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3-aminopyridine
3-pyridylamine

Supplier Sponsors

CAS Number: 462-08-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-322-2
FDA UNII: 69JE8P2L84
Nikkaji Web:J1.535K
Beilstein Number:105692
MDL:MFCD00006400
XlogP3:0.10 (est)
Molecular Weight:94.11682000
Formula:C5 H6 N2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 64.50 °C. @ 760.00 mm Hg
Boiling Point: 252.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.437000 mmHg @ 20.00 °C. (est)
Flash Point: 259.00 °F. TCC ( 126.00 °C. ) (est)
logP (o/w): 0.110
Soluble in:
 water, 1.00E+06 mg/L @ 25 °C (exp)
 water, 9.785e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Carbosynth
For experimental / research use only.
3-Aminopyridine
EMD Millipore
For experimental / research use only.
3-Aminopyridine
Noble Molecular Research
For experimental / research use only.
3-Aminopyridine
Penta International
3-AMINOPYRIDINE
Santa Cruz Biotechnology
For experimental / research use only.
3-Aminopyridine
Sigma-Aldrich: Aldrich
For experimental / research use only.
3-Aminopyridine 99%
TCI AMERICA
For experimental / research use only.
3-Aminopyridine >99.0%(GC)(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-bird - wild LD50 13300 ug/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

intraperitoneal-mouse LD50 28 mg/kg
Journal of Medicinal Chemistry. Vol. 8, Pg. 296, 1965.

intravenous-mouse LD50 24 mg/kg
Annales Pharmaceutiques Francaises. Vol. 26, Pg. 345, 1968.

oral-quail LD50 178 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

Dermal Toxicity:
subcutaneous-mouse LD50 30 mg/kg
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 226, Pg. 163, 1955.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for 3-aminopyridine usage levels up to:
 not for fragrance use.
 
Recommendation for 3-aminopyridine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):462-08-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10009
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
pyridin-3-amine
Chemidplus:0000462088
RTECS:US1650000 for cas# 462-08-8
 
References:
 pyridin-3-amine
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:462-08-8
Pubchem (cid):10009
Pubchem (sid):134973312
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.39.9100
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
3-amino-pyridine
 pyridin-3-amine
 pyridin-3-ylamine
3-pyridinamine
3-pyridylamine
 

Articles:

PubMed:Synthesis, spectroscopic, thermal and structural properties of [M(3-aminopyridine)2Ni(μ-CN)2(CN)2]n (M(II)=Co and Cu) heteropolynuclear cyano-bridged complexes.
PubMed:Fluorescent 1:2 demultiplexer and half-subtractor based on the hydrolysis of N-salicylidene-3-aminopyridine.
PubMed:Fragment-based design of 3-aminopyridine-derived amides as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT).
PubMed:The six-membered-ring azomethine N-((E)-{5-[(E)-(pyridin-3-ylimino)methyl]thiophen-2-yl}methylidene)pyridin-3-amine.
PubMed:catena-Poly[[dichloridomercury(II)]-μ-{N-[(E)-pyridin-2-yl-methyl-idene-κN]pyridin-3-amine-κ(2)N(1):N(3)}].
PubMed:catena-Poly[[[iodidocopper(I)]-{μ-N-[(pyridin-2-yl-κN)methyl-idene]pyridin-3-amine-κ(2)N(3):N(1)}] acetonitrile hemisolvate].
PubMed:Solvation effect on the NH stretching vibrations of solvated aminopyrazine, 2-aminopyridine, and 3-aminopyridine clusters.
PubMed:Radiochemotherapy plus 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) in advanced-stage cervical and vaginal cancers.
PubMed:Bis[μ-N-(pyridin-2-ylmeth-yl)pyridin-3-amine-κ(2) N:N']disilver(I) bis-(perchlorate) dimethyl sulfoxide disolvate.
PubMed:Management of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone-induced methemoglobinemia.
PubMed:5,6-Dimethyl-4-(thio-phen-2-yl)-1H-pyrazolo-[3,4-b]pyridin-3-amine.
PubMed:A phase I and pharmacokinetic study of oral 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) in the treatment of advanced-stage solid cancers: a California Cancer Consortium Study.
PubMed:Ribonucleotide reductase inhibition by metal complexes of Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone): a combined experimental and theoretical study.
PubMed:Phase II trial of the ribonucleotide reductase inhibitor 3-aminopyridine-2-carboxaldehydethiosemicarbazone plus gemcitabine in patients with advanced biliary tract cancer.
PubMed:Anharmonic vibrational analysis of 3,4-diaminopyridine and 3-aminopyridine by density functional theory calculations.
