86516-36-1

Basic information

• Product Name: 1-DANSYLPIPERAZINE
• Synonyms: N,N-Dimethyl-5-(piperazin-1-ylsulfonyl)naphthalen-1-amine;1-Naphthalenamine, N,N-dimethyl-5-(1-piperazinylsulfonyl)-
• CAS NO: 86516-36-1
• Molecular Formula: C₁₆H₂₁N₃O₂S
• Molecular Weight: 319.42
• Mol File: 86516-36-1.mol

Chemical Properties

• Melting Point: 130-135 °C
• Boiling Point: 490.727°C at 760 mmHg
• Flash Point: 250.583°C
• Appearance: /
• Density: 1.263g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.633
• PKA: 7.73±0.10(Predicted)
• CAS DataBase Reference: 1-DANSYLPIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-DANSYLPIPERAZINE(86516-36-1)
• EPA Substance Registry System: 1-DANSYLPIPERAZINE(86516-36-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 86516-36-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H21N3O2S/c1-18(2)15-7-3-6-14-13(15)5-4-8-16(14)22(20,21)19-11-9-17-10-12-19/h3-8,17H,9-12H2,1-2H3

Upstream product

• 110-85-0 piperazine 
• 605-65-2 5-(dimethylamino)naphth-1-ylsulfonyl chloride 

Downstream Products

• 548768-67-8 4-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazine-1-carboxylic acid 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl ester 

Relevant articles and documents

Design and synthesis of NBD-S-dye dyads for fluorescently discriminative detection of biothiols and Cys/Hcy

Based on thiolysis of NBD (7-nitro-1,2,3-benzoxadiazole) thioether, we designed and synthesized fast-response fluorescent probes for discriminative detection of biothiols and Cys/Hcy. Probes treated with GSH/H2S could only release one emission; while reactions with Cys/Hcy generated two. Compared with probe 1, probe 2 exhibited good stability and high sensitivity toward Cys/Hcy in PBS buffer. Moreover, 2 could eliminate the effect of probe consumption by GSH/H2S when used to selectively detect Cys/Hcy and was applied for selective bioimaging of Cys in living mammalian cells successfully.

A fluorescent ammonia sensor based on a porphyrin cobalt(II)-dansyl complex

Detecting and measuring the concentration of ammonia is of interest in many scientific and technological areas. A porphyrin based cobalt(II) complex with a dansyl fluorophore has been synthesized and investigated as a 'turn-on' fluorescent ammonia sensor. Over sixfold increase in fluorescence emission occurs upon the treatment of NH3 to [Co(TPP)(Ds-pip)] sensor solution, resulting from NH3-induced displacement of the axially coordinated fluorophore.

Optimization of ASE and SPE conditions for the HPLC-FLD detection of piperazine in chicken tissues and pork

Accelerated solvent extraction (ASE) and solid-phase extraction (SPE) conditions were optimized by a high-performance liquid chromatography-fluorescence detector (HPLC-FLD) method for the detection of piperazine in chicken tissues and pork. Piperazine residues were determined by precolumn derivatization with trimethylamine and dansyl chloride. Samples were extracted with 2% formic acid in acetonitrile using an ASE apparatus and purified using a Strata-X-C SPE column. The monosubstituted product of the reaction of piperazine with dansyl chloride was 1-dansyl piperazine (1-DNS-piperazine). Chromatographic separations were performed on an Athena C18 column (250?×?4.6?mm, id: 5?μm) with gradient elution using ultrapure water and acetonitrile (5:95, V/V) as the mobile phase. The calibration curves showed good linearity over a concentration range of LOQ-200.0?μg/kg with a coefficient of determination (R2)?≥.9992. The recoveries and relative standard deviations (RSD values) ranged from 78.49% to 97.56% and 1.19% to 5.32%, respectively, across the limit of quantification (LOQ) and 0.5, 1, and 2.0 times the maximum residue limit (MRL; μg/kg). The limits of detection (LODs) and LOQs were 0.96 to 1.85?μg/kg and 3.20 to 5.50?μg/kg, respectively. The method was successfully applied for the validation of animal products in the laboratory.

Quantitative fluorescence ratio imaging of intralysosomal chloride ions with single excitation/dual maximum emission

Fluorescence ratio imaging is currently being used to quantitatively detect biologically active molecules in biosystems; however, two excitations of most existing fluorescent ratiometric probes account for cumbersome operating conditions for imaging. Thus

Synthesis and application of asymmetric disulfamide compound

The invention relates to synthesis and application of an asymmetric disulfamide compound. The asymmetric disulfamide compound is a compound of formula (I) (see details in the specification). Tests show that the ultraviolet absorption spectrum of the asymmetric disulfamide compound reacted with cysteine (Cys) has red shift of 100nm, fluorescence at 577nm can be remarkably improved, at the same time, the fluorescence of a solution can be turned yellow from blue, and other amino acids and sulfur-containing compounds are barely affected. In addition, results of response tests in different pH valuesolutions show that Cys can be selectively detected by using the compound within a pH value range of 5-12. Therefore, the compound provided by the invention can be used as a fluorescent probe for detecting Cys.

