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09278

Sigma-Aldrich

4-[4-(Dimethylamino)phenylazo]benzoic acid N-succinimidyl ester

≥98.0% (HPLC)

Synonym(s):

4-(Dimethylamino)azobenzene-4′-carboxylic acid N-succinimidyl ester, DABCYL-N-succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):
C19H18N4O4
CAS Number:
146998-31-4
Molecular Weight:
366.37
MDL number:
MFCD00467415
UNSPSC Code:
12352108
PubChem Substance ID:
329748752
NACRES:
NA.32

Assay

≥98.0% (HPLC)

form

powder

solubility

DMF: soluble
DMSO: soluble

fluorescence

λex 428 nm; λem 453 nm

storage temp.

−20°C

SMILES string

CN(C)c1ccc(cc1)\N=N\c2ccc(cc2)C(=O)ON3C(=O)CCC3=O

InChI

1S/C19H18N4O4/c1-22(2)16-9-7-15(8-10-16)21-20-14-5-3-13(4-6-14)19(26)27-23-17(24)11-12-18(23)25/h3-10H,11-12H2,1-2H3/b21-20+

InChI key

IBOVDNBDQHYNJI-QZQOTICOSA-N

Application

A useful reagent (similar to MANCYL-SE) for labeling proteins or peptides through their amino-groups by forming stable peptide bonds. The succinimidyl ester is reactive with terminal amines or lysines of peptides and other nucleophiles for fluorescent studies of proteins. Its fluorescent properties (has a characteristic broad and intense visible absorption but has no fluorescence) make it an ideal long wavelength quencher and it has been utilized as an acceptor chromophore in FRET studies.

Analysis Note

Absorption spectra shows a maximum at 453 nm (in methanol). After reaction with butylamine: max. absorption at 428 nm (Lit.)

Other Notes

N-terminal modification of peptides in automated synthesis

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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L L Maggiora et al.
Journal of medicinal chemistry, 35(21), 3727-3730 (1992-10-16)
A general scheme for obtaining a fluorescent donor/acceptor peptide substrate via solid-phase synthesis methodology is presented. The key feature of this method is the design of a glutamic acid derivative that has been modified on the carboxyl side chain with
C García-Echeverría et al.
FEBS letters, 297(1-2), 100-102 (1992-02-03)
A series of new substrates for determining the catalytic activity of cysteine proteinases is described. The rate of hydrolysis by papain was monitored by a fluorescence continuous assay based on internal resonance energy transfer using 5-[(2-aminoethyl)amino]naphtalene-1-sulfonic acid (EDANS) and 4-(4-dimethylaminophenylazo)benzoic

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