PubMed:Synthesis, DNA-PK inhibition, anti-platelet activity studies of 2-(N-substituted-3-aminopyridine)-substituted-1,3-benzoxazines and DNA-PK and PI3K inhibition, homology modelling studies of 2-morpholino-(7,8-di and 8-substituted)-1,3-benzoxazines.
PubMed:Population pharmacokinetics of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (Triapine®) in cancer patients.
PubMed:Two new zinc(II) acetates with 3- and 4-aminopyridine: syntheses and structural properties.
PubMed:Cytotoxic Evaluation of 3-Aminopyridine-2-Carboxaldehyde Thiosemicarbazone, 3-AP, in Peripheral Blood Lymphocytes of Patients with Refractory Solid Tumors using Electron Paramagnetic Resonance.
PubMed:Synthesis and spectroscopic studies of the charge transfer complexes of 2- and 3-aminopyridine.
PubMed:Well-designed strategy to construct helical silver(I) coordination polymers from flexible unsymmetrical bis(pyridyl) ligands: syntheses, structures, and properties.
PubMed:The maximum tolerated dose and biologic effects of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) in combination with irinotecan for patients with refractory solid tumors.
PubMed:Evaluation of electrophilic heteroaromatic substitution: synthesis of heteroaromatic-fused pyrimidine derivatives via sequential three-component heterocyclization.
PubMed:Phase I trial of pelvic radiation, weekly cisplatin, and 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) for locally advanced cervical cancer.
PubMed:Fluorescence properties and cellular distribution of the investigational anticancer drug triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone) and its zinc(II) complex.
PubMed:Three-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of L-tartaric acid with the associative-group monosubstituted pyridines 3-aminopyridine, 3-carboxypyridine (nicotinic acid) and 2-carboxypyridine (picolinic acid).
PubMed:Spectroscopic characterization of charge transfer complexes of 2,3-diaminopyridine with chloranilic acid and dihydroxy-p-benzoquinone in polar solvent.
PubMed:Impact of metal coordination on cytotoxicity of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (triapine) and novel insights into terminal dimethylation.
PubMed:DCLAK11, a multi-tyrosine kinase inhibitor, exhibits potent antitumor and antiangiogenic activity in vitro.
PubMed:The significance of the temporal bond polarizabilty relaxation of 2- and 3-aminopyridine by 514.5 nm excitation for the nonresonant Raman virtual states.
PubMed:Distinct mechanisms of cell-kill by triapine and its terminally dimethylated derivative Dp44mT due to a loss or gain of activity of their copper(II) complexes.
PubMed:PnuC and the utilization of the nicotinamide riboside analog 3-aminopyridine in Haemophilus influenzae.
PubMed:Synaptic facilitation by 3-aminopyridine and its antagonism by verapamil and diltiazem.
PubMed:Two salts of 5-sulfosalicylic acid and 3-aminopyridine.
PubMed:Differential responses of synaptosomal cation movements and respiration to the convulsants penicillin, pentylenetetrazol and 3-aminopyridine.
PubMed:Preparation of 3-aminopyridine 1,N6-ethenoadenine dinucleotide and 3-aminopyridine 1,N6-ethenoadenine dinucleotide phosphate.
PubMed:Studies of yeast alcohol dehydrogenase with 3-aminopyridine monucleotide.
PubMed:Oxidation and cleavage of 3-aminopyridine adenine dinucleotide phosphate with periodate.
PubMed:Periodate-oxidized 3-aminopyridine adenine dinucleotide phosphate as a fluorescent affinity label for pigeon liver malic enzyme.
PubMed:3-aminopyridine 1,N6-ethenoadenine dinucleotide phosphate: a fluorescent reagent for NADP-requiring enzymes.
PubMed:Preparation of 3-aminopyridine adenine dinucleotide and 3-aminopyridine adenine dinucleotide phosphate.
PubMed:A novel diazonium-sulfhydryl reaction in the inactivation of yeast alcohol dehydrogenase by diazotized 3-aminopyridine adenine dinucleotide.
PubMed:Effects of 3-aminopyridine-induced seizures on platelet eicosanoid synthesis.
PubMed:The anticonvulsive effect of non-NMDA antagonist GYKI 52466 on 3-aminopyridine-induced primary and secondary cortical ictal activity in rat.
PubMed:Synthesis, cytotoxicity, antimicrobial and anti-biofilm activities of novel pyrazolo[3,4-b]pyridine and pyrimidine functionalized 1,2,3-triazole derivatives.
PubMed:6-Methyl-pyridin-3-amine.
PubMed:Inhibition of human cancer cell growth by periodate-oxidized 3-aminopyridine adenine dinucleotide phosphate.
PubMed:Early ultrastructural changes in the cerebral cortex of albino rats subjected to 3-aminopyridine seizures.
