aminophenols

Summary

Summary: Phenols substituted in any position by an amino group.

Top Publications

  1. Durmowicz A, Witzmann K, Rosebraugh C, Chowdhury B. Change in sweat chloride as a clinical end point in cystic fibrosis clinical trials: the ivacaftor experience. Chest. 2013;143:14-18 pubmed publisher
    ..Future clinical trials of drugs that are directed to the defective CFTR will need take into account the uncertainty of using even established measurements, such as sweat chloride, as clinical end points...
  2. Foreman B, Tarloff J. Contribution of reactive oxygen species to para-aminophenol toxicity in LLC-PK1 cells. Toxicol Appl Pharmacol. 2008;230:144-9 pubmed publisher
    ..Paradoxically, DMTU exacerbated PAP-induced loss of viability. These data suggest that ROS are generated in cells exposed to PAP but these species are not the predominant cause of cellular injury...
  3. Pizarro J, Folch J, Esparza J, Jordan J, Pallas M, Camins A. A molecular study of pathways involved in the inhibition of cell proliferation in neuroblastoma B65 cells by the GSK-3 inhibitors lithium and SB-415286. J Cell Mol Med. 2009;13:3906-17 pubmed publisher
    ..We conclude that inhibitors of GSK-3 induced cell-cycle arrest, mediated by the phosphorylation of cdc2 and, in the case of SB-415286, SIRT2 expression, which induced apoptosis in a caspase-independent manner...
  4. Van Goor F, Hadida S, Grootenhuis P, Burton B, Cao D, Neuberger T, et al. Rescue of CF airway epithelial cell function in vitro by a CFTR potentiator, VX-770. Proc Natl Acad Sci U S A. 2009;106:18825-30 pubmed publisher
    ..These results support the hypothesis that pharmacological agents that restore or increase CFTR function can rescue epithelial cell function in human CF airway...
  5. Suzuki H, Ohnishi Y, Horinouchi S. Arylamine N-acetyltransferase responsible for acetylation of 2-aminophenols in Streptomyces griseus. J Bacteriol. 2007;189:2155-9 pubmed publisher
  6. Accurso F, Rowe S, Clancy J, Boyle M, Dunitz J, Durie P, et al. Effect of VX-770 in persons with cystic fibrosis and the G551D-CFTR mutation. N Engl J Med. 2010;363:1991-2003 pubmed publisher
    ..VX-770, a CFTR potentiator, has been shown to increase the activity of wild-type and defective cell-surface CFTR in vitro...
  7. Behrens C, Hooker J, Obermeyer A, Romanini D, Katz E, Francis M. Rapid chemoselective bioconjugation through oxidative coupling of anilines and aminophenols. J Am Chem Soc. 2011;133:16398-401 pubmed publisher
    A highly efficient protein bioconjugation method is described involving addition of anilines to o-aminophenols in the presence of sodium periodate. The reaction takes place in aqueous buffer at pH 6...
  8. Hogestatt E, Jonsson B, Ermund A, Andersson D, Björk H, Alexander J, et al. Conversion of acetaminophen to the bioactive N-acylphenolamine AM404 via fatty acid amide hydrolase-dependent arachidonic acid conjugation in the nervous system. J Biol Chem. 2005;280:31405-12 pubmed
  9. Gasowska B, Kafarski P, Wojtasek H. Interaction of mushroom tyrosinase with aromatic amines, o-diamines and o-aminophenols. Biochim Biophys Acta. 2004;1673:170-7 pubmed
    ..These results show that the relative positioning of the amino group and the hydroxy group in o-aminophenols with respect to the side chain is important both for binding to the dicopper center and for catalysis.

More Information

Publications62

  1. Eckford P, Li C, Ramjeesingh M, Bear C. Cystic fibrosis transmembrane conductance regulator (CFTR) potentiator VX-770 (ivacaftor) opens the defective channel gate of mutant CFTR in a phosphorylation-dependent but ATP-independent manner. J Biol Chem. 2012;287:36639-49 pubmed publisher
    ..This work sets the stage for future studies of the structural properties that mediate CFTR gating using VX-770 as a probe...
