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Chemical Compound Review

MOLI001254     phenol

Synonyms: AC1L9P4M
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Disease relevance of phenol

  • However, although the existence of covalently closed circles has been postulated, double-stranded viral DNA purified from virions or infected cells by conventional methods (that is, using proteases and phenol or chloroform) has always been obtained in a linear form [1].
  • When the "fragment reaction" was used as a model assay for peptide bond formation, Escherichia coli ribosomes or 50S subunits retained 20 to 40 percent activity after extensive treatment with proteinase K and SDS, but lost activity after extraction with phenol or exposure to EDTA [2].
  • Ribosomes from the thermophilic eubacterium Thermus aquaticus remained more than 80 percent active after treatment with proteinase K and SDS, which was followed by vigorous extraction with phenol [2].
  • Glycerol teichoic acids were not detected immunochemically or chemically in phenol-water, hot saline (Rantz and Randall), or supernatant fluids of disrupted cells of Streptococcus mitis [3].
  • Venous thrombosis results from some phenol injections [4].

Psychiatry related information on phenol


High impact information on phenol


Chemical compound and disease context of phenol


Biological context of phenol

  • Therefore, the gastric emptying rate of 50- and 200-mL volumes of phenol red solution were measured while monitoring contractile activity [19].
  • Plasmid DNA from a monkey cerebellum cDNA library was hybridized in large excess to radiolabeled monkey cortex cDNA in a phenol emulsion-enhanced reaction [20].
  • A novel experimental system to study mutation in starving bacteria was designed, relying on the activation of a promoterless phenol degradation operon of Pseudomonas putida [21].
  • Cloning and substrate specificity of a human phenol UDP-glucuronosyltransferase expressed in COS-7 cells [22].
  • At the concentrations present in tissue culture media, phenol red causes partial estrogenic stimulation, increasing cell number to 200% and progesterone receptor content to 300% of that found for cells grown in phenol red-free media, thereby reducing the degree to which exogenous estrogen is able to stimulate responses [23].

Anatomical context of phenol

  • Denervation was produced in anesthetized nondiuretic rats by application of phenol to the left renal artery [24].
  • To investigate the nature of this protection, dogs and rabbits were immunized with purified glycolipid prepared by phenol-chloroform-petroleum ether extraction of the "Re" mutant of Salmonella minnesota 595 and opsonophagocytic and bactericidal tests were carried out using lapine peritoneal granulocytes and serum factors [25].
  • During this period, most (97%) of the phenol red was detected in the proximal two-thirds of the small intestine [26].
  • Previous immunohistochemical studies suggested that a phenol transferase induced by polycyclic aromatic hydrocarbons may be differentially expressed in centrilobular hepatocytes of rats [27].
  • We used this technique to measure and time the recovery from the duodenum of a second nonabsorbable marker, phenol red [28].

Associations of phenol with other chemical compounds


Gene context of phenol

  • However, gelatinase B-deficient mice had a normal rate of resolution of acute inflammation elicited by cutaneous phenol [34].
  • The removal of TLR2 lipopeptide components from LPS by phenol re-extraction substantially reduced both the IL-8 and superoxide response of the stimulated neutrophils, indicating that, unlike monocytes, the neutrophil response is preferentially directed to TLR2 ligands [35].
  • This activity is not present in the simple phenol-form PST, SULT1A1, which is otherwise >93% identical to SULT1A3 in amino acid sequence [36].
  • Transgenic expression of TLR2 and TLR6 restored responsiveness to phenol soluble modulin and peptidoglycan in IEC [37].
  • We found that phenol/water-extracts of the two strains use TLRs differently with T. brennaborense-stimulating cells in a TLR-4-dependent fashion, while T. maltophilum-mediated activation apparently involved TLR-2 [38].

