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16858-02-9 | 1,2-Ethanediamine, N,N,N',N'-tetrakis(2-pyridinylmethyl)-
CAS No: 16858-02-9 Catalog No: AG001Y5G MDL No:MFCD00036918
Product Description
Catalog Number:
AG001Y5G
Chemical Name:
1,2-Ethanediamine, N,N,N',N'-tetrakis(2-pyridinylmethyl)-
CAS Number:
16858-02-9
Molecular Formula:
C26H28N6
Molecular Weight:
424.5407
MDL Number:
MFCD00036918
IUPAC Name:
N,N,N',N'-tetrakis(pyridin-2-ylmethyl)ethane-1,2-diamine
InChI:
InChI=1S/C26H28N6/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/h1-16H,17-22H2
InChI Key:
CVRXLMUYFMERMJ-UHFFFAOYSA-N
SMILES:
c1ccc(nc1)CN(Cc1ccccn1)CCN(Cc1ccccn1)Cc1ccccn1
UNII:
R9PTU1U29I
Properties
Complexity:
419
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
424.238g/mol
Formal Charge:
0
Heavy Atom Count:
32
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
424.552g/mol
Monoisotopic Mass:
424.238g/mol
Rotatable Bond Count:
11
Topological Polar Surface Area:
58A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.1
Literature
| Title | Journal |
|---|---|
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| Arsenite binding-induced zinc loss from PARP-1 is equivalent to zinc deficiency in reducing PARP-1 activity, leading to inhibition of DNA repair. | Toxicology and applied pharmacology 20140115 |
| Induction of autophagy and cell death by tamoxifen in cultured retinal pigment epithelial and photoreceptor cells. | Investigative ophthalmology & visual science 20120809 |
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| Zinc maintains prophase I arrest in mouse oocytes through regulation of the MOS-MAPK pathway. | Biology of reproduction 20120701 |
| Zinc enhances adiponectin oligomerization to octadecamers but decreases the rate of disulfide bond formation. | Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine 20120401 |
| Reaction of metal-binding ligands with the zinc proteome: zinc sensors and N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine. | Inorganic chemistry 20120319 |
| Colorimetric and fluorescent signaling of Au3+ by desulfurization of thiocoumarin. | Inorganic chemistry 20120305 |
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| Influence of zinc and zinc chelator on HT-29 colorectal cell line. | Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine 20110201 |
| Exacerbation of diabetes-induced testicular apoptosis by zinc deficiency is most likely associated with oxidative stress, p38 MAPK activation, and p53 activation in mice. | Toxicology letters 20110115 |
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| The zinc-dependent protease activity of the botulinum neurotoxins. | Toxins 20100501 |
| Nitric oxide synthase activation and oxidative stress, but not intracellular zinc dyshomeostasis, regulate ultraviolet B light-induced apoptosis. | Life sciences 20100313 |
| Zinc deficiency suppresses matrix mineralization and retards osteogenesis transiently with catch-up possibly through Runx 2 modulation. | Bone 20100301 |
| Effects of postconditioning with N,N,N'N'-tetrakis-[2-pyridylmethyl]-ethylenediamine in isolated rat hearts. | Korean journal of anesthesiology 20100301 |
| Endogenous zinc mediates apoptotic programmed cell death in the developing brain. | Neurotoxicity research 20100201 |
| Morphine prevents the mitochondrial permeability transition pore opening through NO/cGMP/PKG/Zn2+/GSK-3beta signal pathway in cardiomyocytes. | American journal of physiology. Heart and circulatory physiology 20100201 |
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| Nickel mobilizes intracellular zinc to induce metallothionein in human airway epithelial cells. | American journal of respiratory cell and molecular biology 20090701 |
| N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine induces apoptosis through the activation of caspases-3 and -8 in human platelets. A role for endoplasmic reticulum stress. | Journal of thrombosis and haemostasis : JTH 20090601 |
| Dynamic interaction of hTRPC6 with the Orai1-STIM1 complex or hTRPC3 mediates its role in capacitative or non-capacitative Ca(2+) entry pathways. | The Biochemical journal 20090513 |
| Essential role of p53 in TPEN-induced neuronal apoptosis. | FEBS letters 20090506 |
| Theoretical study of cyclohexane hydroxylation by three possible isomers of [FeIV(O)(R-TPEN)] 2+: does the pentadentate ligand wrapping around the metal center differently lead to the different stability and reactivity? | Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20090501 |
