164204-38-0,MFCD01459907
Catalog No.:AA00ASPI

164204-38-0 | N-[N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]- L-tryptophan,sodium salt (1

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Purity
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1mg
≥98%
in stock  
$123.00   $86.00
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5mg
≥98%
in stock  
$242.00   $169.00
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10mg
≥98%
in stock  
$423.00   $296.00
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25mg
≥98%
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  • Technical Information
  • Properties
  • Literature
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Technical Information
Catalog Number:
AA00ASPI
Chemical Name:
N-[N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]- L-tryptophan,sodium salt (1
CAS Number:
164204-38-0
Molecular Formula:
C23H34N3Na2O10P
Molecular Weight:
589.4835
MDL Number:
MFCD01459907
SMILES:
CC(C[C@@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)NP(=O)(O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)C.[Na].[Na]
Properties
Computed Properties
 
Complexity:
834  
Covalently-Bonded Unit Count:
3  
Defined Atom Stereocenter Count:
7  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
39  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0  
Rotatable Bond Count:
10  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  

Literature

Title: Neurogenic airway microvascular leakage induced by toluene inhalation in rats.

Journal: European journal of pharmacology 20120615

Title: In-silico characterization of ECE-1 inhibitors.

Journal: Computers in biology and medicine 20120401

Title: Antinociceptive effect of [Met5]enkephalin semicarbazide is not affected by dipeptidyl carboxypeptidase-I.

Journal: Journal of peptide science : an official publication of the European Peptide Society 20120201

Title: The role of neutral endopeptidase in caerulein-induced acute pancreatitis.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20111115

Title: Aβ-degrading enzymes: potential for treatment of Alzheimer disease.

Journal: Journal of neuropathology and experimental neurology 20111101

Title: Crystal structure of Mycobacterium tuberculosis zinc-dependent metalloprotease-1 (Zmp1), a metalloprotease involved in pathogenicity.

Journal: The Journal of biological chemistry 20110916

Title: Dendroaspis natriuretic peptide and the designer natriuretic peptide, CD-NP, are resistant to proteolytic inactivation.

Journal: Journal of molecular and cellular cardiology 20110701

Title: Cysteine cathepsins in human carious dentin.

Journal: Journal of dental research 20110401

Title: Intranasal phosphoramidon increases beta-amyloid levels in wild-type and NEP/NEP2-deficient mice.

Journal: Journal of molecular neuroscience : MN 20110301

Title: Endothelin-1 expression by vascular endothelial growth factor in human umbilical vein endothelial cells and aortic smooth muscle cells.

Journal: Hypertension in pregnancy 20110101

Title: Neprilysin-2 is an important β-amyloid degrading enzyme.

Journal: The American journal of pathology 20110101

Title: Bradykinin-induced lung inflammation and bronchoconstriction: role in parainfluenze-3 virus-induced inflammation and airway hyperreactivity.

Journal: The Journal of pharmacology and experimental therapeutics 20101201

Title: Increased endothelial exocytosis and generation of endothelin-1 contributes to constriction of aged arteries.

Journal: Circulation research 20100723

Title: Production of an antigenic peptide by insulin-degrading enzyme.

Journal: Nature immunology 20100501

Title: Diabetes-associated changes and role of N epsilon-(carboxymethyl)lysine in big ET-1-induced coronary vasoconstriction.

Journal: Peptides 20100201

Title: Positron emission tomography of [18F]-big endothelin-1 reveals renal excretion but tissue-specific conversion to [18F]-endothelin-1 in lung and liver.

Journal: British journal of pharmacology 20100201

Title: Intrathecal substance P augments morphine-induced antinociception: possible relevance in the production of substance P N-terminal fragments.

Journal: Peptides 20090901

Title: Neutral endopeptidase inhibition enhances substance P mediated inflammation due to hypomagnesemia.

Journal: Magnesium research 20090901

Title: Functional and molecular characterization of the endothelin system in retinal arterioles.

Journal: Investigative ophthalmology & visual science 20090701

Title: Structure of human endothelin-converting enzyme I complexed with phosphoramidon.

Journal: Journal of molecular biology 20090109

Title: [Changes in the activity of amyloid-degrading metallopeptidases leads to disruption of memory in rats].

Journal: Zhurnal vysshei nervnoi deiatelnosti imeni I P Pavlova 20090101

Title: Role of endogenous endothelin-1 in post-ischemic cardiac dysfunction and norepinephrine overflow in rat hearts.

Journal: European journal of pharmacology 20080904

Title: Homology modeling and site-directed mutagenesis to identify selective inhibitors of endothelin-converting enzyme-2.

Journal: Journal of medicinal chemistry 20080626

Title: Phosphoramidon, an endothelin-converting enzyme inhibitor, attenuates lipopolysaccharide-induced acute lung injury.

Journal: Experimental lung research 20080301

Title: Great increase in antinociceptive potency of [Leu5]enkephalin after peptidase inhibition.

Journal: Journal of pharmacological sciences 20080201

Title: Effects of endothelin-1 1-31 on cell viabililty and [Ca2+]i in cultured neonatal rat cardiomyocytes.

Journal: Physiological research 20080101

Title: Activation of the amyloid cascade by intracerebroventricular injection of the protease inhibitor phosphoramidon.

Journal: Neuro-degenerative diseases 20080101

Title: Metabolic inactivation of the circadian transmitter, pigment dispersing factor (PDF), by neprilysin-like peptidases in Drosophila.

Journal: The Journal of experimental biology 20071201

Title: Characterisation of endothelin converting enzyme-1 shedding from endothelial cells.

Journal: FEBS letters 20070918

Title: The enhancing effects of peptidase inhibitors on the antinociceptive action of [Met5]enkephalin-Arg6-Phe7 in rats.

Journal: Journal of pharmacological sciences 20070901

Title: Potentiation of bradykinin effect by angiotensin-converting enzyme inhibition does not correlate with angiotensin-converting enzyme activity in the rat mesenteric arteries.

