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Chemical Compound Review

p-Aminophenyl     cyclohexatrienamine

Synonyms: AC1L48LB, 4-Aminophenyl, 59000-01-0, para-aminophenyl, Phenyl, 4-amino-, ...
 
 
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Disease relevance of cyclohexatrienamine

 

High impact information on cyclohexatrienamine

  • Two TK isozymes, cytosolic and mitochondrial TKs, were separated better by means of p-aminophenyl 3'-TMP:CH-Sepharose gel affinity column chromatography for precise quantitation of the activity than by polyacrylamide disc gel electrophoresis [3].
  • In contrast, preincubation of 1321N1 cells with the antagonist of the sPLA2 receptor p-aminophenyl-alpha-D-mannopyranoside-bovine serum albumin, blocked cPLA2 activation with a EC50 similar to that described for the inhibition of binding of sPLA2 to its receptor [4].
  • The 24-kilodalton messenger RNA cap-binding protein (CBP) was purified from the rabbit reticulocyte postribosomal supernatant fraction using an affinity resin consisting of the p-aminophenyl gamma-ester of m7GTP coupled to Sepharose [5].
  • Lectin from all stages was purified by absorption to galactose-linked immunoadsorbent or by affinity chromatography on a column of p-aminophenyl-beta-D-lactoside coupled to Sepharose 4B [6].
  • Competitive inhibition studies with [3H]rauwolscine in rat kidney membranes indicate that the affinity for the carboxamide derivatives is inversely related to the length of the carbon spacer arm with rauwolscine 4-aminophenyl carboxamide (zero carbon spacer arm; rau-AMPC) exhibiting the highest affinity (Kd = 2.3 +/- 0.2 nM) [7].
 

Biological context of cyclohexatrienamine

  • Visualization of immobilized antibodies can be achieved with scanning electrochemical microscopy (SECM) by saturation of the antigen binding sites with an alkaline phosphatase-antigen conjugate, which catalyzes hydrolysis of the redox-inactive 4-aminophenyl phosphate to the redox-active 4-aminophenol (PAP) [8].
  • In this study, we demonstrated that the organomercurial compound, 4-aminophenyl mercuric acetate (APMA), which is routinely employed to activate latent MMPs at a concentration of 1000 microM, induces platelet aggregation at low concentration (5 microM) and inhibits agonist-induced platelet aggregation at concentrations >or= 50 microM [9].
  • A conjugate of p-aminophenyl 6-phospho-alpha-D-mannopyranoside and bovine serum albumin was shown to interact with the uptake system for lysosomal enzymes in cultured human diploid fibroblasts [10].
  • The effect of oxidized forms (methemoglobin) of HbS on the kinetics of aggregation of deoxyHbS was also studied because of the presence of 33% metHbS when HbS was modified by 4-aminophenyl disulfide [11].
 

Anatomical context of cyclohexatrienamine

  • In the bacteria, the enzyme reacts with the substrate, p-aminophenyl phosphate, in the periplamic space that separates the outer plasma membrane from the cell wall [12].
  • Its efficiency was similar in comparison to measurements with a probe, derived by diazotization with the p-aminophenyl glycosides of gal-beta 1,3-galNAc and already shown to be a reliable marker for lectin localization in tissue sections and cultured cells [13].
  • Out of beta-gal modified with a series of p-aminophenyl alpha- or beta-glycosides, beta-gal modified with p-aminophenyl beta-D-glucopyranoside (beta-D-Glc beta-gal) was bound to the synaptosomes most effectively, then beta-gal modified with beta-D-galactoside and with alpha-D-mannoside [14].
  • The articular cartilage was removed and homogenized in a Tris buffer, pH 7.5, and then divided into four groups: direct PG extraction, no addition, presence of 1 mM p-aminophenyl mercuric acetate (APMA), and presence of 1 mM APMA and 10 mM o-phenanthroline, incubated for 42 h at 37 degrees C followed by PG extraction [15].
  • Final studies demonstrated that p-aminophenyl-alpha-D-mannopyranoside BSA, a known ligand of the sPLA2 receptor, also selectively released AA from mast cells but not from HL-60 cells [16].
 

Associations of cyclohexatrienamine with other chemical compounds

 

Gene context of cyclohexatrienamine

 

Analytical, diagnostic and therapeutic context of cyclohexatrienamine

  • This fusion protein, which comprised as much as 3% of the total bacterial protein, was purified to greater than 90% homogeneity by affinity chromatography on p-aminophenyl-beta-D-thiogalactoside-Sepharose [26].
  • Western blotting of protein, isolated from the membrane fraction and purified by p-aminophenyl-beta-D-thiogalactoside-agarose column chromatography, revealed a fusion protein monomer of 170 kDa which agrees with the predicted molecular weight [27].
  • Covalent immobilization of oligonucleotides on p-aminophenyl-modified carbon screen-printed electrodes for viral DNA sensing [28].
  • Three beta-N-acetylhexosaminidases [EC 3.2.1.52] and one beta-galactosidase [EC 3.2.1.23] were purified from the culture filtrate of streptococcus 6646 group K by a combination of column chromatographies on p-aminophenyl beta-D-thiogalactopyranoside-substituted Sepharose and N-(paminophenyl)oxamic acid-substituted Sepharose [29].
  • MMP in 9000-g supernatant fraction of lung homogenate was activated by p-aminophenyl mercuric acetate (APMA), and gelatinolytic activity was determined by sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE) followed by Coomassie staining [30].

