JSCS Vol 73, No. 8-9
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J. Serb. Chem. Soc. 73 (8–9) 771–780 (2008)
UDC
547.466.1:547.538–32:547.233:66.097.8; JSCS–3760; doi: 10.2298/JSC0809771F; Original scientific paper
Synthesis of 2-{[2-(2-oxo-1-azacycloalkyl)acetAMido]phenoxy}acetic
acids and their activity as AMinopeptidase M inhibitors
OLDŘICH FARSA, MILAN DOČKAL, JANA KOVÁČIKOVÁ* and MÁRIA BENEŠOVÁ*
Institute of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and
Pharmaceutical Sciences Brno, Palackého 1/3, 612 42 Brno, Czech Republic
*Department of Cellular and Molecular Biology of
Drugs, Faculty of Pharmacy, Comenius University, Kalinčiakova 8, 832 32
Bratislava, Slovak Republic
(Received 21 February, revised 9 May
2008)
A series of 9 phenoxyacetic acids substituted in the o-, m-,
and p-position of benzene ring with
2-(2-oxo-1-azacycloalkyl)acetAMidic moiety containing 5–7-membered w-lactAM
ring was prepared by a 4-step synthetic pro¬cedure. Five selected substances of this series were
tested in vitro for inhibition of
porcine kidney AMinopeptidase M. 2-{4-[2-(2-Oxoperhydroazepin-1-yl)acetAMido]phenoxy}acetic acid exhibited the highest
activity with Ki = 243.6 mM.
Keywords: w-lactAMs; phenoxyacetic acids; AMinopeptidase
M; inhibition.
Full
Article - PDF 395 KB
J. Serb. Chem. Soc. 73 (8–9) 781–791 (2008)
UDC 547.78:615.212:615.276:577.115–39;
JSCS–3761; doi: 10.2298/JSC0809781H;
Original scientific paper
Synthesis of 1-(4-phenoxyphenyl)-3-[5-(substituted
aryl)-1,3,4-oxadiazol-2-yl]propan-1-ones as safer anti-inflAMmatory and
analgesic agents
ASIF HUSAIN, F. J. AHMAD*, MOHD AJMAL and PRIYANKA AHUJA
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, JAMia HAMdard
(HAMdard University), New Delhi–110062, India
*Department of Pharmaceutics, Faculty of Pharmacy,
JAMia HAMdard (HAMdard University), New Delhi–110062, India
(Received 18 September 2007, revised 9
May 2008)
A novel series of
1-(4-phenoxyphenyl)-3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]propan-1-one
was synthesized by reaction of 3-(4-phenoxybenzoyl)propionic acid with several
aryl acid hydrazides in phosphorus oxychloride. The structures of the compounds
were supported by IR, 1H- and 13C-NMR, MS data and
elemental analysis results. These compounds were tested for their
anti-inflAMmatory, analgesic, ulcerogenic and lipid peroxidation actions. A few
compounds were found to have very good anti-inflAMmatory activity in the
carrageenan-induced rat paw edema test, while a fair number of the compounds
showed significant analgesic activity in the acetic acid-induced writhing test.
These new compounds showed very low ulcerogenic action with reduced
malondialdehyde content (MDA), which is one of the by-products of lipid
peroxidation.
Keywords: 1,3,4-oxadiazole;
anti-inflAMmatory; analgesic; ulcerogenic; lipid peroxidation.
