146998-31-4

Basic information

• Product Name: 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER
• Synonyms: DABCYL ACID, SE;DABCYL, SE;DABCYL SUCCINIMIDE ESTER;DABCYL-N-SUCCINIMIDYL ESTER;DABCYL-OSU;DABCYL-NHS;DABCYL N-HYDROXYSUCCINIMIDE ESTER;4-(DIMETHYLAMINO)AZOBENZENE-4'-CARBOXYLIC ACID N-SUCCINIMIDYL ESTER
• CAS NO: 146998-31-4
• Molecular Formula: C₁₉H₁₈N₄O₄
• Molecular Weight: 366.37
• Product Categories: Fluorescent Dyes
• Mol File: 146998-31-4.mol

Chemical Properties

• Melting Point: 242 °C(dec.)
• Boiling Point: 550.702 °C at 760 mmHg
• Flash Point: 286.855 °C
• Appearance: white crystal powder
• Density: 1.306 g/cm³
• Vapor Pressure: 3.56E-12mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO.
• PKA: 3.28±0.10(Predicted)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER(146998-31-4)
• EPA Substance Registry System: 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER(146998-31-4)

Safety Data

• Safety Statements: 24/25
• RIDADR: 3234
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 146998-31-4(Hazardous Substances Data)

Usage

Uses

1. Used in Fluorescent Labeling of Proteins and Peptides:
4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER is used as a non-fluorescent probe for labeling proteins or peptides. Its succinimidyl ester group reacts with terminal amines or lysines of peptides and other nucleophiles, allowing for the fluorescent study of proteins.
2. Used in Fluorescence Resonance Energy Transfer (FRET) Studies:
Due to its fluorescent properties, which include a characteristic broad and intense visible absorption but no fluorescence, 4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER serves as an ideal long wavelength quencher. It has been utilized as an acceptor chromophore in FRET studies, enabling the investigation of protein-protein interactions and conformational changes.
3. Used in Automated Synthesis for N-Terminal Modification of Peptides:
4-((4-(DIMETHYLAMINO)PHENYL)AZO)BENZOIC ACID, SUCCINIMIDYL ESTER is also used for N-terminal modification of peptides in automated synthesis. This application takes advantage of its reactivity with amino groups to introduce specific functional groups or tags to the N-terminus of peptides, which can be useful for various research and diagnostic purposes.

InChI:InChI=1/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+

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 201858-51-7 p-methyl red 

Downstream Products

• 1262962-96-8 C₆₆H₈₀N₇O₅⁽¹⁺⁾*I^(1-) 
• 1262962-97-9 C₆₈H₈₄N₇O₃⁽¹⁺⁾*I^(1-) 
• 1262962-98-0 C₇₀H₈₈N₇O₇⁽¹⁺⁾*I^(1-) 
• 1262962-99-1 C₅₉H₆₇N₆O₂⁽¹⁺⁾*I^(1-) 
• 909729-58-4 C₁₇H₂₁N₅O 
• 146998-27-8 N-α-Fmoc-N-ε-(4,4-dimethylaminoazobenzene-4′carbonyl)-L-lysine 

Relevant articles and documents

Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics

The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans-cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO-linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically relevant concentrations.

ENZYME DETECTION COMPOUND AND MANUFACTURING METHOD OF THE COMPOUND

PROBLEM TO BE SOLVED: To obtain a noel compound for detecting enzyme and a detection method of enzyme using the same and a compound having following structure, R1 and R2 are each independently H, an alkyl group having 1 to 2 carbon atoms, an alkenyl group having 2 carbon atoms or an alkynyl group or a phenyl group having 2 carbon atoms, n is 2 to 12 and X is an amino acid residue. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2018,JPOandINPIT

TUNABLE FLUORESCENCE USING CLEAVABLE LINKERS

The invention relates to cleavable chemistry in general, and in particular, to tunable fluoresence using cleavable linkers present in fluorochrome-quencher conjugates.

Multicolor, one- and two-photon imaging of enzymatic activities in live cells with fluorescently quenched activity-based probes (qABPs)

Fluorescence imaging provides an indispensable way to locate and monitor biological targets within complex and dynamic intracellular environments. Of the various imaging agents currently available, small molecule-based probes provide a powerful tool for live cell imaging, primarily due to their desirable properties, including cell permeability (as a result of their smaller sizes), chemical tractability (e.g., different molecular structures/designs can be installed), and amenability to imaging a wide variety of biological events. With a few exceptions, most existing small molecule probes are however not suitable for in vivo bioimaging experiments in which high-resolution studies of enzyme activity and localization are necessary. In this article, we reported a new class of fluorescently Quenched Activity-Based Probes (qABPs) which are highly modular, and can sensitively image (through multiple enzyme turnovers leading to fluorescence signal amplification) different types of enzyme activities in live mammalian cells with good spatial and temporal resolution. We have also incorporated two-photon dyes into our modular probe design, enabling for the first time activity-based, fluorogenic two-photon imaging of enzyme activities. This, hence, expands the repertoire of smart, responsive probes currently available for live cell bioimaging experiments.

Synthesis of dye-labeled lysine derivatives

The N(ε)-dabcyl-N(α)-(9-fluorenylmethoxy)-carbonyllysine was prepared by reaction of lysine-Cu2+ complex with the N-hydroxysuccinimide (HOSu) activated ester of [4-(4'-dimethylamino)phenylazo]benzoic acid (dabcyl acid) followed by treatment with EDTA and acylation with Fmoc-OSu, and the N(α)tert-butyloxycarbonyl-N(ε)-dabcyllysine was prepared by reaction of N(α)-tertbutyloxycarbonyllysine with dabcyl-OSu.