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H 2 N
O
O
H 2 N
H 3 C
O
O
O
COOH
O
N
O
+
O
m
NH
O
H
O
N
n
H 2 N
0°C-RT
O
(1)
0.1 M NaHCO 3
pH 7.5
NH 2
H 2 N
Cy5.5
H 2 N
HN
Cy5.5
COOH
HN
O
COOH
NH
O
H
O
(2 ) Cy5.5-NHS
NH
O
HN
n
H
O
pH 7.8, 0°C-RT
HN
n
O
O
HN
O
O
O
O
O
O
HN
O
O
O
O
O
O
O
O
m
CH 3
O
O
m
CH 3
O
O
m
CH 3
O
m
CH 3
1) (ICH 2 CO) 2 O
2) GPLGVRGC(Et)K(FITC)CNH 2
(3)
3) Cy5.5-NHS
Cy5.5 -HN-GP LGVR GC(Et)K(FITC)CNH 2
S
Cy5.5
-HN-GP
LGVR
GC(Et)K(FITC)CNH 2
O
S
HN
O
HN
COOH
O
NH
O
H
N
HN
n
O
O
O
HN
O
O
O
O
O
O
O
m
CH 3
O
m
CH 3
Figure 9.5 A schema of PGC-based probe synthesis:
(1)
synthesis of MPEG-bPLL;
(2)
synthesis of cathepsin B/H/L-cleavable PGC-Cy5.5; and
multistep synthesis of
MMP-cleavable PGC carrying peptide linkers with MMP-specific LGVR amino acid se-
quences (shown in italics). Peptide bonds cleavable by cathepsins are shown with an
arrow. Esterase-cleavable bonds are shown with an arrowhead.
(3)
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