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Concept of Nowel Bioadhesive Dental Monomers Based on Natural Amino
Acids
Agnieszka Dąbrowska, Mirosław Gibas
Silesian University of Technology, Department of Organic Chemistry, Bioorganic Chemistry
and Biotechnology , ul. Krzywoustego 4, 44-100 Gliwice, Poland
The effective adhesion of restorative resins to mineralized tooth tissue has been a topic of
active research for nearly 50 years.
Dental bioadhesives are a sort of restorative materials destined to provide sealing and
mechanical stabilization of restoration of a hard tooth tissue made from an artificial filling
material. The prefix bio suggests that a material is at least biocompatible, some healing action
towards neighbouring tissue is desirable as well [1].
The dental adhesive systems are composed of various methacrylate monomers and an
initiating systems; the latter may be either a photoinitiator in light-cured systems or
peroxide/tertiary amine in chemically-cured ones.
Marine organisms such as the common blue mussel Mytilus edulis affix themselves to
surfaces by producing a protein-based glue. Bioadhesion of this animal is remarkably strong,
resisting high shear forces, e.g. on ship hulls or rocks on the coastal surf. This ability results
from a specific structure of a mussel adhesive proteins known as MAP, and of a high content
of hydrophilic amino acids, such as hydroxyproline, proline and 3,4-dihydroxyphenylalanine
(DOPA) in this protein.
NH 3
+
HO
HO
CH 2
NH 3
OH
CH 2
CH3
H3 N
+
CH
C
NH
OH
CH 2
CH 2
CH
O
Ala
C
N
CH
C
Pro
OH
O
Ser
OH
HC
H2C
NH CH C NH
O
O
Lys
CH 2
OH
CH 2
CH C
N CH
O
Tyr
CH C N
CH
O
Hyp
CH 2
CH3
C NH CH C
CH 2
NH
Thr
CH 2
CH C
O
O
Hyp
+
CH 2
NH
CH
O
Dopa
COOH
80
Lys
Figure 1. Sequence of MAP [2]
Up to now several promising results have been reported for the use of MAP as an
attachment factor in vitro cell cultures or as bonding adhesive in transplantation surgery. The
aim of our research is to functionalize these natural amino acids with glicydyl methacrylate in
order to use them as novel bioadhesive dental monomers. We suppose that presence of
hydrophilic functional groups, responsible for adhesion to wet dental surface, and carboncarbon double bonds capable of copolymerization with dental composite material should yield
a new dental bioadhesive system.
Keywords: adhesion; biocompatibility; dental monomers; mussel adhesive proteins
[1] Gibas, T. Kupka, M. Tanasiewicz, W. Malec, Macromol. Symp., 210, 237-240 (2004);
[2] J. Schnurrer, C. M. Lehr, Int. J. Pharm., 141, 251-256 (1996).