  2. Endo Y, Bäckvall J. Biomimetic oxidative coupling of benzylamines and 2-aminophenols: synthesis of benzoxazoles. Chemistry. 2012;18:13609-13 pubmed publisher
    ..This biomimetic oxidation proceeds smoothly under mild conditions and the protocol can also be used for preparing benzimidazoles and benzothiazoles...
  3. Takenaka S, Setyorini E, Kim Y, Murakami S, Aoki K. Constitutive synthesis of enzymes involved in 2-aminophenol metabolism and inducible synthesis of enzymes involved in benzoate, p-hydroxybenzoate, and protocatechuate metabolism in Pseudomonas sp. strain AP-3. Biosci Biotechnol Biochem. 2005;69:1033-5 pubmed
    ..The enzymes responsible for these reactions were shown to be inducible. In contrast, strain AP-3 constitutively expresses the enzymes involved in the metabolism of 2-aminophenol...
  4. Yu H, Burton B, Huang C, Worley J, Cao D, Johnson J, et al. Ivacaftor potentiation of multiple CFTR channels with gating mutations. J Cyst Fibros. 2012;11:237-45 pubmed publisher
    ..The aim of this in vitro study was to determine whether ivacaftor potentiates mutant CFTR with gating defects caused by other CFTR gating mutations...
  5. Ramsey B, Davies J, McElvaney N, Tullis E, Bell S, Drevinek P, et al. A CFTR potentiator in patients with cystic fibrosis and the G551D mutation. N Engl J Med. 2011;365:1663-72 pubmed publisher
    ..Increasing the activity of defective cystic fibrosis transmembrane conductance regulator (CFTR) protein is a potential treatment for cystic fibrosis...
  6. Gaillard M, Vallaeys T, Vorhölter F, Minoia M, Werlen C, Sentchilo V, et al. The clc element of Pseudomonas sp. strain B13, a genomic island with various catabolic properties. J Bacteriol. 2006;188:1999-2013 pubmed
    ..This indicates the dynamic evolution of this type of element and the continued transition between elements with a more pathogenic character and those with catabolic properties...
  7. Das J, Jo K, Lee J, Yang H. Electrochemical immunosensor using p-aminophenol redox cycling by hydrazine combined with a low background current. Anal Chem. 2007;79:2790-6 pubmed
    ..Mouse IgG could be detected at concentrations ranging from 100 fg/mL to 100 microg/mL (i.e., 9 orders of magnitude) in a single assay...
  8. Heravi M, Baghernejad B, Oskooie H. A novel three-component reaction for the synthesis of 3-aryl-4H-benzo [1,4] oxazin-2-amine. Mol Divers. 2009;13:395-8 pubmed publisher
    ..A high yielding and fast method for the synthesis of 3-aryl-4H-benzo [1,4] oxazin-2-amine via one-pot, three component reaction of an aromatic aldehyde, isocyanide and o-aminophenol using p-toluene sulfonic acid as a catalyst is described...
  9. Ren J, Liu D, Tian L, Wei Y, Proksch P, Zeng J, et al. Venezuelines A-G, new phenoxazine-based alkaloids and aminophenols from Streptomyces venezuelae and the regulation of gene target Nur77. Bioorg Med Chem Lett. 2013;23:301-4 pubmed publisher
    Five new phenoxazine-based alkaloids venezuelines A-E (1-5) and two new aminophenols venezuelines F-G (6-7), as well as three known analogues exfoliazone, chandrananimycin D and carboxyexfoliazone were isolated from the fermentation broth ..
  10. Mazor M, Kawano Y, Zhu H, Waxman J, Kypta R. Inhibition of glycogen synthase kinase-3 represses androgen receptor activity and prostate cancer cell growth. Oncogene. 2004;23:7882-92 pubmed
    ..Finally, inhibition of GSK-3 reduced the growth of AR-expressing prostate cancer cell lines. Our observations suggest a potential new therapeutic application for GSK-3 inhibitors in prostate cancer...
