1953-02-2 | 2-(2-sulfanylpropanamido)acetic acid

Packsize	Purity	Availability	Price	Discounted Price
100mg	97%	in stock	$11.00	$8.00
250mg	97%	in stock	$13.00	$9.00
1g	97%	in stock	$16.00	$11.00
5g	97%	in stock	$25.00	$18.00
25g	97%	in stock	$70.00	$49.00
100g	97%	in stock	$152.00	$106.00

Description

• Catalog Number: AB47158
• Chemical Name: 2-(2-sulfanylpropanamido)acetic acid
• CAS Number: 1953-02-2
• Molecular Formula: C5H9NO3S
• Molecular Weight: 163.1949
• MDL Number: MFCD00004861
• SMILES: CC(C(=O)NCC(=O)O)S
• NSC Number: 760416

Computed Properties

• Complexity: 148
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 3
• Undefined Atom Stereocenter Count: 1
• XLogP3: -0.1

Literature

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  Biochemical and biophysical research communications 20041217

• Effect of change in cellular GSH levels on mitochondrial damage and cell viability loss due to mitomycin c in small cell lung cancer cells.

  Biochemical pharmacology 20041101

• N-2-mercaptopropionylglycine, a scavanger of reactive oxygen species, does not modify the early antiarrhythmic effect of ischaemic preconditioning in anaesthetised dogs.

  Cardiovascular drugs and therapy 20041101

• Antioxidant effects of sulfur-containing amino acids.

  Yonsei medical journal 20041031

• Nanoparticles comprising a mixed monolayer for specific bindings with biomolecules.

  Journal of the American Chemical Society 20040929

• Complexation of polysaccharide and monosaccharide with thiolate boronic acid capped on silver nanoparticle.

  Analytical biochemistry 20040915

• HPLC study of tyrosinase inhibition by thiopronine.

  Biomedical chromatography : BMC 20040901

• The protective role of tiopronin in cisplatin ototoxicity in Wistar rats.

  International journal of audiology 20040901

• Transport of meprin subunits through the secretory pathway: role of the transmembrane and cytoplasmic domains and oligomerization.

  The Journal of biological chemistry 20040813

• Liquid chromatography analysis of N-(2-mercaptopropionyl)-glycine in biological samples by ThioGlo 3 derivatization.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040805

• Delayed ischemic preconditioning activates nuclear-encoded electron-transfer-chain gene expression in parallel with enhanced postanoxic mitochondrial respiratory recovery.

  Circulation 20040803

• Exogenous NO triggers preconditioning via a cGMP- and mitoKATP-dependent mechanism.

  American journal of physiology. Heart and circulatory physiology 20040801

• Yellow nail syndrome in rheumatoid arthritis: a drug-induced disease?

  Clinical rheumatology 20040801

• Polyherbal extract of septilin protects mice against whole body lethal dose of gamma radiation.

  Phytotherapy research : PTR 20040801

• Oligonucleotide-displaced organic monolayer-protected silver nanoparticles and enhanced luminescence of their salted aggregates.

  Analytical biochemistry 20040701

• The MAM (meprin/A5-protein/PTPmu) domain is a homophilic binding site promoting the lateral dimerization of receptor-like protein-tyrosine phosphatase mu.

  The Journal of biological chemistry 20040625

• Cardioprotection of interleukin-2 is mediated via kappa-opioid receptors.

  The Journal of pharmacology and experimental therapeutics 20040501

• The role of antioxidants in protection from ototoxic drugs.

  Acta oto-laryngologica. Supplementum 20040501

• Protective effects of alpha-tocopherol and tiopronin against cisplatin-induced ototoxicity.

  Acta oto-laryngologica 20040501

• Exogenous nitric oxide generates ROS and induces cardioprotection: involvement of PKG, mitochondrial KATP channels, and ERK.

