Page last updated: 2024-11-04

mdl 72527

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

MDL 72527: RN given refers to di-HCl; RN for parent cpd not available 6/85; polyamine oxidase inhibitor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3035046
CHEMBL ID4439012
SCHEMBL ID4195463
MeSH IDM0129827

Synonyms (29)

Synonym
mdl 72527
93565-01-6
n,n'-di(buta-2,3-dien-1-yl)butane-1,4-diamine
n1,n4-di(buta-2,3-dienyl)butane-1,4-diamine dihydrochloride
unii-1yvr349gn4
mdl-72527
n1,n4-bis(2,3-butadienyl)-1,4-butanediamine, hydrochloride
mdl-72527da
1,4-butanediamine, n,n'-di-2,3-butadienyl-, dihydrochloride
n,n'-bis(2,3-butadienyl)-1,4-butanediamine dihydrochloride
1yvr349gn4 ,
AKOS015950949
n1,n4-di(buta-2,3-dien-1-yl)butane-1,4-diamine dihydrochloride
1,4-butanediamine, n1,n4-di-2,3-butadien-1-yl-, hydrochloride (1:2)
SCHEMBL4195463
n1,n4-di-2,3-butadienyl-1,4-butanediamine dihydrochloride
DS-2332
(buta-2,3-dien-1-yl)({4-[(buta-2,3-dien-1-yl)amino]butyl})amine dihydrochloride
mfcd13152261
EX-A1094
mdl 72527, >=98% (hplc)
FT-0732900
Q27253225
n,n/'-bis(buta-2,3-dienyl)butane-1,4-diamine;dihydrochloride
CHEMBL4439012
A859738
HY-100621
mdl 72527 (dihydrochloride)
CS-0019799

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Spermine was toxic to BHK-21/C13 cells in the absence of any extracellular metabolism of the amine."( Mechanisms of spermine toxicity in baby-hamster kidney (BHK) cells. The role of amine oxidases and oxidative stress.
Brunton, VG; Grant, MH; Wallace, HM, 1991
)
0.28
" Nevertheless, it exerts toxic effects if it accumulates in cells."( Spermine cytotoxicity to human colon carcinoma-derived cells (CaCo-2).
Duranton, B; Gossé, F; Raul, F; Seiler, N, 2000
)
0.31
" However, the development of lethal toxic effects due to prevention of spermine degradation is a considerable disadvantage of the compound."( Cytotoxicity of the polyamine oxidase inactivator MDL 72527 to cancer cells: comparison with a saturated structural analogue.
Gossé, F; Raul, F; Renault, J; Roussi, S; Seiler, N, 2005
)
0.33
" Pre-treatment with N1,N4-bis(2,3-butadienyl)-1,4-butanediamine (MDL 72527), a lysosomotropic compound, sensitized cells to toxic spermine metabolites."( Toxicity of enzymatic oxidation products of spermine to human melanoma cells (M14): sensitization by heat and MDL 72527.
Agostinelli, E; Arancia, G; Belli, F; Condello, M; Marra, M; Molinari, A; Palmigiani, P; Seiler, N; Vedova, LD, 2006
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysine-specific histone demethylase 1AHomo sapiens (human)IC50 (µMol)100.00000.00312.16029.6000AID1575522
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)200.00000.00002.37899.7700AID1575524
Amine oxidase [flavin-containing] BHomo sapiens (human)IC50 (µMol)200.00000.00001.89149.5700AID1575526
Spermine oxidaseHomo sapiens (human)IC50 (µMol)89.70000.04000.04000.0400AID1575528
REST corepressor 1Homo sapiens (human)IC50 (µMol)100.00001.10001.16001.1900AID1575522
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (55)