Journal: Hypertension (Dallas, Tex. : 1979) 20070701

Title: Functional evidence of des-Arg10-kallidin enzymatic inactivating pathway in isolated human umbilical vein.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20070501

Title: Antagonism of phosphoramidon-induced antinociception in mice by mu- but not kappa-opioid receptor blockers.

Journal: Life sciences 20070417

Title: Effect of chronic ethanol consumption on endothelin-1 generation and conversion of exogenous big-endothelin-1 by the rat carotid artery.

Journal: Alcohol (Fayetteville, N.Y.) 20070301

Title: Neutral endopeptidase up-regulation in isolated human umbilical artery: involvement in desensitization of bradykinin-induced vasoconstrictor effects.

Journal: The Journal of pharmacology and experimental therapeutics 20070201

Title: Expression of NEP2, a soluble neprilysin-like endopeptidase, during embryogenesis in Drosophila melanogaster.

Journal: Peptides 20070101

Title: Inhibition of neutral endopeptidase by thiorphan does not modify coronary vascular responses to angiotensin I, angiotensin II and bradykinin in the isolated guinea pig heart.

Journal: Pharmacological reports : PR 20070101

Title: Big ET-1 processing into vasoactive peptides in arteries and veins.

Journal: Vascular pharmacology 20070101

Title: Neprilysin protects human neuronal progenitor cells against impaired development caused by amyloid-beta peptide.

Journal: Brain research 20061208

Title: Preparation of a protected phosphoramidon precursor via an H-phosphonate coupling strategy.

Journal: Bioorganic & medicinal chemistry letters 20061101

Title: Effects of big endothelin-1 in comparison with endothelin-1 on the microvascular blood flow velocity and diameter of rat mesentery in vivo.

Journal: Microvascular research 20061101

Title: Arrhythmogenic action of endothelin-1(1-31) through conversion to endothelin-1(1-21).

Journal: Experimental biology and medicine (Maywood, N.J.) 20060601

Title: Angiotensin converting enzyme has an inhibitory role in CGRP metabolism in human skin.

Journal: Peptides 20060401

Title: Phosphodiesterase IV and neutral endopeptidase in airways from developing and allergen sensitized rabbits.

Journal: Pulmonary pharmacology & therapeutics 20060101

Title: Blood pressure responses of endothelin-1 1-31 within the rostral ventrolateral medulla through conversion to endothelin-1 1-21.

Journal: Journal of cardiovascular pharmacology 20051201

Title: Role of endothelin-1-dependent up-regulation of leptin in oral mucosal repair.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20051201

Title: Endothelin-1-dependent leptin induction in gastric mucosal inflammatory responses to Helicobacter pylori lipopolysaccharide.

Journal: Biochemical and biophysical research communications 20051104

Title: NEP inhibitors enhance C-type natriuretic peptide-induced relaxation in porcine isolated coronary artery.

Journal: Vascular pharmacology 20051001

Title: Inhibition of neutral endopeptidase (NEP) facilitates neurogenic inflammation.

Journal: Experimental neurology 20050901

Title: Endothelin-1 (1-31) is an intermediate in the production of endothelin-1 after big endothelin-1 administration in vivo.

Journal: Hypertension (Dallas, Tex. : 1979) 20050701

Title: Contribution of endogenous endothelin-1 to basal vascular tone during normal pregnancy and preeclampsia.

Journal: American journal of obstetrics and gynecology 20050701

Title: The role of substance P and bradykinin in the cough reflex and bronchoconstriction in guinea-pigs.

Journal: European journal of pharmacology 20050418

Title: Purification, characterization cloning, and sequencing of metalloendopeptidase from Streptomyces septatus TH-2.

Journal: Archives of biochemistry and biophysics 20050215

Title: Down-regulation does not mediate natriuretic peptide-dependent desensitization of natriuretic peptide receptor (NPR)-A or NPR-B: guanylyl cyclase-linked natriuretic peptide receptors do not internalize.

Journal: Molecular pharmacology 20050101

Title: Effective antiprotease-antibiotic treatment of experimental anthrax.

Journal: BMC infectious diseases 20050101

Title: Further evidence on the anxiogenic-like effect of substance P evaluated in the elevated plus-maze in rats.

Journal: Behavioural brain research 20041005

Title: Despite minimal hemodynamic alterations endotoxemia modulates NOS and p38-MAPK phosphorylation via metalloendopeptidases.

Journal: Molecular and cellular biochemistry 20041001

Title: [Physiological and pathophysiological roles of the endothelin converting enzymes].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20040901

Title: Hypoxia augments TNF-alpha-mediated endothelin-1 release and cell proliferation in human optic nerve head astrocytes.

Journal: Biochemical and biophysical research communications 20040604

Title: Endothelin-induced constriction of the ductus venosus in fetal sheep: developmental aspects and possible interaction with vasodilatory prostaglandin.

Journal: British journal of pharmacology 20040601

Title: [Endothelin].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20040601

Title: A continuous spectrophotometric assay for Pseudomonas aeruginosa LasA protease (staphylolysin) using a two-stage enzymatic reaction.

Journal: Analytical biochemistry 20040515

Title: The effect of phosphoramidon on inflammation-mediated preterm delivery in a mouse model.

Journal: American journal of obstetrics and gynecology 20040201

Title: Signal pathway involved in increased expression of neutral endopeptidase 24.11 by gonadotropin releasing hormone in choriocarcinoma cells.

Journal: Placenta 20040101

Title: [The new class of drugs-- metalloprotease inhibitors -- in the treatment of heart failure].

Journal: Klinicheskaia meditsina 20040101

Title: A low dose of angiotensin II increases inotropism through activation of reverse Na(+)/Ca(2+) exchange by endothelin release.

Journal: Cardiovascular research 20031201

Title: [Protective effects of phosphoramidon on the experimental myocardial injury in rats].

Journal: Hunan yi ke da xue xue bao = Hunan yike daxue xuebao = Bulletin of Hunan Medical University 20031201

Title: Active amino acids of the Kell blood group protein and model of the ectodomain based on the structure of neutral endopeptidase 24.11.