PubMed:Synthesis of novel 1,2,3-triazole tagged pyrazolo[3,4-b]pyridine derivatives and their cytotoxic activity.
PubMed:Complexes of Trypanosoma cruzi sterol 14α-demethylase (CYP51) with two pyridine-based drug candidates for Chagas disease: structural basis for pathogen selectivity.
PubMed:A phase 2 consortium (P2C) trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) for advanced adenocarcinoma of the pancreas.
PubMed:A Phase II study of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) and gemcitabine in advanced pancreatic carcinoma. A trial of the Princess Margaret hospital Phase II consortium.
PubMed:A phase I trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone in combination with gemcitabine for patients with advanced cancer.
PubMed:Phase I and pharmacokinetic study of the ribonucleotide reductase inhibitor, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone, administered by 96-hour intravenous continuous infusion.
PubMed:Site-directed enzyme inactivation studies of 3-aminopyridine 1,N6-ethenoadenine dinucleotide.
PubMed:Selective inactivation of NADPH-cytochrome P-450 (c) reductase by diazotized 3-aminopyridine adenine dinucleotide phosphate.
PubMed:Spectral characterization of a fluorescent nicotinamide adenine dinucleotide analog: 3-aminopyridine adenine dinucleotide.
PubMed:Convulsive effects of 3-aminopyridine on cortical neurones.
PubMed:Studies of 3-aminopyridine adenine dinucleotide phosphate.
PubMed:Phase I study of the ribonucleotide reductase inhibitor 3-aminopyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) in combination with high dose cytarabine in patients with advanced myeloid leukemia.
PubMed:A multicenter phase II trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, Triapine) and gemcitabine in advanced non-small-cell lung cancer with pharmacokinetic evaluation using peripheral blood mononuclear cells.
PubMed:Neuroprotective activity of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (PAN-811), a cancer therapeutic agent.
PubMed:PAN-811 (3-aminopyridine-2-carboxaldehyde thiosemicarbazone), a novel neuroprotectant, elicits its function in primary neuronal cultures by up-regulating Bcl-2 expression.
PubMed:Sensitive determination of propoxur by spectrophotometry using 3-aminopyridine.
PubMed:Potent antibacterial activity of oligo-3-aminopyridine against Staphylococcus aureus and Enterococcus faecalis.
PubMed:Phase I and pharmacokinetic study of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) using a single intravenous dose schedule.
PubMed:Development of a parenteral formulation of an investigational anticancer drug, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone.
PubMed:[Comparison of 2-aminopyridine, 3-aminopyridine and 4-aminopyridine hydrochlorides and iodomethylates by the degree of decrease in curare toxicity].
PubMed:Formation and reactivity of 3-diazopyridinium cations and influence on their reductive electrografting on glassy carbon.
PubMed:Synthesis and biological evaluation of novel alkyl amide functionalized trifluoromethyl substituted pyrazolo[3,4-b]pyridine derivatives as potential anticancer agents.
PubMed:Triapine and a more potent dimethyl derivative induce endoplasmic reticulum stress in cancer cells.
PubMed:Hysteretic Spin Crossover in Two-Dimensional (2D) Hofmann-Type Coordination Polymers.
PubMed:Aminopyridine derivatives controlled the assembly and various properties of Cu-BTC metal-organic frameworks.
PubMed:A dimeric cobalt(II)-suberate complex with 3-aminopyridine.
PubMed:Allergic contact dermatitis to the hair dye 6-methoxy-2-methylamino-3-aminopyridine HCl (INCI HC Blue no. 7) without cross-sensitivity to PPD.
PubMed:Photoinduced electron-transfer processes based on novel bipyridine-Ru(II) complex: properties of cis-[Ru(2,2'-bipyridine)2(5,6-bis(3-amidopyridine)-7-oxanorbornene)](PF6)2 and cis-[Ru(2,2'-bipyridine)2(3-aminopyridine)2](PF6)2 complexes.
PubMed:The conversion of [(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]azines into azine fused thiazole-2-carbonitriles.
PubMed:Synthesis and antimicrobial evaluation of some novel bis-α,β-unsaturated ketones, nicotinonitrile, 1,2-dihydropyridine-3-carbonitrile, fused thieno[2,3-b]pyridine and pyrazolo[3,4-b]pyridine derivatives.
PubMed:A phase I study of the novel ribonucleotide reductase inhibitor 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, Triapine) in combination with the nucleoside analog fludarabine for patients with refractory acute leukemias and aggressive myeloproliferative disorders.
PubMed:Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone) induces apoptosis in ovarian cancer cells.
PubMed:Triapine (3-aminopyridine-2-carboxaldehyde- thiosemicarbazone): A potent inhibitor of ribonucleotide reductase activity with broad spectrum antitumor activity.