Processvia Protein(s)Taxonomy
regulation of double-strand break repair via homologous recombinationLysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of protein ubiquitinationLysine-specific histone demethylase 1AHomo sapiens (human)
regulation of protein localizationLysine-specific histone demethylase 1AHomo sapiens (human)
cellular response to UVLysine-specific histone demethylase 1AHomo sapiens (human)
cellular response to gamma radiationLysine-specific histone demethylase 1AHomo sapiens (human)
DNA repair-dependent chromatin remodelingLysine-specific histone demethylase 1AHomo sapiens (human)
negative regulation of transcription by RNA polymerase IILysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of neuroblast proliferationLysine-specific histone demethylase 1AHomo sapiens (human)
regulation of transcription by RNA polymerase IILysine-specific histone demethylase 1AHomo sapiens (human)
protein demethylationLysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of epithelial to mesenchymal transitionLysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of neuron projection developmentLysine-specific histone demethylase 1AHomo sapiens (human)
cerebral cortex developmentLysine-specific histone demethylase 1AHomo sapiens (human)
negative regulation of protein bindingLysine-specific histone demethylase 1AHomo sapiens (human)
neuron maturationLysine-specific histone demethylase 1AHomo sapiens (human)
negative regulation of DNA bindingLysine-specific histone demethylase 1AHomo sapiens (human)
negative regulation of DNA-binding transcription factor activityLysine-specific histone demethylase 1AHomo sapiens (human)
negative regulation of DNA damage response, signal transduction by p53 class mediatorLysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of cell sizeLysine-specific histone demethylase 1AHomo sapiens (human)
negative regulation of DNA-templated transcriptionLysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of transcription by RNA polymerase IILysine-specific histone demethylase 1AHomo sapiens (human)
guanine metabolic processLysine-specific histone demethylase 1AHomo sapiens (human)
muscle cell developmentLysine-specific histone demethylase 1AHomo sapiens (human)
regulation of androgen receptor signaling pathwayLysine-specific histone demethylase 1AHomo sapiens (human)
response to fungicideLysine-specific histone demethylase 1AHomo sapiens (human)
cellular response to cAMPLysine-specific histone demethylase 1AHomo sapiens (human)
regulation of DNA methylation-dependent heterochromatin formationLysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of cold-induced thermogenesisLysine-specific histone demethylase 1AHomo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorLysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of neural precursor cell proliferationLysine-specific histone demethylase 1AHomo sapiens (human)
positive regulation of stem cell proliferationLysine-specific histone demethylase 1AHomo sapiens (human)
chromatin remodelingLysine-specific histone demethylase 1AHomo sapiens (human)
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
response to xenobiotic stimulusAmine oxidase [flavin-containing] BHomo sapiens (human)
response to toxic substanceAmine oxidase [flavin-containing] BHomo sapiens (human)
response to aluminum ionAmine oxidase [flavin-containing] BHomo sapiens (human)
response to selenium ionAmine oxidase [flavin-containing] BHomo sapiens (human)
negative regulation of serotonin secretionAmine oxidase [flavin-containing] BHomo sapiens (human)
phenylethylamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
substantia nigra developmentAmine oxidase [flavin-containing] BHomo sapiens (human)
response to lipopolysaccharideAmine oxidase [flavin-containing] BHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to ethanolAmine oxidase [flavin-containing] BHomo sapiens (human)
positive regulation of dopamine metabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
hydrogen peroxide biosynthetic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to corticosteroneAmine oxidase [flavin-containing] BHomo sapiens (human)
polyamine biosynthetic processSpermine oxidaseHomo sapiens (human)
polyamine catabolic processSpermine oxidaseHomo sapiens (human)
xenobiotic metabolic processSpermine oxidaseHomo sapiens (human)
spermine catabolic processSpermine oxidaseHomo sapiens (human)
chromatin organizationREST corepressor 1Homo sapiens (human)
negative regulation of gene expressionREST corepressor 1Homo sapiens (human)
erythrocyte differentiationREST corepressor 1Homo sapiens (human)
positive regulation of megakaryocyte differentiationREST corepressor 1Homo sapiens (human)
negative regulation of DNA-templated transcriptionREST corepressor 1Homo sapiens (human)
regulation of transcription by RNA polymerase IIREST corepressor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (31)

