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Chemical Compound Review

AC1MSWFI     carbazole

Synonyms: 9H-carbazolium, 9H-carbazol-9-ium
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Disease relevance of NSC 3498


High impact information on NSC 3498

  • Incorporation of these carbazole-labeled phospholipds into model membranes provides a system that allows the rapid determination of the uptake rates of chlorinated hydrocarbons into model membranes [4].
  • For the mono(imide) receptors, delta H was -5.8 kcal/mol (carbazole) and -9.2 kcal/mol (naphthalene) [5].
  • We examined the chemoprotective effects of KF41399, a novel derivative of carbazole compounds, on severe thrombocytopenia induced by nimustine (ACNU, 45 mg/kg administered for 2 consecutive days intravenously) in mice [2].
  • Differentiation of carbazole catabolic operons by replacement of the regulated promoter via transposition of an insertion sequence [3].
  • Protein-A peroxidase with diaminobenzidine or amino ethyl carbazole as substrate, served to detect binding of anti-human liver ADH antibodies in human liver thin sections, cultured human skin and lung fibroblasts, and HeLa cells [6].

Chemical compound and disease context of NSC 3498


Biological context of NSC 3498


Anatomical context of NSC 3498


Associations of NSC 3498 with other chemical compounds

  • Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. 8. Bis-basic derivatives of carbazole, dibenzofuran, and dibenzothiophene [21].
  • The following five fluorescent probes, each attached to the terminal carbon atom of the fatty acyl residue, were introduced into sphingomyelin: dansyl, pyrene, carbazole, 4-chloro-7-nitrobenz-2-oxa-1,3-diazole, and anthroic acid [22].
  • In a pilot study, results of the direct DMB test for 48 urine specimens agreed with the clinical diagnosis, and quantitative measurements correlated moderately (r = 0.76) with results of a commonly used procedure (carbazole-borate reactivity after precipitation with cetylpyridinium chloride) [23].
  • Partition coefficients for DDE determined by this method were the same as partition coefficients determined for carbazole-labeled membranes using the two-phase analysis [24].
  • Luminescence determination of pharmaceuticals of the tetrahydrocarbazole, carbazole, and 1,4-benzodiazepine class [25].

Gene context of NSC 3498

  • In this study, we use a combination of whole cell transport assays and photoaffinity labeling of Pdr5p with [(125)I]iodoarylazidoprazosin in purified plasma membrane vesicles to study the behavior of two series of novel substrates: trityl (triphenylmethyl) and carbazole derivatives [26].
  • The anti-inflammatory carbazole, LCY-2-CHO, inhibits lipopolysaccharide-induced inflammatory mediator expression through inhibition of the p38 mitogen-activated protein kinase signaling pathway in macrophages [27].
  • The novel antidepressant tetrindole (2,3,3a,4,5,6-hexahydro-8-cyclohexyl-1H[3,2,1-j,k] carbazole) was found to be a selective inhibitor of monoamine oxidase A (MAO A) [28].
  • Real-time competitive PCR and direct counting using the (gfp) marker were employed to monitor the total number of carbazole 1,9a-dioxygenase gene (carAa) and survival of CA10 cells in the soil and soil slurry microcosms [29].
  • The carbazole- and indole-based inhibitors displayed approximately 10-fold preferences over human H-FABP and E-FABP, and are highly selective against I-FABP [30].

Analytical, diagnostic and therapeutic context of NSC 3498

  • Significant increases in the induction of neoplastic lesions were found in the livers and forestomachs of mice given carbazole as compared to the control groups [1].
  • Surface plasmon resonance biosensor analysis of carbazole binding to an oligomer with an AATT central sequence indicated that the 2,7 NH compound has the largest binding constant [31].
  • The effect of carbazole on upstream pathways in human psoriasis was determined, and carbazole was shown to inhibit signal transducer and activator of transcription (stat)3-mediated transcription, which has been shown to be relevant in human psoriasis [32].
  • We sought S-100 protein in sections prepared from formalin-fixed paraffin-embedded tumor and normal tissues by an immunoperoxidase technique with a rabbit anti-bovine S-100 protein antiserum as first antibody and aminoethyl carbazole as developer [33].
  • Glycosaminoglycans were extracted by papain digestion and analysed by cellulose acetate electrophoresis, the carbazole assay for uronic acid and the dimethylmethylene blue dye-binding assay for sulphated glycosaminoglycans [34].