  11. Flume P, Liou T, Borowitz D, Li H, Yen K, Ordonez C, et al. Ivacaftor in subjects with cystic fibrosis who are homozygous for the F508del-CFTR mutation. Chest. 2012;142:718-724 pubmed publisher
  12. MacAulay K, Blair A, Hajduch E, Terashima T, Baba O, Sutherland C, et al. Constitutive activation of GSK3 down-regulates glycogen synthase abundance and glycogen deposition in rat skeletal muscle cells. J Biol Chem. 2005;280:9509-18 pubmed
  13. Pettit R. Cystic fibrosis transmembrane conductance regulator-modifying medications: the future of cystic fibrosis treatment. Ann Pharmacother. 2012;46:1065-75 pubmed publisher
    ..To review and evaluate cystic fibrosis transmembrane conductance regulator (CFTR) modulators for the treatment of cystic fibrosis (CF)...
  14. Cross D, Culbert A, Chalmers K, Facci L, Skaper S, Reith A. Selective small-molecule inhibitors of glycogen synthase kinase-3 activity protect primary neurones from death. J Neurochem. 2001;77:94-102 pubmed
  15. Coghlan M, Culbert A, Cross D, Corcoran S, Yates J, Pearce N, et al. Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription. Chem Biol. 2000;7:793-803 pubmed
    ..This report describes the identification and characterisation of potent and selective small molecule inhibitors of GSK-3...
  16. Kadiyala V, Nadeau L, Spain J. Construction of Escherichia coli strains for conversion of nitroacetophenones to ortho-aminophenols. Appl Environ Microbiol. 2003;69:6520-6 pubmed
    ..We tested the hypothesis that constructed strains might accumulate the aminophenols from nitroacetophenones and other nitroaromatic compounds...
  17. Park H, Kim H. Genetic and structural organization of the aminophenol catabolic operon and its implication for evolutionary process. J Bacteriol. 2001;183:5074-81 pubmed
    ..The evolutionary process of the AP operon suggests how bacteria have efficiently acquired genetic diversity and expanded their metabolic capabilities by modular type gene transfer...
  18. Ohkuma Y, Kawanishi S. Oxidative DNA damage induced by a metabolite of carcinogenic o-anisidine: enhancement of DNA damage and alteration in its sequence specificity by superoxide dismutase. Arch Biochem Biophys. 2001;389:49-56 pubmed
    ..We consider that SOD may increase the frequency of mutations due to DNA damage induced by o-aminophenol and thus increase its carcinogenic potential...
  19. Shao R, Tarloff J. Lack of correlation between para-aminophenol toxicity in vivo and in vitro in female Sprague-Dawley rats. Fundam Appl Toxicol. 1996;31:268-78 pubmed
    ..These observations suggest that PAP nephrotoxicity may be mediated by PAP-GSH conjugates rather than autooxidation of PAP in the kidney...
  20. Song H, Chen T. p-Aminophenol-induced liver toxicity: tentative evidence of a role for acetaminophen. J Biochem Mol Toxicol. 2001;15:34-40 pubmed
    ..The results suggest the roles of GSH and N-acetylation of PAP to APAP in PAP-induced hepatotoxicity...
  21. Parameswaran R, Ramakrishnan P, Moreton S, Xia Z, Hou Y, Lee D, et al. Repression of GSK3 restores NK cell cytotoxicity in AML patients. Nat Commun. 2016;7:11154 pubmed publisher
    ..Finally, GSK3-inhibited NK cells show significant efficacy in human AML mouse models. Overall, our work provides mechanistic insights into the AML-NK dysfunction and a potential NK cell therapy strategy. ..
  22. Li D, Zhang J, Hou Y, Liu L, Liu S, Liu W. Crystallization and preliminary crystallographic analysis of 2-aminophenol 1,6-dioxygenase complexed with substrate and with an inhibitor. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2012;68:1337-40 pubmed publisher
    ..24, b=48.39, c=108.55?Å, ?=109.57°. All X-ray data sets collected from diffraction-quality crystals were suitable for structure determination...