Processvia Protein(s)Taxonomy
telomeric DNA bindingLysine-specific histone demethylase 1AHomo sapiens (human)
p53 bindingLysine-specific histone demethylase 1AHomo sapiens (human)
chromatin bindingLysine-specific histone demethylase 1AHomo sapiens (human)
transcription coactivator activityLysine-specific histone demethylase 1AHomo sapiens (human)
protein bindingLysine-specific histone demethylase 1AHomo sapiens (human)
oxidoreductase activityLysine-specific histone demethylase 1AHomo sapiens (human)
enzyme bindingLysine-specific histone demethylase 1AHomo sapiens (human)
nuclear receptor coactivator activityLysine-specific histone demethylase 1AHomo sapiens (human)
demethylase activityLysine-specific histone demethylase 1AHomo sapiens (human)
histone demethylase activityLysine-specific histone demethylase 1AHomo sapiens (human)
histone H3K4 demethylase activityLysine-specific histone demethylase 1AHomo sapiens (human)
histone H3K9 demethylase activityLysine-specific histone demethylase 1AHomo sapiens (human)
identical protein bindingLysine-specific histone demethylase 1AHomo sapiens (human)
MRF bindingLysine-specific histone demethylase 1AHomo sapiens (human)
flavin adenine dinucleotide bindingLysine-specific histone demethylase 1AHomo sapiens (human)
nuclear androgen receptor bindingLysine-specific histone demethylase 1AHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingLysine-specific histone demethylase 1AHomo sapiens (human)
telomeric repeat-containing RNA bindingLysine-specific histone demethylase 1AHomo sapiens (human)
DNA-binding transcription factor bindingLysine-specific histone demethylase 1AHomo sapiens (human)
FAD-dependent H3K4me/H3K4me3 demethylase activityLysine-specific histone demethylase 1AHomo sapiens (human)
promoter-specific chromatin bindingLysine-specific histone demethylase 1AHomo sapiens (human)
transcription factor bindingLysine-specific histone demethylase 1AHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
electron transfer activityAmine oxidase [flavin-containing] BHomo sapiens (human)
identical protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
polyamine oxidase activitySpermine oxidaseHomo sapiens (human)
norspermine:oxygen oxidoreductase activitySpermine oxidaseHomo sapiens (human)
N1-acetylspermine:oxygen oxidoreductase (N1-acetylspermidine-forming) activitySpermine oxidaseHomo sapiens (human)
spermine:oxygen oxidoreductase (spermidine-forming) activitySpermine oxidaseHomo sapiens (human)
chromatin bindingREST corepressor 1Homo sapiens (human)
protein bindingREST corepressor 1Homo sapiens (human)
enzyme bindingREST corepressor 1Homo sapiens (human)
transcription corepressor activityREST corepressor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
chromatinLysine-specific histone demethylase 1AHomo sapiens (human)
nucleusLysine-specific histone demethylase 1AHomo sapiens (human)
chromosome, telomeric regionLysine-specific histone demethylase 1AHomo sapiens (human)
nucleusLysine-specific histone demethylase 1AHomo sapiens (human)
nucleoplasmLysine-specific histone demethylase 1AHomo sapiens (human)
transcription regulator complexLysine-specific histone demethylase 1AHomo sapiens (human)
protein-containing complexLysine-specific histone demethylase 1AHomo sapiens (human)
DNA repair complexLysine-specific histone demethylase 1AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial envelopeAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] BHomo sapiens (human)
dendriteAmine oxidase [flavin-containing] BHomo sapiens (human)
neuronal cell bodyAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
nucleoplasmSpermine oxidaseHomo sapiens (human)
cytosolSpermine oxidaseHomo sapiens (human)
nuclear membraneSpermine oxidaseHomo sapiens (human)
intracellular membrane-bounded organelleSpermine oxidaseHomo sapiens (human)
nucleusREST corepressor 1Homo sapiens (human)
nucleoplasmREST corepressor 1Homo sapiens (human)
transcription repressor complexREST corepressor 1Homo sapiens (human)
DNA repair complexREST corepressor 1Homo sapiens (human)
histone deacetylase complexREST corepressor 1Homo sapiens (human)
transcription regulator complexREST corepressor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1575522Inhibition of recombinant LSD1/CoREST (unknown origin) incubated for 30 mins to 4 hrs by fluorescence based assay2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
AID1575527Inhibition of SMOX (unknown origin) assessed as decrease in spermidine formation using spermine as substrate at 10 uM treated with compound 2 mins prior to substrate addition followed by further incubation for 1 hr by HPLC analysis relative to control2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
AID1575521Inhibition of recombinant LSD1/CoREST (unknown origin) at 10 uM incubated for 30 mins to 4 hrs by fluorescence based assay relative to control2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
AID1575525Inhibition of MAOB (unknown origin) using luminogenic substrate at 10 uM incubated for 1 hr by luminescence based assay relative to control2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
AID1575524Inhibition of MAOA (unknown origin) using luminogenic substrate incubated for 1 hr by luminescence based assay2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
AID1575526Inhibition of MAOB (unknown origin) using luminogenic substrate incubated for 1 hr by luminescence based assay2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
AID1575529Inhibition of PAOX (unknown origin) assessed as decrease in spermidine formation using N-acetylspermine as substrate at 10 uM treated with compound 2 mins prior to substrate addition followed by further incubation for 1 hr by HPLC analysis relative to con2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
AID1575523Inhibition of MAOA (unknown origin) using luminogenic substrate at 10 uM incubated for 1 hr by luminescence based assay relative to control2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
AID1575528Inhibition of SMOX (unknown origin) assessed as decrease in spermidine formation using spermine as substrate treated with compound 2 mins prior to substrate addition followed by further incubation for 1 hr by HPLC analysis2019MedChemComm, May-01, Volume: 10, Issue:5
Dual inhibitors of LSD1 and spermine oxidase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (75)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (8.00)18.7374
1990's29 (38.67)18.2507
2000's25 (33.33)29.6817
2010's12 (16.00)24.3611
2020's3 (4.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other82 (97.62%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]