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D9689

Sigma-Aldrich

DABCYL SE

solid

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Synonym(s):
4-([4-(Dimethylamino)phenyl]­azo)­benzoic acid succinimidyl ester
Empirical Formula (Hill Notation):
C19H18N4O4
Molecular Weight:
366.37
MDL number:
MFCD00467415
UNSPSC Code:
12171500
PubChem Substance ID:
24894321

form

solid

mol wt

apparent mol wt 366.38

shipped in

dry ice

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

Non-fluorescent acceptor in fluorescent resonance energy transfer applications.
This succinimidyl ester is useful for preparation of quenched fluorogenic substrates for proteases.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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E D Matayoshi et al.
Science (New York, N.Y.), 247(4945), 954-958 (1990-02-23)
The 11-kD protease (PR) encoded by the human immunodeficiency virus 1 (HIV-1) is essential for the correct processing of viral polyproteins and the maturation of infectious virus, and is therefore a target for the design of selective acquired immunodeficiency syndrome
J O Capobianco et al.
Analytical biochemistry, 204(1), 96-102 (1992-07-01)
A fluorescent method for monitoring the activity of the secreted Candida carboxyl (aspartic) proteinase (EC 3.4.23.6) was developed using a fluorogenic substrate based on resonance energy transfer. The fluorescent assay was used to monitor proteinase production, purification, and inhibition. The
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
Automated Synthesis of Fluorogenic Protease Substrates: Design of Probes for Alzheimers Disease-Associated Proteases.
Wang, G.T., et al.
Bioorganic & Medicinal Chemistry Letters, 2, 1665-1665 (1992)
M W Pennington et al.
Peptide research, 7(2), 72-76 (1994-03-01)
Interleukin 1 beta converting enzyme (ICE) is responsible for processing an inactive 31-kDa precursor to the active, mature 17-kDa Il-1 beta with cleavage occurring between the Asp116-Ala117 amide bond. We have prepared a peptide substrate that contains the protease cleavage

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