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Merck

D4008

Sigma-Aldrich

Dansylcadaverine

≥97% (TLC)

Sinónimos:

N-(5-Amino­pentyl)-5-di­methyl­amino­naphtha­lene-1-sulfon­amide, N-(Dimethyl­amino­naphtha­lene­sulfonyl)-1,5-pentane­diamine, Monodansyl cadaverine

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About This Item

Fórmula empírica (notación de Hill):
C17H25N3O2S
Número de CAS:
Peso molecular:
335.46
Beilstein/REAXYS Number:
2951070
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.32
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Quality Level

assay

≥97% (TLC)

form

powder

storage temp.

−20°C

SMILES string

CN(C)c1cccc2c(cccc12)S(=O)(=O)NCCCCCN

InChI

1S/C17H25N3O2S/c1-20(2)16-10-6-9-15-14(16)8-7-11-17(15)23(21,22)19-13-5-3-4-12-18/h6-11,19H,3-5,12-13,18H2,1-2H3

Inchi Key

MLEBFEHOJICQQS-UHFFFAOYSA-N

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General description

Dansylcadaverine, also called as monodansylcadaverine (MDC), is a lysosomotropic agent. It is present in acidic and lipid rich regions. Dansylcadaverine also acts as a solvent polarity probe.[1] It inhibits vesicular transport and decreases the rotavirus sequestering in L cells, when pre-treated.[2]

Application

Dansylcadaverine in methanol has a reported λex of 335 nm and λem of 512 nm. It has been used:
  • as an endocytosis inhibitor in human proximal tubular HK-2 cells,(62) mouse J774A.1 macrophages and human A549 epithelial cells(63)
  • to label autophagic vacuoles in cardiomyocytes for fluorescence microscopy studies(64)
  • in monodansylcadaverine (MDC) staining of fibroblasts in Ankylosing spondylitis (AS) samples(65)

Biochem/physiol Actions

The autofluorescent dye dansylcadaverine, or monodansylcadaverine (MDC), is commonly used to monitor autophagy. MDC preferentially accumulates in autophagic vacuoles due to a combination of ion trapping and specific interactions with membrane lipids.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.
air sensitive, handled under inert gas

Other Notes

Solubility of dansylcadaverine is tested in methanol (10 mg/mL). It has also been reported that dansylcadaverine is soluble in DMSO and acetic acid.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Fluorescence properties and staining behavior of monodansylpentane, a structural homologue of the lysosomotropic agent monodansylcadaverine
Niemann A, et al.
The Journal of Histochemistry and Cytochemistry, 49(2), 177-185 (2001)
Dansylcadaverine and cytochalasin D enhance rotavirus infection of murine L cells
Bass DM, et al.
Virology, 212(2), 429-437 (1995)
P J Davies et al.
Diabetes care, 7 Suppl 1, 35-41 (1984-05-01)
It has been suggested that cellular transglutaminases may play an important role in the process of receptor-mediated endocytosis. We have examined this premise by investigating the receptor-mediated endocytosis of two proteins, epidermal growth factor and alpha 2 macroglobulin in cells
Shih T Khew et al.
Biomaterials, 31(16), 4600-4608 (2010-03-13)
Transglutaminase (TGase)-modified proteins are commonly observed in a wide range of biological systems. Therefore, the identification of TGase substrates and respective consensus sites may contribute to a better understanding of the physiological role of TGase. In this study, we identified
Melissa S Hillwig et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(3), 1093-1098 (2011-01-05)
RNase T2 enzymes are conserved in most eukaryotic genomes, and expression patterns and phylogenetic analyses suggest that they may carry out an important housekeeping role. However, the nature of this role has been elusive. Here we show that RNS2, an

Questions

1–5 of 5 Questions  
  1. Can I use Dansylcadaverine D4008 for detection of autophagy using flow cytometry? if Yes which laser should we use to detect the MDC signal? Di you have any recommendations regarding the final concentration of MDC for detection of autophagy in lymphocyte?

    1 answer
    1. Unfortunately, no data for Product D4008's use with flow cytometry application is determined. However, several academic publications associated with this product's use in flow cytometry experiments may provide details that can assist with the experimental design. Please see the link to those publications below:
      https://scholar.google.com/scholar?hl=en&as_sdt=0%2C26&q=%22Dansylcadaverine%22+%22D4008%22+%22flow+cytometry%22&btnG=

      Helpful?

  2. What is the solution stability of Product D4008, Dansylcadaverine?

    1 answer
    1. According to one source a stock solution of monodansylcadaverine was prepared in methanol at 50 mM and stored frozen at -20°C.  No time frame for long-term solution stability was given.

      Helpful?

  3. What is Product D4008, Dansylcadaverine, soluble in?

    1 answer
    1. We test the solubility of this product in acetic acid at a concentration of 50 mg/mL, with the application of heat and sonication. It has also been reported as being soluble in methanol and DMSO. We have not validated this claim in our labs.

      Helpful?

  4. Can Dansylcadaverine be use as a marker of autophagic vacuoles?

    1 answer
    1. Dansylcadaverine is a lysosomotropic compound that can be used for the identification of autophagic vacuoles.  Please refer to the literature for application-specific protocols.

      Helpful?

  5. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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