Journal: Blood 20031015

Title: Metalloendopeptidase inhibition regulates phosphorylation of p38-mitogen-activated protein kinase and nitric oxide synthase in heart after endotoxemia.

Journal: Shock (Augusta, Ga.) 20031001

Title: The role of endothelin converting enzyme inhibition during group B streptococcus-induced pulmonary hypertension in newborn piglets.

Journal: Pediatric research 20030901

Title: Cerebral angiogenesis and expression of VEGF after subarachnoid hemorrhage (SAH) in rats.

Journal: Brain research 20030815

Title: Isolation and characterization of a zinc-containing metalloprotease expressed by Vibrio tubiashii.

Journal: Canadian journal of microbiology 20030801

Title: The effects of phosphoramidon on the expression of human endothelin-converting enzyme-1 (ECE-1) isoforms.

Journal: Journal of cardiovascular pharmacology 20030701

Title: [D-Val22]big ET-1[16-38] inhibits endothelin-converting enzyme activity: a promising concept in the prevention of cerebral vasospasm.

Journal: Neurosurgical review 20030501

Title: Pseudomonas aeruginosa elastase degrades surfactant proteins A and D.

Journal: American journal of respiratory cell and molecular biology 20030401

Title: Vasospasm following subarachnoid hemorrhage: evidence against functional upregulation of protein kinase C constrictor pathway.

Journal: Neurological research 20030401

Title: Binding of a new bioactive 31-amino-acid endothelin-1 to an endothelin ET(B) or ET(B)-like receptor in porcine lungs.

Journal: European journal of pharmacology 20030328

Title: Peptidases prevent mu-opioid receptor internalization in dorsal horn neurons by endogenously released opioids.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20030301

Title: Effects of kinins on mammalian spermatozoa and the impact of peptidolytic enzymes.

Journal: Andrologia 20030201

Title: Effect of endothelin-1 (1-31) on the renal resistance vessels.

Journal: The journal of medical investigation : JMI 20030201

Title: Role of tachykinins in the bronchoconstriction induced by HCl intraesophageal instillation in the rabbit.

Journal: Life sciences 20030124

Title: Action of three ectopeptidases on corticotropin-releasing factor: metabolism and functional aspects.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20030101

Title: Attenuation of renal ischemia/reperfusion injury by a triple drug combination therapy.

Journal: Journal of nephrology 20030101

Title: Cardioprotective effects of phosphoramidon on myocardial structure and function in murine Chagas' disease.

Journal: International journal for parasitology 20021101

Title: The mechanisms for tachykinin-induced contractions of the rabbit corpus cavernosum.

Journal: British journal of pharmacology 20021101

Title: Effect of endothelin-converting enzyme inhibitors on big endothelin-1 induced contraction in isolated rat basilar artery.

Journal: Acta neurochirurgica 20021101

Title: Combination therapy of N-acetylcysteine, sodium nitroprusside and phosphoramidon attenuates ischemia-reperfusion injury in rat kidney.

Journal: Molecular and cellular biochemistry 20021101

Title: Attenuation of ischemia/reperfusion induced MAP kinases by N-acetyl cysteine, sodium nitroprusside and phosphoramidon.

Journal: Molecular and cellular biochemistry 20021101

Title: The increased proliferation of cultured neuroblastoma cells treated with vasoactive intestinal peptide is enhanced by simultaneous inhibition of neutral endopeptidase.

Journal: Regulatory peptides 20021015

Title: Effect of quercetin on plasma extravasation in rat CNS and dura mater by ACE and NEP inhibition.

Journal: Phytotherapy research : PTR 20020901

Title: Endothelin-converting enzyme activity in human cerebral circulation.

Journal: Neurosurgery 20020801

Title: Characterization of PgPepO, a bacterial homologue of endothelin-converting enzyme-1.

Journal: Clinical science (London, England : 1979) 20020801

Title: Expression, purification and characterization of the monomeric and dimeric forms of soluble bovine endothelin converting enzyme-1a.

Journal: Clinical science (London, England : 1979) 20020801

Title: Phosphoramidon treatment improves the consequences of chagasic heart disease in mice.

Journal: Clinical science (London, England : 1979) 20020801

Title: Pressor and pulmonary responses to ET-1(1-31) in guinea-pigs.

Journal: British journal of pharmacology 20020701

Title: Possible involvement of placental peptidases that degrade gonadotropin-releasing hormone (GnRH) in the dynamic pattern of placental hCG secretion via GnRH degradation.

Journal: Placenta 20020701

Title: Vasospasm following subarachnoid hemorrhage: evidence against functional upregulation of Rho kinase constrictor pathway.

Journal: Neurological research 20020601

Title: Inhibition of endothelin-1 improves survival and vasculopathy in rat cardiac transplants treated with cyclosporine.

Journal: Transplantation 20020415

Title: Substance P induced preprotachykinin-a mRNA, neutral endopeptidase mRNA and substance P in cultured normal fibroblasts.

Journal: International archives of allergy and immunology 20020401

Title: Enhancement of neurokinin A-induced smooth muscle contraction in human urinary bladder by mucosal removal and phosphoramidon: relationship to peptidase inhibition.

Journal: European journal of pharmacology 20020308

Title: Endothelin-1[1-31]: a novel autocrine-paracrine regulator of human adrenal cortex secretion and growth.

Journal: The Journal of clinical endocrinology and metabolism 20020101

Title: Endothelin-converting enzyme activity in vascular smooth muscle preparations in vitro.

Journal: Methods in molecular biology (Clifton, N.J.) 20020101

Title: Zinc and Manduca sexta hemocyte functions.

Journal: Journal of insect science (Online) 20020101

Title: Soluble recombinant neprilysin induces aggrecanase-mediated cleavage of aggrecan in cartilage explant cultures.

Journal: Archives of biochemistry and biophysics 20011215

Title: The role of substance P release in the lung with esophageal acid.

