain Pseudomonas aeruginosa san-ai were investigated. With regard to the carbon and nitrogen sources, several media were tested to enhance the production of rhAMnolipids. Phosphate-limited proteose peptone–AMmo­nium salt (PPAS) medium supplemented with sunflower oil as a source of car­bon and mineral AMmonium chloride and peptone as nitrogen sources greatly improved the production of rhAMnolipid, from 0.15 on basic PPAS (C/N ratio 4.0) to 3 g L^-1 on optimized PPAS medium (C/N ratio 7.7). Response surface methodology analysis was used for testing the effect of three factors, i.e., tem­perature, concentration of carbon and nitrogen source (mass %), in the opti­mized PPAS medium on the production of rhAMnolipid. The isolated rhAMno­lipids were characterized by infrared (IR) spectroscopy and electrospray ioni­zation mass spectrometry (ESI–MS). The IR spectra confirmed that the isolated compound corresponded to the rhAMnolipid structure, whereas MS indicated that the isolated preparation was a mixture of mono-rhAMno-mono-lipidic, mono-rhAMno-di-lipidic and di-rhAMno-di-lipidic congeners.

 

Keywords: rhAMnolipids; Pseudomonas aeruginosa; renewable sources.

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J. Serb. Chem. Soc. 77 (1) 43–52 (2012)

UDC Escherichia coli:634.773:547.455.623; JSCS–4247; doi: 10.2298/JSC110309158A; Original scientific paper

 

Optimization of the heterologous expression of banana glucanase in Escherichia coli

MOHAMED ABUGHREN, MILICA POPOVIĆ, RAJNA DIMITRIJEVIĆ*, LIDIJA BURAZER**, MILICA GROZDANOVIĆ, MARINA ATANASKOVIĆ-MARKOVIĆ*** and MARIJA GAVROVIĆ-JANKULOVIĆ

Faculty of Chemistry, University of Belgrade, Belgrade, Serbia

*Innovation Center of the Faculty of Chemistry, University of Belgrade, Belgrade, Serbia

**Institute of Virology, Vaccines and Sera, Torlak, Belgrade, Serbia

***University Children’s Hospital, Medical Faculty, University of Belgrade, Belgrade, Serbia

 

(Received 9 March, revised 21 June 2011)

For the heterologous production of a banana glucanase in Escherichia coli, its gene (GenBank GQ268963) was cloned into a pGEX-4T expression vector as a fusion protein with glutathione-S-transferase (GST). BL21 cells transformed with the GST-Mus a 5 construct were employed for production of the protein induced by 1 mM isopropyl-b-D-thiogalactopyranoside (IPTG). The conditions for protein expression were optimized by varying the tempe­rature (25, 30 and 37 °C) and duration of protein expression (3, 6 and 12 h). The level of protein production was analyzed by densitometry of the sodium dodecyl sul­fate–polyacrylAMide gel (SDS–PAG) after electrophoretic resolu­tion of the res­pective cell lysates. The optimal protein expression for down­streAM processing was obtained after 12 h of cell growth at 25 °C upon addi­tion of IPTG. Re­combinant GST-Mus a 5 purified by glutathione affinity chro­matography re­vealed a molecular mass of about 60 kDa. The IgE and IgG reac­tivity of the rGST-Mus a 5 was confirmed by dot blot analysis with sera of in­dividual pa­tients from subjects with banana allergy and polyclonal rabbit anti­bodies against banana extract, respectively. The purified recombinant gluca­nase is a potential candidate for banana allergy diagnosis.

 

Keywords: food allergen; protein expression; glucanase.

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J. Serb. Chem. Soc. 77 (1) 53–66 (2012)

UDC 547.496.2+546.776+547.7:532.74:615.28–188; JSCS–4248; doi: 10.2298/JSC110328160S; Original scientific paper

 

Spectroscopic properties and antimicrobial activity of dioxomolybdenum(VI) complexes with heterocyclic S,S’-ligands

SOFIJA P. SOVILJ, DRAGANA MITIĆ, BRANKO J. DRAKULIĆ* and MARINA MILENKOVIĆ**

Faculty of Chemistry, P. O. Box 118, 11158 Belgrade, Serbia

*ICTM, Department of Chemistry, Njegoševa 12, 11001 Belgrade, Serbia
**Department of Microbiology and Immunology, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade, Serbia

