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D4008

Sigma-Aldrich

Dansylcadaverine

≥97% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H25N3O2S
CAS Number:
10121-91-2
Molecular Weight:
335.46
Beilstein:
2951070
EC Number:
233-326-9
MDL number:
MFCD00042704
UNSPSC Code:
12352108
PubChem Substance ID:
24893805
NACRES:
NA.32

Quality Level

100

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. It inhibits vesicular transport and decreases the rotavirus sequestering in L cells, when pre-treated.

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL2227
BCCJ4973
BCCG9380
BCCD6440
BCCC7667

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

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

    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.

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

    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.

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

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

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Dansylcadaverine and cytochalasin D enhance rotavirus infection of murine L cells
Bass DM, et al.
Virology, 212(2), 429-437 (1995)
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)
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
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
Raúl A Almeida et al.
Veterinary research communications, 35(2), 89-101 (2011-01-06)
Research on mastitis in dairy cows caused by Escherichia coli has reported the emergence of strains capable of inducing chronic mastitis and that these strains adhered to and internalized into bovine mammary epithelial cells better than strains of E. coli
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