Journal: The American journal of medicine 20011203

Title: Effect of neutral endopeptidase inhibitor on bradykinin-induced bronchoconstriction.

Journal: Life sciences 20011121

Title: In vitro contractile effects of neurokinin receptor blockade in the human ureter.

Journal: The Journal of urology 20011001

Title: Differential effects of U46619 on renal regional hemodynamics in the rat: involvement of endothelin.

Journal: The Journal of pharmacology and experimental therapeutics 20011001

Title: Determination of bradykinin in rat urine by coupled-column high pressure liquid chromatography with precolumn derivatization with a water-soluble fluorogenic reagent.

Journal: Analytical biochemistry 20011001

Title: Roles of mast cells and sensory nerves in cutaneous vascular hyperpermeability and scratching behavior induced by poly-L-arginine in rats.

Journal: European journal of pharmacology 20010817

Title: A proteinase inhibitor decreases tumor growth in a laparoscopic rat model.

Journal: Surgical endoscopy 20010801

Title: Deletion of neutral endopeptidase exacerbates intestinal inflammation induced by Clostridium difficile toxin A.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20010801

Title: Changes in the expression of tachykinin receptors in the rat uterus during the course of pregnancy.

Journal: Biology of reproduction 20010801

Title: Degradation of the Alzheimer's amyloid beta peptide by endothelin-converting enzyme.

Journal: The Journal of biological chemistry 20010706

Title: Neprilysin degrades both amyloid beta peptides 1-40 and 1-42 most rapidly and efficiently among thiorphan- and phosphoramidon-sensitive endopeptidases.

Journal: The Journal of biological chemistry 20010615

Title: Soluble CD44 inhibits melanoma tumor growth by blocking cell surface CD44 binding to hyaluronic acid.

Journal: Oncogene 20010607

Title: Effect of ECE and NEP inhibition on cigarette smoke-induced cell proliferation in the rat lung.

Journal: Inhalation toxicology 20010601

Title: Endothelium-dependent relaxation in response to low concentrations of bradykinin is enhanced by phosphoramidon, bosentan and BQ-123 in bovine coronary arteries in vitro.

Journal: Japanese journal of pharmacology 20010601

Title: The lungs as an anti-inflammatory organ of the body.

Journal: Critical care medicine 20010501

Title: A three-dimensional model of endothelin-converting enzyme (ECE) based on the X-ray structure of neutral endopeptidase 24.11 (NEP).

Journal: Protein engineering 20010501

Title: Isoprostaglandin E2 type-III (8-iso-prostaglandin E2) evoked contractions in the human internal mammary artery.

Journal: Life sciences 20010413

Title: Phosphoramidon-sensitive endothelin-converting enzymes modulate cerebral blood flow and neural damage of hypoxic rats.

Journal: Neuroscience letters 20010330

Title: Reverse mode of the Na+-Ca2+ exchange after myocardial stretch: underlying mechanism of the slow force response.

Journal: Circulation research 20010302

Title: Interactions of human matrix metalloproteinase 7 (matrilysin) with the inhibitors thiorphan and R-94138.

Journal: Journal of biochemistry 20010301

Title: Antinociceptive effect produced by intracerebroventricularly administered dynorphin A is potentiated by p-hydroxymercuribenzoate or phosphoramidon in the mouse formalin test.

Journal: Brain research 20010209

Title: Neutral endopeptidase terminates substance P-induced inflammation in allergic contact dermatitis.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20010115

Title: Mitogen-activated protein kinase activity regulation role of angiotensin and endothelin systems in vascular smooth muscle cells.

Journal: European journal of pharmacology 20010105

Title: Effect of phosphoramidon on brain tissue angiogenesis in the chronic phase of vasospasm after subarachnoid hemorrhage in the rat.

Journal: Medical science monitor : international medical journal of experimental and clinical research 20010101

Title: Role of endothelin-converting enzyme-1 in the suppression of constitutive nitric oxide synthase in rat gastric mucosal injury by indomethacin.

Journal: Scandinavian journal of gastroenterology 20001101

Title: Pharmacological characterization of a novel sulfonylureid-pyrazole derivative, SM-19712, a potent nonpeptidic inhibitor of endothelin converting enzyme.

Journal: Japanese journal of pharmacology 20000901

Title: Morphine preconditioning attenuates neutrophil activation in rat models of myocardial infarction.

Journal: Cardiovascular research 19981201

Title: Influence of several peptidase inhibitors on the pro-inflammatory effects of substance P, capsaicin and collagenase.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19961101

Title: In vitro metabolism of an insect neuropeptide by neural membrane preparations from Lymantria dispar.

Journal: Peptides 19960101

Title: Regulation of N-formyl-methionyl-leucyl-phenylalanine receptor recycling by surface membrane neutral endopeptidase-mediated degradation of ligand.

Journal: Journal of leukocyte biology 19951001

Title: Brain cathepsin B but not metalloendopeptidases degrade rAPP751 with production of amyloidogenic fragments. Comparison with synthetic peptides emulating beta- and gamma-secretase sites.

Journal: International journal of peptide and protein research 19950101

Title: Purification and characterization of a neutral zinc endopeptidase secreted by Flavobacterium meningosepticum.

Journal: Archives of biochemistry and biophysics 19940515

Title: Degradation of bradykinin by neutral endopeptidase (EC 3.4.24.11) in cultured human endothelial cells.

Journal: European journal of clinical chemistry and clinical biochemistry : journal of the Forum of European Clinical Chemistry Societies 19930501

Title: Jurkat T cells express a functional neutral endopeptidase activity (CALLA) involved in T cell activation.

Journal: The EMBO journal 19921101

Title: Functional reactivity of different central opioid receptor systems following clomipramine treatments.

Journal: Pharmacological research 19900101

Title: Neuropeptide-degrading endopeptidase activity of locust (Schistocerca gregaria) synaptic membranes.

Journal: The Biochemical journal 19881101

Title: Effects of bestatin and phosphoramidon on the hypertensive response to physostigmine in the rat.