  23. Chen C, Teng W, Hahn J. Nanoband electrode for high-performance in-channel amperometric detection in dual-channel microchip capillary electrophoresis. Electrophoresis. 2011;32:838-43 pubmed publisher
    ..The effect of sample injection time and data acquisition time on separation efficiency was investigated, and an attractive separation efficiency was achieved with a plate number up to 17,500...
  24. Gillespie J, Ulici V, Dupuis H, Higgs A, DiMattia A, Patel S, et al. Deletion of glycogen synthase kinase-3? in cartilage results in up-regulation of glycogen synthase kinase-3? protein expression. Endocrinology. 2011;152:1755-66 pubmed publisher
    ..To our knowledge, this is the first tissue in which such a compensatory mechanism is described. Thus, our study provides important new insights into both skeletal development and the biology of GSK-3 proteins...
  25. Aluotto S, Tynan H, Maggio C, Falzone M, Mukherjee A, Gullo V, et al. Development of a semi-defined medium supporting production of platensimycin and platencin by Streptomyces platensis. J Antibiot (Tokyo). 2013;66:51-4 pubmed publisher
    ..It yields suitable production of the compounds, as shown by agar diffusion assays, bioautography and HPLC. The antibiotics were located in the extracellular broths and not in the mycelia...
  26. Orii C, Takenaka S, Murakami S, Aoki K. Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: A different modified meta-cleavage pathway for 2-aminophenols. Biosci Biotechnol Biochem. 2006;70:2653-61 pubmed
    ..This proposed metabolic pathway differs considerably from the modified meta-cleavage pathway of 2-aminophenol and those previously reported for methyl- and chloro-derivatives...
  27. Hernandez S, Kergaravat S, Pividori M. Enzymatic electrochemical detection coupled to multivariate calibration for the determination of phenolic compounds in environmental samples. Talanta. 2013;106:399-407 pubmed publisher
    ..6 to 1.4 × 10(-6) mol L(-1). Recoveries for prediction samples were higher than 85%. These compounds were analyzed simultaneously in spiked samples and in water samples collected close to tanneries and landfills...
  28. Nicolaou K, Tria G, Edmonds D. Total synthesis of platencin. Angew Chem Int Ed Engl. 2008;47:1780-3 pubmed publisher
  29. Belfield K, Bondar M, Haniff H, Mikhailov I, Luchita G, Przhonska O. Superfluorescent squaraine with efficient two-photon absorption and high photostability. Chemphyschem. 2013;14:3532-42 pubmed publisher
    ..The quantum chemical study of 1 revealed the simulated vibronic nature of the 1PA and 2PA spectra were in good agreement with experimental data; this may provide the ability to predict potential advanced photonic materials...
  30. Alexandre E, Kiguti L, Calmasini F, Silva F, da Silva K, Ferreira R, et al. Mirabegron relaxes urethral smooth muscle by a dual mechanism involving ?3 -adrenoceptor activation and ?1 -adrenoceptor blockade. Br J Pharmacol. 2016;173:415-28 pubmed publisher
    ..This article is commented on by Michel, M. C., pp. 429-430 of this issue. To view this commentary visit http://dx.doi.org/10.1111/bph.13379...
  31. Mie Y, Kowata K, Hirano Y, Niwa O, Mizutani F. Comparison of enzymatic recycling electrodes for measuring aminophenol: development of a highly sensitive natriuretic peptide assay system. Anal Sci. 2008;24:577-82 pubmed
    ..ANPs from serum samples at ppt-levels were determined appropriately using the present assay system...
  32. Wu J, Sun C, Jiang C, Liu Z, Liu S. A novel 2-aminophenol 1,6-dioxygenase involved in the degradation of p-chloronitrobenzene by Comamonas strain CNB-1: purification, properties, genetic cloning and expression in Escherichia coli. Arch Microbiol. 2005;183:1-8 pubmed
    ..The enzyme was actively synthesized when the genes coding for the ORF9 and ORF10 were cloned into Escherichia coli...
