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Merck

D4008

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
UNSPSC Code:
12352108
NACRES:
NA.32
PubChem Substance ID:
24893805
EC Number:
233-326-9
Beilstein/REAXYS Number:
2951070
MDL number:
MFCD00042704

Key Documents

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InChI key

MLEBFEHOJICQQS-UHFFFAOYSA-N

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

SMILES string

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

assay

≥97% (TLC)

form

powder

storage temp.

−20°C

Quality Level

100

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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP1166
BCCL2227
BCCJ4973
BCCG9380
BCCD6440

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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)
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
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
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
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