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58337-38-5,MFCD00151066
Catalog No.:AA00EBIS

58337-38-5 | Ehna hydrochloride

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5mg
≥95%
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10mg
≥95%
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25mg
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500mg
98% by HPLC
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1000mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00EBIS
Chemical Name:
Ehna hydrochloride
CAS Number:
58337-38-5
Molecular Formula:
C28H48Cl2N10O2
Molecular Weight:
627.6525
MDL Number:
MFCD00151066
SMILES:
CCCCCC[C@@H](n1cnc2c1ncnc2N)[C@@H](O)C.CCCCCC[C@H](n1cnc2c1ncnc2N)[C@H](O)C.Cl.Cl
NSC Number:
263164
Properties
Computed Properties
 
Complexity:
291  
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
7  

Literature

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Journal: Journal of cellular physiology 20121101

Title: Measurement of deoxyinosine adduct: Can it be a reliable tool to assess oxidative or nitrosative DNA damage?

Journal: Toxicology letters 20121017

Title: Adenosine-mediated cardiovascular toxicity in amitriptyline-poisoned rats.

Journal: Drug and chemical toxicology 20121001

Title: On-pump inhibition of es-ENT1 nucleoside transporter and adenosine deaminase during aortic crossclamping entraps intracellular adenosine and protects against reperfusion injury: role of adenosine A1 receptor.

Journal: The Journal of thoracic and cardiovascular surgery 20120701

Title: The adenosine deaminases of Plasmodium vivax and Plasmodium falciparum exhibit surprising differences in ligand specificity.

Journal: Journal of molecular graphics & modelling 20120501

Title: Distinctive immunoregulatory effects of adenosine on T cells of older humans.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20120301

Title: Dynein dysfunction disrupts intracellular vesicle trafficking bidirectionally and perturbs synaptic vesicle docking via endocytic disturbances a potential mechanism underlying age-dependent impairment of cognitive function.

Journal: The American journal of pathology 20120201

Title: Adenosine activation of A(2B) receptor(s) is essential for stimulated epithelial ciliary motility and clearance.

Journal: American journal of physiology. Lung cellular and molecular physiology 20110801

Title: Inhibition of ATP release from erythrocytes: a role for EPACs and PKC.

Journal: Microcirculation (New York, N.Y. : 1994) 20110201

Title: Erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA) blocks differentiation and maintains the expression of pluripotency markers in human embryonic stem cells.

Journal: The Biochemical journal 20101215

Title: The blockade of adenosine deaminase ameliorates chronic experimental colitis through the recruitment of adenosine A2A and A3 receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20101101

Title: Rapid determination of adenosine deaminase kinetics using fast-scan cyclic voltammetry.

Journal: Physical chemistry chemical physics : PCCP 20100914

Title: Mechanisms regulating the nuclear translocation of p38 MAP kinase.

Journal: Journal of cellular biochemistry 20100815

Title: Strategy to fabricate an electrochemical aptasensor: application to the assay of adenosine deaminase activity.

Journal: Analytical chemistry 20100415

Title: A novel mouse model for sudden unexpected death in epilepsy (SUDEP): role of impaired adenosine clearance.

Journal: Epilepsia 20100301

Title: The effects of dynein inhibition on the autophagic pathway in glioma cells.

Journal: Neuropathology : official journal of the Japanese Society of Neuropathology 20100201

Title: Caspase-4 activation in association with decreased adenosine deaminase activity may be a factor for gastric ulcer.

Journal: Digestion 20100101

Title: Influence of an adenosine deaminase inhibitor, erythro-9-(2-hydroxy-3-nonyl) adenine hydrochloride, on 5-HT2CR mRNA editing in primary cultured cortical cells.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Purinergic modulation in the development of the rat uncrossed retinotectal pathway.

Journal: Neuroscience 20091110

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: Dynein motor contributes to stress granule dynamics in primary neurons.

Journal: Neuroscience 20090317

Title: Adenosine as an endogenous regulating factor of hippocampal sharp waves.

Journal: Hippocampus 20090201

Title: Shared requirement for dynein function and intact microtubule cytoskeleton for normal surface expression of cardiac potassium channels.

Journal: American journal of physiology. Heart and circulatory physiology 20090101

Title: Kinetic characterization of adenosine deaminase activity in zebrafish (Danio rerio) brain.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20080901

Title: Conformational change of adenosine deaminase during ligand-exchange in a crystal.

Journal: Biochemical and biophysical research communications 20080815

Title: [Conformation of adenosine deaminase in complexes with inhibitors: application of selective quenching of fluorescence emission].

