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useful for imaging vesicle acidification.
135
Linking a cyanine dye that is sus-
ceptible to oxidation to a more stable dye can be used to prepare fluorogenic
sensors for oxidative stress based on FRET.
136
Finally, like many other clas-
ses of dyes, appending chelating moieties such as BAPTA can yield fluo-
rogenic ion sensors based on PeT.
137
Although compounds such as
88
have been prepared,
the
long wavelength of
the
cyanine dye
766/782 nm) decreases the efficiency of the PeT process.
130
Thus, molecule
88
exhibits high basal fluorescence and only a modest
threefold increase in fluorescence upon calcium ion binding.
137
(
l
max
/
l
ΒΌ
em
11. OTHER FLUOROGENIC SCAFFOLDS
11.1. Overview
As shown in
Fig. 1.9
, several other fluorophore types have been used to
construct fluorogenic molecules. Derivatives of polycyclic aromatic com-
pounds such as the pyrene-based 8-hydroxypyrene-1,3,6-trisulfonic acid
(HPTS,
89
) and the amino-naphthalimide Lucifer Yellow (
90
) are widely used
O
NHNH
2
-
O
3
S
OH
O
N
+
H
2
N
O
O
O
N
O
Cl
NH
Cl
N
CO
2
H
N
O
H
-
O
3
S
SO
3
-
O
-
O
3
S
SO
3
-
NH
2
CO
2
-
89
90
91
92
93
Enzyme substrates
Photoactivatable fluorophores
O
O
Cl
Cl
-
O
3
S
O
NH
NH
Cl
Cl
NO
2
N
N
H
2
N
2-
O
3
PO
O
98
94
95
-
O
3
S
SO
3
-
peptide
N
O
O
Indicators
O
N
O
O
N
OH
96
OH
O
HO
O
O
N
N
O
HO
O
NH
100
O
O
NH
2
S
99
N
H
O
OTIPS
97
Figure 1.9 Other scaffolds for fluorogenic molecules.
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