Full Article - PDF 388 KB
J. Serb.
Chem. Soc. 73 (8–9) 793–804 (2008)
UDC 577.175.2:577.354; JSCS–3762; doi:
10.2298/JSC0809793M; Original scientific paper
Lectin-induced alterations of the
interaction of insulin and insulin-like growth factor 1 receptors with their
ligands
ROMANA MASNIKOSA, ANNA J. NIKOLIC and OLGICA NEDIC
INEP – Institute for the Application of
Nuclear Energy, University of Belgrade, Banatska 31b, 11080
Belgrade, Serbia
(Received 16 October 2007, revised 15 January 2008)
In order
to study whether the carbohydrate moieties of the human placental IGF-I
receptor (IGF1R), IGF-II receptor (IGF2R) and insulin receptors (IRs) play a
role in ligand binding, solubilised cell membrane preparations were incubated
with 125I-labelled IGF-I, IGF-II and insulin in the presence of
lectins with different sugar specificities. Three incubation procedures were
tested: ligand-first, co-incubation and lectin-first incubation. Wheat germ
agglutinin (WGA), concanavalin A (Con A) and phytohaemagglutinin (PHA) altered
the binding of IGF-I and insulin to their high-affinity receptors in a lectin
specific and dose-dependent manner, whereas these lectins did not affect the
interaction of IGF-II with its receptor(s). Moreover, the sAMe lectins either
inhibited or enhanced IGF-I and insulin binding, depending on the incubation
scheme. These results also suggest that IR-A and IR-B from human placenta might
be differently glycosylated.
Keywords:
IGF1R; IGF2R; IR; WGA; Con A; PHA.
Full Article - PDF 655 KB
J. Serb. Chem. Soc. 73 (8–9) 805–813 (2008)
UDC 577.112:54.02:519.2; JSCS–3763; doi:
10.2298/JSC0809805P;
Original scientific paper
Structural features of proteins as
reflected by statistical scaling laws
LAURA PITULICE, ADRIANA ISVORAN and ADRIAN CHIRIAC
Department of Chemistry, West University of Timisoara, 16 Pestallozi, 300115,
Timisoara, Romania
(Received 31 December 2007, revised 28
March 2008)
Within this paper, statistical scaling laws for the
radius of gyration with the residues number, the surface area with the probe
radii and the backbone length with the interval of residues for a set of 60
proteins are revealed. The proteins belong to three different structural
classes: alpha, beta and alpha plus beta class (20 proteins for each)
according to the SCOP database classification, which takes into account the
composition in the elements of their secondary structure. The shape and the
surface roughness of proteins seem to be independent of the protein content in
the secondary structure elements. On the contrary, the protein packing density
shows a strong correlation with this composition.
Keywords: protein; backbone; fractal dimension; radius of
gyration; scaling law.
Full Article - PDF 566 KB
UDC
546.472+547.466.23:543.422.25:615.28–188; JSCS–3764; doi:
10.2298/JSC0809815M;
Original scientific paper
Synthesis, NMR, DFT and antimicrobial studies of Zn(II) complexes with N-benzyloxycarbonyl-S-alanine
DRAGANA M.
MITIC, DJENANA U. MIODRAGOVIC, DUSAN M. SLADIC, ZELJKO J. VITNIK, ZORAN M.
MIODRAGOVIC, KATARINA K. ANDJELKOVIC, MILANKA Dj. RADULOVIC* and NENAD O.
JURANIC**
Faculty of
Chemistry, University of Belgrade, Studentski trg 12–16, 11001 Belgrade, Serbia
*Centre of Chemistry,
Institute of Chemistry, Technology and Metallurgy, Njegoseva 12, 11000
Belgrade, Serbia
**Mayo Clinic
and Foundation, Rochester, 59905 Minnesota, USA
(Received 23 January, revised 1 April 2008)
In this study, the first complexes of Zn(II) with the N-benzyl-oxycarbonyl-S-alaninato
ligand (N-Boc-S-ala) were synthesized. The new complexes were
characterized by elemental analysis, conductometric measurements, IR, 1H-NMR,
13C-NMR and 2D-NMR spectroscopy. On the basis of the
experimental data, tetrahedral geometry of the Zn(II)
complexes was proposed. A very good agreement between the NMR and DFT
calculated data was obtained. Investigation of antimicrobial activity of the
newly synthesized complexes was also performed. It was established that [Zn(N-Boc-S-ala)2] was selective and acts
only on Candida albicans.
Keywords: antimicrobial activity; DFT;
N-benzyloxycarbonyl-S-alanine; NMR; Zn(II) complexes.
