M2949
MDL 72527
≥98% (HPLC), spermine oxidase SMO inhibitor, powder
Synonym(s):
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
Empirical Formula (Hill Notation):
C12 H20 N2·2 HCl
CAS Number:
Molecular Weight:
265.22
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
MDL 72527, ≥98% (HPLC)
SMILES string
Cl.Cl.C=C=CCNCCCCNCC=C=C
InChI key
ITVRWVVFVHINOH-UHFFFAOYSA-N
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
assay
≥98% (HPLC)
form
powder
color
white to brown
solubility
H2O: 15 mg/mL, clear
storage temp.
room temp
Quality Level
Related Categories
Biochem/physiol Actions
MDL 72527is an inhibitor of polyamine oxidase (spermine oxidase SMO).
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.
signalword
Warning
hcodes
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
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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
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
Nikolaus Seiler et al.
Progress in drug research. Fortschritte der Arzneimittelforschung. Progres des recherches pharmaceutiques, 59, 1-40 (2002-12-03)
Polyamine oxidase is a FAD-dependent amine oxidase, which is constitutively expressed in nearly all tissues of the vertebrate organism. In 1985, N1,N4-bis(2,3-butadienyl)-1,4-butanediamine (MDL 72527) was designed as a selective enzyme-activated irreversible inhibitor of polyamine oxidase (EC 1.5.3.11). It inactivates, at
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