Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 5, pp. 931−934.
Pleiades Publishing, Ltd., 2009.
Original Russian Text
R.Kh. Mudarisova, E.I. Kulish, S.V. Kolesov, Yu.B. Monakova, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 5,
A Study of the Interaction of Chitosan with Cefazolin
R. Kh. Mudarisova
, E. I. Kulish
, S. V. Kolesov
, and Yu. B. Monakova
Institute of Organic Chemistry, Ufa Scientiﬁ c Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia
Bashkir State University, Ufa, Bashkortostan, Russia
Received October 8, 2008
Abstract—Some aspects of the complexation of chitosan with an antibiotic cefazolin were studied. The optimal
conditions for synthesis of the complexes were found. Their composition and physicochemical properties were
Chitosan, a polyaminosaccharide of natural origin,
possesses a number of unique properties, owing to which
it ﬁ nds wide use in medicine. The solubility of chitosan in
weakly acid aqueous solutions, its ﬁ lm-forming capacity,
and presence of primary amino groups in the composition
of this polysaccharide enable its use for fabrication of
membranes and ﬁ lm coatings containing immobilized
medicinal compounds [1–6]. Recently, a considerable
researchers’ attention has been given to analysis of
complexes formed by chitosan and medicinal substances
[7, 8]. The reason is that the biopolymer not only prolongs
the action of medicinal agents, diminishes their toxicity,
and enhances the curing effect, but also provides efﬁ cient
supply of preparations to target organs.
The aim of the study was to analyze the interaction of
chitosan (CTS) with a derivative of cefalosporinic acid,
cefazolin (CFZ), which exhibits an antimicrobial effect
, and to obtain ﬁ lms with controllable release of the
medicinal agent on their basis.
The CTS used in the study was produced from shells
of the Far-Eastern crab and had the following parameters:
initial number-average degree of polymerization Pn 680,
degree of deacetylation 70–75%, and moisture content
4.5%. A pharmaceutical preparation of CFZ was used
without additional puriﬁ cation.
IR spectra of the samples were recorded with Specord-
M 80 and Shimadzu spectrometers (KBr pellets, ﬁ lms) in
the range 700–3600 cm
. UV spectra of all the samples
were recorded relative to water in 1-cm-thick quartz
cuvettes with a Specord M-40 spectrophotometer in the
range 220–350 nm. As solvent served 0.1, 1, 10, and
70% acetic acid (AA).
H NMR spectra were recorded
with a Bruker AM-300 instrument (working frequency
300 MHz, solvent D
O). The pH value of the solutions
was monitored with an ANION 4100 pH-meter.
The interaction products were obtained by mixing
cefazolin and chitosan in acetic acid of various
concentrations (1, 10, 70%) at T = 25°C in the course of
1 h. The compounds synthesized were puriﬁ ed by double
reprecipitation of the reaction solution into isopropanol
(at a 1 : 5 volume ratio of the reaction mixture and
isopropanol), followed by washing of the precipitated
complex with isopropanol. Further, the precipitate was
dried in a vacuum to constant weight.
Films were produced from a 2% solution of the
CTS–CFZ complex, with a 1 : 1 molar ratio of the
components, in 1, 10, and 70% acetic acid by casting
onto glass, with the subsequent drying in air at room
temperature. The thickness of the ﬁ lms was the same
(0.1 mm) in all the experiments. The kinetics of CFZ
release from ﬁ lm samples placed in an aqueous solution
was studied photometrically with a Specord M-40 on
the basis of the absorption band of CFZ at λ = 270 nm.
To preclude dissolution in water, chitosan ﬁ lms were
preliminarily treated with a 5% solution of an anionic
surfactant, sodium dodecyl sulfate. The time of keeping
the ﬁ lms in the surfactant solution was 10 min.