IAEDANS

IAEDANS
Names
Preferred IUPAC name
5-{[2-(2-Iodoacetamido)ethyl]amino}naphthalene-1-sulfonic acid
Other names
5-[2-[(2-Iodo-1-oxoethyl)amino]ethylamino]-1-naphthalenesulfonic acid
1,5-IAEDANS
Identifiers
CAS Number
  • 36930-63-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:58984 checkY
ChemSpider
  • 82727 checkY
ECHA InfoCard 100.048.418 Edit this at Wikidata
PubChem CID
  • 91621
UNII
  • 6V7G304M5M checkY
CompTox Dashboard (EPA)
  • DTXSID10190421 Edit this at Wikidata
InChI
  • InChI=1S/C14H15IN2O4S/c15-9-14(18)17-8-7-16-12-5-1-4-11-10(12)3-2-6-13(11)22(19,20)21/h1-6,16H,7-9H2,(H,17,18)(H,19,20,21) checkY
    Key: ZMERMCRYYFRELX-UHFFFAOYSA-N checkY
  • InChI=1/C14H15IN2O4S/c15-9-14(18)17-8-7-16-12-5-1-4-11-10(12)3-2-6-13(11)22(19,20)21/h1-6,16H,7-9H2,(H,17,18)(H,19,20,21)
    Key: ZMERMCRYYFRELX-UHFFFAOYAI
  • O=S(=O)(O)c1cccc2c1cccc2NCCNC(=O)CI
Properties
Chemical formula
C14H15IN2O4S
Molar mass 434.25 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

IAEDANS is an organic fluorophore (fluorescent molecule).[1] It stands for 5-({2-[(iodoacetyl)amino]ethyl}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 (DMF) or buffer above pH 6 and reacts primarily with thiols.

The absorption spectrum IAEDANS overlaps well with the emission spectrum of tryptophan, making it useful as an acceptor in FRET experiments. It can also be used as a resonance energy donor to fluorophores such as fluorescein, Alexa Fluor 488, Oregon Green, and BODIPY FL.

References

  1. ^ Takashi, R; Duke, J; Ue, K; Morales, M.F (1976). "Defining the "fast-reacting" thiols of myosin by reaction with 1,5 IAEDANS". Archives of Biochemistry and Biophysics. 175 (1): 279–83. doi:10.1016/0003-9861(76)90509-9. PMID 133635.
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