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Chemical Compound Review

p-Nitraniline     4-nitroaniline

Synonyms: p-Nitroanilina, p-Nitroaniline, Developer P, PubChem2098, LS-39, ...
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Disease relevance of Shinnippon Fast Red GG Base


High impact information on Shinnippon Fast Red GG Base

  • This medium did not cause cleavage of p-nitroaniline from the tripeptide substrate, and 83% of added FVIII procoagulant activity remained after 48 hr [6].
  • When the synthetic tripeptide was incubated in contact with cultured endothelial cells, 7.3 +/- 0.8 X 10(-10) moles of p-nitroaniline/hr was released; moreover, only 47% of the added FVIII procoagulant activity remained after 48 hr [6].
  • The AMC and pNA groups give insights into the leaving group binding site (P') of cathepsin B. These studies show for the first time that at least seven dissociable groups are involved in substrate binding and hydrolysis in cathepsin B activity [7].
  • Analysis of the observed molar transition energies indicates that for 4-nitroaniline and N,N-dimethyl-4-nitroaniline the stabilization of the zwitterionic excited states of such push-pull molecules is on the order of 2.0 kcal mol(-1) per mol of added salt [8].
  • A new solid ionic crystal MALDI matrix was synthesized which combined the lipid response enhancing UV-absorber p-nitroaniline with the protonating agent butyric acid [9].

Chemical compound and disease context of Shinnippon Fast Red GG Base


Biological context of Shinnippon Fast Red GG Base

  • Protease activity was quantitated by the hydrolysis of p-nitroaniline from the substrate, N-benzoyl-phenylalanyl-valyl-arginyl-p-nitroanilide and by degradation of the procoagulant activity of added purified plasma FVIII/vWF protein [6].
  • A comparative assessment of reductive amination and cleavage of these linkers under conditions of multiple synthesis indicated that both were applicable to a broad range of primary amines including aniline and 4-nitroaniline [11].
  • The three diaminobenzenes and 4-nitroaniline were mutagenic only with metabolic activation [12].
  • It is rate-determining with the ester substrate, but with the 4-nitroaniline acylation is and this is even more pronounced with the amide [13].
  • A novel method to characterize the activity and reaction kinetics of the immobilized enzyme has been developed based on the frontal analysis of enzymatic reaction products, which was performed by the on-line monitoring of the absorption at 410 nm of p-nitroaniline from the hydrolysis of N-alpha-benzoyl-DL-arginine-p-nitroanilide (BAPNA) [14].

Anatomical context of Shinnippon Fast Red GG Base

  • To address these limitations, a series of 4-nitroaniline mustards bearing hydrophilic side chains attached via an electron-withdrawing carboxamide group was prepared and evaluated for hypoxia-selective cytotoxicity against Chinese hamster cell lines [15].
  • Metabolism of 4-nitroaniline by rat liver microsomes [16].
  • The localization of gamma-glutamyl transferase (GGT) in the intact rat liver was studied by a new approach in which the chromogenic gamma-glutamyl donor substrate of GGT gamma-glutamyl-p-nitroanilide is perfused through the portal vein to yield p-nitroaniline, which is monitored spectrophotometrically [17].
  • Infusion of glutathione (GSH), the natural substrate of GGT, was shown to markedly reduce or to abolish the formation of p-nitroaniline without entering the liver cells, indicating the existence of a GGT ectoactivity accessible to the sinusoidal circulation [17].
  • An enzymatic activity with releases p-nitroaniline from 3-carboxypropionyl-trialanine p-nitroanilide (Suc[Ala]3NA) was characterized in blood plasma of patients with Tangier disease [18].

Associations of Shinnippon Fast Red GG Base with other chemical compounds


Gene context of Shinnippon Fast Red GG Base

  • Kallikrein-like activity was expressed as picomoles of p-nitroaniline liberated per minute per milligram of protein [24].
  • In the standard method, we defined the activity of h-TM forming 0.1 micromol of p -nitroaniline per min in the reaction as 1 JRS Unit [25].
  • Due to the low equilibrium population of the X-cis-Pro-Phe-pNA isomer (the PPIase substrate), in conjunction with the low solubility of p-nitroaniline generated by chymotrypsin hydrolysis, substrate concentrations in the saturating region are not experimentally attainable [26].
  • Conditions were chosen such that the rate of para-nitroaniline release from the substrate is directly proportional to the concentration of tPA [27].
  • The scu-PA solution was activated by plasmin to two-chain u-PA, which releases p-nitroaniline from pyro-Glu-Gly-Arg-pNA, and the optical density at 405 nm was measured [28].