Journal: Biofizika 20080101

Title: The adenosine deaminase inhibitor erythro-9-[2-hydroxyl-3-nonyl]-adenine decreases intestinal permeability and protects against experimental sepsis: a prospective, randomised laboratory investigation.

Journal: Critical care (London, England) 20080101

Title: Inhibition of adenosine deaminase attenuates inflammation in experimental colitis.

Journal: The Journal of pharmacology and experimental therapeutics 20070801

Title: Methotrexate and erythro-9-(2-hydroxynon-3-yl) adenine therapy for rat adjuvant arthritis and the effect of methotrexate on in vivo purine metabolism.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20070601

Title: Modulation of ischaemic contracture in mouse hearts: a 'supraphysiological' response to adenosine.

Journal: Experimental physiology 20070101

Title: Anandamide inhibits endothelin-1 production by human cultured endothelial cells: a new vascular action of this endocannabinoid.

Journal: Pharmacology 20070101

Title: Effects of phosphodiesterase (PDE) inhibitors on human ether-a-go-go related gene (hERG) channel activity.

Journal: Journal of applied toxicology : JAT 20070101

Title: Fine-tuning modulation of myenteric motoneurons by endogenous adenosine: on the role of secreted adenosine deaminase.

Journal: Autonomic neuroscience : basic & clinical 20060630

Title: Solid-phase enzyme activity assay utilizing an entrapped fluorescence-signaling DNA aptamer.

Journal: Angewandte Chemie (International ed. in English) 20060512

Title: The role of adenosine in chondrocyte death in murine osteoarthritis and in a murine chondrocyte cell line.

Journal: Osteoarthritis and cartilage 20060501

Title: Cyclic guanosine monophosphate compartmentation in rat cardiac myocytes.

Journal: Circulation 20060501

Title: Moderate hypoxia induces xanthine oxidoreductase activity in arterial endothelial cells.

Journal: Free radical biology & medicine 20060315

Title: Compartmentalized phosphodiesterase-2 activity blunts beta-adrenergic cardiac inotropy via an NO/cGMP-dependent pathway.

Journal: Circulation research 20060203

Title: Assay of adenosine deaminase isoforms by HPLC.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060202

Title: A new chemical tool for exploring the physiological function of the PDE2 isozyme.

Journal: Bioorganic & medicinal chemistry letters 20060115

Title: Extracellular inosine participates in tumor necrosis factor-alpha induced nitric oxide production in cultured Sertoli cells.

Journal: Molecular and cellular biochemistry 20060101

Title: Adenosine down-regulates giant depolarizing potentials in the developing rat hippocampus by exerting a negative control on glutamatergic inputs.

Journal: Journal of neurophysiology 20051001

Title: Adenosine and deoxyadenosine induces apoptosis in oestrogen receptor-positive and -negative human breast cancer cells via the intrinsic pathway.

Journal: Cell proliferation 20051001

Title: Reduction in interaction between cGMP and cAMP in dog ventricular myocytes with hypertrophic failure.

Journal: American journal of physiology. Heart and circulatory physiology 20050901

Title: Dynein mutations impair autophagic clearance of aggregate-prone proteins.

Journal: Nature genetics 20050701

Title: Effects of various selective phosphodiesterase inhibitors on carbachol-induced contraction and cyclic nucleotide contents in the guinea pig gall bladder.

Journal: The Journal of veterinary medical science 20050701

Title: Structural determinants for inhibitor specificity and selectivity in PDE2A using the wheat germ in vitro translation system.

Journal: Biochemistry 20050614

Title: Adenosine-dependent induction of glutathione peroxidase 1 in human primary endothelial cells and protection against oxidative stress.

Journal: Circulation research 20050429

Title: The phosphodiesterase 3 inhibitor cilostamide enhances inotropic responses to glucagon but not to dobutamine in rat ventricular myocardium.

Journal: European journal of pharmacology 20050411

Title: Differential effects of cGMP produced by soluble and particulate guanylyl cyclase on mouse ventricular myocytes.

Journal: Experimental biology and medicine (Maywood, N.J.) 20050401

Title: Protective effect of adenosine and purine nucleos(t)ides against the death by hydrogen peroxide and glucose deprivation in rat primary astrocytes.

Journal: Neuroscience research 20050101

Title: Macrophages are a source of extracellular adenosine deaminase-2 during inflammatory responses.

Journal: Clinical and experimental immunology 20041001

Title: Effects of the sGC stimulator BAY 41-2272 are not mediated by phosphodiesterase 5 inhibition.