  American journal of physiology. Heart and circulatory physiology 20040401

• The effects of ionizing radiation on DNA: the role of thiols as radioprotectors.

  Life sciences 20040326

• Evidence of myofibrillar protein oxidation induced by postischemic reperfusion in isolated rat hearts.

  American journal of physiology. Heart and circulatory physiology 20040301

• ROS-mediated ERK activation in delayed protection from anoxic preconditioning in neonatal rat cardiomyocytes.

  Chinese medical journal 20040301

• Reactive oxygen species precede protein kinase C-delta activation independent of adenosine triphosphate-sensitive mitochondrial channel opening in sevoflurane-induced cardioprotection.

  Anesthesiology 20040301

• Remote preconditioning by infrarenal aortic occlusion is operative via delta1-opioid receptors and free radicals in vivo in the rat heart.

  Cardiovascular research 20040215

• Bradykinin induces mitochondrial ROS generation via NO, cGMP, PKG, and mitoKATP channel opening and leads to cardioprotection.

  American journal of physiology. Heart and circulatory physiology 20040101

• Delayed cardioprotection is mediated via a non-peptide delta opioid agonist, SNC-121, independent of opioid receptor stimulation.

  Basic research in cardiology 20040101

• Activation of mitochondrial ATP-sensitive potassium channels delays ischemia-induced cellular uncoupling in rat heart.

  Acta pharmacologica Sinica 20040101

• Au nanoparticle-enhanced surface plasmon resonance sensing of biocatalytic transformations.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20031215

• A simple and sensitive chemiluminescence method for the determination of tiopronin for a pharmaceutical formulation.

  Journal of pharmaceutical and biomedical analysis 20031204

• Urinary excretion of total cystine and the dibasic amino acids arginine, lysine and ornithine in relation to genetic findings in patients with cystinuria treated with sulfhydryl compounds.

  Urological research 20031201

• Studies of urinary cystine precipitation in vitro: ontogeny of cystine nephrolithiasis and identification of meso-2,3-dimercaptosuccinic acid as a potential therapy for cystinuria.

  Molecular genetics and metabolism 20031201

• The cardioprotective effect of sevoflurane depends on protein kinase C activation, opening of mitochondrial K(+)(ATP) channels, and the production of reactive oxygen species.

  Anesthesia and analgesia 20031101

• Inhibition of endogenous thioredoxin in the heart increases oxidative stress and cardiac hypertrophy.

  The Journal of clinical investigation 20031101

• Cardiac nerves affect myocardial stunning through reactive oxygen and nitric oxide mechanisms.

  Circulation research 20031031

• Heterophase ligand exchange and metal transfer between monolayer protected clusters.

  Journal of the American Chemical Society 20030924

• Adenosine and opioid receptor-mediated cardioprotection in the rat: evidence for cross-talk between receptors.

  American journal of physiology. Heart and circulatory physiology 20030701

• Cystine crystal volume determination: a useful tool in the management of cystinuric patients.

  Urological research 20030701

• Modifications of myosin-regulatory light chain correlate with function of stunned myocardium.

  Journal of molecular and cellular cardiology 20030701

• Oxygen dependency of the adrenergic Na/H exchange in rainbow trout erythrocytes is diminished by a hydroxyl radical scavenger.

  Acta physiologica Scandinavica 20030601

• 3-Aminopropanal, formed during cerebral ischaemia, is a potent lysosomotropic neurotoxin.

  The Biochemical journal 20030415

• Mitochondrial adenosine triphosphate-regulated potassium channel opening acts as a trigger for isoflurane-induced preconditioning by generating reactive oxygen species.

  Anesthesiology 20030401

• [An observation of the effects of Tiopronin on the oxygen free radicals in severely scalded rats receiving delayed fluid resuscitation].

  Zhonghua shao shang za zhi = Zhonghua shaoshang zazhi = Chinese journal of burns 20030401

• Cardiac ischemia causes inhibition of the Na/K ATPase by a labile cytosolic compound whose production is linked to oxidant stress.