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| On the use of fluorescent probes to distinguish Ca2+ from Zn2+ in models of excitotoxicity. | Cell calcium 20070901 |
| Potentiation of acid-sensing ion channels by sulfhydryl compounds. | American journal of physiology. Cell physiology 20070601 |
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| Ca2+ release from the sarcoplasmic reticulum activated by the low affinity Ca2+ chelator TPEN in ventricular myocytes. | Cell calcium 20070201 |
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| Cellular Zn depletion by metal ion chelators (TPEN, DTPA and chelex resin) and its application to osteoblastic MC3T3-E1 cells. | Nutrition research and practice 20070101 |
| Zinc modulates cytokine-induced lung epithelial cell barrier permeability. | American journal of physiology. Lung cellular and molecular physiology 20061201 |
| Clioquinol, a Cu(II)/Zn(II) chelator, inhibits both ubiquitination and asparagine hydroxylation of hypoxia-inducible factor-1alpha, leading to expression of vascular endothelial growth factor and erythropoietin in normoxic cells. | The Journal of biological chemistry 20061110 |
| Reduced nonprotein thiols inhibit activation and function of MMP-9: implications for chemoprevention. | Free radical biology & medicine 20061015 |
| Diverse effects of zinc on NF-kappaB and AP-1 transcription factors: implications for prostate cancer progression. | Carcinogenesis 20061001 |
| Apo-metallothionein emerging as a major player in the cellular activities of metallothionein. | Experimental biology and medicine (Maywood, N.J.) 20061001 |
| Cytotoxicity of nitric oxide is alleviated by zinc-mediated expression of antioxidant genes. | Experimental biology and medicine (Maywood, N.J.) 20061001 |
| Inhibition of cyclooxygenase-2 expression by zinc-chelator in retinal ischemia. | Vision research 20060901 |
| Endothelial response to stress from exogenous Zn2+ resembles that of NO-mediated nitrosative stress, and is protected by MT-1 overexpression. | American journal of physiology. Cell physiology 20060901 |
| Toll-like receptor-mediated regulation of zinc homeostasis influences dendritic cell function. | Nature immunology 20060901 |
| Zinc is required for Fc epsilon RI-mediated mast cell activation. | Journal of immunology (Baltimore, Md. : 1950) 20060715 |
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| Zinc-dependent multi-conductance channel activity in mitochondria isolated from ischemic brain. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20060621 |
| The zinc chelator, N,N,N',N'-tetrakis (2-pyridylmethyl) ethylenediamine, increases the level of nonfunctional HIF-1alpha protein in normoxic cells. | Biochemical and biophysical research communications 20060519 |
| Flow cytometric measurement of labile zinc in peripheral blood mononuclear cells. | Analytical biochemistry 20060515 |
| Intracellular zinc release and ERK phosphorylation are required upstream of 12-lipoxygenase activation in peroxynitrite toxicity to mature rat oligodendrocytes. | The Journal of biological chemistry 20060407 |
| Selenium prevents diabetes-induced alterations in [Zn2+]i and metallothionein level of rat heart via restoration of cell redox cycle. | American journal of physiology. Heart and circulatory physiology 20060301 |
| Apoptosis may underlie the pathology of zinc-deficient skin. | Immunology and cell biology 20060201 |
| Protective effect of zinc against ischemic neuronal injury in a middle cerebral artery occlusion model. | Journal of pharmacological sciences 20060201 |
| Cytosolic labile zinc: a marker for apoptosis in the developing rat brain. | The European journal of neuroscience 20060101 |
| Apoptotic neuronal changes enhanced by zinc chelator--TPEN in organotypic rat hippocampal cultures exposed to anoxia. | Folia neuropathologica 20060101 |
| Effect of the zinc chelator N,N,N',N'-tetrakis (2-pyridylmethyl)ethylenediamine (TPEN) on hippocampal mossy fiber calcium signals and on synaptic transmission. | Biological research 20060101 |
| Neuritic outgrowth from goldfish retinal explants, interaction of taurine and zinc. | Advances in experimental medicine and biology 20060101 |
| New example of a non-heme mononuclear iron(IV) oxo complex. Spectroscopic data and oxidation activity. | Inorganic chemistry 20051212 |
| Inhibition of the catalytic activity of hypoxia-inducible factor-1alpha-prolyl-hydroxylase 2 by a MYND-type zinc finger. | Molecular pharmacology 20051201 |