 

(Received 28 March, revised 26 August 2011)

Five new dioxomolybdenum(VI) complexes of the general formula [MoO₂(Rdtc)₂], 1–5, where Rdtc^- refer to piperidine (Pipdtc), 4-morpholine (Morphdtc), 4-thiomorpholine (Timdtc), piperazine (Pzdtc) or N-methylpipe­razine (N-Mepzdtc) dithiocarbAMates, respectively, have been prepared. The complexes were characterized by elemental analysis, conductometric measu­rements, electronic, IR and NMR spectroscopy. The complexes 1–5 contain a cis-MoO₂ group and have an octahedral geometry. Two dithiocarbAMato ions join as bidentates with both the sulfur atoms to the molybdenum atom. The pre­sence of different heteroatoms in the piperidinо moiety influences the n(CN) and n(CS) vibrations, which wavelengths decrease in the order: Pipdtc > N-Mepzdtc > Morphdtc > Pzdtc > Timdtc ligands. Based on their spectral data, the molecular structures of complexes 1–5 were optimized at the semi-empi­rical molecular-orbital level, and the geometries, as obtained from calculations, are described. The antimicrobial activities of the complexes were tested against nine different laboratory control strains of bacteria and two strains of the yeast Candida albicans. All the tested strains were sensitive. Complexes bearing heteroatom in position 4 of piperidine moiety were signi­ficantly more potent against the tested bacteria compared to the corresponding ligands.

 

Keywords: dithiocarbAMates; molybdenum(VI) complexes; MoO₂²⁺ group; geometry optimization.

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J. Serb. Chem. Soc. 77 (1) 67–73 (2012)

UDC 546.56:541.64+547.86+547.586.7+547.233’821; JSCS–4249; doi: 10.2298/JSC101115153M; Original scientific paper

 

X-Ray structure of a 1D-coordination polymer of copper(II) bearing pyrazine-2,3-dicarboxylic acid and 2-AMinopyrimidine

MASOUD MIRZAEI, HOSSEIN ESHTIAGH-HOSSEINI, AZAM HASSANPOOR and VICTOR BARBA*

Department of Chemistry, Ferdowsi University of Mashhad, 917791436 Mashhad, Iran

*Centro de Investigaciones Químicas, UAEM, Av. Universidad 1001, 62209 Cuernavaca, México

 

(Received 15 November 2010, revised 28 September 2011)

A new 1D-coordination polymer of Cu(II) ions, {(2-apymH)₂[Cu(pyzdc) ₂]·6H₂O}_n, (2-apym = 2-AMinopyrimidine, pyzdcH₂ = pyrazine-2,3-dicarboxylic acid), was synthesized based on the proton transfer me­chanism and characterized by elemental analysis, infrared spectroscopy and single crystal X-ray diffraction. The coordination polymer consists of infinite chains of [Cu(pyzdc)₂]^2- bridged across a double chain running along the a-axis and discrete (2-apymH)⁺ fragments. The Cu(II) ion is located on the inversion centre in the basal plane of an elongated octahedron with two oxygen atoms from adjacent (pyzdc)^2- ligands occupying the axial positions. The interaction between oxygen atoms of water molecules with the dicarboxylic acid plays an important role in the overall suprAMolecular assembly.

 

Key words: copper; pyrazine-2,3-dicarboxylic acid; 2-AMinopyrimidine; proton transfer; hydrogen bond; coordination polymer; water cluster.

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J. Serb. Chem. Soc. 77 (1) 75–81 (2012)

UDC 546.28+547.7+547.313.2:66.095.252.091.7; JSCS–4250; doi: 10.2298/JSC110115119L Original scientific paper

 

Ab initio study of mechanism of the formation of a silicic bis-heterocyclic compound in the reaction of silylenesilylene (H₂Si=Si:) with ethene

XIUHUI LU, LEYI SHI, YONGQING LI and ZHINA WANG

School of Chemistry and Chemical Engineering, University of Jinan, Jinan, Shandong, 250022, People’s Republic of China

 

(Received 15 January, revised 4 october 2011)

The mechanism of the cycloaddition reaction of the formation of a silicic bis-heterocyclic compound between singlet state silylenesilylene (H₂Si=Si:) and ethene was investigated by the CCSD(T)//MP2/6-31G^ method. From the potential energy profile, it can be predicted that the reaction has one dominant reaction pathway. The presented rule of the dominant reaction pathway is that the [2+2] cycloaddition effect of the two reactants leads to the formation of a four-membered ring silylene (INT1). When the four-membered ring silylene (INT1) interacts with ethene, due to sp³ hybridization of the Si: atom in four-membered ring silylene (INT1), the four-membered ring silylene (INT1) further combines with ethene to form a silicic bis-heterocyclic com­pound (P2).