Full Article - PDF 916 KB
J. Serb. Chem. Soc. 73 (8–9) 825–834 (2008)
UDC 547.462.3+541.183:661.183.8; JSCS–3765; doi:
10.2298/JSC0809825G; Original scientific paper
Adsorption of itaconic acid from aqueous solutions onto alumina
JELENA J. GULICOVSKI, LJILJANA S. CEROVIC, SLOBODAN K.
MILONJIC and IVANKA G. POPOVIC*
The Vinča Institute of
Nuclear Sciences, P.O. Box 522, 11001 Belgrade, Serbia
*Faculty of Technology and
Metallurgy, P.O. Box 3503, 11120 Belgrade, Serbia
(Received 18 February 2008)
Itaconic acid, IA (C5H6O4),
was investigated as a potential flocculant for the aqueous processing of
alumina powders. The adsorption of IA, as a function of its concentration and
pH value of the solution, onto the alumina surface was studied by the solution
depletion method. The stability of the suspensions in the presence of itaconic
acid was evaluated in light of the surface charge of the alumina powder used,
the degree of dissociation of IA, as well as the sedimentation behavior and
rheology of the suspensions. It was found that the adsorption process is
extremely pH dependent; the maximum adsorption of IA onto alumina surface
occurring at a pH close to the value of the first IA dissociation constant, pKa1. Also, IA does not
influence the value of the point of zero charge of alumina. It was shown that
IA represents an efficient flocculant for concentrated acidic alumina
suspensions.
Keywords: alumina; itaconic acid;
adsorption; stability; flocculation; suspension.
Full Article - PDF 385 KB
J. Serb. Chem. Soc. 73 (8–9) 835–843 (2008)
UDC 546.185+546.268.5:541.183:549.525.2; JSCS–3766; doi: 10.2298/JSC0809835P; Original
scientific paper
Sorption of phosphates and thiocyanates on isomorphic substituted
Mg/Zn–Al-type hydrotalcites
RODICA PODE,
EVELINE POPOVICI*, LAURA COCHECI, ERIKA REISZ, ELENA MIHAELA SEFTEL* and VASILE
PODE
Faculty of
Industrial Chemistry and Environmental Engineering, University “Politehnica” of
Timisoara, Victoriei Sq. 2, 300006 Timisoara, Romania
*Faculty of
Chemistry, “Al. I. Cuza” University of Iasi, Carol I Blvd. 11, 700506 Iasi,
Romania
(Received 15 April 2007, revised 15 March
2008)
The sorption equilibriums of phosphate and
thiocyanate anions on isomorphic substituted Mg/Zn–Al-type hydrotalcites were
investigated in this study. Langmuir and Freundlich isotherms were used to
interpret the equilibrium data for phosphate. The sorption equilibriums of
phosphate on Mg3Al, Mg2ZnAl and Mg1.5Zn1.5Al
hydrotalcites were well described by the Langmuir isotherm. The highest maximum
sorption capacities for these adsorbents were as follows: 111, 101 and 95 mg g-1.
The equilibrium constant and standard Gibbs energy changes were also calculated
from the sorption data. Standard Gibbs energy changes of about –20 kJ mol-1
indicated that the process might be considered as physical adsorption. The
sorption equilibriums of phosphate on isomorphic substituted sAMples of MgZn2Al
and Zn3Al were well described by the Freundlich isotherm.
Thiocyanate showed a relative low affinity for the studied materials, as
indicated by both the “S”-shaped isotherms and low sorption capacities. The
sorption of phosphate and thiocyanate on the investigated hydrotalcites showed
a continuous decrease of the sorption capacity in the following order: Mg3Al
> Mg2ZnAl > Mg1.5Zn1.5Al > MgZn2Al
> Zn3Al.
Keywords: Mg/Zn–Al-type hydrotalcites; sorption;
equilibrium; phosphate; thiocyanate.
