Skip to Content
Merck
All Photos(1)

Documents

M2949

Sigma-Aldrich

MDL 72527

≥98% (HPLC)

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C12 H20 N2·2 HCl
CAS Number:
93565-01-6
Molecular Weight:
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

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Enzo Agostinelli et al.
International journal of oncology, 35(3), 485-498 (2009-07-30)
It has been confirmed that multidrug resistant (MDR) human melanoma cells are more sensitive than their wild-type counterparts to H2O2 and aldehydes, the products of bovine serum amine oxidase (BSAO)-catalyzed oxidation of spermine. The metabolites formed by BSAO and spermine
S M Oredsson et al.
Biochemical Society transactions, 35(Pt 2), 405-409 (2007-03-21)
Reduction of cellular polyamine pools results in inhibition of cell proliferation and sometimes in induction of cell death. Reduction of cellular polyamine pools can be achieved by several strategies involving all the mechanisms of polyamine homoeostasis, i.e. biosynthesis, catabolism and
B Duranton et al.
Cell biology and toxicology, 18(6), 381-396 (2002-12-18)
N1,N4-bis(2,3-butadienyl)-1,4-butanediamine (MDL 72527) was considered to be a selective inactivator of FAD-dependent tissue polyamine oxidase. Recently MDL 72527 was reported to induce apoptosis in transformed hematopoietic cells through lysosomotropic effects. Since it is the only useful inhibitor of polyamine oxidase
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service