Journal: Fundamental & clinical pharmacology 19870101

Title: Enkephalinase inhibition suppresses naloxone-induced jumping in morphine-dependent mice.

Journal: Archives internationales de pharmacodynamie et de therapie 19861001

Title: Kukkola PJ, et al. Differential structure-activity relationships of phosphoramidon analogues for inhibition of three metalloproteases: endothelin-converting enzyme, neutral endopeptidase, and angiotensin-converting enzyme.J CardiovascPharmacol. 1995;26Suppl 3:S65-8.

Title: Sun Q, et al. Synthesis and enzymatic evaluation of phosphoramidon and its β anomer: Anomerization of α-l-rhamnose triacetate upon phosphitylation.Bioorg Med Chem. 2013 Nov 1;21(21):6778-87.

Title: Hanson LR, et al. Intranasal phosphoramidon increases beta-amyloid levels in wild-type and NEP/NEP2-deficient mice.J MolNeurosci. 2011 Mar;43(3):424-7.

Title: Bhavsar TM, et al. Phosphoramidon, an endothelin-converting enzyme inhibitor, attenuates lipopolysaccharide-induced acute lung injury.Exp Lung Res. 2008 Mar;34(3):141-54.

Title: Matsumaru K, et al. Phosphoramidon, an inhibitor of endothelin-converting enzyme, prevents indomethacin-induced gastric mucosal damage in rats.Life Sci. 1998;62(7):PL79-84.

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Tags:164204-38-0 Molecular Formula|164204-38-0 MDL|164204-38-0 SMILES|164204-38-0 N-[N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]- L-tryptophan,sodium salt (1
Catalog No.: AA00ASPI
164204-38-0,MFCD01459907
164204-38-0 | N-[N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]- L-tryptophan,sodium salt (1
Pack Size: 1mg
Purity: ≥98%
in stock
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Pack Size: 5mg
Purity: ≥98%
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$242.00 $169.00
Pack Size: 10mg
Purity: ≥98%
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$423.00 $296.00
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Purity: ≥98%
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Technical Information
Catalog Number: AA00ASPI
Chemical Name: N-[N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]- L-tryptophan,sodium salt (1
CAS Number: 164204-38-0
Molecular Formula: C23H34N3Na2O10P
Molecular Weight: 589.4835
MDL Number: MFCD01459907
SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)NP(=O)(O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)C.[Na].[Na]
Properties
Complexity: 834  
Covalently-Bonded Unit Count: 3  
Defined Atom Stereocenter Count: 7  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 39  
Hydrogen Bond Acceptor Count: 11  
Hydrogen Bond Donor Count: 6  
Isotope Atom Count: 0  
Rotatable Bond Count: 10  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
Literature fold

Title: Neurogenic airway microvascular leakage induced by toluene inhalation in rats.

Journal: European journal of pharmacology20120615

Title: In-silico characterization of ECE-1 inhibitors.

Journal: Computers in biology and medicine20120401

Title: Antinociceptive effect of [Met5]enkephalin semicarbazide is not affected by dipeptidyl carboxypeptidase-I.

Journal: Journal of peptide science : an official publication of the European Peptide Society20120201

Title: The role of neutral endopeptidase in caerulein-induced acute pancreatitis.

Journal: Journal of immunology (Baltimore, Md. : 1950)20111115

Title: Aβ-degrading enzymes: potential for treatment of Alzheimer disease.

Journal: Journal of neuropathology and experimental neurology20111101

Title: Crystal structure of Mycobacterium tuberculosis zinc-dependent metalloprotease-1 (Zmp1), a metalloprotease involved in pathogenicity.

Journal: The Journal of biological chemistry20110916

Title: Dendroaspis natriuretic peptide and the designer natriuretic peptide, CD-NP, are resistant to proteolytic inactivation.

Journal: Journal of molecular and cellular cardiology20110701

Title: Cysteine cathepsins in human carious dentin.

Journal: Journal of dental research20110401

Title: Intranasal phosphoramidon increases beta-amyloid levels in wild-type and NEP/NEP2-deficient mice.

Journal: Journal of molecular neuroscience : MN20110301

Title: Endothelin-1 expression by vascular endothelial growth factor in human umbilical vein endothelial cells and aortic smooth muscle cells.

Journal: Hypertension in pregnancy20110101

Title: Neprilysin-2 is an important β-amyloid degrading enzyme.

Journal: The American journal of pathology20110101

Title: Bradykinin-induced lung inflammation and bronchoconstriction: role in parainfluenze-3 virus-induced inflammation and airway hyperreactivity.

Journal: The Journal of pharmacology and experimental therapeutics20101201

Title: Increased endothelial exocytosis and generation of endothelin-1 contributes to constriction of aged arteries.

Journal: Circulation research20100723

Title: Production of an antigenic peptide by insulin-degrading enzyme.

Journal: Nature immunology20100501

Title: Diabetes-associated changes and role of N epsilon-(carboxymethyl)lysine in big ET-1-induced coronary vasoconstriction.

Journal: Peptides20100201

Title: Positron emission tomography of [18F]-big endothelin-1 reveals renal excretion but tissue-specific conversion to [18F]-endothelin-1 in lung and liver.

Journal: British journal of pharmacology20100201

Title: Intrathecal substance P augments morphine-induced antinociception: possible relevance in the production of substance P N-terminal fragments.

Journal: Peptides20090901

Title: Neutral endopeptidase inhibition enhances substance P mediated inflammation due to hypomagnesemia.

Journal: Magnesium research20090901

Title: Functional and molecular characterization of the endothelin system in retinal arterioles.

Journal: Investigative ophthalmology & visual science20090701

Title: Structure of human endothelin-converting enzyme I complexed with phosphoramidon.

Journal: Journal of molecular biology20090109

Title: [Changes in the activity of amyloid-degrading metallopeptidases leads to disruption of memory in rats].

Journal: Zhurnal vysshei nervnoi deiatelnosti imeni I P Pavlova20090101

Title: Role of endogenous endothelin-1 in post-ischemic cardiac dysfunction and norepinephrine overflow in rat hearts.