PubMed:In vitro and in vivo radiosensitization induced by the ribonucleotide reductase inhibitor Triapine (3-aminopyridine-2-carboxaldehyde-thiosemicarbazone).
PubMed:Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone; 3-AP): an inhibitor of ribonucleotide reductase with antineoplastic activity.
PubMed:Synthesis and biological evaluation of a water soluble phosphate prodrug of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP).
PubMed:Uridine modulates neuronal activity and inhibits spike-wave discharges of absence epileptic Long Evans and Wistar Albino Glaxo/Rijswijk rats.
PubMed:3-[(E)-(Pyridin-3-yl-imino)-meth-yl]phenol.
PubMed:Synthesis and binding of 3-aminopyridine derivatives at central nicotinic receptors.
PubMed:Selective inactivation of rabbit muscle glycerophosphate dehydrogenase by diazotized 3-aminopyridine adenine dinucleotide.
PubMed:Experimental evaluation of anti-inflammatory activity of 3,4-dimethoxyphenylethylamino-3-aminopyridine (Compound 64-92).
PubMed:Interactions of 3-aminopyridine adenine dinucleotide with dehydrogenases.
PubMed:Mechanistic studies of semicarbazone triapine targeting human ribonucleotide reductase in vitro and in mammalian cells: tyrosyl radical quenching not involving reactive oxygen species.
PubMed:Bis(3-aminopyridine-kappaN)(4,4'-dimethyl-2,2'-bipyridine-kappa2N,N')(perchlorato-kappaO)copper(II) perchlorate.
PubMed:Ribonucleotide reductase inhibition restores platinum-sensitivity in platinum-resistant ovarian cancer: a Gynecologic Oncology Group Study.
PubMed:Emissive behavior, cytotoxic activity, cellular uptake, and PEGylation properties of new luminescent rhenium(I) polypyridine poly(ethylene glycol) complexes.
PubMed:Deoxynucleoside salvage facilitates DNA repair during ribonucleotide reductase blockade in human cervical cancers.
PubMed:Kinetic studies on the oxidation of oxyhemoglobin by biologically active iron thiosemicarbazone complexes: relevance to iron-chelator-induced methemoglobinemia.
PubMed:Radiosensitization of human cervical cancer cells by inhibiting ribonucleotide reductase: enhanced radiation response at low-dose rates.
PubMed:Triapine-mediated ABCB1 induction via PKC induces widespread therapy unresponsiveness but is not underlying acquired triapine resistance.
PubMed:Trypanotoxic activity of thiosemicarbazone iron chelators.
PubMed:Role of ruthenium oxidation states in ligand-to-ligand charge transfer processes.
PubMed:A phase II trial of sequential ribonucleotide reductase inhibition in aggressive myeloproliferative neoplasms.
PubMed:Molecular docking study of the binding of aminopyridines within the K+ channel.
PubMed:Studies of NAD kinase and NMN:ATP adenylyltransferase in Haemophilus influenzae.
PubMed:Ribonucleotide reductase inhibition enhances chemoradiosensitivity of human cervical cancers.
PubMed:Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules.
PubMed:In vitro evaluation of nicotinamide riboside analogs against Haemophilus influenzae.
PubMed:Probing the dynamic nature of water molecules and their influences on ligand binding in a model binding site.
PubMed:Triapine disrupts CtIP-mediated homologous recombination repair and sensitizes ovarian cancer cells to PARP and topoisomerase inhibitors.
PubMed:Alkyl substituted 2'-benzoylpyridine thiosemicarbazone chelators with potent and selective anti-neoplastic activity: novel ligands that limit methemoglobin formation.
PubMed:Two different hydrogen bond donor ligands together: a selectivity improvement in organometallic {Re(CO)3} anion hosts.
PubMed:Synthesis of 3-hydroxypyridines using ruthenium-catalyzed ring-closing olefin metathesis.
PubMed:Regioselective cobalt-catalyzed formation of bicyclic 3- and 4-aminopyridines.
PubMed:A phase I study of prolonged infusion of triapine in combination with fixed dose rate gemcitabine in patients with advanced solid tumors.
PubMed:Aryl- and heteroaryl-thiosemicarbazone derivatives and their metal complexes: a pharmacological template.
PubMed:Iron-targeting antitumor activity of gallium compounds and novel insights into triapine(®)-metal complexes.
PubMed:Mechanisms underlying reductant-induced reactive oxygen species formation by anticancer copper(II) compounds.
PubMed:Iron chelators for the treatment of cancer.
PubMed:Selective effects of subarachnoid hemorrhage on cerebral vascular responses to 4-aminopyridine in rats.