Analytical, diagnostic and therapeutic context of phenol


  1. Covalently closed circles of adenovirus 5 DNA. Ruben, M., Bacchetti, S., Graham, F. Nature (1983) [Pubmed]
  2. Unusual resistance of peptidyl transferase to protein extraction procedures. Noller, H.F., Hoffarth, V., Zimniak, L. Science (1992) [Pubmed]
  3. Absence of glycerol teichoic acids in certain oral streptococci. Rosan, B. Science (1978) [Pubmed]
  4. Venous thrombosis results from some phenol injections. Macek, C. JAMA (1983) [Pubmed]
  5. Measurement of alkaline phosphatase isoenzymes in individual mouse bone marrow fibroblast cells based on capillary electrophoresis with on-capillary enzyme-catalyzed reaction and electrochemical detection. Sun, X., Jin, W., Li, D., Bai, Z. Electrophoresis (2004) [Pubmed]
  6. Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia. McDonald, T.A., Holland, N.T., Skibola, C., Duramad, P., Smith, M.T. Leukemia (2001) [Pubmed]
  7. Human phenol sulfotransferases SULT1A2 and SULT1A1: genetic polymorphisms, allozyme properties, and human liver genotype-phenotype correlations. Raftogianis, R.B., Wood, T.C., Weinshilboum, R.M. Biochem. Pharmacol. (1999) [Pubmed]
  8. Congophilia in cerebral amyloidosis is modified by inactivation procedures on slow transmissible pathogens. Tashima, T., Kitamoto, T., Tateishi, J., Sato, Y. Brain Res. (1986) [Pubmed]
  9. Cisapride stimulates antral motility and decreases biliary reflux in patients with severe dyspepsia. Rezende-Filho, J., Di Lorenzo, C., Dooley, C.P., Valenzuela, J.E. Dig. Dis. Sci. (1989) [Pubmed]
  10. Hepatitis B virus contains protein attached to the 5' terminus of its complete DNA strand. Gerlich, W.H., Robinson, W.S. Cell (1980) [Pubmed]
  11. Titanium-containing mesoporous molecular sieves for catalytic oxidation of aromatic compounds. Tanev, P.T., Chibwe, M., Pinnavaia, T.J. Nature (1994) [Pubmed]
  12. Steroid sulfatase: molecular biology, regulation, and inhibition. Reed, M.J., Purohit, A., Woo, L.W., Newman, S.P., Potter, B.V. Endocr. Rev. (2005) [Pubmed]
  13. Molecules from Staphylococcus aureus that bind CD14 and stimulate innate immune responses. Kusunoki, T., Hailman, E., Juan, T.S., Lichenstein, H.S., Wright, S.D. J. Exp. Med. (1995) [Pubmed]
  14. Endotoxin protein: a B-cell mitogen and polyclonal activator of C3H/HeJ lymphocytes. Sultzer, B.M., Goodman, G.W. J. Exp. Med. (1976) [Pubmed]
  15. Results of sympathetic denervation in the canine heart: supersensitivity that may be arrhythmogenic. Inoue, H., Zipes, D.P. Circulation (1987) [Pubmed]
  16. Inhibition of N-methyl-N-nitrosourea-induced mutagenicity and DNA methylation by ellagic acid. Dixit, R., Gold, B. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  17. Interaction of phenol red with estrogenic and antiestrogenic action on growth of human breast cancer cells ZR-75-1 and T-47-D. Glover, J.F., Irwin, J.T., Darbre, P.D. Cancer Res. (1988) [Pubmed]
  18. Characterization of a polysaccharide antigen from Bacteroides gingivalis. Schifferle, R.E., Reddy, M.S., Zambon, J.J., Genco, R.J., Levine, M.J. J. Immunol. (1989) [Pubmed]
  19. The influence of the interdigestive migrating myoelectric complex on the gastric emptying of liquids. Oberle, R.L., Chen, T.S., Lloyd, C., Barnett, J.L., Owyang, C., Meyer, J., Amidon, G.L. Gastroenterology (1990) [Pubmed]
  20. Phenol emulsion-enhanced DNA-driven subtractive cDNA cloning: isolation of low-abundance monkey cortex-specific mRNAs. Travis, G.H., Sutcliffe, J.G. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  21. Promoter-creating mutations in Pseudomonas putida: a model system for the study of mutation in starving bacteria. Kasak, L., Hõrak, R., Kivisaar, M. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  22. Cloning and substrate specificity of a human phenol UDP-glucuronosyltransferase expressed in COS-7 cells. Harding, D., Fournel-Gigleux, S., Jackson, M.R., Burchell, B. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  23. Phenol red in tissue culture media is a weak estrogen: implications concerning the study of estrogen-responsive cells in culture. Berthois, Y., Katzenellenbogen, J.A., Katzenellenbogen, B.S. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  24. Effects of acute unilateral renal denervation in the rat. Bello-Reuss, E., Colindres, R.E., Pastoriza-Muñoz, E., Mueller, R.A., Gottschalk, C.W. J. Clin. Invest. (1975) [Pubmed]
