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M2949

Sigma-Aldrich

MDL 72527

≥98% (HPLC)

Synonyma:

CPC-200, MDL-72527DA, N,N′-Bis(2,3-butadienyl)-1,4-butanediamine dihydrochloride, N1,N4-Bis(2,3-butadienyl)-1,4-butanediamine hydrochloride

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About This Item

Empirický vzorec (Hillův zápis):
C12 H20 N2·2 HCl
Číslo CAS:
93565-01-6
Molekulová hmotnost:
265.22
MDL number:
MFCD13152261
UNSPSC Code:
12352200
PubChem Substance ID:
329817958
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to brown

solubility

H2O: 15 mg/mL, clear

storage temp.

room temp

SMILES string

Cl.Cl.C=C=CCNCCCCNCC=C=C

InChI

1S/C12H20N2.2ClH/c1-3-5-9-13-11-7-8-12-14-10-6-4-2;;/h5-6,13-14H,1-2,7-12H2;2*1H

InChI key

ITVRWVVFVHINOH-UHFFFAOYSA-N

Biochem/physiol Actions

MDL 72527is an inhibitor of polyamine oxidase (spermine oxidase SMO). It blocks the production of H2O2 and increases the cells survival. Polyamine catabolism is one of the major causes of the ROS production of prostate cells in general and androgen-induced enhancement of ROS in androgen-dependent CaP cells in particular. Reports suggest that androgen stimulation of prostate cancer results in accumulation of ROS, which lead to progression of cancer, such progression is control by MDL 72527.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Agmatine sulfate salt ≥97%, powder

Sigma-Aldrich

A7127

Agmatine sulfate salt

Chlorhexidine ≥99.5%

Sigma-Aldrich

282227

Chlorhexidine

Spermine ≥97%

Sigma-Aldrich

S3256

Spermine

Gelatin from bovine skin Type B, powder, BioReagent, suitable for cell culture

Sigma-Aldrich

G9391

Gelatin from bovine skin

Francine Gossé et al.
International journal of oncology, 29(2), 423-428 (2006-07-06)
Apple procyanidins have chemopreventive properties in a model of colon cancer, they affect intracellular signalling pathways, and trigger apoptosis in a human adenocarcinoma-derived metastatic cell line (SW620). In the present study we investigated relationships between procyanidin-induced alterations in polyamine metabolism
Tianyun Wu et al.
Biochemical and biophysical research communications, 326(2), 483-490 (2004-12-08)
Murine N(1)-acetylated polyamine oxidase (mPAO) was treated with N,N'-bis-(prop-2-ynyl)-1,4-diaminobutane, a poor substrate and inhibitor for the enzyme, with K(m) and K(i) values in the millimolar range. Apparently, its oxidation produces prop-2-ynal, which reacts with amino acyl nucleophiles. Using a steady-state
Enzo Agostinelli et al.
Biochemical and biophysical research communications, 340(3), 840-844 (2005-12-29)
MDL 72527 was considered a selective inhibitor of FAD-dependent polyamine oxidases. In the present communication, we demonstrate that MDL 72527 inactivates bovine serum amine oxidase, a copper-containing, TPQ-enzyme, time-dependently at 25 degrees C. In striking contrast, the enzyme remained active
Stamatiki Roussi et al.
International journal of oncology, 29(6), 1549-1554 (2006-11-08)
7beta-OHsitosterol and 7beta-OHcholesterol are natural compounds of plant and animal cells with high structural similarity. Recently it was reported that both compounds induced apoptosis on human colon cancer cells by targeting different signalling pathways. Our study aimed at comparing their
M E Maldonado-Celisa et al.
Cellular and molecular life sciences : CMLS, 65(9), 1425-1434 (2008-04-01)
We showed previously that inhibition of polyamine catabolism with the polyamine oxidase inhibitor MDL 72527 (MDL) potentiates the apoptotic effects of apple procyanidins (Pcy) in SW620 cells. Here we report that Pcy caused an activation of the intrinsic apoptotic pathway
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