30432

Sigma-Aldrich

Dansylcadaverine

BioReagent, suitable for fluorescence, ≥99.0% (HPLC)

Synonym(s):
N-(5-Amino­pentyl)-5-di­methyl­amino­naphtha­lene-1-sulfon­amide, Monodansyl cadaverine, N-(Dimethyl­amino­naphtha­lene­sulfonyl)-1,5-pentane­diamine
Empirical Formula (Hill Notation):
C17H25N3O2S
CAS Number:
Molecular Weight:
335.46
Beilstein/REAXYS Number:
2951070
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

product line

BioReagent

assay

≥99.0% (HPLC)

mp

137-140 °C

fluorescence

λex 335 nm; λem 518 nm in methanol
λex 338 nm; λem 500 nm (Reaction product)

suitability

suitable for fluorescence

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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Application

Dansylcadaverine (MDC), an autofluorescent dye, is used to monitor autophagy. MDC accumulates in autophagic vacuoles due to a combination of ion trapping and specific interactions with membrane lipids.

Biochem/physiol Actions

Inhibitor of the fibrin-stabilizing fator; Inhibitor of epidermal growth factor (EGF) internalization; Fluorescent substrate for the assay of transamidating enzymes.
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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Transamidating enzymes. I. Rapid chromatographic assays.
L Lorand et al.
Analytical biochemistry, 44(1), 207-220 (1971-11-01)
Fibrin-stabilizing factor inhibitors. 3. Sulphonamides related to monodansylcadaverine.
J L Nilsson et al.
Acta pharmaceutica Suecica, 8(5), 497-504 (1971-11-01)
H T Haigler et al.
The Journal of biological chemistry, 255(4), 1239-1241 (1980-02-25)
The binding and internalization of 125I-epidermal growth factor (125I-EGF) was studied in cultures of BALB 3T3 cells using a novel method that involved removal of cell-surface hormone by treatment with acetic acid under conditions that did not remove internalized hormone....
S N Murthy et al.
The Journal of biological chemistry, 269(36), 22907-22911 (1994-09-09)
Elevating the intracellular concentration of Ca2+ ions in human erythrocytes leads to the formation of membrane-associated polymers, composed of skeletal and cytoplasmic proteins. The anion transporter band 3 serves as a membrane anchor for this N epsilon-(gamma-glutamyl)lysine cross-linked polymer. The...
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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