  33. Takahashi N, Honda T, Ohba T. Anticancer and superoxide scavenging activities of p-alkylaminophenols having various length alkyl chains. Bioorg Med Chem. 2006;14:409-17 pubmed
    ..These results indicate that anticancer activity of p-alkylaminophenols correlated with the inhibitory activity of lipid peroxidation, but not with the superoxide scavenging activity...
  34. Gangula A, Podila R, M R, Karanam L, Janardhana C, Rao A. Catalytic reduction of 4-nitrophenol using biogenic gold and silver nanoparticles derived from Breynia rhamnoides. Langmuir. 2011;27:15268-74 pubmed publisher
    ..Efficient reduction of 4-nitrophenol (4-NP) to 4-aminophenol (4-AP) in the presence of AuNPs (or AgNPs) and NaBH(4) was observed and was found to depend upon the nanoparticle size or the stem extract concentration used for synthesis...
  35. de Jesus Rodrigues Santos W, Lima P, Tarley C, Kubota L. A catalytically active molecularly imprinted polymer that mimics peroxidase based on hemin: application to the determination of p-aminophenol. Anal Bioanal Chem. 2007;389:1919-29 pubmed
    ..1 and 3.2% for solutions of 4-APh of 50 and 500 micromol L(-1), respectively. Recoveries of 96-111% from water samples (tap water and river water) spiked with 4-APh were achieved, thus illustrating the accuracy of the proposed system...
  36. Arai T, Wasai M, Yokoyama N. Easy access to fully functionalized chiral tetrahydro-?-carboline alkaloids. J Org Chem. 2011;76:2909-12 pubmed publisher
  37. Schulz D, Ohlendorf B, Zinecker H, Schmaljohann R, Imhoff J. Eutypoids B-E produced by a Penicillium sp. strain from the North Sea. J Nat Prod. 2011;74:99-101 pubmed publisher
    ..The eutypoids were neither cytotoxic nor antibacterial, but inhibited the activity of glycogen synthase kinase-3?...
  38. Peineau S, Taghibiglou C, Bradley C, Wong T, Liu L, Lu J, et al. LTP inhibits LTD in the hippocampus via regulation of GSK3beta. Neuron. 2007;53:703-17 pubmed
    ..We conclude that the regulation of GSK3beta activity provides a powerful mechanism to preserve information encoded during LTP from erasure by subsequent LTD, perhaps thereby permitting the initial consolidation of learnt information...
  39. Tewari B, Boodhoo M. Removal of p-aminophenol and p-nitrophenol from aqueous solution through adsorption on antimony, cadmium, and zirconium ferrocyanides. J Colloid Interface Sci. 2005;289:328-32 pubmed
    ..The interaction followed the Langmuir type of adsorption in general. The p-nitrophenol was found to have greater affinity for the antimony, cadmium, and zirconium ferrocyanides then the p-aminophenol...
  40. Zhang L, Hu J, Zhu R, Zhou Q, Chen J. Degradation of paracetamol by pure bacterial cultures and their microbial consortium. Appl Microbiol Biotechnol. 2013;97:3687-98 pubmed publisher
    ..The exact roles of each of the strains in the consortium need to be further elucidated...
  41. Virant Young D, Thomas J, Woiderski S, Powers M, Carlier J, McCarty J, et al. Cystic Fibrosis: A Novel Pharmacologic Approach to Cystic Fibrosis Transmembrane Regulator Modulation Therapy. J Am Osteopath Assoc. 2015;115:546-55 pubmed publisher
    ..Drug therapy monitoring, adverse effects, and indications for discontinuation must also be considered. ..
  42. Vijay Kumar H, Naik N. Synthesis and antioxidant properties of some novel 5H-dibenz[b,f]azepine derivatives in different in vitro model systems. Eur J Med Chem. 2010;45:2-10 pubmed publisher
    A series of 5H-dibenz[b,f]azepine containing different aminophenols and substituted aminophenols were synthesized...
  43. Otari S, Patil R, Nadaf N, Ghosh S, Pawar S. Green synthesis of silver nanoparticles by microorganism using organic pollutant: its antimicrobial and catalytic application. Environ Sci Pollut Res Int. 2014;21:1503-13 pubmed publisher
    ..The as-prepared AgNPs showed excellent catalytic activity in reduction of 4-nitrophenol to 4-aminophenol by NaBH4. By manufacturing magnetic alginate beads, the reusability of the AgNPs for the catalytic reaction has been demonstrated. ..