  25. Functional role of antibody against "core" glycolipid of Enterobacteriaceae. Young, L.S., Stevens, P., Ingram, J. J. Clin. Invest. (1975) [Pubmed]
  26. A physiological role of peptide YY on exocrine pancreatic secretion in rats. Jin, H., Cai, L., Lee, K., Chang, T.M., Li, P., Wagner, D., Chey, W.Y. Gastroenterology (1993) [Pubmed]
  27. Lobular distribution of human liver phenol and bilirubin uridine 5'-diphosphate glucuronosyltransferase messenger RNAs. Chen, F., Zhou, J., Ritter, J.K., Bondy, C.A., Owens, I.S. Gastroenterology (1996) [Pubmed]
  28. Control of gastric emptying by osmolality of duodenal contents in man. Meeroff, J.C., Go, V.L., Phillips, S.F. Gastroenterology (1975) [Pubmed]
  29. Gastric pacemakers. Sarna, S.K., Bowes, K.L., Daniel, E.E. Gastroenterology (1976) [Pubmed]
  30. The 3'-terminal exon of the family of steroid and phenol sulfotransferase genes is spliced at the N-terminal glycine of the universally conserved GXXGXXK motif that forms the sulfonate donor binding site. Chiba, H., Komatsu, K., Lee, Y.C., Tomizuka, T., Strott, C.A. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  31. Role of the integument in insect defense: pro-phenol oxidase cascade in the cuticular matrix. Ashida, M., Brey, P.T. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  32. Isolation and characterization of germ line DNA from mouse sperm. Shiurba, R., Nandi, S. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  33. Molecular cloning and heterologous expression of a cDNA encoding berbamunine synthase, a C--O phenol-coupling cytochrome P450 from the higher plant Berberis stolonifera. Kraus, P.F., Kutchan, T.M. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  34. Matrix metalloproteinase deficiencies affect contact hypersensitivity: stromelysin-1 deficiency prevents the response and gelatinase B deficiency prolongs the response. Wang, M., Qin, X., Mudgett, J.S., Ferguson, T.A., Senior, R.M., Welgus, H.G. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  35. Role of toll-like receptor 2 (TLR2) in neutrophil activation: GM-CSF enhances TLR2 expression and TLR2-mediated interleukin 8 responses in neutrophils. Kurt-Jones, E.A., Mandell, L., Whitney, C., Padgett, A., Gosselin, K., Newburger, P.E., Finberg, R.W. Blood (2002) [Pubmed]
  36. Structure-function relationships in the stereospecific and manganese-dependent 3,4-dihydroxyphenylalanine/tyrosine-sulfating activity of human monoamine-form phenol sulfotransferase, SULT1A3. Pai, T.G., Oxendine, I., Sugahara, T., Suiko, M., Sakakibara, Y., Liu, M.C. J. Biol. Chem. (2003) [Pubmed]
  37. Human intestinal epithelial cells are broadly unresponsive to Toll-like receptor 2-dependent bacterial ligands: implications for host-microbial interactions in the gut. Melmed, G., Thomas, L.S., Lee, N., Tesfay, S.Y., Lukasek, K., Michelsen, K.S., Zhou, Y., Hu, B., Arditi, M., Abreu, M.T. J. Immunol. (2003) [Pubmed]
  38. Involvement of lipopolysaccharide binding protein, CD14, and Toll-like receptors in the initiation of innate immune responses by Treponema glycolipids. Schröder, N.W., Opitz, B., Lamping, N., Michelsen, K.S., Zähringer, U., Göbel, U.B., Schumann, R.R. J. Immunol. (2000) [Pubmed]
  39. Teichoic acids of group D streptococci with special reference to strains from pig meningitis (Streptococcus suis). Elliott, S.D., McCarty, M., Lancefield, R.C. J. Exp. Med. (1977) [Pubmed]
  40. Heterogeneous atrial denervation creates substrate for sustained atrial fibrillation. Olgin, J.E., Sih, H.J., Hanish, S., Jayachandran, J.V., Wu, J., Zheng, Q.H., Winkle, W., Mulholland, G.K., Zipes, D.P., Hutchins, G. Circulation (1998) [Pubmed]
  41. Specific cloning of DNA fragments absent from the DNA of a male patient with an X chromosome deletion. Kunkel, L.M., Monaco, A.P., Middlesworth, W., Ochs, H.D., Latt, S.A. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  42. Murine cytomegalovirus infects spermatogenic cells. Dutko, F.J., Oldstone, M.B. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
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