Fluorescent Environment-Sensitive Dyes as Reporters of Biomolecular Interactions - Progress in Molecular Biology and Translational Science - page 40

Table 2.1 Properties of common solvatochromic fluorescent dyes a

Apolar
solvent
(Toluene)

Polar solvent
(MeOH)

l Abs (nm)
(MeOH)

« max
(MeOH)

l Fluo
(nm)

QY
(%)

l Fluo
(nm)

QY
(%)

D n Fluo
(cm - 1 ) Dye Refs.

308 b 695 c 0.1 c 476 Fluoroprobe 12,000 46 6620 14

<

FR0 396 43,000 570 19 434 98 5500 15

Dapoxyl Ò
derivatives

373 28,000 584 39 457 86 4760 16

Prodan 361 18,400 498 51 417 55 3900 17

3MC-2 445 29,000 597 1.4 485 68 3870 18

6DMN 382 8000 589 1.2 491 21 3390 19

12,100 d Anthradan 456 604 41 507 58 3170 20

12 e 457 c 62 c 4DMP 396 6500 534 3160 21

Dansyl
derivatives

335 4600 526 49 471 81 2220 22

Nile Red 553 45,000 632 38 569 90 1750 23

NBD 465 22,000 541 - 529 - 420 24

a

l Abs , absorption maximum; e max , absorption coefficient (M -1 cm -1 ); l Fluo , fluorescence maximum; QY,
fluorescence quantum yield; MeOH, methanol; d n Fluo , band shift in response to change of solvent from
toluene to methanol.
b

Data in cyclohexane.
c Tetrahydrofuran.
d

Acetonitrile.

e
Dioxane.

brightness and red-shifted absorption, together with high fluorescence
solvatochromism.
To label biomolecules with solvatochromic dyes, their amino or thiol-
reactive derivatives are commonly used. In solvatochromic labels, the
fluorophore should be connected to the reactive group through the shortest
possible linker, in order to localize it precisely at the labeling site of a
biomolecule of interest. However, the most efficient method of site-specific
protein labeling corresponds to the direct introduction of the amino acid
derivative of the solvatochromic dye into the peptide. This can be achieved
by solid-state peptide synthesis or by using cellular protein synthesis