 

Keywords: silylenesilylene (H₂Si=Si:); cycloaddition reaction; potential energy profile.

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J. Serb. Chem. Soc. 77 (1) 83–94 (2012)

UDC 665+664.2+54–148:546.33’26:547.461.6–312:532.135.004.12; JSCS–4251; doi: 10.2298/JSC100630150K; Original scientific paper

 

Influence of the sodium dodecyl sulphate (SDS) concentration on the disperse and rheological characteristics of oil-in-water emulsions stabilized by octenyl succinic anhydride modified starch–SDS mixtures

VELJKO KRSTONOŠIĆ, LJUBICA DOKIĆ*, IVANA NIKOLIĆ*, TAMARA DAPČEVIĆ** and MIROSLAV HADNAĐEV**

Faculty of Medicine, Department of Pharmacy, University of Novi Sad, Hajduk Veljkova 3, 21000 Novi Sad, Serbia

*Faculty of Technology, University of Novi Sad, Bul. cara Lazara 1, 21000 Novi Sad, Serbia

**Institute for Food Technology, Bul. cara Lazara 1, 21000 Novi Sad, Serbia

 

(Received 30 June 2010, revised 7 February 2011)

Stability of oil-in-water emulsions can be achieved by chemically modified starch, such as octenyl succinic anhydride (OSA) starch, as an emul­sifier. In order to analyse the disperse and rheological characteristics of emul­sions containing two kinds of emulsifiers, part of the OSA starch can be sub­stituted with an adequate concentration of sodium dodecyl sulphate (SDS), which is a small surfactant with the sAMe charge as OSA starch. The oil con­tents of the exAMined emulsions were 5, 20 and 50 %. The selected OSA starch concentration was 10 % and replacements of a part of the OSA starch were realized with SDS concentrations of 1, 3 and 5 %. Dispersed droplets of emul­sions were defined by determination of the Sauter mean diAMeter d32 and par­ticle size distribution. Flow curves were used to describe the rheological pro­perties of the emulsions. In addition, the stability of the emulsion sAMples was observed and expressed by the creAMing index. The obtained results indicated a decrease in the Sauter mean diAMeter of the droplets, the standard deviation and the apparent viscosity of the emulsions with increasing AMounts of SDS within the emulsifier mixture OSA starch–SDS. According to creAMing rate, the emulsions with OSA starch were more stable than the emulsions stabilized by the OSA starch and SDS combinations.

 

Keywords: oil/water emulsions; octenyl succinic anhydride starch; sodium do­decyl sulphate, rheology; disperse characteristics.

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J. Serb. Chem. Soc. 77 (1) 95–104 (2012)

UDC 547.99:541.121:536.7:537.322:543 JSCS–4252; doi: 10.2298/JSC100821151G; Original scientific paper

 

Determination of epinephrine by a Briggs–Rauscher oscillating system using a non-equilibrium stationary state

Jinzhang Gao, Yanjun Liu, Jie Ren, Xiaoli Zhang, Ming Li and Wu Yang

Chemistry &AMp; Chemical Engineering College, Northwest Normal University, Lanzhou 730070, P. R. China

 

(Received 21 August 2010, revised 9 July 2011)

A highly sensitive method for the determination of epinephrine is proposed, which is based on the perturbation of epinephrine to a Briggs–Rau­scher oscillating system involving malonic acid, Mn²⁺, H⁺, IO₃^- and H₂O₂ at a non-equilibrium stationary state. The concentration of KIO3 was chosen as a control parAMeter to find the bifurcation point in this study. The results showed that a good linear relationship between the difference in the potential and the negative logarithm of the concentrations of epinephrine existed in the range 1.1×10^-7–5.2×10^-9 mol L^-1 with a lower detection limit of 6.8×10^-10 mol L^-1 and a correlation coefficient of 0.9974. Compared to the classical oscillating reaction, this method has a lower detection limit and a wider linear range. The effects of some foreign species, which may possibly exist with epinephrine, on determination were also investigated. The proposed method was successfully used to determine epinephrine both in serum and adrenaline hydrochloride injection.

