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Chemical Compound Review

Indoxyl     1H-indol-3-ol

Synonyms: PubChem7264, indole-3-ol, indol-3-ol, SureCN155191, SureCN156061, ...
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Disease relevance of C05658


High impact information on C05658


Chemical compound and disease context of C05658


Biological context of C05658


Anatomical context of C05658


Associations of C05658 with other chemical compounds

  • Current results indicate that this process involves the conversion of endogenous indole to indoxyl by the P450 [20].
  • The organisms were catalase, urease, alkaline phosphatase, and nitrate negative but oxidase and indoxyl acetate positive [21].
  • Among the organic anions examined, hippuric acid, para-hydroxyhippuric acid, ortho-hydroxyhippuric acid, indoxyl sulphate and indoleacetic acid showed a high affinity for hOAT1 expressed in the OK cells [22].
  • Afterward, liquid chromatography-electrospray mass spectrometry, using the selected ion monitoring mode and internal standard (2-MeO-DIBOA, indoxyl-beta-D-glucoside, and quercetin-3-O-rutinoside) quantification method was performed [23].
  • Enzyme histochemical stains for alkaline and acid phosphatase, leucine, aminopeptidase, succinic dehydrogenase, and indoxyl and nonspecific esterase were positive in the areas of subcutaneous fat necrosis [24].

Gene context of C05658

  • When indoxyl was incubated with SULT1A1*2, a human recombinant aryl SULT, an apparent Km value of 5.6 +/- 1.8 microM was obtained [25].
  • Immunohistochemistry was performed using antibodies against indoxyl sulfate, hOAT1, and hOAT3 [26].
  • Attachment of an indoxyl residue rather than a PNP group to the maltoheptaoside did not affect the substrate response to pancreatic or salivary isoenzyme activity [27].
  • All strains of N. brasiliensis, N. otitidiscavarium, and N. farcinica were positive for indoxyl phosphate, whereas strains of N. nova and N. asteroides sensu stricto were always negative [28].
  • An oral sorbent reduces overload of indoxyl sulphate and gene expression of TGF-beta1 in uraemic rat kidneys [18].

