Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C26H28N6.4ClHO4 |
| Molecular Weight | 826.375 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCl(=O)(=O)=O.OCl(=O)(=O)=O.OCl(=O)(=O)=O.OCl(=O)(=O)=O.C(CN(CC1=NC=CC=C1)CC2=NC=CC=C2)N(CC3=CC=CC=N3)CC4=CC=CC=N4
InChI
InChIKey=JKBQPGLRYWUSND-UHFFFAOYSA-N
InChI=1S/C26H28N6.4ClHO4/c1-5-13-27-23(9-1)19-31(20-24-10-2-6-14-28-24)17-18-32(21-25-11-3-7-15-29-25)22-26-12-4-8-16-30-26;4*2-1(3,4)5/h1-16H,17-22H2;4*(H,2,3,4,5)
| Molecular Formula | C26H28N6 |
| Molecular Weight | 424.5407 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClHO4 |
| Molecular Weight | 100.459 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
N,N,N',N'-TETRAKIS(2-PYRIDYLMETHYL)ETHYLENEDIAMINE (TPEN) is a heavy metal chelator with strong affinities for Zn2+, Fe2+, and Mn2+. TPEN inhibits lamin assembly, destabilizes nuclear architecture and may independently protect nuclei from apoptosis in vitro. TPEN prevents HIF-1alpha from interacting with CBP, so reducing expression of HIF-1alpha target genes. TPEN was able to pass through the blood-brain barrier and the neuronal membrane, leading to successful intracellular zinc chelation - zinc chelation could be a potentially effective way for ischemic stroke treatment. TPEN exhibits robust anti-tumor activity in vivo in colon cancer mouse xenografts. In vivo experiments show that TPEN-loaded, aptamer-targeted liposomes reduce tumor growth in a human prostate cancer xenograft model.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Zinc modulates cytokine-induced lung epithelial cell barrier permeability. | 2006-12 |
|
| Diverse effects of zinc on NF-kappaB and AP-1 transcription factors: implications for prostate cancer progression. | 2006-10 |
|
| Toll-like receptor-mediated regulation of zinc homeostasis influences dendritic cell function. | 2006-09 |
|
| Endothelial response to stress from exogenous Zn2+ resembles that of NO-mediated nitrosative stress, and is protected by MT-1 overexpression. | 2006-09 |
|
| Inhibition of cyclooxygenase-2 expression by zinc-chelator in retinal ischemia. | 2006-09 |
|
| Zinc is required for Fc epsilon RI-mediated mast cell activation. | 2006-07-15 |
|
| Zinc-dependent multi-conductance channel activity in mitochondria isolated from ischemic brain. | 2006-06-21 |
|
| The zinc chelator, N,N,N',N'-tetrakis (2-pyridylmethyl) ethylenediamine, increases the level of nonfunctional HIF-1alpha protein in normoxic cells. | 2006-05-19 |
|
| Flow cytometric measurement of labile zinc in peripheral blood mononuclear cells. | 2006-05-15 |
|
| Intracellular zinc release and ERK phosphorylation are required upstream of 12-lipoxygenase activation in peroxynitrite toxicity to mature rat oligodendrocytes. | 2006-04-07 |
|
| Selenium prevents diabetes-induced alterations in [Zn2+]i and metallothionein level of rat heart via restoration of cell redox cycle. | 2006-03 |
|
| Protective effect of zinc against ischemic neuronal injury in a middle cerebral artery occlusion model. | 2006-02 |
|
| Apoptosis may underlie the pathology of zinc-deficient skin. | 2006-02 |
|
| Cytosolic labile zinc: a marker for apoptosis in the developing rat brain. | 2006-01 |
|
| Apoptotic neuronal changes enhanced by zinc chelator--TPEN in organotypic rat hippocampal cultures exposed to anoxia. | 2006 |
|
| New example of a non-heme mononuclear iron(IV) oxo complex. Spectroscopic data and oxidation activity. | 2005-12-12 |
|
| Taurine and zinc modulate outgrowth from goldfish retinal explants. | 2005-12 |
|
| Inhibition of the catalytic activity of hypoxia-inducible factor-1alpha-prolyl-hydroxylase 2 by a MYND-type zinc finger. | 2005-12 |
|
| Comparative sensitivity of rat cerebellar neurons to dysregulation of divalent cation homeostasis and cytotoxicity caused by methylmercury. | 2005-11-01 |
|
| Dynamics of SNARE assembly and disassembly during sperm acrosomal exocytosis. | 2005-10 |
|
| Selective zinc sensor molecules with various affinities for Zn2+, revealing dynamics and regional distribution of synaptically released Zn2+ in hippocampal slices. | 2005-07-27 |
|
| Caspase-3 dependent cleavage and activation of skeletal muscle phosphorylase b kinase. | 2005-07 |
|
| ZINC-mediated gene expression offers protection against H2O2-induced cytotoxicity. | 2005-06-15 |