  1. Carcinogenic effect of carbazole in the liver of (C57BL/6N x C3H/HeN)F1 mice. Tsuda, H., Hagiwara, A., Shibata, M., Ohshima, M., Ito, N. J. Natl. Cancer Inst. (1982) [Pubmed]
  2. Chemoprotective effects of KF41399, a derivative of carbazole compounds, on nimustine-induced thrombocytopenia. Shiotsu, Y., Yamashita, K., Kanai, F., Ikuina, Y., Murakata, C., Teramura, M., Mizoguchi, H., Tamaoki, T., Akinaga, S. Blood (2000) [Pubmed]
  3. Differentiation of carbazole catabolic operons by replacement of the regulated promoter via transposition of an insertion sequence. Miyakoshi, M., Urata, M., Habe, H., Omori, T., Yamane, H., Nojiri, H. J. Biol. Chem. (2006) [Pubmed]
  4. Pesticide uptake into membranes measured by fluorescence quenching. Omann, G., Lakowicz, J.R. Science (1977) [Pubmed]
  5. Hydrogen bonding in water using synthetic receptors. Kato, Y., Conn, M.M., Rebek, J. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  6. Immunohistochemical localization of human liver alcohol dehydrogenase in liver tissue, cultured fibroblasts, and HeLa cells. Buehler, R., Hess, M., Von Wartburg, J.P. Am. J. Pathol. (1982) [Pubmed]
  7. Complete nucleotide sequence of carbazole/dioxin-degrading plasmid pCAR1 in Pseudomonas resinovorans strain CA10 indicates its mosaicity and the presence of large catabolic transposon Tn4676. Maeda, K., Nojiri, H., Shintani, M., Yoshida, T., Habe, H., Omori, T. J. Mol. Biol. (2003) [Pubmed]
  8. Simultaneous biodetoxification of s, N, and o pollutants by engineering of a carbazole-degrading gene cassette in a recombinant biocatalyst. Yu, B., Ma, C., Zhou, W., Zhu, S., Wang, Y., Qu, J., Li, F., Xu, P. Appl. Environ. Microbiol. (2006) [Pubmed]
  9. Indigenous and enhanced mineralization of pyrene, benzo[a]pyrene, and carbazole in soils. Grosser, R.J., Warshawsky, D., Vestal, J.R. Appl. Environ. Microbiol. (1991) [Pubmed]
  10. The association of elevated urinary total to sulfated glycosaminoglycan ratio and high molecular mass hyaluronic acid with interstitial cystitis. Wei, D.C., Politano, V.A., Selzer, M.G., Lokeshwar, V.B. J. Urol. (2000) [Pubmed]
  11. Discovery and optimization of a series of carbazole ureas as NPY5 antagonists for the treatment of obesity. Block, M.H., Boyer, S., Brailsford, W., Brittain, D.R., Carroll, D., Chapman, S., Clarke, D.S., Donald, C.S., Foote, K.M., Godfrey, L., Ladner, A., Marsham, P.R., Masters, D.J., Mee, C.D., O'Donovan, M.R., Pease, J.E., Pickup, A.G., Rayner, J.W., Roberts, A., Schofield, P., Suleman, A., Turnbull, A.V. J. Med. Chem. (2002) [Pubmed]
  12. Detection of quadruplex DNA structures in human telomeres by a fluorescent carbazole derivative. Chang, C.C., Kuo, I.C., Ling, I.F., Chen, C.T., Chen, H.C., Lou, P.J., Lin, J.J., Chang, T.C. Anal. Chem. (2004) [Pubmed]
  13. Genetic characterization and evolutionary implications of a car gene cluster in the carbazole degrader Pseudomonas sp. strain CA10. Nojiri, H., Sekiguchi, H., Maeda, K., Urata, M., Nakai, S., Yoshida, T., Habe, H., Omori, T. J. Bacteriol. (2001) [Pubmed]
  14. Characterization of the Replication, Maintenance, and Transfer Features of the IncP-7 Plasmid pCAR1, Which Carries Genes Involved in Carbazole and Dioxin Degradation. Shintani, M., Yano, H., Habe, H., Omori, T., Yamane, H., Tsuda, M., Nojiri, H. Appl. Environ. Microbiol. (2006) [Pubmed]
  15. Cell apoptosis induced by a synthetic carbazole compound LCY-2-CHO is mediated through activation of caspase and mitochondrial pathways. Hsu, M.J., Chao, Y., Chang, Y.H., Ho, F.M., Huang, L.J., Huang, Y.L., Luh, T.Y., Chen, C.P., Lin, W.W. Biochem. Pharmacol. (2005) [Pubmed]
  16. Biosynthetic incorporation of fluorescent carbazolylundecanoic acid into membrane phospholipids of LM cells and determination of quenching constants and partition coefficients of hydrophobic quenchers. Omann, G.M., Glaser, M. Biochemistry (1984) [Pubmed]
  17. Comparative efficacy evaluation of dicationic carbazole compounds, nitazoxanide, and paromomycin against Cryptosporidium parvum infections in a neonatal mouse model. Blagburn, B.L., Drain, K.L., Land, T.M., Kinard, R.G., Moore, P.H., Lindsay, D.S., Patrick, D.A., Boykin, D.W., Tidwell, R.R. Antimicrob. Agents Chemother. (1998) [Pubmed]