| Taurine and zinc modulate outgrowth from goldfish retinal explants. | Neurochemical research 20051201 |
| Neuronal zinc stores are modulated by non-steroidal anti-inflammatory drugs: an optical analysis in cultured hippocampal neurons. | Brain research 20051102 |
| Comparative sensitivity of rat cerebellar neurons to dysregulation of divalent cation homeostasis and cytotoxicity caused by methylmercury. | Toxicology and applied pharmacology 20051101 |
| Dynamics of SNARE assembly and disassembly during sperm acrosomal exocytosis. | PLoS biology 20051001 |
| Selective zinc sensor molecules with various affinities for Zn2+, revealing dynamics and regional distribution of synaptically released Zn2+ in hippocampal slices. | Journal of the American Chemical Society 20050727 |
| Caspase-3 dependent cleavage and activation of skeletal muscle phosphorylase b kinase. | Molecular and cellular biochemistry 20050701 |
| ZINC-mediated gene expression offers protection against H2O2-induced cytotoxicity. | Toxicology and applied pharmacology 20050615 |
| N,N,N',N'-tetrakis(2-pyridylmethyl)-ethylenediamine improves myocardial protection against ischemia by modulation of intracellular Ca2+ homeostasis. | The Journal of pharmacology and experimental therapeutics 20050601 |
| Keap1, the sensor for electrophiles and oxidants that regulates the phase 2 response, is a zinc metalloprotein. | Biochemistry 20050510 |
| Simultaneous detection of [metal(II)-tpen]2+ as kinetically inert cationic complexes using pre-capillary derivatization electrophoresis: an application to biological samples. | The Analyst 20050501 |
| Search of chemical scaffolds for novel antituberculosis agents. | Journal of biomolecular screening 20050401 |
| Acid-sensing properties in rat gastric sensory neurons from normal and ulcerated stomach. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20050309 |
| Mechanisms of apoptosis in human retinal pigment epithelium induced by TNF-alpha in conditions of heavy metal ion deficiency. | Investigative ophthalmology & visual science 20050301 |
| Tetrakis(2-quinolinylmethyl)ethylenediamine (TQEN) as a new fluorescent sensor for zinc. | Dalton transactions (Cambridge, England : 2003) 20050207 |
| TPEN attenuates hepatic apoptotic ischemia/ reperfusion injury and remote early cardiac dysfunction. | Apoptosis : an international journal on programmed cell death 20050101 |
| Expression of apoptosis-related proteins in model of anoxia in vitro. | Folia neuropathologica 20050101 |
| Zinc has ambiguous effects on chromium (VI)-induced oxidative stress and apoptosis. | Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS) 20050101 |
| The mammalian Zip5 protein is a zinc transporter that localizes to the basolateral surface of polarized cells. | The Journal of biological chemistry 20041203 |
| Peroxynitrite-induced neuronal apoptosis is mediated by intracellular zinc release and 12-lipoxygenase activation. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20041124 |
| Measurement of presynaptic zinc changes in hippocampal mossy fibers. | Brain research 20041105 |
| 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. | Dalton transactions (Cambridge, England : 2003) 20041021 |
| Development of a zinc ion-selective luminescent lanthanide chemosensor for biological applications. | Journal of the American Chemical Society 20041006 |
| Fungal susceptibility to zinc deprivation. | The Journal of laboratory and clinical medicine 20041001 |
| Actions of zinc at mature Golgi cell to granule cell synapses in cerebellum of rats and mice. | Neuroscience letters 20040826 |
| Differential regulation of zinc efflux transporters ZnT-1, ZnT-5 and ZnT-7 gene expression by zinc levels: a real-time RT-PCR study. | Biochemical pharmacology 20040815 |
| Peroxisome proliferator activated receptors alpha and gamma require zinc for their anti-inflammatory properties in porcine vascular endothelial cells. | The Journal of nutrition 20040701 |
| Hippocampal mossy fiber calcium transients are maintained during long-term potentiation and are inhibited by endogenous zinc. | Brain research 20040409 |
| Heparin-binding epidermal growth factor cleavage mediates zinc-induced epidermal growth factor receptor phosphorylation. | American journal of respiratory cell and molecular biology 20040401 |
| Unliganded human mutant alpha 7 nicotinic receptors are modulated by Ca2+ and trace levels of Zn2+. | Neuropharmacology 20040401 |
| 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. | Cell calcium 20040401 |