Journal: European journal of pharmacology20080904

Title: Homology modeling and site-directed mutagenesis to identify selective inhibitors of endothelin-converting enzyme-2.

Journal: Journal of medicinal chemistry20080626

Title: Phosphoramidon, an endothelin-converting enzyme inhibitor, attenuates lipopolysaccharide-induced acute lung injury.

Journal: Experimental lung research20080301

Title: Great increase in antinociceptive potency of [Leu5]enkephalin after peptidase inhibition.

Journal: Journal of pharmacological sciences20080201

Title: Effects of endothelin-1 1-31 on cell viabililty and [Ca2+]i in cultured neonatal rat cardiomyocytes.

Journal: Physiological research20080101

Title: Activation of the amyloid cascade by intracerebroventricular injection of the protease inhibitor phosphoramidon.

Journal: Neuro-degenerative diseases20080101

Title: Metabolic inactivation of the circadian transmitter, pigment dispersing factor (PDF), by neprilysin-like peptidases in Drosophila.

Journal: The Journal of experimental biology20071201

Title: Characterisation of endothelin converting enzyme-1 shedding from endothelial cells.

Journal: FEBS letters20070918

Title: The enhancing effects of peptidase inhibitors on the antinociceptive action of [Met5]enkephalin-Arg6-Phe7 in rats.

Journal: Journal of pharmacological sciences20070901

Title: Potentiation of bradykinin effect by angiotensin-converting enzyme inhibition does not correlate with angiotensin-converting enzyme activity in the rat mesenteric arteries.

Journal: Hypertension (Dallas, Tex. : 1979)20070701

Title: Functional evidence of des-Arg10-kallidin enzymatic inactivating pathway in isolated human umbilical vein.

Journal: Naunyn-Schmiedeberg's archives of pharmacology20070501

Title: Antagonism of phosphoramidon-induced antinociception in mice by mu- but not kappa-opioid receptor blockers.

Journal: Life sciences20070417

Title: Effect of chronic ethanol consumption on endothelin-1 generation and conversion of exogenous big-endothelin-1 by the rat carotid artery.

Journal: Alcohol (Fayetteville, N.Y.)20070301

Title: Neutral endopeptidase up-regulation in isolated human umbilical artery: involvement in desensitization of bradykinin-induced vasoconstrictor effects.

Journal: The Journal of pharmacology and experimental therapeutics20070201

Title: Expression of NEP2, a soluble neprilysin-like endopeptidase, during embryogenesis in Drosophila melanogaster.

Journal: Peptides20070101

Title: Inhibition of neutral endopeptidase by thiorphan does not modify coronary vascular responses to angiotensin I, angiotensin II and bradykinin in the isolated guinea pig heart.

Journal: Pharmacological reports : PR20070101

Title: Big ET-1 processing into vasoactive peptides in arteries and veins.

Journal: Vascular pharmacology20070101

Title: Neprilysin protects human neuronal progenitor cells against impaired development caused by amyloid-beta peptide.

Journal: Brain research20061208

Title: Preparation of a protected phosphoramidon precursor via an H-phosphonate coupling strategy.

Journal: Bioorganic & medicinal chemistry letters20061101

Title: Effects of big endothelin-1 in comparison with endothelin-1 on the microvascular blood flow velocity and diameter of rat mesentery in vivo.

Journal: Microvascular research20061101

Title: Arrhythmogenic action of endothelin-1(1-31) through conversion to endothelin-1(1-21).

Journal: Experimental biology and medicine (Maywood, N.J.)20060601

Title: Angiotensin converting enzyme has an inhibitory role in CGRP metabolism in human skin.

Journal: Peptides20060401

Title: Phosphodiesterase IV and neutral endopeptidase in airways from developing and allergen sensitized rabbits.

Journal: Pulmonary pharmacology & therapeutics20060101

Title: Blood pressure responses of endothelin-1 1-31 within the rostral ventrolateral medulla through conversion to endothelin-1 1-21.

Journal: Journal of cardiovascular pharmacology20051201

Title: Role of endothelin-1-dependent up-regulation of leptin in oral mucosal repair.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society20051201

Title: Endothelin-1-dependent leptin induction in gastric mucosal inflammatory responses to Helicobacter pylori lipopolysaccharide.

Journal: Biochemical and biophysical research communications20051104

Title: NEP inhibitors enhance C-type natriuretic peptide-induced relaxation in porcine isolated coronary artery.

Journal: Vascular pharmacology20051001

Title: Inhibition of neutral endopeptidase (NEP) facilitates neurogenic inflammation.

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Title: Endothelin-1 (1-31) is an intermediate in the production of endothelin-1 after big endothelin-1 administration in vivo.

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Title: Contribution of endogenous endothelin-1 to basal vascular tone during normal pregnancy and preeclampsia.

Journal: American journal of obstetrics and gynecology20050701

Title: The role of substance P and bradykinin in the cough reflex and bronchoconstriction in guinea-pigs.

Journal: European journal of pharmacology20050418

Title: Purification, characterization cloning, and sequencing of metalloendopeptidase from Streptomyces septatus TH-2.

Journal: Archives of biochemistry and biophysics20050215

Title: Down-regulation does not mediate natriuretic peptide-dependent desensitization of natriuretic peptide receptor (NPR)-A or NPR-B: guanylyl cyclase-linked natriuretic peptide receptors do not internalize.

Journal: Molecular pharmacology20050101

Title: Effective antiprotease-antibiotic treatment of experimental anthrax.

Journal: BMC infectious diseases20050101

Title: Further evidence on the anxiogenic-like effect of substance P evaluated in the elevated plus-maze in rats.

Journal: Behavioural brain research20041005

Title: Despite minimal hemodynamic alterations endotoxemia modulates NOS and p38-MAPK phosphorylation via metalloendopeptidases.

Journal: Molecular and cellular biochemistry20041001

Title: [Physiological and pathophysiological roles of the endothelin converting enzymes].

