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Chemical Compound Review

Ketole     1H-indole

Synonyms: indole, Indol, Benzopyrrole, SureCN698, CHEMBL15844, ...
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Disease relevance of Benzopyrrole

  • Among the 23 isolates tested, three of Bacteroides fragilis thetaiotaomicron and one Citrobacter sp. were indole positive [1].
  • The rolB gene of Agrobacterium rhizogenes, whose expression stimulates the formation of roots by transformed plant tissues and other growth alterations in transgenic plants, codes for a beta-glucosidase able to hydrolyse indole-beta-glucosides [2].
  • The phytoalexin camalexin, an indole derivative, is produced by Arabidopsis in response to infection with the bacterial pathogen Pseudomonas syringae [3].
  • The ability of indole derivatives to facilitate RNA polymerase transcription of the L-arabinose operon in Escherichia coli was shown to require the catabolite activator protein (CAP) as well as the araC gene product [4].
  • Treatment of cells expressing reporter constructs with ESE sequences demonstrated that selected indole derivatives mediate inhibition of ESE usage in vivo and prevent early splicing events required for HIV replication [5].

Psychiatry related information on Benzopyrrole

  • Ibogaine, an indole alkaloid that causes hallucinations, tremor, and ataxia, produces cerebellar neurotoxicity in rats, manifested by degeneration of Purkinje cells aligned in narrow parasagittal bands that are coextensive with activated glial cells [6].
  • The changes of indole levels induced by food deprivation were compared to their known function in the brain and the individual segments of the GIT [7].
  • Ibogaine, an indole alkaloid, has been proposed for treatment of drug addiction, yet its mechanism, site of action, and possible neurotoxicity have not been determined [8].
  • These results indicate that 4,5-DKT is a novel indole neurotoxin which exhibits a striking propensity for medial limbic system structures including some of those affected in dementia of the Alzheimer type [9].
  • The effect of environmental photoperiodicity on indole rhythms and locomotor activity in sighted and eye covered chickens [10].

High impact information on Benzopyrrole

  • SIN1/MIP1 Maintains rictor-mTOR Complex Integrity and Regulates Akt Phosphorylation and Substrate Specificity [11].
  • A new class of indole leukotriene inhibitor has been described that inhibits the formation of cellular leukotrienes but has no direct inhibitory effect on soluble 5-LO activity [12].
  • Identification of the TRiC/CCT Substrate Binding Sites Uncovers the Function of Subunit Diversity in Eukaryotic Chaperonins [13].
  • Moreover, functional enzyme activity was directly correlated to IFN-gamma resistance through an indole rescue mechanism [14].
  • This suppressive effect of indole on bladder tumorigenesis contrasted markedly with its failure to suppress tumors at other sites such as nasal sinuses, trachea, esophagus, and fore-stomach [15].

Chemical compound and disease context of Benzopyrrole


Biological context of Benzopyrrole

  • The protein encoded by the rolB plant oncogene hydrolyses indole glucosides [2].
  • Both sar1 and sar3 mutations affect the localization of the transcriptional repressor AXR3/INDOLE ACETIC ACID17, providing a likely explanation for suppression of the phenotype conferred by axr1 [21].
  • More than 100 insect-responsive genes potentially involved in defense were identified, including genes involved in pathogenesis, indole glucosinolate metabolism, detoxification and cell survival, and signal transduction [22].
  • We have investigated the magnitude and timescale of fluctuations within the core of a protein using the exchange kinetics of indole and benzene binding to engineered hydrophobic cavities in T4 lysozyme [23].
  • Since deblocking was done with piperidine and the peptide was removed from the resin by treatment with ethanolamine, this synthetic protocol prevented oxidation of the indole rings of this tryptophan-rich peptide and reduced truncations produced by acid hydrolysis [24].

Anatomical context of Benzopyrrole

  • Total indole levels were significantly increased in the mucosa (p less than 0.02) and circular muscle (p less than 0.05) of the constipated patients [25].
  • Skatole and indole, the benzopyrrole volatiles believed to be responsible for fecal odor, in fact elaborated a napthalenelike "mothball" odor in the crystalline state as well as after purging from feces [26].
  • CONCLUSIONS: Substrate availability modulates nucleoside transporter expression (CNT1) in rat jejunum in vivo [27].
  • Dihydroteleocidin B, an indole alkaloid tumor promoter, stimulates confluent, quiescent mouse 3T3-L1 fibroblasts to initiate DNA synthesis and undergo cell division [28].
  • Increase in the synthesis of a Mr 32,000 protein in BALB/c 3T3 cells treated with tumor-promoting indole alkaloids or polyacetates [29].