|
| N,N,N',N'-tetrakis(2-pyridylmethyl)-ethylenediamine improves myocardial protection against ischemia by modulation of intracellular Ca2+ homeostasis. | 2005-06 |
|
| Keap1, the sensor for electrophiles and oxidants that regulates the phase 2 response, is a zinc metalloprotein. | 2005-05-10 |
|
| Simultaneous detection of [metal(II)-tpen]2+ as kinetically inert cationic complexes using pre-capillary derivatization electrophoresis: an application to biological samples. | 2005-05 |
|
| Search of chemical scaffolds for novel antituberculosis agents. | 2005-04 |
|
| Acid-sensing properties in rat gastric sensory neurons from normal and ulcerated stomach. | 2005-03-09 |
|
| Mechanisms of apoptosis in human retinal pigment epithelium induced by TNF-alpha in conditions of heavy metal ion deficiency. | 2005-03 |
|
| Tetrakis(2-quinolinylmethyl)ethylenediamine (TQEN) as a new fluorescent sensor for zinc. | 2005-02-07 |
|
| TPEN attenuates hepatic apoptotic ischemia/ reperfusion injury and remote early cardiac dysfunction. | 2005-01 |
|
| Zinc has ambiguous effects on chromium (VI)-induced oxidative stress and apoptosis. | 2005 |
|
| Expression of apoptosis-related proteins in model of anoxia in vitro. | 2005 |
|
| The mammalian Zip5 protein is a zinc transporter that localizes to the basolateral surface of polarized cells. | 2004-12-03 |
|
| Peroxynitrite-induced neuronal apoptosis is mediated by intracellular zinc release and 12-lipoxygenase activation. | 2004-11-24 |
|
| Measurement of presynaptic zinc changes in hippocampal mossy fibers. | 2004-11-05 |
|
| XAS characterization of end-on and side-on peroxoiron(III) complexes of the neutral pentadentate N-donor ligand N-methyl-N,N',N'-tris(2-pyridylmethyl)ethane-1,2-diamine. | 2004-10-21 |
|
| Development of a zinc ion-selective luminescent lanthanide chemosensor for biological applications. | 2004-10-06 |
|
| Fungal susceptibility to zinc deprivation. | 2004-10 |
|
| Actions of zinc at mature Golgi cell to granule cell synapses in cerebellum of rats and mice. | 2004-08-26 |
|
| Differential regulation of zinc efflux transporters ZnT-1, ZnT-5 and ZnT-7 gene expression by zinc levels: a real-time RT-PCR study. | 2004-08-15 |
|
| Peroxisome proliferator activated receptors alpha and gamma require zinc for their anti-inflammatory properties in porcine vascular endothelial cells. | 2004-07 |
|
| Hippocampal mossy fiber calcium transients are maintained during long-term potentiation and are inhibited by endogenous zinc. | 2004-04-09 |
|
| Evaluation, using targeted aequorins, of the roles of the endoplasmic reticulum and its (Ca2++Mg2+)ATP-ases in the activation of store-operated Ca2+ channels in liver cells. | 2004-04 |
|
| Unliganded human mutant alpha 7 nicotinic receptors are modulated by Ca2+ and trace levels of Zn2+. | 2004-04 |
|
| Crosstalk between nitric oxide and zinc pathways to neuronal cell death involving mitochondrial dysfunction and p38-activated K+ channels. | 2004-02-05 |
|
| Divalent cations regulate acidity within the lumen and tubulovesicle compartment of gastric parietal cells. | 2004-01 |
|
| Depletion of endogenous zinc stores induces oxidative stress and cell death in human melanoma cells. | 2004 |
|
| Intracellular zinc fluctuations modulate protein tyrosine phosphatase activity in insulin/insulin-like growth factor-1 signaling. | 2003-12-10 |
|
| Regulation of zinc homeostasis by inducible NO synthase-derived NO: nuclear metallothionein translocation and intranuclear Zn2+ release. | 2003-11-25 |
Patents
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 05:51:02 GMT 2025
by
admin
on
Wed Apr 02 05:51:02 GMT 2025
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| Record UNII |
447DAN30LD
|
| Record Status |
Validated (UNII)
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| Record Version |
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m11846
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139065867
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163088-76-4
Created by
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447DAN30LD
Created by
admin on Wed Apr 02 05:51:02 GMT 2025 , Edited by admin on Wed Apr 02 05:51:02 GMT 2025
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PARENT -> SALT/SOLVATE |