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• [Cystinuria - Cystine Stones: Recommendations for Diagnosis, Therapy and Follow-up].

  Aktuelle Urologie 20030301

• The cardioprotective and mitochondrial depolarising properties of exogenous nitric oxide in mouse heart.

  Cardiovascular research 20030201

• Effects of N-(2-mercaptopropionyl)-glycine on mitochondrial function in ischemic-reperfused heart.

  Cardiovascular research 20030201

• Involvement of reactive oxygen species in cardiac preconditioning in rats.

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  Hinyokika kiyo. Acta urologica Japonica 20030201

• Paradoxical effects of thiol reagents on Jurkat cells and a new thiol-sensitive mutant form of human mitochondrial superoxide dismutase.

  Cancer research 20030101

• Effects of sulfhydryl compounds on pancreatic cytoprotection in acute necrotic pancreatitis.

  Chinese medical journal 20030101

• Possible underlying mechanism for hydrogen peroxide-induced electromechanical suppression in human atrial myocardium.

  Journal of pharmacological sciences 20030101

• Enhancement of antiradiation potential of some aminothiols by beta-carotene.

  Annals of nutrition & metabolism 20030101

• Meprin proteolytic complexes at the cell surface and in extracellular spaces.

  Biochemical Society symposium 20030101

• Protective effect of N2-mercaptopropionylglycine on rats and dogs liver during ischemia/reperfusion process.

  Arquivos de gastroenterologia 20030101

• Mechanism of preconditioning by isoflurane in rabbits: a direct role for reactive oxygen species.

  Anesthesiology 20021201

• Glyceraldehyde phosphate dehydrogenase oxidation during cardiac ischemia and reperfusion.

  Journal of molecular and cellular cardiology 20021101

• The new MATH: homology suggests shared binding surfaces in meprin tetramers and TRAF trimers.

  FEBS letters 20021023

• Infarct size limitation by nicorandil: roles of mitochondrial K(ATP) channels, sarcolemmal K(ATP) channels, and protein kinase C.

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• Acetylcholine leads to free radical production dependent on K(ATP) channels, G(i) proteins, phosphatidylinositol 3-kinase and tyrosine kinase.

  Cardiovascular research 20020815

• The relative order of mK(ATP) channels, free radicals and p38 MAPK in preconditioning's protective pathway in rat heart.

  Cardiovascular research 20020815

• Yellow nail syndrome associated with thiol compound therapy for rheumatoid arthritis. Two case reports.

  Joint, bone, spine : revue du rhumatisme 20020601

• The protective role of thiola and soybean seeds against the genotoxicity induced by potassium dichromate in mice.

  Mutation research 20020527

• Oxygen radicals trigger activation of NF-kappaB and AP-1 and upregulation of ICAM-1 in reperfused canine heart.

  American journal of physiology. Heart and circulatory physiology 20020501

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  Nihon Naika Gakkai zasshi. The Journal of the Japanese Society of Internal Medicine 20020410

• Free-radical production triggered by hyperthermia contributes to heat stress-induced cardioprotection in isolated rat hearts.

  British journal of pharmacology 20020401

• Isoflurane preconditions myocardium against infarction via release of free radicals.

  Anesthesiology 20020401

• Effect of treatment on ventricular function and troponin I proteolysis in reperfused myocardium.

  Journal of molecular and cellular cardiology 20020401

• The antioxidant N-2-mercaptopropionyl glycine attenuates left ventricular hypertrophy in in vivo murine pressure-overload model.

  Journal of the American College of Cardiology 20020306

• Investigation of nail permeation enhancement by chemical modification using water as a probe.

  Journal of pharmaceutical sciences 20020201

• Acetylcholine attenuates cardiomyocyte oxidant stress during simulated ischemia and reoxygenation.

