Biomedical Engineering Reference
In-Depth Information
undergoes a substitution reaction with the incoming nucleophile,
forming the desired product [20].
R
1
O
HN
O
O
NH
OH
OH
OH
O
OH
OH
NH
O
NH
O
HO
O
HO
O
HO
O
HO
O
O
O
O
O
O
O
O
HO
O
HO
O
HO
O
O
O
O
NH
NH
OH
O
x
O
O
O
O
O
OH
OH
HN
R
3
R
2
OH
Dopamine
R
1
SH
CDH
SH
Cystamine
HDMA
R
2
NHNH
2
O
OH
S
CH
2 4
NH
2
NH
2
NHNH
2
ADH
S
Tyramine
PDPH
S
N
OH
O
S
VS
O
S
S
Iodine
I
O
O
n
HA
O
O
AEMA
O
O
Aldehyde
R
3
O
H
O
APMA
Glycidyl
methacrylate
O
O
Figure 8.1
Selective primary modification of carboxyl group on
HA. AEMA: 2-aminoethyl methacrylate hydrochloride; ADH:
adipic acid dihydrazide; APMA: 2-aminoethyl methacrylate;
CDH: carbodihydrazide; HDMA: hexane-1,6-diamine; PDPH:
pyridyldithioethylamine; SH: thiol; and VS: vinyl sulfonyl
8.3.1.1 Amidation of Hyaluronic Acid
Small molecule drugs, peptides, polymers and other molecules
containing primary amine groups have been conjugated to HA
via
the above-mentioned EDC chemistry. Some of the examples
are as follows: Darr and Calabro synthesised tyramine-substituted
HA which undergoes enzymatic crosslinking with horseradish
peroxidase and hydrogen peroxide [21]. Oommen and co-workers
prepared doxorubicin (Dox)-HA NP by direct conjugation of the
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