Analytical, diagnostic and therapeutic context of Shinnippon Fast Red GG Base

  • Sensitive determination of carbohydrates labelled with p-nitroaniline by capillary electrophoresis with photometric detection using a 406 nm light-emitting diode [29].
  • We have coupled diazotized p-nitroaniline to catecholamines, derivatives, and metabolites and examined the reaction products by thin-layer chromatography and physico-chemical methods (ultraviolet spectra, mass spectroscopy, nuclear magnetic resonance) [2].
  • The release of p-nitroaniline was more prolonged, but still showed little dependence on microsphere size [30].
  • Glycosylamination was performed with p-nitroaniline in DMSO-formic acid-water, where the whole mixture of oligosaccharide derivatives was isolated by reversed phase HPLC on Hamilton PRP-1 and separated into single glycosylamines on Shandon Hypersil ODS [31].
  • 4. Given the relatively high frequency of organic acidurias, particularly methylmalonic aciduria, in intensive care unit populations, it is suggested that the p-nitroaniline reaction be incorporated into the battery of chemical urine tests [32].


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  3. Acetyl-coenzyme A: arylamine N-acetyltransferases in microorganisms: screening and isolation of an enzyme from Bacillus cereus. Hasmann, M.J., Seidl, P.H., Engelhardt, G., Schleifer, K.H. Arch. Microbiol. (1986) [Pubmed]
  4. Simultaneous determination of Pseudomonas aeruginosa elastase, human leukocyte elastase and cathepsin G activities by micellar electrokinetic chromatography. Viglio, S., Luisetti, M., Zanaboni, G., Döring, G., Worlitzsch, D., Cetta, G., Iadarola, P. Journal of chromatography. A. (1999) [Pubmed]
  5. Mechanism-based comparisons of acute toxicities elicited by industrial organic chemicals in procaryotic and eucaryotic systems. Jaworska, J.S., Schultz, T.W. Ecotoxicol. Environ. Saf. (1994) [Pubmed]
  6. The effect of cultured endothelial cells on factor VIII procoagulant activity. Stead, N.W., McKee, P.A. Blood (1979) [Pubmed]
  7. Characterization of recombinant rat cathepsin B and nonglycosylated mutants expressed in yeast. New insights into the pH dependence of cathepsin B-catalyzed hydrolyses. Hasnain, S., Hirama, T., Tam, A., Mort, J.S. J. Biol. Chem. (1992) [Pubmed]
  8. Electrostatic modulation by ionic aggregates: charge transfer transitions in solutions of lithium perchlorate-diethyl ether. Pocker, Y., Spyridis, G.T. J. Am. Chem. Soc. (2002) [Pubmed]
  9. MALDI-TOF MS of phosphorylated lipids in biological fluids using immobilized metal affinity chromatography and a solid ionic crystal matrix. Ham, B.M., Jacob, J.T., Cole, R.B. Anal. Chem. (2005) [Pubmed]
  10. Subchronic inhalation toxicity of p-nitroaniline and p-nitrochlorobenzene in rats. Nair, R.S., Johannsen, F.R., Levinskas, G.J., Terrill, J.B. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1986) [Pubmed]
  11. Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin approach. Bui, C.T., Bray, A.M., Pham, Y., Campbell, R., Ercole, F., Rasoul, F.A., Maeji, N.J. Mol. Divers. (1998) [Pubmed]
  12. Genotoxic activity of important nitrobenzenes and nitroanilines in the Ames test and their structure-activity relationship. Assmann, N., Emmrich, M., Kampf, G., Kaiser, M. Mutat. Res. (1997) [Pubmed]
  13. Mechanism of carboxypeptidase-Y-catalysed peptide semisynthesis. Christensen, U., Drøhse, H.B., Mølgaard, L. Eur. J. Biochem. (1992) [Pubmed]
  14. On-line characterization of the activity and reaction kinetics of immobilized enzyme by high-performance frontal analysis. Jiang, H., Zou, H., Wang, H., Ni, J., Zhang, Q., Zhang, Y. Journal of chromatography. A. (2000) [Pubmed]
  15. Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells. Palmer, B.D., Wilson, W.R., Cliffe, S., Denny, W.A. J. Med. Chem. (1992) [Pubmed]