| Crosstalk between nitric oxide and zinc pathways to neuronal cell death involving mitochondrial dysfunction and p38-activated K+ channels. | Neuron 20040205 |
| Endogenous zinc inhibits GABA(A) receptors in a hippocampal pathway. | Journal of neurophysiology 20040201 |
| Divalent cations regulate acidity within the lumen and tubulovesicle compartment of gastric parietal cells. | Gastroenterology 20040101 |
| Depletion of endogenous zinc stores induces oxidative stress and cell death in human melanoma cells. | Acta medica (Hradec Kralove) 20040101 |
| Intracellular zinc fluctuations modulate protein tyrosine phosphatase activity in insulin/insulin-like growth factor-1 signaling. | Experimental cell research 20031210 |
| Regulation of zinc homeostasis by inducible NO synthase-derived NO: nuclear metallothionein translocation and intranuclear Zn2+ release. | Proceedings of the National Academy of Sciences of the United States of America 20031125 |
| A reassessment of the effects of luminal [Ca2+] on inositol 1,4,5-trisphosphate-induced Ca2+ release from internal stores. | The Journal of biological chemistry 20031010 |
| Inositol 1,4,5-trisphosphate receptor ubiquitination is mediated by mammalian Ubc7, a component of the endoplasmic reticulum-associated degradation pathway, and is inhibited by chelation of intracellular Zn2+. | The Journal of biological chemistry 20031003 |
| Zinc modulates PPARgamma signaling and activation of porcine endothelial cells. | The Journal of nutrition 20031001 |
| Zinc chelators inhibit eotaxin, RANTES, and MCP-1 production in stimulated human airway epithelium and fibroblasts. | American journal of physiology. Lung cellular and molecular physiology 20030901 |
| Hg2+ signaling in trout hepatoma (RTH-149) cells: involvement of Ca2+-induced Ca2+ release. | Cell calcium 20030901 |
| Zinc deficiency induces oxidative DNA damage and increases p53 expression in human lung fibroblasts. | The Journal of nutrition 20030801 |
| N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine inhibits ligand binding to certain G protein-coupled receptors. | European journal of pharmacology 20030801 |
| Zinc-induced changes in ionic currents of cardiomyocytes. | Biological trace element research 20030701 |
| A global view of the selectivity of zinc deprivation and excess on genes expressed in human THP-1 mononuclear cells. | Proceedings of the National Academy of Sciences of the United States of America 20030610 |
| Ubiquitination and proteasomal degradation of endogenous and exogenous inositol 1,4,5-trisphosphate receptors in alpha T3-1 anterior pituitary cells. | The Journal of biological chemistry 20030110 |
| N,N,N ',N '-Tetrakis(2-pyridylmethyl)ethylenediamine and its analogues as hypodentate ligands. Synthesis and characterization of the rhodium(III), ruthenium(II), and palladium(II) complexes. | Inorganic chemistry 20021202 |
| Requirement of caspase and p38MAPK activation in zinc-induced apoptosis in human leukemia HL-60 cells. | European journal of biochemistry 20021201 |
| Zinc is involved in the expression of a nuclear-encoded alternative oxidase gene in the yeast Hansenula anomala. | Bioscience, biotechnology, and biochemistry 20021201 |
| Calreticulin differentially modulates calcium uptake and release in the endoplasmic reticulum and mitochondria. | The Journal of biological chemistry 20021129 |
| Involvement of redox events in caspase activation in zinc-depleted airway epithelial cells. | Biochemical and biophysical research communications 20021004 |
| In situ chelation of Ca(2+) in intracellular stores induces capacitative Ca(2+) entry in bovine adrenal chromaffin cells. | Annals of the New York Academy of Sciences 20021001 |
| Role of Zn(2+) in oxidative stress caused by endotoxin challenge. | European journal of pharmacology 20020920 |
| A novel, cell-permeable, fluorescent probe for ratiometric imaging of zinc ion. | Journal of the American Chemical Society 20020911 |
| DNA damage-induced [Zn(2+)](i) transients: correlation with cell cycle arrest and apoptosis in lymphoma cells. | American journal of physiology. Cell physiology 20020801 |
| Time course and magnitude of the calcium release induced by bright light in salamander rods. | The Journal of physiology 20020801 |
| Implication of extracellular zinc exclusion by recombinant human calprotectin (MRP8 and MRP14) from target cells in its apoptosis-inducing activity. | Mediators of inflammation 20020601 |
| Developmental profiles of glutamate receptors and synaptic transmission at a single synapse in the mouse auditory brainstem. | The Journal of physiology 20020501 |