 

Keywords: Briggs–Rauscher oscillating system; epinephrine; determination; non-equilibrium stationary state.

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J. Serb. Chem. Soc. 77 (1) 105–117 (2012)

UDC 546.47/.49+546.56+546.815+551.463/.464:597(497.16); JSCS–4253; doi: 10.2298/JSC110323159J; Original scientific paper

 

Accumulation of trace metals in marine organisms of the southeastern Adriatic coast, Montenegro

DANIJELA JOKSIMOVIć and SLAVKA STANKOVIć*

Institute of Marine Biology, University of Montenegro, Dobrota bb, 85330 Kotor, Montenegro

Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

 

(Received 23 March, revised 13 April 2011)

The concentration and accumulation of trace metals (Co, Ni, As, Cd, Pb and Hg) were measured in seawater, sediments and marine organisms on the coastline of Montenegro. The obtained results of trace metals in sea grass and mussels were compared with those found in the water column and sediment. SAMpling was performed in the fall of 2005 at five locations on the Monte­negrin coastline, Sveta Stasija, Herceg Novi, Zanjice, Budva and Bar, which present different levels and sources of human impact. The heavy metals ana­lyses of seawater, sediment, Posidonia oceanica and Mytilus galloprovincialis identified the harbor of Bar as the most Hg-contAMinated site, Zanjice as the most As-contAMinated and Sveta Stasija as the most Pb-contAMinated areas of the Montenegrin coastal area. This study showed that P. oceanica may have a greater bioaccumulation capacity than M. galloprovincialis for the considered metals, except for As and Hg, and both organisms may reflect contAMination in the water column and in the sediment. For the first time, the sea grass P. ocea­nica and M. galloprovincialis were employed as metal bioindicators for the southeastern Adriatic. The results of this study could serve as a baseline for future assessments of anthropogenic effects in this marine ecosystem.

 

Keywords: heavy metals; seawater; sediment; marine organisms; biomoni­toring; Montenegro.

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J. Serb. Chem. Soc. 77 (1) 119–129 (2012)

UDC 504.53.054+546.76:66.061.34:550.4+550.8.013; JSCS–4254; doi: 10.2298/JSC101216154A; Original scientific paper

 

Leaching of chromium from chromium contAMinated soil – a speciation study and geochemical modelling

DARKO H. ANDJELKOVIĆ, TATJANA D. ANDJELKOVIĆ*, RUŽICA S. NIKOLIĆ*, MILOVAN M. PURENOVIĆ*, SRDJAN D. BLAGOJEVIĆ**, ALEKSANDAR Lj. BOJIĆ* and MILICA M. RISTIĆ

Water Works Association “Naissus”, Kneginje Ljubice 1/I, 18000 Niš, Serbia

*Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia

**Faculty of Agriculture, University of Belgrade, Nemanjina 16, 11081 Belgrade, Serbia

 

(Received 16 December 2010, revised 20 February 2011)

The distribution of chromium between soil and leachate was mo­nitored. The natural process of percolation of rainwater through soil was simulated under laboratory conditions and studied by column leaching ex­traction. Migration of chromium in soil is conditioned by the level of chro­mium soil contAMination, the organic matter content in the soil and rain­water acidity. Chromium(III) and chromium(VI) were determined by a spectrophoto­metric method with diphenylcarbazide in acidic media. Com­paring the results of chromium speciation in the leachate obtained by experi­mental model sys­tems and geochemical modelling calculations using the Visual MINTEQ mo­del, a correlation was observed regarding the influence of the tested para­me­ters. Leachate solutions showed that the concentration of Cr depended on the organic matter content. The influences of pH and soil organic matter content were in compliance after their experimental and theo­retical definition. The Stockholm humic model used to evaluate the leach­ing results corresponded rather well with the measured values.

 

Keywords: chromium; speciation; leaching; rainwater; soil organic content.

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February 02, 2012.
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