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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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