References

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  3. Activity of the cytosolic isozyme of thymidine kinase in human primary lung tumors with reference to malignancy. Yusa, T., Yamaguchi, Y., Ohwada, H., Hayashi, Y., Kuroiwa, N., Morita, T., Asanagi, M., Moriyama, Y., Fujimura, S. Cancer Res. (1988) [Pubmed]
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  9. The organomercurial 4-aminophenylmercuric acetate, independent of matrix metalloproteinases, induces dose-dependent activation/inhibition of platelet aggregation. Rosenfeldt, M.T., Valentino, M., Labruzzo, S., Scudder, L., Pavlaki, M., Cao, J., Vacirca, J., Bahou, W.F., Zucker, S. Thromb. Haemost. (2005) [Pubmed]
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  11. Kinetics of polymerization of hemoglobin S modified by thiol reagents and by oxidation. Domenget, C., Garel, M.C., Rhoda, M.D., Caburi-Martin, J., Galacteros, F., Beuzard, Y. Biochim. Biophys. Acta (1985) [Pubmed]
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  13. Conjugation of p-aminophenyl glycosides with squaric acid diester to a carrier protein and the use of neoglycoprotein in the histochemical detection of lectins. Tietze, L.F., Schröter, C., Gabius, S., Brinck, U., Goerlach-Graw, A., Gabius, H.J. Bioconjug. Chem. (1991) [Pubmed]
  14. Binding of specific glycoconjugates to human brain synaptosomes: studies using glycosylated beta-galactosidase. Naoi, M., Iwashita, T., Nagatsu, T. Neurosci. Lett. (1987) [Pubmed]
  15. Immunological analysis of proteoglycan structural changes in the early stage of experimental osteoarthritic canine cartilage lesions. Pelletier, J.P., Martel-Pelletier, J., Mehraban, F., Malemud, C.J. J. Orthop. Res. (1992) [Pubmed]
  16. Mechanisms that account for the selective release of arachidonic acid from intact cells by secretory phospholipase A2. Fonteh, A.N., Samet, J.M., Surette, M., Reed, W., Chilton, F.H. Biochim. Biophys. Acta (1998) [Pubmed]
  17. Generation and reactivity of the 4-aminophenyl cation by photolysis of 4-chloroaniline. Guizzardi, B., Mella, M., Fagnoni, M., Freccero, M., Albini, A. J. Org. Chem. (2001) [Pubmed]
  18. A novel alpha-arylation of ketones, aldehydes, and esters via a photoinduced SN1 reaction through 4-aminophenyl cations. Fraboni, A., Fagnoni, M., Albini, A. J. Org. Chem. (2003) [Pubmed]
  19. Flow injection electrochemical enzyme immunoassay for theophylline using a protein A immunoreactor and p-aminophenyl phosphate-p-aminophenol as the detection system. Palmer, D.A., Edmonds, T.E., Seare, N.J. The Analyst. (1992) [Pubmed]
  20. Preparation and characterisation of homogeneous neurotoxin type A from Clostridium botulinum. Its inhibitory action on neuronal release of acetylcholine in the absence and presence of beta-bungarotoxin. Tse, C.K., Dolly, J.O., Hambleton, P., Wray, D., Melling, J. Eur. J. Biochem. (1982) [Pubmed]
  21. Differential MMP-2 activity of ligament cells under mechanical stretch injury: an in vitro study on human ACL and MCL fibroblasts. Zhou, D., Lee, H.S., Villarreal, F., Teng, A., Lu, E., Reynolds, S., Qin, C., Smith, J., Sung, K.L. J. Orthop. Res. (2005) [Pubmed]
  22. Co-purification of thymidylate kinase and cytosolic thymidine kinase from human term placenta by affinity chromatography. Tamiya, N., Yusa, T., Yamaguchi, Y., Tsukifuji, R., Kuroiwa, N., Moriyama, Y., Fujimura, S. Biochim. Biophys. Acta (1989) [Pubmed]
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  26. Expression in Escherichia coli of a cloned DNA sequence encoding the pre-S2 region of hepatitis B virus. Offensperger, W., Wahl, S., Neurath, A.R., Price, P., Strick, N., Kent, S.B., Christman, J.K., Acs, G. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  27. The MAK11 protein is essential for cell growth and replication of M double-stranded RNA and is apparently a membrane-associated protein. Icho, T., Wickner, R.B. J. Biol. Chem. (1988) [Pubmed]
  28. Covalent immobilization of oligonucleotides on p-aminophenyl-modified carbon screen-printed electrodes for viral DNA sensing. Ruffien, A., Dequaire, M., Brossier, P. Chem. Commun. (Camb.) (2003) [Pubmed]
  29. Purification and characterization of beta-N-acetylhexosaminidases and beta-galactosidase from Streptococcus 6646 K. Kiyohara, T., Terao, T., Shioiri-Nakano, K., Osawa, T. J. Biochem. (1976) [Pubmed]
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