  16. Metabolism of 4-nitroaniline by rat liver microsomes. Anderson, M.M., Mays, J.B., Mitchum, R.K., Hinson, J.A. Drug Metab. Dispos. (1984) [Pubmed]
  17. Gamma-glutamyl transferase ectoactivity in the intact rat liver: effect of chronic alcohol consumption. Speisky, H., Israel, Y. Alcohol (1990) [Pubmed]
  18. Characterization of metalloelastase-like activity from the plasma of a patient with Tangier disease. Hornebeck, W., Homsy, R., Ayrault-Jarrier, M., Stanislavski, L., Robert, L. Biol. Chem. Hoppe-Seyler (1991) [Pubmed]
  19. Photoinactivation of peptide transport in Saccharomyces cerevisiae. Becker, J.M., Dunsmore, K.P., Steinfeld, A.S., Naider, F. Biochemistry (1982) [Pubmed]
  20. A new technique for detecting oxytocinase activity in electrophoresis gels. Roy, A.C., Saha, N., Tan, S.M., Kamarul, F.Z., Ratnam, S.S. Electrophoresis (1992) [Pubmed]
  21. Purification and properties of gamma-glutamyltranspeptidase from Proteus mirabilis. Nakayama, R., Kumagai, H., Tochikura, T. J. Bacteriol. (1984) [Pubmed]
  22. Ion soft-landing into liquids: Protein identification, separation, and purification with retention of biological activity. Gologan, B., Takáts, Z., Alvarez, J., Wiseman, J.M., Talaty, N., Ouyang, Z., Cooks, R.G. J. Am. Soc. Mass Spectrom. (2004) [Pubmed]
  23. Computer simulation of the linear and nonlinear optical susceptibilities of p-nitroaniline in cyclohexane, 1,4-dioxane, and tetrahydrofuran in quadrupolar approximation. I. Molecular polarizabilities and hyperpolarizabilities. Reis, H., Grzybowski, A., Papadopoulos, M.G. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  24. Distribution of tonin- and kallikrein-like activities in rat brain. Lopes, E.S., Sumitani, M., Juliano, L., Beraldo, W.T., Pesquero, J.L. Brain Res. (1997) [Pubmed]
  25. Establishment of a standard assay method for human thrombomodulin and determination of the activity of the Japanese reference standard. Niimi, S., Oshizawa, T., Naotsuka, M., Ohba, S., Yokozawa, A., Murata, T., Hayakawa, T. Biologicals (2002) [Pubmed]
  26. Determination of kinetic constants for peptidyl prolyl cis-trans isomerases by an improved spectrophotometric assay. Kofron, J.L., Kuzmic, P., Kishore, V., Colón-Bonilla, E., Rich, D.H. Biochemistry (1991) [Pubmed]
  27. A spectrophotometric solid-phase fibrin-tissue plasminogen activator activity assay (SOFIA-tPA) for high-fibrin-affinity tissue plasminogen activators. Angles-Cano, E. Anal. Biochem. (1986) [Pubmed]
  28. Assay method for single-chain urokinase-type plasminogen activator. Matsuo, O., Ueshima, S., Okada, K., Fukao, H., Ohgaki, M., Watanabe, R., Arimura, H. Hematologic pathology. (1989) [Pubmed]
  29. Sensitive determination of carbohydrates labelled with p-nitroaniline by capillary electrophoresis with photometric detection using a 406 nm light-emitting diode. Momenbeik, F., Johns, C., Breadmore, M.C., Hilder, E.F., Macka, M., Haddad, P.R. Electrophoresis (2006) [Pubmed]
  30. Microsphere size, precipitation kinetics and drug distribution control drug release from biodegradable polyanhydride microspheres. Berkland, C., Kipper, M.J., Narasimhan, B., Kim, K.K., Pack, D.W. Journal of controlled release : official journal of the Controlled Release Society. (2004) [Pubmed]
  31. Efficient HPLC separation of N-p-nitrophenylglycosylamines derived from complex oligosaccharide mixtures. Human orosomucoid as a model. Kurth, H., Lehmann, J. Biomed. Chromatogr. (1986) [Pubmed]
  32. Detection of inborn errors of metabolism in unselected patients from pediatric intensive care units in Porto Alegre, Brazil: evaluation of screening techniques. Wannmacher, C.M., Wajner, M., Buchalter, M.S., Dutra-Filho, C.S., Pellini, V.B., Pedroso, D.L., Branco, F.S., Goldani, M.Z., Bolner, A.R. Braz. J. Med. Biol. Res. (1987) [Pubmed]
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