PubMed:Effects of intracellularly applied aminopyridine on firing activities and synaptic responses of electrophysiologically identified cell types in the motor cortex of cats.
PubMed:Interaction of 4-aminopyridine with [3H]phencyclidine receptors in rat brain homogenates.
PubMed:[Presynaptic effects of aminopyridines on the neuromuscular junction of vertebrates].
PubMed:A study of the action of tetanus toxin at rat soleus neuromuscular junctions.
PubMed:Actions of potassium channel blockers on guinea-pig lateral olfactory tract axons.
PubMed:Stimulation of substantia nigra pars reticulata suppresses neocortical seizures.
PubMed:Structural requirements of the ASBT by 3D-QSAR analysis using aminopyridine conjugates of chenodeoxycholic acid.
PubMed:A dose escalation and pharmacodynamic study of triapine and radiation in patients with locally advanced pancreas cancer.
PubMed:Modulating radiation resistance by inhibiting ribonucleotide reductase in cancers with virally or mutationally silenced p53 protein.
PubMed:Methemoglobin formation by triapine, di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone (Dp44mT), and other anticancer thiosemicarbazones: identification of novel thiosemicarbazones and therapeutics that prevent this effect.
PubMed:Coenzyme binding during catalysis is beneficial for the stability of 4-hydroxyacetophenone monooxygenase.
PubMed:Interaction of 2-Amino-, 3-Amino-, and 4-Aminopyridines with Chromium and Manganese Ferrocyanides.
PubMed:Pyridine-Containing schiff base derivatives for the struxtural determination of long-chain aldehydes by gas chromatography combined with mass spectrometry.
PubMed:Kinetic studies of Haemophilus influenzae 6-phosphogluconate dehydrogenase.
PubMed:The anticancer thiosemicarbazones Dp44mT and triapine lack inhibitory effects as catalytic inhibitors or poisons of DNA topoisomerase IIα.
PubMed:PAN-811 provides neuroprotection against glutamate toxicity by suppressing activation of JNK and p38 MAPK.
PubMed:Examining the out-of-center distortion in the [NbOF5]2- anion.
PubMed:Photodependent inhibition of bovine spleen NAD+ glycohydrolase by 8-azido carbocyclic analogs of NAD+.
PubMed:Effect of pyridine nucleotide on the oxidative half-reaction of Escherichia coli thioredoxin reductase.
PubMed:Anticonvulsive effect of urethane on aminopyridine-induced epileptiform activity.
PubMed:Methylenetetrahydrofolate dehydrogenase - methenyltetrahydrofolate cyclohydrolase - formyltetrahydrofolate synthetase from porcine liver: evidence to support a common dehydrogenase-cyclohydrolase site.
PubMed:Comutagenic effect of norharman with aminopyridine derivatives.
PubMed:Effect of epileptogenic agents on the incorporation of 3H-glycine into proteins in the cat's cerebral cortex.
PubMed:Development of new mitomycin C and porfiromycin analogues.
PubMed:Reactions of the Neurospora crassa nitrate reductase with NAD(P) analogs.
PubMed:Uridine release during aminopyridine-induced epilepsy.
PubMed:Phase II study of 3-AP Triapine in patients with recurrent or metastatic head and neck squamous cell carcinoma.
PubMed:Magnetism and crystal structure of an N3O3-coordinated iron(II) complex.
PubMed:Conformational change of Arabidopsis thaliana thioredoxin reductase after binding of pyridine nucleotide and thioredoxin.
PubMed:Thioredoxin reductase-thioredoxin fusion enzyme from Mycobacterium leprae: comparison with the separately expressed thioredoxin reductase.
PubMed:Evidence for two conformational states of thioredoxin reductase from Escherichia coli: use of intrinsic and extrinsic quenchers of flavin fluorescence as probes to observe domain rotation.
PubMed:Binding of the 2',5'-ADP subsite stimulates cyclohydrolase activity of human NADP(+)-dependent methylenetetrahydrofolate dehydrogenase/cyclohydrolase.
PubMed:Inactivation of rat ovarian 20 alpha-hydroxysteroid dehydrogenase by N-alkylmaleimides.
PubMed:Interaction of Triapine and related thiosemicarbazones with iron(III)/(II) and gallium(III): a comparative solution equilibrium study.
PubMed:The iron-chelating drug triapine causes pronounced mitochondrial thiol redox stress.
PubMed:PAN-811 inhibits oxidative stress-induced cell death of human Alzheimer's disease-derived and age-matched olfactory neuroepithelial cells via suppression of intracellular reactive oxygen species.
PubMed:Synthesis, a case of isostructural packing, and antimicrobial activity of silver(I)quinoxaline nitrate, silver(I)(2,5-dimethylpyrazine) nitrate and two related silver aminopyridine compounds.