Analytical, diagnostic and therapeutic context of C05658


  1. A furan fatty acid and indoxyl sulfate are the putative inhibitors of thyroxine hepatocyte transport in uremia. Lim, C.F., Bernard, B.F., de Jong, M., Docter, R., Krenning, E.P., Hennemann, G. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  2. Determination of indoxyl sulfate in plasma of patients with renal failure by use of ion-pairing liquid chromatography. Stanfel, L.A., Gulyassy, P.F., Jarrard, E.A. Clin. Chem. (1986) [Pubmed]
  3. Indoxyl sulfate induces complex redox alterations in mesangial cells. Gelasco, A.K., Raymond, J.R. Am. J. Physiol. Renal Physiol. (2006) [Pubmed]
  4. Evaluation of indoxyl-beta-D-glucuronide as a chromogen in media specific for Escherichia coli. Haines, J.R., Covert, T.C., Rankin, C.C. Appl. Environ. Microbiol. (1993) [Pubmed]
  5. Indoxyl sulfate stimulates proliferation of rat vascular smooth muscle cells. Yamamoto, H., Tsuruoka, S., Ioka, T., Ando, H., Ito, C., Akimoto, T., Fujimura, A., Asano, Y., Kusano, E. Kidney Int. (2006) [Pubmed]
  6. Uremic toxins of organic anions up-regulate PAI-1 expression by induction of NF-kappaB and free radical in proximal tubular cells. Motojima, M., Hosokawa, A., Yamato, H., Muraki, T., Yoshioka, T. Kidney Int. (2003) [Pubmed]
  7. Effect of protein-bound uraemic toxins on the thermodynamic characteristics of human albumin. Sarnatskaya, V.V., Lindup, W.E., Niwa, T., Ivanov, A.I., Yushko, L.A., Tjia, J., Maslenny, V.N., Korneeva, L.N., Nikolaev, V.G. Biochem. Pharmacol. (2002) [Pubmed]
  8. Comparison of three rapid methods, tributyrine, 4-methylumbelliferyl butyrate, and indoxyl acetate, for rapid identification of Moraxella catarrhalis. Speeleveld, E., Fossépré, J.M., Gordts, B., Van Landuyt, H.W. J. Clin. Microbiol. (1994) [Pubmed]
  9. Phylogeny of Helicobacter isolates from bird and swine feces and description of Helicobacter pametensis sp. nov. Dewhirst, F.E., Seymour, C., Fraser, G.J., Paster, B.J., Fox, J.G. Int. J. Syst. Bacteriol. (1994) [Pubmed]
  10. Contributions of hippurate, indoxyl sulfate, and o-hydroxyhippurate to impaired ligand binding by plasma in azotemic humans. Gulyassy, P.F., Jarrard, E., Stanfel, L.A. Biochem. Pharmacol. (1987) [Pubmed]
  11. Differentiation of macrophages from Lewis lung carcinoma tumour cells in tissue sections by their alpha-naphthyl butyrate esterase activity. Brown, R., Wolman, M. Histochem. J. (1981) [Pubmed]
  12. Resolution of alkaline phosphatase isoenzymes in serum by isoelectric focusing in immobilized pH gradients. Sinha, P.K., Bianchi-Bosisio, A., Meyer-Sabellek, W., Righetti, P.G. Clin. Chem. (1986) [Pubmed]
  13. Oxidation of indole by cytochrome P450 enzymes. Gillam, E.M., Notley, L.M., Cai, H., De Voss, J.J., Guengerich, F.P. Biochemistry (2000) [Pubmed]
  14. Cloning and expression of a Ralstonia eutropha HF39 gene mediating indigo formation in Escherichia coli. Drewlo, S., Brämer, C.O., Madkour, M., Mayer, F., Steinbüchel, A. Appl. Environ. Microbiol. (2001) [Pubmed]
  15. Total synthesis of the Kopsia lapidilecta alkaloid (+/-)-lapidilectine B. Pearson, W.H., Lee, I.Y., Mi, Y., Stoy, P. J. Org. Chem. (2004) [Pubmed]
  16. Organic acids and the uremic syndrome: protein metabolite hypothesis in the progression of chronic renal failure. Niwa, T. Semin. Nephrol. (1996) [Pubmed]
  17. Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. Ohtsuki, S., Asaba, H., Takanaga, H., Deguchi, T., Hosoya, K., Otagiri, M., Terasaki, T. J. Neurochem. (2002) [Pubmed]
  18. An oral sorbent reduces overload of indoxyl sulphate and gene expression of TGF-beta1 in uraemic rat kidneys. Miyazaki, T., Aoyama, I., Ise, M., Seo, H., Niwa, T. Nephrol. Dial. Transplant. (2000) [Pubmed]
  19. Involvement of Indoxyl Sulfate in Renal and Central Nervous System Toxicities During Cisplatin-induced Acute Renal Failure. Iwata, K., Watanabe, H., Morisaki, T., Matsuzaki, T., Ohmura, T., Hamada, A., Saito, H. Pharm. Res. (2007) [Pubmed]
  20. What makes P450s work? Searches for answers with known and new P450s. Guengerich, F.P., Parikh, A., Yun, C.H., Kim, D., Nakamura, K., Notley, L.M., Gillam, E.M. Drug Metab. Rev. (2000) [Pubmed]
  21. Helicobacter winghamensis sp. nov., a novel Helicobacter sp. isolated from patients with gastroenteritis. Melito, P.L., Munro, C., Chipman, P.R., Woodward, D.L., Booth, T.F., Rodgers, F.G. J. Clin. Microbiol. (2001) [Pubmed]
  22. Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake. Motojima, M., Hosokawa, A., Yamato, H., Muraki, T., Yoshioka, T. Br. J. Pharmacol. (2002) [Pubmed]
  23. Determination of benzoxazinone derivatives in plants by combining pressurized liquid extraction-solid-phase extraction followed by liquid chromatography-electrospray mass spectrometry. Villagrasa, M., Guillamón, M., Eljarrat, E., Barceló, D. J. Agric. Food Chem. (2006) [Pubmed]
  24. Association of islet cell carcinoma of the pancreas with subcutaneous fat necrosis. Millns, J.L., Evans, H.L., Winkelmann, R.K. The American Journal of dermatopathology. (1979) [Pubmed]
  25. Sulfation of indoxyl by human and rat aryl (phenol) sulfotransferases to form indoxyl sulfate. Banoglu, E., King, R.S. European journal of drug metabolism and pharmacokinetics. (2002) [Pubmed]
  26. Accumulation of Indoxyl Sulfate in OAT1/3-Positive Tubular Cells in Kidneys of Patients With Chronic Renal Failure. Taki, K., Nakamura, S., Miglinas, M., Enomoto, A., Niwa, T. Journal of renal nutrition : the official journal of the Council on Renal Nutrition of the National Kidney Foundation. (2006) [Pubmed]
  27. Alpha-amylase determination with the Reflotron reagent carrier system: use of whole blood, plasma, and serum, and effect of isoenzymes. Bais, R., Badenoch, J., Bayer, P.M., Foo, Y., Keller, H., Koller, P.U., Leinberger, R., Weidemann, G., Rosalki, S.B. Clin. Chem. (1989) [Pubmed]
  28. Novel method for rapid identification of Nocardia species by detection of preformed enzymes. Biehle, J.R., Cavalieri, S.J., Felland, T., Zimmer, B.L. J. Clin. Microbiol. (1996) [Pubmed]
  29. Indoxyl-beta-D-glucuronide, the primary emitter of low-level chemiluminescence in plasma of hemodialysis patients. Agatsuma, S., Sekino, H., Nagoshi, T., Watanabe, H. Clin. Chem. (1994) [Pubmed]
  30. Accumulation of indoxyl sulfate, an inhibitor of drug-binding, in uremic serum as demonstrated by internal-surface reversed-phase liquid chromatography. Niwa, T., Takeda, N., Tatematsu, A., Maeda, K. Clin. Chem. (1988) [Pubmed]
  31. Chemiluminescent enzyme immunoassay of prostate-specific antigen based on indoxyl phosphate substrate. Albrecht, S., Brandl, H., Steinke, M., Freidt, T. Clin. Chem. (1994) [Pubmed]
  32. Evaluation of the indoxyl acetate hydrolysis test for rapid differentiation of Campylobacter, Helicobacter, and Wolinella species. Popovic-Uroic, T., Patton, C.M., Nicholson, M.A., Kiehlbauch, J.A. J. Clin. Microbiol. (1990) [Pubmed]
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