Full Article - PDF 380 KB
J. Serb. Chem. Soc. 73
(8–9) 845–859 (2008)
UDC
546.26–033.5+547.261+66.094.3:546.92+544.478; JSCS–3767; doi:
10.2298/JSC0809845S; Original scientific paper
Influence of surface
morphology on methanol oxidation at a glassy carbon-supported Pt catalyst
S. STEVANOVIC, D.
TRIPKOVIC, A. KOWAL*, D. MINIC**, V. M. JOVANOVIC and A. TRIPKOVIC
ICTM – Center for
Electrochemistry, University of Belgrade, Njegoseva 12, P. O. Box 473, 1100
Belgrade, Serbia
*Institute of Catalysis and
Surface Chemistry, Polish Academy of Science, Krakow, Niezapominajek 8, 30-239,
Poland
**Faculty of Physical
Chemistry, University of Belgrade, Studentski trg 12, 1100 Belgrade, Serbia
(Received 20 December 2007,
revised 14 March 2008)
Platinum supported on
glassy carbon (GC) was used as a model system for studying the influence of the
surface morphology of a Pt catalyst on methanol oxidation in alkaline and
acidic solutions. Platinum was deposited by the potential step method on GC
sAMples from H2SO4 + H2PtCl6
solution under the sAMe conditions with loadings from 10 to 80 mg cm-2.
AFM and STM images
of the GC/Pt electrodes showed that the Pt was deposited in the form of 3D agglomerates
composed of spherical particles. Longer deposition times resulted in increased
growth of Pt forms and a decrease in the specific area of the Pt. The real
surface area of Pt increased with loading but the changes were almost
negligible at higher loadings. Nevertheless, both the specific and mass
activity of platinum supported on glassy carbon for methanol oxidation in
acidic and in alkaline solutions exhibit a volcanic dependence with respect to
the platinum loading. The increase in the activity can be explained by the
increasing the particle size with the loading and thus an increase in the
contiguous Pt sites available for adsorption and decomposition of methanol.
However, the decrease in the activity of the catalyst with further increase of loading
and particle size after reaching the maximum is related to the decrease of
active sites available for methanol adsorption and their accessibility as a
result of more close proximity and pronounced coalescence of the Pt particles.
Keywords: glassy carbon; methanol oxidation; electrochemical
Pt deposition; surface morphology.
Full Article - PDF 859 KB
J. Serb. Chem. Soc. 73
(8–9) 861–870 (2008)
UDC
669.1–492.2+66.087:541.135–32; JSCS–3768, doi:
10.2298/JSC0809861M; Original scientific paper
Electrodeposition of Fe
powder from acid electrolytes
VESNA M. MAKSIMOVIC, LJUBICA J. PAVLOVIC*,
BORKA M. JOVIC** and MIOMIR G. PAVLOVIC*
Institute of Nuclear
Sciences Vinca, University of Belgrade, P.O. Box 522, 11000 Belgrade, Serbia
*Institute of
Electrochemistry ICTM, University of Belgrade, Njegoseva 12, 11000 Belgrade,
Serbia
**Institute for
Multidisciplinary Research, P.O. Box 33, 11030 Belgrade, Serbia
(Received 17 December 2007,
revised 27 February 2008)
Polarization
characteristics of the electrodeposition processes of Fe powders from sulfate
and chloride electrolytes and the morphology of the obtained powders were
investigated. The morphology depended on the anion presence in the electrolyte
but not on the current density in the investigated range. A characteristic
feature of the dendritic powder with cauliflower endings obtained from sulfate
electrolyte is the presence of cone-like cavities and the crystallite
morphology of the powders surface. On the other hand, Fe powders
electrodeposited from chloride electrolyte appear in the form of agglomerates.
A soap solution treatment applied as a method of washing and drying provides
good protection from oxidation of the powders.
Keywords: Fe powder; morphology; polarization diagrAMs.
