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Chemical Compound Review

quinolone     1H-quinolin-2-one

Synonyms: Quinolinol, Carbostyril, Quinolinone, Quinolin-2-ol, quinolin-2-one, ...
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Disease relevance of Carbostyril

  • Highly purified tetanus toxin at 2.5 x 10(5) 50% lethal doses per ml lost all toxicity in 40 mM PTL or 150 mM DPD but was not detectably affected by 100 mM HQL (the highest concentration possible) [1].
  • In two calves suffering from Adema disease, the bovine parallel to Acrodermatitis enteropathica, hydroxyquinoline supplementation resulted in an increase in intestinal 65Zn absorption, while picolinic acid had no such effect [2].
  • 2-Oxoquinoline 8-monooxygenase is a Rieske non-heme iron oxygenase that catalyzes the NADH-dependent oxidation of the N-heterocyclic aromatic compound 2-oxoquinoline to 8-hydroxy-2-oxoquinoline in the soil bacterium Pseudomonas putida 86 [3].
  • Rebamipide, a gastroprotective drug, is a compound selected from over 500 amino acid analogs of 2(1H)-quinolinone tested for gastroprotective action and for efficacy to heal experimental gastric ulcers [4].
  • In the case of patients with impetigo, hydrocortisone/potassium hydroxyquinoline sulphate proved significantly more effective than the other combination, the success rates being 92% and 74%, respectively [5].

Psychiatry related information on Carbostyril


High impact information on Carbostyril


Chemical compound and disease context of Carbostyril


Biological context of Carbostyril


Anatomical context of Carbostyril

  • In the iron-loaded hepatocyte cultures, the three hydroxyquinoline chelators, although showing diversity in terms of lipophilicity, appeared to be very similar in their capacity to chelate iron [17].
  • Preincubation of membranes with either of the carbostyril congeners followed by washing reduced specific [125I]CYP binding capacity without changing the KD value for the remaining receptors [18].
  • The interaction of the carbostyril derivatives 5-[2-[[1-(4-aminophenyl)-2-methyl-prop-2-yl]amino]-1-hydroxyethyl]- 8-hydroxycarbostyril (carbo-amine) and 5-[2-[[3-[4-(bromoacetamido)phenyl]-2-methylprop-2-yl]amino]-1- hydroxyethyl]-8-hydroxycarbostyril (carbo-Br) with the rat reticulocyte beta-adrenoreceptor system has been partially characterized [18].
  • Studies on 2-oxoquinoline derivatives as blood platelet aggregation inhibitors. I. Alkyl 4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrates and related compounds [19].
  • A microiontophoretic study was performed to investigate the effects of a newly synthesized quinolinone derivative, 7-[3-(4-(2,3-dimethylphenyl) piperazinyl) propoxy] 2-(1H)-quinolinone (OPC-4392), on neuronal activities of the ventral tegmental area (VTA) of rats anesthetized with chloral hydrate [20].

Associations of Carbostyril with other chemical compounds

  • Derivatives carrying a substituent in the para position of the phenyl group of 8-hydroxy-5-[2-[(1-phenyl-2-methylprop-2-yl)amino]-1-hydroxyethyl] carbostyril (10) were prepared and their effects on beta-adrenoceptors evaluated in vitro [21].
  • Plasma was acidified to the optimal pH (6.0) of angiotensin l generation with the least possible dilution, by using a single addition of hydrochloric acid and the enzyme inhibitor hydroxyquinoline [22].
  • Four new hexadendate chelators, three hydroxyquinoline-based, Csox, O-Trensox, Cox750, and one catecholate-based CacCam-which have comparable skeletal structures and pFe, but widely different partition coefficients, (Kpart), 0.01, 0.02, 1 and 3.2 respectively, have been tested for their iron chelating efficacy in vitro by two methods [17].
  • Characteristics of antitumor activity of 3,4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]- 2(1H)-quinolinone (vesnarinone) against a human adenoid squamous carcinoma-forming cell line grown in athymic nude mice [23].
  • An in vitro system was used for growing this fruit, showing that the presence in the incubation medium of sucrose or hydroxyquinoline hemisulfate has no effect on the bioformation of these compounds [24].

Gene context of Carbostyril

  • The novel hydroxyquinoline-containing tetrapodal ligand forms water soluble and stable chelates and is a good sensitizer of the NIR luminescence of its Nd(III) and Yb(III) complexes; its easy synthesis opens the way for potential biomedical applications [25].
  • Several carbostyril-based beta-agonists have been shown to bind tightly to and slowly dissociate from the beta2-adrenoceptor (beta2AR) [26].
  • The medium is supplemented with a recently described chromogenic substrate, hydroxyquinoline-beta-D-glucuronide, for beta-glucuronidase enzyme [27].
  • Synthesis of 3-ureido derivatives of coumarin and 2-quinolone as potent acyl-CoA: cholesterol acyltransferase inhibitors [28].
  • Hydroxyquinoline causes a marked increase in renal weight, the development of wedge-shaped foci with severely dilated tubule segments, and a simultaneous reduction in dehydrogenases, alkaline phosphatase, and alpha-naphthyl esterase [29].