Journal: Circulation 20040921

Title: Effects of various selective phosphodiesterase inhibitors on carbachol-induced contraction and cyclic nucleotide contents in guinea pig taenia coli.

Journal: The Journal of veterinary medical science 20040901

Title: Adenosine induces apoptosis in the human gastric cancer cells via an intrinsic pathway relevant to activation of AMP-activated protein kinase.

Journal: Biochemical pharmacology 20040515

Title: Nitric oxide inhibits arginine-vasotocin-induced increase of water osmotic permeability in frog urinary bladder.

Journal: Pflugers Archiv : European journal of physiology 20040501

Title: High and low gain switches for regulation of cAMP efflux concentration: distinct roles for particulate GC- and soluble GC-cGMP-PDE3 signaling in rabbit atria.

Journal: Circulation research 20040416

Title: Adenosine deaminase 2 from chicken liver: purification, characterization, and N-terminal amino acid sequence.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20040201

Title: Extracellular inosine is modulated by H2O2 and protects sertoli cells against lipoperoxidation and cellular injury.

Journal: Free radical research 20040101

Title: Phosphoinositide 3-kinase is involved in Xenopus and Labrus melanophore aggregation.

Journal: Cellular signalling 20031201

Title: Positive inotropic effect of the inhibition of cyclic GMP-stimulated 3',5'-cyclic nucleotide phosphodiesterase (PDE2) on guinea pig left atria in eu- and hyperthyroidism.

Journal: General physiology and biophysics 20031201

Title: Negative functional effects of cyclic GMP are altered by cyclic AMP phosphodiesterases in rabbit cardiac myocytes.

Journal: European journal of pharmacology 20031114

Title: Extracellular ATP and adenosine induce cell apoptosis of human hepatoma Li-7A cells via the A3 adenosine receptor.

Journal: British journal of pharmacology 20031101

Title: A simple technique for reducing edge effect in cell-based assays.

Journal: Journal of biomolecular screening 20031001

Title: Endogenous adenosine modulation of 22Na uptake by rat brain synaptosomes.

Journal: Neurochemical research 20031001

Title: Phosphorylation of the vasodilator-stimulated phosphoprotein (VASP) by the anti-platelet drug, cilostazol, in platelets.

Journal: Platelets 20030901

Title: An angiogenic switch in macrophages involving synergy between Toll-like receptors 2, 4, 7, and 9 and adenosine A(2A) receptors.

Journal: The American journal of pathology 20030801

Title: VEGF-induced HUVEC migration and proliferation are decreased by PDE2 and PDE4 inhibitors.

Journal: Thrombosis and haemostasis 20030801

Title: Comparative actions of diazepam and other phosphodiesterase inhibitors on the effects of noradrenaline in rat myocardium.

Journal: Pharmacology & toxicology 20030701

Title: Tracer adenosine: a novel myocardial flow marker.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20030401

Title: Inhibition of ovarian steroidogenesis by cyclic GMP in a fly.

Journal: The Journal of endocrinology 20030401

Title: Structure-based de novo design of non-nucleoside adenosine deaminase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20030324

Title: Extracellular purines from cells of seminiferous tubules.

Journal: Molecular and cellular biochemistry 20030301

Title: Activation of A(3) receptors by endogenous adenosine inhibits synaptic transmission during hypoxia in rat cortical neurons.

Journal: Restorative neurology and neuroscience 20030101

Title: Broad spectrum anticonvulsant activity of BW534U87: possible role of an adenosine-dependent mechanism.

Journal: Pharmacology, biochemistry, and behavior 20021201

Title: Adenosine A(2a) receptor-mediated inhibition of rod opsin mRNA expression in tiger salamander.

Journal: Journal of neurochemistry 20021101

Title: Effects of an adenosine kinase inhibitor and an adenosine deaminase inhibitor on accumulation of extracellular adenosine by equine articular chondrocytes.

Journal: American journal of veterinary research 20021101

Title: Hydrolysis of N-methyl-D-aspartate receptor-stimulated cAMP and cGMP by PDE4 and PDE2 phosphodiesterases in primary neuronal cultures of rat cerebral cortex and hippocampus.

Journal: The Journal of pharmacology and experimental therapeutics 20020701

Title: Natriuretic peptide receptor-B in adult rat ventricle is predominantly confined to the nonmyocyte population.

Journal: American journal of physiology. Heart and circulatory physiology 20020601

Title: Mechanisms of apoptosis induced by purine nucleosides in astrocytes.

Journal: Glia 20020501

Title: Differential regulation of human platelet responses by cGMP inhibited and stimulated cAMP phosphodiesterases.