PubMed:A Ferrous-Triapine complex mediates formation of reactive oxygen species that inactivate human ribonucleotide reductase.
PubMed:Inhibitors of ribonucleotide reductase. Comparative effects of amino- and hydroxy-substituted pyridine-2-carboxaldehyde thiosemicarbazones.
PubMed:Electron paramagnetic resonance study of peripheral blood mononuclear cells from patients with refractory solid tumors treated with Triapine.
PubMed:Future of toxicology--iron chelators and differing modes of action and toxicity: the changing face of iron chelation therapy.
PubMed:Structure-function relationships for a new series of pyridine-2-carboxaldehyde thiosemicarbazones on ribonucleotide reductase activity and tumor cell growth in culture and in vivo.
PubMed:Synthesis and antitumor activity of amino derivatives of pyridine-2-carboxaldehyde thiosemicarbazone.
PubMed:Inhibitory mechanisms of heterocyclic carboxaldehyde thiosemicabazones for two forms of human ribonucleotide reductase.
PubMed:Insights into the origin of solid-state photochromism and thermochromism of N-salicylideneanils: the intriguing case of aminopyridines.
PubMed:A phase II trial of triapine (NSC# 663249) and gemcitabine as second line treatment of advanced non-small cell lung cancer: Eastern Cooperative Oncology Group Study 1503.
PubMed:Toward a facile one-step construction of quantum dots containing Zn8S cores.
PubMed:Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald-Hartwig C-N cross-coupling.
PubMed:Synthesis and characterization of the face-sharing bioctahedral [Mo2O6F3]3- anion.
PubMed:catena-Poly[bis[(eta2-1-allyl-3-aminopyridinium)copper(I)]-di-mu-chloro-copper(I)-di-mu-chloro-copper(I)-di-mu-chloro].
PubMed:Three new polynuclear copper(II) complexes with the symmetric [Cu(mu1,1-N3)2Cu]2+ core and pyridine derivatives: syntheses, structure, and magnetic behavior.
PubMed:The nature of the receptor site for the reversible K+ channel blocking by aminopyridines.
PubMed:Pharmacological characterization of the discriminative stimulus effects of the potassium channel blocker 4-aminopyridine in rats.
PubMed:Equilibrium analyses of the active-site asymmetry in enterococcal NADH oxidase: role of the cysteine-sulfenic acid redox center.
PubMed:Mapping of residues in the NADP(H)-binding site of proton-translocating nicotinamide nucleotide transhydrogenase from Escherichia coli. A study of structure and function.
PubMed:Crystallization and preliminary X-ray diffraction studies of homoserine dehydrogenase from Saccharomyces cerevisiae.
PubMed:Characterization of H. parasuis periplasmic nucleotide pyrophosphatase as a potential target enzyme for inhibition of growth.
PubMed:The olivocerebellar projection mediates ibogaine-induced degeneration of Purkinje cells: a model of indirect, trans-synaptic excitotoxicity.
PubMed:The cyclic GMP-mediated calcium release pathway in sea urchin eggs is not required for the rise in calcium during fertilization.
PubMed:Nitric oxide synthase inhibitor facilitates aminopyridine induced neocortical seizure.
PubMed:Regulation of membrane potential and diameter by voltage-dependent K+ channels in rabbit myogenic cerebral arteries.
PubMed:DT-diaphorase. Redox potential, steady-state, and rapid reaction studies.
PubMed:ADP-ribosylation and de-ADP-ribosylation of the rho protein by Clostridium botulinum exoenzyme C3. Regulation by EDTA, guanine nucleotides and pH.
PubMed:Kinetic mechanism of the endogenous lactate dehydrogenase activity of duck epsilon-crystallin.
PubMed:On the active form of 4-aminopyridine: block of K+ currents in rabbit Schwann cells.
PubMed:An aminopyridine-sensitive, early outward current recorded in vivo in neurons of the precruciate cortex of cats using single-electrode voltage-clamp techniques.
PubMed:Analysis of the molecular electrostatic potential for the prediction of N-oxidation and biological activity of substituted pyridines.
PubMed:Phorbol esters that activate protein kinase C induce long-term changes of membrane excitability and postsynaptic currents in neocortical neurons.
PubMed:Modulation of aminopyridine block of potassium currents in squid axon.
PubMed:Intramembranous organization of lobster excitatory neuromuscular synapses.
PubMed:Electrophysiological study of mammalian neurons from ventral mesencephalon grown in primary dissociated cell culture.
PubMed:Potential use of biaromatic L-phenylalanyl derivatives as therapeutic agents in the treatment of sickle cell disease.