  Pharmacology 20020101

• Blockade of angiotensin II type 1 receptors suppressed free radical production and preserved coronary endothelial function in the rabbit heart after myocardial infarction.

  Journal of cardiovascular pharmacology 20020101

• Oxidant species trigger late preconditioning against myocardial stunning in conscious rabbits.

  American journal of physiology. Heart and circulatory physiology 20020101

• Evaluation of genotoxic and cytotoxic potential of thiola (N-2-mercaptopropionylglycine), a medicine used in the treatment of humans contaminated with mercury.

  Environmental and molecular mutagenesis 20020101

• Modulation of c-myc and c-fos gene expression in regenerating rat liver by 2-mercaptopropionylglycine.

  Cell biology international 20020101

• Oxygen radicals mediate ultrastructural and metabolic protection of preconditioning in vivo in pig hearts.

  Experimental and clinical cardiology 20020101

• Reactive oxygen species in mechanical stress-induced cardiac hypertrophy.

  Biochemical and biophysical research communications 20011214

• Bucillamine prevents myocardial reperfusion injury.

  Journal of cardiovascular pharmacology 20011201

• Brief murine myocardial I/R induces chemokines in a TNF-alpha-independent manner: role of oxygen radicals.

  American journal of physiology. Heart and circulatory physiology 20011201

• [A clinical trial of oxymatrine in treating chronic viral hepatitis type B].

  Zhonghua nei ke za zhi 20011201

• Acute alcohol-induced protection against infarction in rabbit hearts: differences from and similarities to ischemic preconditioning.

  Journal of molecular and cellular cardiology 20011101

• In-vitro studies of aluminium-induced toxicity on kidney proximal tubular cells.

  Journal of inorganic biochemistry 20011101

• Attenuation of the acute adriamycin-induced cardiac and hepatic oxidative toxicity by N-(2-mercaptopropionyl) glycine in rats.

  Free radical research 20011101

• 15-deoxy-Delta 12,14-prostaglandin J2 induces apoptosis of human hepatic myofibroblasts. A pathway involving oxidative stress independently of peroxisome-proliferator-activated receptors.

  The Journal of biological chemistry 20011012

• Reactive oxygen intermediates induce monocyte chemotactic protein-1 in vascular endothelium after brief ischemia.

  The American journal of pathology 20011001

• A comparison of the effects of potassium citrate and sodium bicarbonate in the alkalinization of urine in homozygous cystinuria.

  Urological research 20011001

• Cystine analyses of separate day and night urine as a basis for the management of patients with homozygous cystinuria.

  Urological research 20011001

• Lead induced spermatoxicity in mouse and MPG treatment.

  Journal of environmental biology 20011001

• Mitochondrial K(ATP) channel opening protects a human atrial-derived cell line by a mechanism involving free radical generation.

  Cardiovascular research 20010901

• Antioxidant changes in the hypertrophied heart due to energy metabolic disorder.

  Basic research in cardiology 20010901

• Acetylcholine, bradykinin, opioids, and phenylephrine, but not adenosine, trigger preconditioning by generating free radicals and opening mitochondrial K(ATP) channels.

  Circulation research 20010803

• Essential role of oxygen radicals in delayed pharmacological preconditioning.

  Journal of molecular and cellular cardiology 20010801

• BW373U86, a delta opioid agonist, partially mediates delayed cardioprotection via a free radical mechanism that is independent of opioid receptor stimulation.

  Journal of molecular and cellular cardiology 20010801

• Menadione mimics the infarct-limiting effect of preconditioning in isolated rat hearts.

  American journal of physiology. Heart and circulatory physiology 20010801

• Solid phase assay of urine cystine supersaturation in the presence of cystine binding drugs.

  The Journal of urology 20010801

• Cystine calculi in children: the results of a metabolic evaluation and response to medical therapy.

  The Journal of urology 20010601

• [Nephrotic syndrome and anasarca status, secondary to treatment with tiopronin in a case of cystinuria].