Full Article - PDF 1.175 KB
J. Serb. Chem. Soc. 73
(8–9) 871–878 (2008)
UDC 546.137–32+543.551:546.11'98+541.135.5; JSCS–3769, doi:
10.2298/JSC0809871D; Original scientific paper
Determination of relative
acidity scales for some dipolar aprotic solvents by coulometry using a
hydrogen–palladium electrode
RADMILA M. DZUDOVIC and LJILJANA N. JAKSIC*
Faculty of Sciences,
University of Kragujevac, Radoja
Domanovica 12, P. O. Box 60, 34000 Kragujevac, Serbia
*Faculty of Mining and
Geology, University of Belgrade, Djusina 7, 11000 Belgrade, Serbia
(Received 30 July 2007,
revised 13 February 2008)
A
coulometric–potentiometric procedure for the determination of relative acidity
scales of acetone, methylethyl ketone, methyl-isobutyl ketone and propylene
carbonate is described. The range of the relative acidity scale of a solvent
was determined from the difference between the half-neutralization potential of
perchloric acid and that of tetrabutylAMmonium hydroxide. The perchloric acid
was generated in situ from a hydrogen–palladium electrode in presence of
sodium perchlorate or tetrabutylAMmonium perchlorate as the supporting
electrolyte. The electrode pairs glass–SCE and (H2/Pd)ind–SCE were applied for the measurement of the
half-neutralization potentials of the acid and base. A wider range of relative
acidity scale of the solvents was obtained with the glass–SCE electrode pair
and tetrabutylAMmonium perchlorate as the sup-porting electrolyte.
Keywords: relative acidity scale; coulometric generation of
perchloric acid; hydrogen–palladium electrode; non-aqueous solvents.
Full Article - PDF 367 KB
J. Serb. Chem. Soc. 73
(8–9) 879–890 (2008)
UDC
615.275:544.4+535.243+543.062:615.1.004.12; JSCS–3770, doi:
10.2298/JSC0809879M; Original scientific paper
Quantitative analysis of
ibuprofen in pharmaceuticals and human control serum using kinetic
spectrophotometry
SNEZANA S. MITIC, GORDANA Z. MILETIC,
ALEKSANDRA N. PAVLOVIC, BILJANA B. ARSIC and VALENTINA V. ZIVANOVIC*
Faculty of Sciences and
Mathematics, Department of Chemistry, University of Nis, Visegradska 33, P. O.
Box 224, 18000 Nis, Serbia
*High Agriculture School,
Cirila i Metodija 1, 18400 Prokuplje, Serbia
(Received 3 October 2007,
revised 25 March 2008)
The aim of this work was to
develop a new kinetic spectrophoto-metric method for the determination of
ibuprofen in pharmaceutical for-mulations. Ibuprofen was determined in an
acidic ethanolic medium by monitoring the rate of appearance of
1-nitroso-2-naphthol, resulting from the displacement by ibuprofen of Co(III) from the tris(1-nitroso-2-naptholato)cobalt(III)
complex. The optimum operating conditions regarding reagent concentrations and
temperature were established. The tangent method was adopted for constructing
the calibration curve, which was found to be linear over the concentration
range 0.21–1.44 and 1.44–2.06 µg ml-1. The optimized conditions
yielded a theoretical detection limit of 0.03 µg ml-1 based on the 3.3 S0
criterion. The interference effects of the usual excipients of powdery drugs,
foreign ions and AMino acids on the reaction rate were studied in order to
assess the selectivity of the method. The developed procedure was successfully
applied for the rapid determination of ibuprofen in commercial pharmaceutical
formulations and human control serum. The unique features of this procedure are
that the determination can be performed at room temperature and the analysis
time is short. The newly developed method is simple, inexpensive and efficient
for use in the analysis of a large number of sAMples.
Keywords: ibuprofen; kinetic spectrophotometry; validation;
pharmaceutical preparation.
