IAEDANS is an organic
fluorophore
A fluorophore (or fluorochrome, similarly to a chromophore) is a fluorescent chemical compound that can re-emit light upon light excitation. Fluorophores typically contain several combined aromatic groups, or planar or cyclic molecules with ...
(
fluorescent
Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation. It is a form of luminescence. In most cases, the emitted light has a longer wavelength, and therefore a lower photon energy, th ...
molecule
A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bio ...
).
It stands for 5-(amino)naphthalene-1-sulfonic acid. It is widely used as a marker in fluorescence spectroscopy.
1,5-IAEDANS has a peak excitation wavelength of 336 nm and a peak emission wavelength of 490 nm. The extinction coefficient of the dye is 5700. It is soluble in
dimethylformamide
Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the maj ...
(DMF) or buffer above pH 6 and reacts primarily with
thiol
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...
s.
The absorption spectrum IAEDANS overlaps well with the emission spectrum of
tryptophan
Tryptophan (symbol Trp or W)
is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromati ...
, making it useful as an acceptor in
FRET
A fret is any of the thin strips of material, usually metal wire, inserted laterally at specific positions along the neck or fretboard of a stringed instrument. Frets usually extend across the full width of the neck. On some historical instru ...
experiments. It can also be used as a resonance energy donor to fluorophores such as
fluorescein
Fluorescein is an organic compound and dye based on the xanthene tricyclic structural motif, formally belonging to triarylmethine dyes family. It is available as a dark orange/red powder slightly soluble in water and alcohol. It is widely use ...
, Alexa Fluor 488, Oregon Green, and
BODIPY
BODIPY is the technical common name of a chemical compound with formula , whose molecule consists of a boron difluoride group joined to a dipyrromethene group ; specifically, the compound 4,4-difluoro-4-bora-3a,4a-diaza-''s''-indacene in the ...
FL.
References
Sulfonic acids
Fluorescent dyes
Organoiodides
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