Associations of Benzopyrrole with other chemical compounds


Gene context of Benzopyrrole


Analytical, diagnostic and therapeutic context of Benzopyrrole


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  3. Arabidopsis PAD3, a gene required for camalexin biosynthesis, encodes a putative cytochrome P450 monooxygenase. Zhou, N., Tootle, T.L., Glazebrook, J. Plant Cell (1999) [Pubmed]
  4. Metabolite gene regulation of the L-arabinose operon in Escherichia coli with indoleacetic acid and other indole derivatives. Kline, E.L., Brown, C.S., Bankaitis, V., Montefiori, D.C., Craig, K. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  5. Selective modification of alternative splicing by indole derivatives that target serine-arginine-rich protein splicing factors. Soret, J., Bakkour, N., Maire, S., Durand, S., Zekri, L., Gabut, M., Fic, W., Divita, G., Rivalle, C., Dauzonne, D., Nguyen, C.H., Jeanteur, P., Tazi, J. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
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  11. SIN1/MIP1 Maintains rictor-mTOR Complex Integrity and Regulates Akt Phosphorylation and Substrate Specificity. Jacinto, E., Facchinetti, V., Liu, D., Soto, N., Wei, S., Jung, S.Y., Huang, Q., Qin, J., Su, B. Cell (2006) [Pubmed]
  12. Identification and isolation of a membrane protein necessary for leukotriene production. Miller, D.K., Gillard, J.W., Vickers, P.J., Sadowski, S., Léveillé, C., Mancini, J.A., Charleson, P., Dixon, R.A., Ford-Hutchinson, A.W., Fortin, R. Nature (1990) [Pubmed]
  13. Identification of the TRiC/CCT Substrate Binding Sites Uncovers the Function of Subunit Diversity in Eukaryotic Chaperonins. Spiess, C., Miller, E.J., McClellan, A.J., Frydman, J. Mol. Cell (2006) [Pubmed]
  14. Polymorphisms in Chlamydia trachomatis tryptophan synthase genes differentiate between genital and ocular isolates. Caldwell, H.D., Wood, H., Crane, D., Bailey, R., Jones, R.B., Mabey, D., Maclean, I., Mohammed, Z., Peeling, R., Roshick, C., Schachter, J., Solomon, A.W., Stamm, W.E., Suchland, R.J., Taylor, L., West, S.K., Quinn, T.C., Belland, R.J., McClarty, G. J. Clin. Invest. (2003) [Pubmed]
  15. Suppression of dibutylnitrosamine-induced bladder carcinomas in hamsters by dietary indole. Matsumoto, M., Oyasu, R., Hopp, M.L., Kitajima, T. J. Natl. Cancer Inst. (1977) [Pubmed]
  16. Conformational and ligand binding properties of the isolated domains from the beta 2 subunit of Escherichia coli tryptophan synthetase investigated by the reactivity of their cysteines. Goldberg, M.E., Högberg-Raibaud, A. J. Biol. Chem. (1979) [Pubmed]
  17. Some effects of indole on the interaction of amino acids with tryptophanase. Kazarinoff, M.N., Snell, E.E. J. Biol. Chem. (1980) [Pubmed]
  18. Molecular basis defining human Chlamydia trachomatis tissue tropism. A possible role for tryptophan synthase. Fehlner-Gardiner, C., Roshick, C., Carlson, J.H., Hughes, S., Belland, R.J., Caldwell, H.D., McClarty, G. J. Biol. Chem. (2002) [Pubmed]
  19. Dodecaprenyl Phosphate-Galacturonic Acid as a Donor Substrate for Lipopolysaccharide Core Glycosylation in Rhizobium leguminosarum. Kanjilal-Kolar, S., Raetz, C.R. J. Biol. Chem. (2006) [Pubmed]
  20. Crystal Structure of Aminopeptidase N (Proteobacteria Alanyl Aminopeptidase) from Escherichia coli and Conformational Change of Methionine 260 Involved in Substrate Recognition. Ito, K., Nakajima, Y., Onohara, Y., Takeo, M., Nakashima, K., Matsubara, F., Ito, T., Yoshimoto, T. J. Biol. Chem. (2006) [Pubmed]
  21. The Arabidopsis SUPPRESSOR OF AUXIN RESISTANCE proteins are nucleoporins with an important role in hormone signaling and development. Parry, G., Ward, S., Cernac, A., Dharmasiri, S., Estelle, M. Plant Cell (2006) [Pubmed]
  22. A conserved transcript pattern in response to a specialist and a generalist herbivore. Reymond, P., Bodenhausen, N., Van Poecke, R.M., Krishnamurthy, V., Dicke, M., Farmer, E.E. Plant Cell (2004) [Pubmed]
  23. Access of ligands to cavities within the core of a protein is rapid. Feher, V.A., Baldwin, E.P., Dahlquist, F.W. Nat. Struct. Biol. (1996) [Pubmed]
  24. Solid-phase peptide synthesis and solid-state NMR spectroscopy of [Ala3-15N][Val1]gramicidin A. Fields, G.B., Fields, C.G., Petefish, J., Van Wart, H.E., Cross, T.A. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  25. Serotonin and 5-hydroxyindoleacetic acid are increased in the sigmoid colon in severe idiopathic constipation. Lincoln, J., Crowe, R., Kamm, M.A., Burnstock, G., Lennard-Jones, J.E. Gastroenterology (1990) [Pubmed]
  26. Gas-chromatographic and mass-spectrometric analysis of the odor of human feces. Moore, J.G., Jessop, L.D., Osborne, D.N. Gastroenterology (1987) [Pubmed]
  27. Nutritional regulation of nucleoside transporter expression in rat small intestine. Valdés, R., Ortega, M.A., Casado, F.J., Felipe, A., Gil, A., Sánchez-Pozo, A., Pastor-Anglada, M. Gastroenterology (2000) [Pubmed]
  28. Mouse 3T3-L1 cell variants unable to respond to mitogenic stimulation of dihydroteleocidin B: genetic evidence for the synergism of tumor promoters with growth factors. Shimizu, Y., Fujiki, H., Sugimura, T., Shimizu, N. Cancer Res. (1986) [Pubmed]
  29. Increase in the synthesis of a Mr 32,000 protein in BALB/c 3T3 cells treated with tumor-promoting indole alkaloids or polyacetates. Hiwasa, T., Fujiki, H., Sugimura, T., Sakiyama, S. Cancer Res. (1983) [Pubmed]
  30. CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis. Bak, S., Tax, F.E., Feldmann, K.A., Galbraith, D.W., Feyereisen, R. Plant Cell (2001) [Pubmed]
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