  Archivos espanoles de urologia 20010601

• Real-time measurement of intracellular reactive oxygen species using Mito tracker orange (CMH2TMRos).

  Bioscience reports 20010601

• Drug-induced cholestasis.

  Seminars in gastrointestinal disease 20010401

• Signal transduction of flumazenil-induced preconditioning in myocytes.

  American journal of physiology. Heart and circulatory physiology 20010301

• The cytotoxic effects of diesel exhaust particles on human pulmonary artery endothelial cells in vitro: role of active oxygen species.

  Free radical biology & medicine 20010301

• Fluorescence quenching properties and chemiluminescence responses of alpha-ketothiols derivatized with o-phthalaldehyde and primary amino compounds.

  Luminescence : the journal of biological and chemical luminescence 20010101

• Cystinuria in the dog: clinical studies during 14 years of medical treatment.

  Journal of veterinary internal medicine 20010101

• Prophylaxia of cystine calculosis by alpha-mercaptopropionyl-glycine administered continuously or every other day.

  Bollettino della Societa italiana di biologia sperimentale 20010101

• Inhibition of tat-mediated HIV-1-LTR transactivation and virus replication by sulfhydryl compounds with chelating properties.

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  Presse medicale (Paris, France : 1983) 19990501

• Role of H2O2 and heme-containing O2 sensors in hypoxic regulation of tyrosine hydroxylase gene expression.

  The American journal of physiology 19980101

• Urinary excretion of free cystine and the tiopronin-cysteine-mixed disulfide during long term tiopronin treatment of cystinuria.

  Nephron 19950101

• Nicotine exacerbates postischemic contractile dysfunction of 'stunned' myocardium in the canine model. Possible role of free radicals.

  Circulation 19940301

• [Results of treatment of cystinuria and cystine lithiasis with alpha-mercaptopropionylglycine. Apropos of 40 patients].

  Journal d'urologie 19940101

• Pharmacokinetics of oral tiopronin.

  European journal of clinical pharmacology 19930101

• The pharmacokinetics of tiopronin and its principal metabolite (2-mercaptopropionic acid) after oral administration to healthy volunteers.

  European journal of clinical pharmacology 19920101

• A case of nephrotic syndrome due to alpha-mercaptopropionyl glycine in a patient with familial cystinuria.

  Nihon Jinzo Gakkai shi 19900801

• Modulation of myoglobin-H2O2-mediated peroxidation reactions by sulfhydryl compounds.

  Laboratory investigation; a journal of technical methods and pathology 19881201

• Naloxone-reversible antidiarrheal effects of enkephalinase inhibitors.

  European journal of pharmacology 19871201

• Management of cystine nephrolithiasis with alpha-mercaptopropionylglycine.

  The Journal of urology 19861101

• Pharmacological properties of acetorphan, a parenterally active 'enkephalinase' inhibitor.

  The Journal of pharmacology and experimental therapeutics 19860601

• Toxicity due to remission inducing drugs in rheumatoid arthritis. Association with HLA-B35 and Cw4 antigens.

  The Journal of rheumatology 19860201

• Angiotensin-converting enzyme inhibitors potentiate the analgesic activity of [Met]-enkephalin-Arg6-Phe7 by inhibiting its degradation in mouse brain.

  Molecular pharmacology 19851201

• Thiorphan and analogs: lack of correlation between potency to inhibit 'enkephalinase A' in vitro and analgesic potency in vivo.

  The Journal of pharmacology and experimental therapeutics 19850801

• Myopathy due to mercaptopropionyl glycine.

  British medical journal (Clinical research ed.) 19821002

• [Cystine stone therapy with mercapto-propyonyl-glycine (MPG) (Thiola) (author's transl)].

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• Treatment of cystinuria with Thiola (alpha-mercaptopropionyl glycine).

  European urology 19750101