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Title: Hypoxia augments TNF-alpha-mediated endothelin-1 release and cell proliferation in human optic nerve head astrocytes.

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Title: Endothelin-induced constriction of the ductus venosus in fetal sheep: developmental aspects and possible interaction with vasodilatory prostaglandin.

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Title: A continuous spectrophotometric assay for Pseudomonas aeruginosa LasA protease (staphylolysin) using a two-stage enzymatic reaction.

Journal: Analytical biochemistry20040515

Title: The effect of phosphoramidon on inflammation-mediated preterm delivery in a mouse model.

Journal: American journal of obstetrics and gynecology20040201

Title: Signal pathway involved in increased expression of neutral endopeptidase 24.11 by gonadotropin releasing hormone in choriocarcinoma cells.

Journal: Placenta20040101

Title: [The new class of drugs-- metalloprotease inhibitors -- in the treatment of heart failure].

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Title: A low dose of angiotensin II increases inotropism through activation of reverse Na(+)/Ca(2+) exchange by endothelin release.

Journal: Cardiovascular research20031201

Title: [Protective effects of phosphoramidon on the experimental myocardial injury in rats].

Journal: Hunan yi ke da xue xue bao = Hunan yike daxue xuebao = Bulletin of Hunan Medical University20031201

Title: Active amino acids of the Kell blood group protein and model of the ectodomain based on the structure of neutral endopeptidase 24.11.

Journal: Blood20031015

Title: Metalloendopeptidase inhibition regulates phosphorylation of p38-mitogen-activated protein kinase and nitric oxide synthase in heart after endotoxemia.

Journal: Shock (Augusta, Ga.)20031001

Title: The role of endothelin converting enzyme inhibition during group B streptococcus-induced pulmonary hypertension in newborn piglets.

Journal: Pediatric research20030901

Title: Cerebral angiogenesis and expression of VEGF after subarachnoid hemorrhage (SAH) in rats.

Journal: Brain research20030815

Title: Isolation and characterization of a zinc-containing metalloprotease expressed by Vibrio tubiashii.

Journal: Canadian journal of microbiology20030801

Title: The effects of phosphoramidon on the expression of human endothelin-converting enzyme-1 (ECE-1) isoforms.

Journal: Journal of cardiovascular pharmacology20030701

Title: [D-Val22]big ET-1[16-38] inhibits endothelin-converting enzyme activity: a promising concept in the prevention of cerebral vasospasm.

Journal: Neurosurgical review20030501

Title: Pseudomonas aeruginosa elastase degrades surfactant proteins A and D.

Journal: American journal of respiratory cell and molecular biology20030401

Title: Vasospasm following subarachnoid hemorrhage: evidence against functional upregulation of protein kinase C constrictor pathway.

Journal: Neurological research20030401

Title: Binding of a new bioactive 31-amino-acid endothelin-1 to an endothelin ET(B) or ET(B)-like receptor in porcine lungs.

Journal: European journal of pharmacology20030328

Title: Peptidases prevent mu-opioid receptor internalization in dorsal horn neurons by endogenously released opioids.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20030301

Title: Effects of kinins on mammalian spermatozoa and the impact of peptidolytic enzymes.

Journal: Andrologia20030201

Title: Effect of endothelin-1 (1-31) on the renal resistance vessels.

Journal: The journal of medical investigation : JMI20030201

Title: Role of tachykinins in the bronchoconstriction induced by HCl intraesophageal instillation in the rabbit.

Journal: Life sciences20030124

Title: Action of three ectopeptidases on corticotropin-releasing factor: metabolism and functional aspects.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology20030101

Title: Attenuation of renal ischemia/reperfusion injury by a triple drug combination therapy.

Journal: Journal of nephrology20030101

Title: Cardioprotective effects of phosphoramidon on myocardial structure and function in murine Chagas' disease.

Journal: International journal for parasitology20021101

Title: The mechanisms for tachykinin-induced contractions of the rabbit corpus cavernosum.

Journal: British journal of pharmacology20021101

Title: Effect of endothelin-converting enzyme inhibitors on big endothelin-1 induced contraction in isolated rat basilar artery.

Journal: Acta neurochirurgica20021101

Title: Combination therapy of N-acetylcysteine, sodium nitroprusside and phosphoramidon attenuates ischemia-reperfusion injury in rat kidney.

Journal: Molecular and cellular biochemistry20021101

Title: Attenuation of ischemia/reperfusion induced MAP kinases by N-acetyl cysteine, sodium nitroprusside and phosphoramidon.

Journal: Molecular and cellular biochemistry20021101

Title: The increased proliferation of cultured neuroblastoma cells treated with vasoactive intestinal peptide is enhanced by simultaneous inhibition of neutral endopeptidase.

Journal: Regulatory peptides20021015

Title: Effect of quercetin on plasma extravasation in rat CNS and dura mater by ACE and NEP inhibition.

Journal: Phytotherapy research : PTR20020901

Title: Endothelin-converting enzyme activity in human cerebral circulation.

Journal: Neurosurgery20020801

Title: Characterization of PgPepO, a bacterial homologue of endothelin-converting enzyme-1.

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Title: Expression, purification and characterization of the monomeric and dimeric forms of soluble bovine endothelin converting enzyme-1a.

Journal: Clinical science (London, England : 1979)20020801

Title: Phosphoramidon treatment improves the consequences of chagasic heart disease in mice.

Journal: Clinical science (London, England : 1979)20020801

Title: Pressor and pulmonary responses to ET-1(1-31) in guinea-pigs.

Journal: British journal of pharmacology20020701

Title: Possible involvement of placental peptidases that degrade gonadotropin-releasing hormone (GnRH) in the dynamic pattern of placental hCG secretion via GnRH degradation.

Journal: Placenta20020701

Title: Vasospasm following subarachnoid hemorrhage: evidence against functional upregulation of Rho kinase constrictor pathway.