PubMed:Actions of adenine dinucleotides on the vas deferens, guinea-pig taenia caeci and bladder.
PubMed:Calcium-dependent action potentials in mouse spinal cord neurons in cell culture.
PubMed:Properties of tetraethylammonium ion-resistant K+ channels in the photoreceptor membrane of the giant barnacle.
PubMed:On modelling the variability of interspike intervals during epileptic unit activity.
PubMed:Cancerostatics. IV. On the synthesis of some noval 1-Azacarbazole derivatives as antineoplastic agents.
PubMed:A study of tetanic and post-tetanic potentiation of miniature end-plate potentials at the frog neuromuscular junction.
PubMed:Barium ions block the acetylcholine evoked slow H-response in the neurones of Helix pomatia L.
PubMed:Effects of phenytoin on the cyclic nucleotide system in the motor nerve terminal.
PubMed:The actions of aminopyridines on avian muscle.
PubMed:The potentiating effects of 4-aminopyridine on adrenergic transmission in the rabbit vas deferens.
PubMed:Effect of novel arecoline thiazolidinones as muscarinic receptor 1 agonist in Alzheimer's dementia models.
PubMed:Theoretical prediction of relative and absolute pKa values of aminopyridines.
PubMed:Surface complexation modeling of the sorption of 2-, 3-, and 4-aminopyridine by montmorillonite.
PubMed:Rational modelling of the voltage-dependent K+ channel inactivation by aminopyridines.
PubMed:Topoisomerase II antagonism and anticancer activity of coordinated derivatives of [RuCl(2)(C(6)H(6))(dmso)].
PubMed:Apoptosis induced by picolinic acid-related compounds in HL-60 cells.
PubMed:General rules for the packing of hydrogen-bonded crystals as derived from the analysis of squaric acid anions: aminoaromatic nitrogen base co-crystals.
PubMed:Theoretical analysis of the molecular determinants responsible for the K(+) channel blocking by aminopyridines.
PubMed:Determination of the midpoint potential of the FAD and FMN flavin cofactors and of the 3Fe-4S cluster of glutamate synthase.
PubMed:Effects of chronic, intrauterine organic and inorganic mercury intoxication on the epileptogenicity of developing rat.
PubMed:Synthesis and characterization of a fluorescent substrate for the N-arachidonoylethanolamine (anandamide) transmembrane carrier.
PubMed:Chronic low-dose maternal exposure to methylmercury enhances epileptogenicity in developing rats.
PubMed:Porcine recombinant dihydropyrimidine dehydrogenase: comparison of the spectroscopic and catalytic properties of the wild-type and C671A mutant enzymes.
PubMed:Nitric oxide synthase inhibitor facilitates focal seizures induced by aminopyridine in rat.
PubMed:Inhibition studies on the involvement of flavoprotein reductases in menadione- and nitrofurantoin-stimulated oxyradical production by hepatic microsomes of flounder (Platichthys flesus).
PubMed:Matrix isolation applied to the 252Cf plasma-desorption mass spectrometry of underivatized oligosaccharides.
PubMed:Adsorption of aminopyridines to phosphatidylserine membranes.
PubMed:Nonpolar interactions in the modification of an essential sulfhydryl of sorbitol dehydrogenase by N-alkylmaleimides.
PubMed:Properties of depolarizing plateau potentials in aminopyridine-induced ictal seizure foci of cat motor cortex.
PubMed:The reactivity of chicken liver xanthine dehydrogenase with molecular oxygen.
PubMed:Transient outward current (IA) in clonal anterior pituitary cells: blockade by aminopyridine analogs.
PubMed:Mechanism of aminopyridine-induced ictal seizure activity in the cat neocortex.
PubMed:Modelling the interaction of small organic molecules with biomacromolecules. II. A generalized concept for biological interactions.
PubMed:The effects of aminopyridines on the cortical evoked potentials.
PubMed:Drosophila mutants reveal two components of fast outward current.
PubMed:Barbiturate reduction of calcium-dependent action potentials: correlation with anesthetic action.
PubMed:Tetrodotoxin-resistant propagating action potentials in presynaptic axon of the lobster.
PubMed:Comparative study of aminopyridine-induced seizure activities in primary and mirror foci of cat's cortex.
PubMed:Aminopyridine--induced seizure activity.
PubMed:Calcium channels in the high resistivity axonal membrane of photoreceptors of the giant barnacle.
PubMed:Aminopyridine-induced seizure activity.
PubMed:Tetrodotoxin-resistant dendritic spikes in avian Purkinje cells.
PubMed:Purification and kinetic characterization of Haemophilus parasuis malate dehydrogenase.
PubMed:Purification and properties of milk xanthine dehydrogenase.
