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M2949

Sigma-Aldrich

MDL 72527

≥98% (HPLC)

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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
Empirical Formula (Hill Notation):
C12 H20 N2·2 HCl
CAS Number:
Molecular Weight:
265.22
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
P750585610S2876
MDL 72527 ≥98% (HPLC)

M2949

MDL 72527

Putrescine dihydrochloride ≥98% (TLC)

P7505

Putrescine dihydrochloride

Spermine tetrahydrochloride ≥99.0% (AT), powder or crystals

85610

Spermine tetrahydrochloride

Spermine tetrahydrochloride powder or crystals

S2876

Spermine tetrahydrochloride

assay

≥98% (HPLC)

assay

≥98% (TLC)

assay

≥99.0% (AT)

assay

-

Quality Level

100

Quality Level

400

Quality Level

300

Quality Level

-

storage temp.

room temp

storage temp.

-

storage temp.

room temp

storage temp.

room temp

solubility

H2O: 15 mg/mL, clear

solubility

H2O: soluble 100 mg/mL, clear, colorless

solubility

H2O: 0.1 g/mL, clear

solubility

water, high purity: 100 mg/ml

color

white to brown

color

-

color

-

color

-

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

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


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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
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
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
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

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