Chitosan: A Versatile Biomaterial

ELVAN YILMAZ
Department o/Chemistry, Faculty 0/Arts and Sciences, Eastern Medite"anean University,
Famagusta, Northern Cyprus, Mersin 10, TURKEY

1. INTRODUCTION
Chitosan is an amino polysaccharide with a wide range of biomedical
applications in addition to various other uses in food and nutrition, textile
and paper industries, cosmetics, photography and water engineering.
Chitosan is a functional polymer, which is readily soluble in dilute acid
solutions. In contrast to other polysaccharides that are either neutral or
anionic, chitosan acts as a polycation in solution. It has complex fonnation
and ion adsorption properties. Chitosan is a very versatile material in terms
of its chemical, physical and biological properties. It is a non-toxic,
mucoadhesive, biodegradable, and biocompatible polymer.
Biomedical applications of chitosan and its derivatives ranging from
pharmaceutical uses to tissue engineering have been reported. It has been
shown to be useful in oral, injectable, nasal, ophthalmic, transdermal, and
implantable drug administration fonns. It has also been found to act as a
drug absorption enhancer, hypocholesterolemic agent, a wound-healing
accelerator, a blood anticoagulant, and an antimicrobial agent. Its film
forming property has been exploited in the design of artificial kidney
membranes and artificial skin. More recent biomedical applications of
chitosan include protein, gene, and vaccine delivery, owing to its
microparticle and complex forming abilities together with its
mucoadhesivity. Porous chitosan scaffolds have proven to be promising for
use in cell transplantation and tissue regeneration.

Biomaterials: From Molecules to Engineered Tissues, edited by

N. HasJrci and V. Haslrcl, Kluwer AcademicIPlenum Publishers, 2004 59
60 Elvan Yilmaz

2. SOURCES AND PREPARATION OF CHITIN AND

CHITOSAN

The precursor of chitosan is chitin, the second most abundant

polysaccharide in nature after cellulose. Cellulose is mainly synthesized in
plants, while chitin is synthesized mainly in lower animals. It is estimated
that about 10 giga tons of chitin are produced and degraded in the biosphere
each year. Chitin is found in the outer shells of crustaceans such as crabs and
shrimps. These shells contain 20-50% chitin on a dry weight basis. Chitin is
isolated from crab and shrimp waste available from seafood processing
industries. Other potential sources of chitin production include krill,
crayfish, insects, clams, oysters, jellyfish, algae and fungi. Chitin found in
crustacean shells is known as a-chitin. Squid pens also contain chitin that is
known as ~-chitin. Chitosan is commonly produced by deacetylation of a-
chitin in 40-50% aqueous alkali solution, usually sodium hydroxide, at 60-
120°C for a few hours Chitosan obtained in this way may have a degree of
deacetylation up to 0.95 1•

3. PHYSICO-CHEMICAL PROPERTIES OF
CIDTOSAN

Biological properties and activities of chitosan depend largely on its

physicochemical properties such as the degree of deacetylation, crystallinity,
molecular weight, and high charge density in solution, as well as chemical
reactivity and ease of fabrication into different forms.
The chemical structure of chitin is similar to that of cellulose having
acetamide (-NH-CO-CH3) groups at C-2 positions instead of the hydroxyl
groups (-OH) present in cellulose. Chitosan is the deacetylated form of chitin
in which a fraction of acetamide groups have been replaced with
amine (-NH2) groups. Chitin is a polymer of ~ (1-+ 4) linked 2-acetamido-2-
deoxy-D-glucose units while chitosan is a copolymer of ~ (1-+4) linked to 2-
acetamido-2-deoxy-D-glucose and 2-amino-2-deoxy-D-glucose units.
Chemical structure of chitosan is shown in Figure 1. The degree of
deacetylation of polymers cited as chitosan changes between 40 to 100%.
The presence of amino groups in chitosan structure is an advantage over
cellulose since it provides it with a chemical activity suitable for a wider
range of modification reactions and a unique biological functionality.
The degree of deacetylation of chitosan can be determined by elemental
analysis, hydrolysis of acetamide groups, titration of free amine groups, dye
adsorption, IR, UV-VIS or NMR spectroscopy' 3. Metal adsorption capacity
of chitosan depends largely on the degree of deacetylation. Free amine