PubMed:Rapid reaction studies on the reduction and oxidation of chicken liver xanthine dehydrogenase by the xanthine/urate and NAD/NADH couples.
PubMed:Simultaneous inactivation of the catalytic activities of yeast glutathione reductase by N-alkylmaleimides.
PubMed:Formation of a tyrosyl radical in xanthine oxidase.
PubMed:Quinone reductase reaction catalyzed by Streptococcus faecalis NADH peroxidase.
PubMed:Lipoamide dehydrogenase from pig heart. Pyridine nucleotide induced changes in monoalkylated two-electron reduced enzyme.
PubMed:Evaluation of mRNA by Q-RTPCR and protein expression by AQUA of the M2 subunit of ribonucleotide reductase (RRM2) in human tumors.
PubMed:A phase I study of Triapine in combination with doxorubicin in patients with advanced solid tumors.
PubMed:Iron chelators as therapeutic agents for the treatment of cancer.
PubMed:Interactions of nicotinamide-adenine dinucleotide phosphate analogues and fragments with pigeon liver malic enzyme. Synergistic effect between the nicotinamide and adenine moieties.
PubMed:Overexpression of the multidrug resistance genes mdr1, mdr3, and mrp in L1210 leukemia cells resistant to inhibitors of ribonucleotide reductase.
PubMed:Analogues of NADP(+) as inhibitors and coenzymes for NADP(+) malic enzyme from maize leaves.
PubMed:The streptococcal flavoprotein NADH oxidase. II. Interactions of pyridine nucleotides with reduced and oxidized enzyme forms.
PubMed:A new era for ribonucleoside reductase inhibition.
PubMed:Chelators at the cancer coalface: desferrioxamine to Triapine and beyond.
PubMed:A class of iron chelators with a wide spectrum of potent antitumor activity that overcomes resistance to chemotherapeutics.
PubMed:Developmental clinical trials: building one step at a time.
PubMed:A multifunctional cytoprotective agent that reduces neurodegeneration after ischemia.
PubMed:Mechanisms of Ca2+ liberation at fertilization.
PubMed:Drug-induced haemolysis and methaemoglobinaemia in glucose 6-phosphate dehydrogenase deficiency.
PubMed:Platelet function and its clinical significance in the myelodysplastic syndromes.
PubMed:Phase I and pharmacokinetic study of triapine, a potent ribonucleotide reductase inhibitor, administered daily for five days in patients with advanced solid tumors.
PubMed:Examination of the antiproliferative activity of iron chelators: multiple cellular targets and the different mechanism of action of triapine compared with desferrioxamine and the potent pyridoxal isonicotinoyl hydrazone analogue 311.
PubMed:The role of iron in cell cycle progression and the proliferation of neoplastic cells.
PubMed:The function of NADPH bound to Catalase.
PubMed:Using periodate-oxidized nucleotide as affinity label for the nucleotide site of proteins.
PubMed:Phase II study of Triapine in patients with metastatic renal cell carcinoma: a trial of the National Cancer Institute of Canada Clinical Trials Group (NCIC IND.161).
PubMed:Phase I and pharmacokinetic study of Triapine, a potent ribonucleotide reductase inhibitor, in adults with advanced hematologic malignancies.
PubMed:The synergistic interaction of gemcitabine and cytosine arabinoside with the ribonucleotide reductase inhibitor triapine is schedule dependent.
PubMed:Rediscovery of the susceptibility of G6PD deficient persons to methemoglobinemia from oxidant drugs, and to hemolysis from methylene blue.
PubMed:Recognition and management of methemoglobinemia and hemolysis in a G6PD-deficient patient on experimental anticancer drug Triapine.
PubMed:Triapine and cytarabine is an active combination in patients with acute leukemia or myelodysplastic syndrome.
PubMed:Clinical trials referral resource. Current clinical trials investigating 3-AP.
PubMed:Clinical trials referral resource. Current clinical trials investigating Triapine.
PubMed:Stable suppression of the R2 subunit of ribonucleotide reductase by R2-targeted short interference RNA sensitizes p53(-/-) HCT-116 colon cancer cells to DNA-damaging agents and ribonucleotide reductase inhibitors.
PubMed:Phase I and pharmacodynamic study of Triapine, a novel ribonucleotide reductase inhibitor, in patients with advanced leukemia.
PubMed:Syntheses and antitumor activities of potent inhibitors of ribonucleotide reductase: 3-amino-4-methylpyridine-2-carboxaldehyde-thiosemicarba-zone (3-AMP), 3-amino-pyridine-2-carboxaldehyde-thiosemicarbazone (3-AP) and its water-soluble prodrugs.
PubMed:Glutamate synthase: identification of the NADPH-binding site by site-directed mutagenesis.
 
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