605-65-2 Usage
Description
Dansyl chloride, also known as 5-Dimethylaminonaphthalene-1-sulfonyl chloride (CAS 605-65-2), is a fluorogenic reagent that is widely used in the field of biochemistry and biophysical studies. It is non-fluorescent until it reacts with amines, forming Dansyl amides which exhibit environmentally sensitive fluorescence quantum yields, emission maxima, and large Stokes shifts. This unique property has made Dansyl chloride an important tool for various applications in research and analysis.
Uses
Used in Biochemistry and Biomedical Research:
Dansyl chloride is used as a reagent for fluorescent labeling of amines, amino acids, and proteins. This application is particularly useful for the detection and analysis of these biomolecules in various research and diagnostic settings.
Used in Chromatography:
Dansyl chloride is employed as a fluorogenic reagent for N-terminal derivatization of amino acids and peptides, which is essential for their detection by reverse phase high performance liquid chromatography (HPLC). This technique is widely used in the separation, identification, and quantification of these molecules.
Used in Column Chromatography and HPLC:
Dansyl chloride is utilized in column chromatography and HPLC for the fluorescent labeling of proteins, N-terminal amino acids, and peptides. This allows for the efficient separation and detection of these biomolecules, which is crucial for various analytical and preparative purposes.
Used in Synthesis of Derivatives:
Dansyl chloride acts as a precursor for the synthesis of other derivatives, such as dansyl amide. These derivatives can be used in various applications, including the development of new fluorescent probes and labels for biological research.
Biochem/physiol Actions
Dansyl chloride is a sulfonyl chloride compound. It is used to end tag amino groups of peptides and proteins. Dansyl chloride is used for derivatization of free amino acids and amines in neural samples and biological fluids. It is used to study fluorescent conjugates of albumin, protein conformational changes studies and active site characterization.
Safety Profile
Poison by intravenous
route, When heated to decomposition it
emits very toxic fumes of Cland NOx
Check Digit Verification of cas no
The CAS Registry Mumber 605-65-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 5 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 605-65:
(5*6)+(4*0)+(3*5)+(2*6)+(1*5)=62
62 % 10 = 2
So 605-65-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H12ClNO2S/c1-14(2)11-7-3-6-10-9(11)5-4-8-12(10)17(13,15)16/h3-8H,1-2H3
605-65-2Relevant articles and documents
Mendel
, p. 340,341 (1970)
Degradable conjugates from oxanorbornadiene reagents
Kislukhin, Alexander A.,Higginson, Cody J.,Hong, Vu P.,Finn
supporting information; experimental part, p. 6491 - 6497 (2012/05/07)
Oxanorbornadienedicarboxylate (OND) reagents were explored for purposes of binding and releasing drugs from serum albumins as representative macromolecular carriers. Being highly reactive Michael acceptors, ONDs form adducts with thiols and amines, which then undergo retro-Diels-Alder fragmentation. A study of more than 30 model adducts revealed a number of modifications that can be used to influence adduct stability. For the most reactive OND linkers, the labeling of the single available bovine serum albumin (BSA) cysteine residue was complete within minutes at a mid-micromolar concentration of reactants. While a selectivity of greater than 1000-fold for thiol over amine was observed with model amino acids, the labeling of protein amines with ONDs is fast enough to be practical, as demonstrated by the reaction with thiol-depleted BSA. The OND-amine adducts were found to be up to 15 times more stable than OND-thiol adducts, and to be sensitive to acid by virtue of a stereochemically dependent acceleration of cycloreversion. The release rate of fluorescent cargo from serum albumins was tuned by selecting the coupling partners: the available half-lives ranged from 40 min to 7 days at 37 °C. Such versatility of release profiles from protein carriers, controlled by the nature of the OND linkage, is a useful addition to the drug delivery toolbox.
Activatable probes and methods for in vivo gene detection
-
, (2008/06/13)
Probes for detecting a target polynucleotide are provided. One aspect provides a molecular beacon probe set wherein the donor molecular beacon comprises a quantum dot and an acceptor molecular beacon comprises at least one reporter. The probes optionally comprise a protein transduction domain, targeting signal, or a combination thereof. Methods for detecting target polynucleotides using the disclosed probes are also provided.