Journal: Thrombosis and haemostasis 20020501

Title: Does endogenous or exogenous adenosine facilitate the functional recovery of the cochlea after ischemia?

Journal: The Annals of otology, rhinology, and laryngology 20020401

Title: Phosphodiesterase inhibitors cause relaxation of the internal anal sphincter in vitro.

Journal: Diseases of the colon and rectum 20020401

Title: Erythro- and threo-2-hydroxynonyl substituted 2-phenyladenines and 2-phenyl-8-azaadenines: ligands for A1 adenosine receptors and adenosine deaminase.

Journal: Farmaco (Societa chimica italiana : 1989) 20020301

Title: NO-cGMP pathway increases the hyperpolarisation-activated current, I(f), and heart rate during adrenergic stimulation.

Journal: Cardiovascular research 20011201

Title: Effect of adenosine receptor blockade on pial arteriolar dilation during sciatic nerve stimulation.

Journal: American journal of physiology. Heart and circulatory physiology 20011101

Title: Cardioprotection with adenosine metabolism inhibitors in ischemic-reperfused mouse heart.

Journal: Cardiovascular research 20011001

Title: Protection from reperfusion injury after cardiac transplantation by inhibition of adenosine metabolism and nucleotide precursor supply.

Journal: Circulation 20010918

Title: Inhibition of adenosine deaminase attenuates endotoxin-induced release of cytokines in vivo in rats.

Journal: Shock (Augusta, Ga.) 20010901

Title: Enhanced oral bioavailability of 2'- beta-fluoro-2',3'-dideoxyadenosine (F-ddA) through local inhibition of intestinal adenosine deaminase.

Journal: Pharmaceutical research 20010901

Title: Local response of L-type Ca(2+) current to nitric oxide in frog ventricular myocytes.

Journal: The Journal of physiology 20010701

Title: Tryptophan environment in adenosine deaminase. I. Enzyme modification with N-bromosuccinimide in the presence of adenosine and EHNA analogues.

Journal: Biochimica et biophysica acta 20010309

Title: Renal interstitial adenosine metabolism during ischemia in dogs.

Journal: American journal of physiology. Renal physiology 20010201

Title: NO Inhibits NaCl absorption by rat thick ascending limb through activation of cGMP-stimulated phosphodiesterase.

Journal: Hypertension (Dallas, Tex. : 1979) 20010201

Title: Regulation of cardiac calcium current by NO and cGMP-modulating agents.

Journal: Pflugers Archiv : European journal of physiology 20010201

Title: Activation of presynaptic A1-receptors by endogenous adenosine inhibits acetylcholine release in the guinea-pig ileum.

Journal: Journal of autonomic pharmacology 20010201

Title: Evidence against a major role of adenosine in oxygen-dependent regulation of erythropoietin in rats.

Journal: Kidney international 19970801

Title: Rapid regulation of PDE-2 and PDE-4 cyclic AMP phosphodiesterase activity following ligation of the T cell antigen receptor on thymocytes: analysis using the selective inhibitors erythro-9-(2-hydroxy-3-nonyl)-adenine (EHNA) and rolipram.

Journal: Cellular signalling 19960201

Title: Evaluation of the effects of erythro-9(2-hydroxy-3-nonyl) adenine (EHNA) on HIV-1 production in vitro.

Journal: Biochemical and biophysical research communications 19891016

Title: Effects of chirality in 9-(2-hydroxy-3-nonyl)adenine upon deoxyribonucleic acid synthesis in herpes simplex virus-infected cells.

Journal: Biochemical pharmacology 19831201

Title: Podzuweit T, et al. Isozyme selective inhibition of cGMP-stimulated cyclic nucleotide phosphodiesterases by erythro-9-(2-hydroxy-3-nonyl) adenine.Cell Signal. 1995 Sep;7(7):733-8.

Title: Michie AM, et al. Rapid regulation of PDE-2 and PDE-4 cyclic AMP phosphodiesterase activity following ligation of the T cell antigen receptor on thymocytes: analysis using the selective inhibitors erythro-9-(2-hydroxy-3-nonyl)-adenine (EHNA) and rolipram.Cell Signal. 1996 Feb;8(2):97-110.

Title: Blázquez-Bermejo C, et al. Increased dNTP pools rescue mtDNA depletion in human POLG-deficient fibroblasts. FASEB J. 2019 Jun;33(6):7168-7179.

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Tags:58337-38-5 Molecular Formula|58337-38-5 MDL|58337-38-5 SMILES|58337-38-5 Ehna hydrochloride