Full Article - PDF 400 KB
J. Serb. Chem. Soc. 73
(8–9) 891–913 (2008)
UDC
546.26+539.24:621.315.59:519.17; JSCS–3771, doi:
10.2298/JSC0808891M; Review paper
Carbon nanotubes
SLOBODAN N. MARINKOVIC
Vinca Institute of Nuclear
Sciences, P.O. Box 522, Belgrade, Serbia
(Received 14 March, revised
17 May 2008)
Nanotubes, the last in the
focus of scientists in a series of “all carbon” materials discovered over the last
several decades are the most interesting and have the greatest potential. This
review aims at presenting in a concise manner the considerable AMount of
knowledge accumulated since the discovery of this AMazing form of solid carbon,
particularly during the last 15 years. The topics include methods of synthesis,
mathematical description, characterization by RAMan
spectroscopy, most important properties and applications. Problems related to
the determination of CNT properties, as well as difficulties regarding their
applications, in particular scaling, which would lead to their utilization, are
outlined.
Keywords: carbon nanotubes; single-wall nanotubes;
multi-wall nanotubes; intercalation; doping; graphene.
Full Article - PDF 676 KB
J. Serb. Chem. Soc. 73
(8–9) 915–921 (2008)
UDC
678.744+66.095.26:541.131:536.7; JSCS–3772, doi:
10.2298/JSC0809915K; Short communication
Short communication
The thermal stability of poly(methyl methacrylate) prepared by RAFT polymerisation
LYNNE KATSIKAS, MILENA AVRAMOVIC, RUBÉN DARÍO
BETANCOURT CORTÉS, MILOŠ MILOVANOVIC*, MELINA T. KALAGASIDIS-KRUSIC and IVANKA
G. POPOVIC
Faculty of Technology and
Metallurgy,University of Belgrade, Belgrade, Searbia
*Institute of Chemistry,
Technology and Metallurgy, University of Belgrade, Belgrade, Serbia
(Received 10 June 2008)
Poly(methyl methacrylate), PMMA,
was prepared by reversible addition–fragmentation chain transfer, RAFT,
polymerisation using 2-(2-cyanopropyl)-dithiobenzoate, CPDB, as the RAFT agent.
The thermal stability of the resulting polymer approached that of anionically
prepared PMMA, as determined by thermogravimetry. This was the consequence of
the RAFT prepared polymer having no head-to-head links and no chain end double
bonds, which are responsible for the relatively low thermal stability of
radically prepared PMMA.
Keywords: thermogravimetry; stability; RAFT; PMMA.
Full Article - PDF 332 KB
J. Serb. Chem. Soc. 73 (8–9)
923–934 (2008)
UDC
504.55.054:549.25:613.001.24(497.11); JSCS–3773, doi:
10.2298/JSC0809923G; Original scientific paper
Potential health risk
assessment for soil heavy metal contAMination in the central zone of Belgrade
(Serbia)
IVAN GRZETIC and RABIA H. AHMED GHARIANI
University of Belgrade –
Faculty of Chemistry, Studentski trg 16, 11000 Belgrade, Serbia
(Received 17 March, revised
14 May 2008)
An investigation of the
soil quality in the centre of Belgrade was performed to define how seriously
the soil is polluted. On the basis of the heavy metal content (Zn, Cd, Pb, Co,
Ni, Cu, Cr and Mn), the potential health risk assessment calculated for a
lifetime of exposure (ingestion and inhalation), based on the USEPA model, was
determined as the cumulative carcinogenic and non-carcinogenic risk for
children and adults. The study proved that soil contAMination in Belgrade is
not insignificant; risk assessment indicated that the carcinogenic risk is
completely insignificant but the cumulative non-carcinogenic risk tends to
becAMe significant, mainly for children, since it approaches unacceptable
values. There is no particularly dangerous single heavy metal, but their
cumulative effect, expressed as Child Soil Ingestion Hazardous Index, is for
concern.
Keywords: health risk assessment; soil pollution; heavy
metals; Belgrade.
Full Article - PDF 462 KB
Full Article - PDF 119 KB
Copyright
&AMp; copy; SHD 2008.
August 14, 2008.
For more information contact: JSCS@tmf.bg.ac.yu