  18. Inhibition of lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages by a synthetic carbazole, LCY-2-CHO. Tsao, L.T., Lee, C.Y., Huang, L.J., Kuo, S.C., Wang, J.P. Biochem. Pharmacol. (2002) [Pubmed]
  19. Model for focal demyelination of the spinal dorsal columns of transgenic MBP-LacZ mice by phototargeted ablation of oligodendrocytes. Vanderluit, J.L., Bourque, J.A., Peterson, A.C., Tetzlaff, W. J. Neurosci. Res. (2000) [Pubmed]
  20. Effects of aspirin and related drugs in vitamin E-deficient rats. Machlin, L.J., Gabriel, E., Horn, L.R., Woo, D., Filipski, R., Brin, M., Nelson, J. J. Nutr. (1980) [Pubmed]
  21. Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. 8. Bis-basic derivatives of carbazole, dibenzofuran, and dibenzothiophene. Albrecht, W.L., Fleming, R.W., Horgan, S.W., Mayer, G.D. J. Med. Chem. (1977) [Pubmed]
  22. A fluorometric determination of sphingomyelinase by use of fluorescent derivatives of sphingomyelin, and its application to diagnosis of Niemann-Pick disease. Gatt, S., Dinur, T., Barenholz, Y. Clin. Chem. (1980) [Pubmed]
  23. Diagnostic test for mucopolysaccharidosis. I. Direct method for quantifying excessive urinary glycosaminoglycan excretion. Whitley, C.B., Ridnour, M.D., Draper, K.A., Dutton, C.M., Neglia, J.P. Clin. Chem. (1989) [Pubmed]
  24. Dynamic quenchers in fluorescently labeled membranes. Theory for quenching in a three-phase system. Omann, G.M., Glaser, M. Biophys. J. (1985) [Pubmed]
  25. Luminescence determination of pharmaceuticals of the tetrahydrocarbazole, carbazole, and 1,4-benzodiazepine class. de Silva, J.A., Strojny, N., Stika, K. Anal. Chem. (1976) [Pubmed]
  26. The role of hydrogen bond acceptor groups in the interaction of substrates with Pdr5p, a major yeast drug transporter. Hanson, L., May, L., Tuma, P., Keeven, J., Mehl, P., Ferenz, M., Ambudkar, S.V., Golin, J. Biochemistry (2005) [Pubmed]
  27. The anti-inflammatory carbazole, LCY-2-CHO, inhibits lipopolysaccharide-induced inflammatory mediator expression through inhibition of the p38 mitogen-activated protein kinase signaling pathway in macrophages. Ho, F.M., Lai, C.C., Huang, L.J., Kuo, T.C., Chao, C.M., Lin, W.W. Br. J. Pharmacol. (2004) [Pubmed]
  28. Monoamine oxidase inhibition by novel antidepressant tetrindole. Medvedev, A.E., Kirkel, A.A., Kamyshanskaya, N.S., Moskvitina, T.A., Axenova, L.N., Gorkin, V.Z., Andreeva, N.I., Golovina, S.M., Mashkovsky, M.D. Biochem. Pharmacol. (1994) [Pubmed]
  29. Enhanced degradation of carbazole and 2,3-dichlorodibenzo-p-dioxin in soils by Pseudomonas resinovorans strain CA10. Widada, J., Nojiri, H., Yoshida, T., Habe, H., Omori, T. Chemosphere (2002) [Pubmed]
  30. Discovery of inhibitors of human adipocyte fatty acid-binding protein, a potential type 2 diabetes target. Lehmann, F., Haile, S., Axen, E., Medina, C., Uppenberg, J., Svensson, S., Lundbäck, T., Rondahl, L., Barf, T. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  31. Effects of compound structure on carbazole dication-DNA complexes: tests of the minor-groove complex models. Tanious, F.A., Ding, D., Patrick, D.A., Bailly, C., Tidwell, R.R., Wilson, W.D. Biochemistry (2000) [Pubmed]
  32. Carbazole is a naturally occurring inhibitor of angiogenesis and inflammation isolated from antipsoriatic coal tar. Arbiser, J.L., Govindarajan, B., Battle, T.E., Lynch, R., Frank, D.A., Ushio-Fukai, M., Perry, B.N., Stern, D.F., Bowden, G.T., Liu, A., Klein, E., Kolodziejski, P.J., Eissa, N.T., Hossain, C.F., Nagle, D.G. J. Invest. Dermatol. (2006) [Pubmed]
  33. Detection of S-100 protein as an aid to the identification of melanocytic tumors. Cochran, A.J., Wen, D.R., Herschman, H.R., Gaynor, R.B. Int. J. Cancer (1982) [Pubmed]
  34. Glycosaminoglycans of human rotator cuff tendons: changes with age and in chronic rotator cuff tendinitis. Riley, G.P., Harrall, R.L., Constant, C.R., Chard, M.D., Cawston, T.E., Hazleman, B.L. Ann. Rheum. Dis. (1994) [Pubmed]
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