3-aminopyridine
3-pyridylamine
Identification
| Name | 3-aminopyridine |
| CAS Number | 462-08-8 |
| EINECS | 207-322-2 |
| FDA UNII | 69JE8P2L84 |
| Molecular Formula | C5 H6 N2 |
| Molecular Weight | 94.11682000 |
| MDL Number | MFCD00006400 |
| Nikkaji Number | J1.535K |
| Beilstein | 105692 |
| XlogP3 | 0.10 (est) |
Regulatory
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) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-bird - wild LD50 13300 ug/kg |
| Dermal Toxicity | subcutaneous-mouse LD50 30 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
Penta International Corporation
Chemistry innovation
At Penta, our products and services help businesses do business better.
Potential Uses
Natural Occurrence
Synonyms
3-
amino-pyridine
pyridin-3-amine
pyridin-3-ylamine
3-
pyridinamine
3-
pyridylamine
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.