Journal: Neurological research20020601

Title: Inhibition of endothelin-1 improves survival and vasculopathy in rat cardiac transplants treated with cyclosporine.

Journal: Transplantation20020415

Title: Substance P induced preprotachykinin-a mRNA, neutral endopeptidase mRNA and substance P in cultured normal fibroblasts.

Journal: International archives of allergy and immunology20020401

Title: Enhancement of neurokinin A-induced smooth muscle contraction in human urinary bladder by mucosal removal and phosphoramidon: relationship to peptidase inhibition.

Journal: European journal of pharmacology20020308

Title: Endothelin-1[1-31]: a novel autocrine-paracrine regulator of human adrenal cortex secretion and growth.

Journal: The Journal of clinical endocrinology and metabolism20020101

Title: Endothelin-converting enzyme activity in vascular smooth muscle preparations in vitro.

Journal: Methods in molecular biology (Clifton, N.J.)20020101

Title: Zinc and Manduca sexta hemocyte functions.

Journal: Journal of insect science (Online)20020101

Title: Soluble recombinant neprilysin induces aggrecanase-mediated cleavage of aggrecan in cartilage explant cultures.

Journal: Archives of biochemistry and biophysics20011215

Title: The role of substance P release in the lung with esophageal acid.

Journal: The American journal of medicine20011203

Title: Effect of neutral endopeptidase inhibitor on bradykinin-induced bronchoconstriction.

Journal: Life sciences20011121

Title: In vitro contractile effects of neurokinin receptor blockade in the human ureter.

Journal: The Journal of urology20011001

Title: Differential effects of U46619 on renal regional hemodynamics in the rat: involvement of endothelin.

Journal: The Journal of pharmacology and experimental therapeutics20011001

Title: Determination of bradykinin in rat urine by coupled-column high pressure liquid chromatography with precolumn derivatization with a water-soluble fluorogenic reagent.

Journal: Analytical biochemistry20011001

Title: Roles of mast cells and sensory nerves in cutaneous vascular hyperpermeability and scratching behavior induced by poly-L-arginine in rats.

Journal: European journal of pharmacology20010817

Title: A proteinase inhibitor decreases tumor growth in a laparoscopic rat model.

Journal: Surgical endoscopy20010801

Title: Deletion of neutral endopeptidase exacerbates intestinal inflammation induced by Clostridium difficile toxin A.

Journal: American journal of physiology. Gastrointestinal and liver physiology20010801

Title: Changes in the expression of tachykinin receptors in the rat uterus during the course of pregnancy.

Journal: Biology of reproduction20010801

Title: Degradation of the Alzheimer's amyloid beta peptide by endothelin-converting enzyme.

Journal: The Journal of biological chemistry20010706

Title: Neprilysin degrades both amyloid beta peptides 1-40 and 1-42 most rapidly and efficiently among thiorphan- and phosphoramidon-sensitive endopeptidases.

Journal: The Journal of biological chemistry20010615

Title: Soluble CD44 inhibits melanoma tumor growth by blocking cell surface CD44 binding to hyaluronic acid.

Journal: Oncogene20010607

Title: Effect of ECE and NEP inhibition on cigarette smoke-induced cell proliferation in the rat lung.

Journal: Inhalation toxicology20010601

Title: Endothelium-dependent relaxation in response to low concentrations of bradykinin is enhanced by phosphoramidon, bosentan and BQ-123 in bovine coronary arteries in vitro.

Journal: Japanese journal of pharmacology20010601

Title: The lungs as an anti-inflammatory organ of the body.

Journal: Critical care medicine20010501

Title: A three-dimensional model of endothelin-converting enzyme (ECE) based on the X-ray structure of neutral endopeptidase 24.11 (NEP).

Journal: Protein engineering20010501

Title: Isoprostaglandin E2 type-III (8-iso-prostaglandin E2) evoked contractions in the human internal mammary artery.

Journal: Life sciences20010413

Title: Phosphoramidon-sensitive endothelin-converting enzymes modulate cerebral blood flow and neural damage of hypoxic rats.

Journal: Neuroscience letters20010330

Title: Reverse mode of the Na+-Ca2+ exchange after myocardial stretch: underlying mechanism of the slow force response.

Journal: Circulation research20010302

Title: Interactions of human matrix metalloproteinase 7 (matrilysin) with the inhibitors thiorphan and R-94138.

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Title: Antinociceptive effect produced by intracerebroventricularly administered dynorphin A is potentiated by p-hydroxymercuribenzoate or phosphoramidon in the mouse formalin test.

Journal: Brain research20010209

Title: Neutral endopeptidase terminates substance P-induced inflammation in allergic contact dermatitis.

Journal: Journal of immunology (Baltimore, Md. : 1950)20010115

Title: Mitogen-activated protein kinase activity regulation role of angiotensin and endothelin systems in vascular smooth muscle cells.

Journal: European journal of pharmacology20010105

Title: Effect of phosphoramidon on brain tissue angiogenesis in the chronic phase of vasospasm after subarachnoid hemorrhage in the rat.

Journal: Medical science monitor : international medical journal of experimental and clinical research20010101

Title: Role of endothelin-converting enzyme-1 in the suppression of constitutive nitric oxide synthase in rat gastric mucosal injury by indomethacin.

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Title: Pharmacological characterization of a novel sulfonylureid-pyrazole derivative, SM-19712, a potent nonpeptidic inhibitor of endothelin converting enzyme.

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Title: Morphine preconditioning attenuates neutrophil activation in rat models of myocardial infarction.

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Title: Influence of several peptidase inhibitors on the pro-inflammatory effects of substance P, capsaicin and collagenase.

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Title: In vitro metabolism of an insect neuropeptide by neural membrane preparations from Lymantria dispar.

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Title: Brain cathepsin B but not metalloendopeptidases degrade rAPP751 with production of amyloidogenic fragments. Comparison with synthetic peptides emulating beta- and gamma-secretase sites.

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Title: Degradation of bradykinin by neutral endopeptidase (EC 3.4.24.11) in cultured human endothelial cells.

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