  44. Bhalla V, Gupta A, Kumar M. Nanoaggregates of a pentacenequinone derivative as reactors for the preparation of palladium nanoparticles. Chem Commun (Camb). 2012;48:11862-4 pubmed publisher
    ..Further, the combination of catalytic quantities of palladium nanoparticles with NaBH(4) smoothly reduces 4-nitrophenol to 4-aminophenol in aqueous medium...
  45. Yu Y, Addai Mensah J, Losic D. Synthesis of self-supporting gold microstructures with three-dimensional morphologies by direct replication of diatom templates. Langmuir. 2010;26:14068-72 pubmed publisher
    ..offering more efficient catalytic, optical, or magnetic properties...
  46. Dejaegher B, Bloomfield M, Smeyers Verbeke J, Vander Heyden Y. Validation of a fluorimetric assay for 4-aminophenol in paracetamol formulations. Talanta. 2008;75:258-65 pubmed publisher
    ..They were found acceptable to assay the low amounts of 4-aminophenol in paracetamol tablets...
  47. Rowe S, Liu B, Hill A, Hathorne H, Cohen M, Beamer J, et al. Optimizing nasal potential difference analysis for CFTR modulator development: assessment of ivacaftor in CF subjects with the G551D-CFTR mutation. PLoS ONE. 2013;8:e66955 pubmed publisher
    ..8 mV). Therefore, we have confirmed an assay of reasonable reproducibility for detecting chloride-transport improvements in response to CFTR modulation...
  48. Ensafi A, Dadkhah Tehrani S, Karimi Maleh H. A voltammetric sensor for the simultaneous determination of L-cysteine and tryptophan using a p-aminophenol-multiwall carbon nanotube paste electrode. Anal Sci. 2011;27:409 pubmed
    ..3 and 5.7 µmol L(-1), respectively. The proposed method is also used for the determination of L-cysteine and tryptophan in urine, river water, blood plasma, and serum samples using standard addition methods...
  49. Bai Y, Peng Y, Yin W, Liu H, Liu F, Duan S, et al. p-Aminophenol and p-paraphenylenediamine induce injury and apoptosis of human HK-2 proximal tubular epithelial cells. J Nephrol. 2012;25:481-9 pubmed publisher
    ..However, the regulation and implication of the nephrotoxic injury resulting from p-aminophenol (PAP) and p-paraphenylenediamine (PPD), the main components of oxidized hair dye, remain unknown...
  50. Smanski M, Yu Z, Casper J, Lin S, Peterson R, Chen Y, et al. Dedicated ent-kaurene and ent-atiserene synthases for platensimycin and platencin biosynthesis. Proc Natl Acad Sci U S A. 2011;108:13498-503 pubmed publisher
  51. Kendig D, Tarloff J. Inactivation of lactate dehydrogenase by several chemicals: implications for in vitro toxicology studies. Toxicol In Vitro. 2007;21:125-32 pubmed
    ..These studies suggest that LDH that is released into the incubation medium is susceptible to degradation when reactive chemicals are present...
  52. Hosseiny Davarani S, Kalate Bojdi M, Mehdinia A. A new way for synthesis of phenoxazine and diphenoxazine derivatives via electrochemical method. Chem Pharm Bull (Tokyo). 2011;59:1209-13 pubmed
    ..The products were derived with good yield and purity using controlled-potential electrochemical oxidation of 1a, b in the presence of 3a and 3b at the graphite electrode in an undivided cell...
  53. Lee G, Park I, Kwon K, Kwon T, Seo J, Chang W, et al. Electrochemical detection of high-sensitivity CRP inside a microfluidic device by numerical and experimental studies. Biomed Microdevices. 2012;14:375-84 pubmed publisher
    ..Furthermore, the results described in this study should be useful for the design and optimization of electrochemical immunoassay chips for the detection of target proteins...