| NMDA receptor-mediated currents in rat cerebellar granule and unipolar brush cells. | Journal of neurophysiology 20020401 |
| [Role of intracellular zinc in programmed cell death]. | Pathologie-biologie 20020401 |
| pH dependence and compartmentalization of zinc transported across plasma membrane of rat cortical neurons. | American journal of physiology. Cell physiology 20020201 |
| Nitric oxide-induced changes in intracellular zinc homeostasis are mediated by metallothionein/thionein. | American journal of physiology. Lung cellular and molecular physiology 20020201 |
| L-type calcium channels reduce ROS generation in cerebellar granule cells following kainate exposure. | Synapse (New York, N.Y.) 20020101 |
| Multiple pathways of neuroprotection against oxidative stress and excitotoxic injury in immature primary hippocampal neurons. | Brain research. Developmental brain research 20011231 |
| Cellular zinc content is a major determinant of iron chelator-induced apoptosis of thymocytes. | Blood 20011215 |
| Mechanism of apoptosis induced by zinc deficiency in peripheral blood T lymphocytes. | Apoptosis : an international journal on programmed cell death 20011201 |
| Effects of intracellular zinc depletion on metallothionein and ZIP2 transporter expression and apoptosis. | Journal of leukocyte biology 20011001 |
| Extreme zinc-binding thermodynamics of the metal sensor/regulator protein, ZntR. | Journal of the American Chemical Society 20010905 |
| Characteristics of a store-operated calcium-permeable channel: sarcoendoplasmic reticulum calcium pump function controls channel gating. | The Journal of biological chemistry 20010810 |
| The role of zinc binding in the biological activity of botulinum toxin. | The Journal of biological chemistry 20010720 |
| Role of cellular zinc in programmed cell death: temporal relationship between zinc depletion, activation of caspases, and cleavage of Sp family transcription factors. | Biochemical pharmacology 20010701 |
| Role of zinc in pulmonary endothelial cell response to oxidative stress. | American journal of physiology. Lung cellular and molecular physiology 20010701 |
| Femtomolar sensitivity of metalloregulatory proteins controlling zinc homeostasis. | Science (New York, N.Y.) 20010629 |
| Reassembly of the tight junction after oxidative stress depends on tyrosine kinase activity. | The Journal of biological chemistry 20010622 |
| Modulation of caspase-3 activity by zinc ions and by the cell redox state. | Experimental cell research 20010610 |
| p38 activation is required upstream of potassium current enhancement and caspase cleavage in thiol oxidant-induced neuronal apoptosis. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20010515 |
| Receptor-operated osteoclast calcium sensing. | Endocrinology 20010501 |
| Enzymatic autocatalysis of botulinum A neurotoxin light chain. | Journal of protein chemistry 20010401 |
| Cleavage of SNAP-25 by botulinum toxin type A requires receptor-mediated endocytosis, pH-dependent translocation, and zinc. | The Journal of pharmacology and experimental therapeutics 20010301 |
| Comparative effects of metal chelating agents on the neuronal cytotoxicity induced by copper (Cu+2), iron (Fe+3) and zinc in the hippocampus. | Brain research 20010216 |
| Depletion of intracellular zinc and copper with TPEN results in apoptosis of cultured human retinal pigment epithelial cells. | Investigative ophthalmology & visual science 20010201 |
| High-affinity zinc potentiation of inhibitory postsynaptic glycinergic currents in the zebrafish hindbrain. | Journal of neurophysiology 20010201 |
| [Transition metals and nitric oxide production in human endothelial cells]. | Comptes rendus de l'Academie des sciences. Serie III, Sciences de la vie 20010101 |
| 2-Aminoethoxydiphenyl borate (2-APB) inhibits capacitative calcium entry independently of the function of inositol 1,4,5-trisphosphate receptors. | Receptors & channels 20010101 |
| Apoptosis induced by cadmium in human lymphoma U937 cells through Ca2+-calpain and caspase-mitochondria- dependent pathways. | The Journal of biological chemistry 20001215 |
| Effector caspases are dispensable for the early nuclear morphological changes during chemical-induced apoptosis. | Journal of cell science 20000901 |
| Zinc protects against apoptosis of endothelial cells induced by linoleic acid and tumor necrosis factor alpha. | The American journal of clinical nutrition 20000101 |
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