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30432

Sigma-Aldrich

Dansylcadaverine

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

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:
57648439
NACRES:
NA.32

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
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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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.
Qi Jiang et al.
The Journal of urology, 188(4), 1361-1368 (2012-08-22)
Androgen receptor has a critical role in prostate cancer development and progression. Cell death via autophagy may also contribute to prostate cancer progression. We determined the role and regulatory effects of androgen receptor on the autophagy process of prostate cancer
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
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