N?-Acryloyllysine Piperazides as Irreversible Inhibitors of Transglutaminase 2: Synthesis, Structure-Activity Relationships, and Pharmacokinetic Profiling

Transglutaminase 2 (TGase 2)-catalyzed transamidation represents an important post-translational mechanism for protein modification with implications in physiological and pathophysiological conditions, including fibrotic and neoplastic processes. Consequently, this enzyme is considered a promising target for the diagnosis of and therapy for these diseases. In this study, we report on the synthesis and kinetic characterization of N?-acryloyllysine piperazides as irreversible inhibitors of TGase 2. Systematic structural modifications on 54 new compounds were performed with a major focus on fluorine-bearing substituents due to the potential of such compounds to serve as radiotracer candidates for positron emission tomography. The determined inhibitory activities ranged from 100 to 10?000 M-1 s-1, which resulted in comprehensive structure-activity relationships. Structure-activity correlations using various substituent parameters accompanied by covalent docking studies provide an advanced understanding of the molecular recognition for this inhibitor class within the active site of TGase 2. Selectivity profiling of selected compounds for other transglutaminases demonstrated an excellent selectivity toward transglutaminase 2. Furthermore, an initial pharmacokinetic profiling of selected inhibitors was performed, including the assessment of potential membrane permeability and liver microsomal stability.

A fast, highly selective and sensitive dansyl-based fluorescent sensor for copper (II) ions and its imaging application in living cells

Since the copper ions (Cu2+) play a fatal role in many foundational physiological processes, it is important to develop a simple, highly sensitive and selective sensor for Cu2+detection in living systems. Herein, an intramolecular charge transfer (ICT) and dansyl-based fluorescent chemosensor 1 was designed, synthesized and characterized for the sensitive and selective quantification of Cu2+. It exhibited remarkable fluorescence quenching upon addition of Cu2+over other selected metal ions, attributed to the complex formation between 1 and Cu2+with the association constant 6.7?×?105?M?1. The sensor 1 showed a fast and linear response towards Cu2+in the concentration range from 0 to 12.5?×?10?6?mol?L?1with the detection limit of 2.5?×?10?7?mol?L?1. This detection could be carried out in a wide pH range of 5.0–14. Furthermore, sensor 1 can be used for detecting Cu2+in living cells.

TG2 INHIBITOR COMPOUNDS AND USES THEREOF

There are provided Tissue Transglutaminase (TG2) inhibitor compounds, and compositions and methods of use thereof for the prevention or treatment of a cancer. Compounds of Formula I, and pharmaceutically acceptable salts thereof, are provided: Formula (I).

Structure-Activity Relationships of Potent, Targeted Covalent Inhibitors That Abolish Both the Transamidation and GTP Binding Activities of Human Tissue Transglutaminase

Human tissue transglutaminase (hTG2) is a multifunctional enzyme. It is primarily known for its calcium-dependent transamidation activity that leads to formation of an isopeptide bond between glutamine and lysine residues found on the surface of proteins, but it is also a GTP binding protein. Overexpression and unregulated hTG2 activity have been associated with numerous human diseases, including cancer stem cell survival and metastatic phenotype. Herein, we present a series of targeted covalent inhibitors (TCIs) based on our previously reported Cbz-Lys scaffold. From this structure-activity relationship (SAR) study, novel irreversible inhibitors were identified that block the transamidation activity of hTG2 and allosterically abolish its GTP binding ability with a high degree of selectivity and efficiency (kinact/KI > 105 M-1 min-1). One optimized inhibitor (VA4) was also shown to inhibit epidermal cancer stem cell invasion with an EC50 of 3.9 μM, representing a significant improvement over our previously reported "hit" NC9.

A fluorescent turn-on H2S-responsive probe: Design, synthesis and application

Hydrogen sulfide (H2S) is considered as the third signaling molecule in vivo and it plays an important role in various physiological processes and pathological processes in vivo, such as vasodilation, apoptosis, neurotransmission, ischemia/reperfusion-induced injury, insulin secretion and inflammation. Developing a highly selective and sensitive method that can detect H2S in the biological system is very important. In this work, a colorimetric and "turn-on" fluorescent probe is developed. Furthermore, this probe displays a highly selective response to H2S in aqueous solution and possesses good capability for bioimaging H2S without interference in living cells. The results suggest that a H2S-selective probe has good water-solubility, biocompatibility and cell-penetrability and can serve as an efficient tool for probing H2S in the cell level.