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M2949

Sigma-Aldrich

MDL 72527

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C12 H20 N2·2 HCl
Numéro CAS:
93565-01-6
Poids moléculaire :
265.22
Numéro MDL:
MFCD13152261
Code UNSPSC :
12352200
ID de substance PubChem :
329817958
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to brown

Solubilité

H2O: 15 mg/mL, clear

Température de stockage

room temp

Chaîne SMILES 

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

Clé InChI

ITVRWVVFVHINOH-UHFFFAOYSA-N

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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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