Analytical, diagnostic and therapeutic context of Carbostyril


  1. Inactivation of botulinum and tetanus toxins by chelators. Bhattacharyya, S.D., Sugiyama, H. Infect. Immun. (1989) [Pubmed]
  2. Zinc absorption in cattle with a dietary picolinic acid supplement. Flagstad, T. J. Nutr. (1981) [Pubmed]
  3. 2-Oxoquinoline 8-monooxygenase oxygenase component: active site modulation by Rieske-[2Fe-2S] center oxidation/reduction. Martins, B.M., Svetlitchnaia, T., Dobbek, H. Structure (Camb.) (2005) [Pubmed]
  4. Rebamipide: overview of its mechanisms of action and efficacy in mucosal protection and ulcer healing. Arakawa, T., Kobayashi, K., Yoshikawa, T., Tarnawski, A. Dig. Dis. Sci. (1998) [Pubmed]
  5. A clinical trial of hydrocortisone/potassium hydroxyquinoline sulphate ('Quinocort') in the treatment of infected eczema and impetigo in general practice. Jaffé, G.V., Grimshaw, J.J. Pharmatherapeutica. (1986) [Pubmed]
  6. Design, microwave-assisted synthesis, and photophysical properties of small molecule organic antennas for luminescence resonance energy transfer. Lee, H.K., Cao, H., Rana, T.M. Journal of combinatorial chemistry. (2005) [Pubmed]
  7. RNA synthesis and control of cell division in the yeast S. cerevisiae. Johnston, G.C., Singer, R.A. Cell (1978) [Pubmed]
  8. 6-hydroxyquinoline-N-oxides: a new class of "super" photoacids. Solntsev, K.M., Clower, C.E., Tolbert, L.M., Huppert, D. J. Am. Chem. Soc. (2005) [Pubmed]
  9. Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists. Raitio, K.H., Savinainen, J.R., Vepsäläinen, J., Laitinen, J.T., Poso, A., Järvinen, T., Nevalainen, T. J. Med. Chem. (2006) [Pubmed]
  10. Effects of 2 quinolone antibacterials, temafloxacin and enoxacin, on theophylline pharmacokinetics. Sörgel, F., Mahr, G., Granneman, G.R., Stephan, U., Nickel, P., Muth, P. Clinical pharmacokinetics. (1992) [Pubmed]
  11. Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds. Moon, M.W., Morris, J.K., Heier, R.F., Chidester, C.G., Hoffmann, W.E., Piercey, M.F., Althaus, J.S., Von Voigtlander, P.F., Evans, D.L., Figur, L.M. J. Med. Chem. (1992) [Pubmed]
  12. Effect of OPC-8212 (2(1H)-quinolinone), a new inotropic agent, on myocardial energy metabolism in patients with coronary heart disease. Nanto, S., Kodama, K., Kimura, Y., Masuyama, T., Mishima, M., Hamanaka, Y., Hori, M., Inoue, M. Jpn. Circ. J. (1988) [Pubmed]
  13. Synthesis and aldose reductase inhibitory activity of substituted 2-oxoquinoline-1-acetic acid derivatives. DeRuiter, J., Brubaker, A.N., Whitmer, W.L., Stein, J.L. J. Med. Chem. (1986) [Pubmed]
  14. Neuroprotection by a novel brain permeable iron chelator, VK-28, against 6-hydroxydopamine lession in rats. Shachar, D.B., Kahana, N., Kampel, V., Warshawsky, A., Youdim, M.B. Neuropharmacology (2004) [Pubmed]
  15. On the inhibition of the b-c1 segment on the mitochondrial respiratory chain by quinone analogues and hydroxyquinoline derivatives. Papa, S., Izzo, G., Guerrieri, F. FEBS Lett. (1982) [Pubmed]
  16. Effect of 7-(3-[4-(2,3-dimethylphenyl)piperazinyl]propoxy)- 2(1H)-quinolinone (OPC-4392), a newly synthesized agonist for presynaptic dopamine D2 receptor, on tyrosine hydroxylation in rat striatal slices. Kiuchi, K., Hirata, Y., Minami, M., Nagatsu, T. Life Sci. (1988) [Pubmed]
  17. New 8-hydroxyquinoline and catecholate iron chelators: influence of their partition coefficient on their biological activity. Henry, C., Rakba, N., Imbert, D., Thomas, F., Baret, P., Serratrice, G., Gaude, D., Pierre, J.L., Ward, R.J., Crichton, R.R., Lescoat, G. Biochem. Pharmacol. (2001) [Pubmed]
  18. Carbostyril-based beta-adrenergic agonists: evidence for long lasting or apparent irreversible receptor binding and activation of adenylate cyclase activity in vitro. Standifer, K.M., Pitha, J., Baker, S.P. Naunyn Schmiedebergs Arch. Pharmacol. (1989) [Pubmed]
  19. Studies on 2-oxoquinoline derivatives as blood platelet aggregation inhibitors. I. Alkyl 4-(2-oxo-1,2,3,4-tetrahydro-6-quinolyloxy)butyrates and related compounds. Nishi, T., Yamamoto, K., Shimizu, T., Kanbe, T., Kimura, Y., Nakagawa, K. Chem. Pharm. Bull. (1983) [Pubmed]
  20. D-2 receptor-mediated inhibition by a substituted quinolinone derivative, 7-[3-(4-(2,3-dimethylphenyl)piperazinyl)propoxy]-2(1H)-quinolinone (OPC-4392), of dopaminergic neurons in the ventral tegmental area. Momiyama, T., Sasa, M., Takaori, S. Life Sci. (1990) [Pubmed]
  21. Carbostyril derivatives having potent beta-adrenergic agonist properties. Milecki, J., Baker, S.P., Standifer, K.M., Ishizu, T., Chida, Y., Kusiak, J.W., Pitha, J. J. Med. Chem. (1987) [Pubmed]
  22. Radioimmunoassay of plasma renin activity. Fyhrquist, F., Soveri, P., Puutula, L., Stenman, U.H. Clin. Chem. (1976) [Pubmed]
  23. Characteristics of antitumor activity of 3,4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]- 2(1H)-quinolinone (vesnarinone) against a human adenoid squamous carcinoma-forming cell line grown in athymic nude mice. Sato, M., Harada, K., Bando, T., Shirakami, T., Nakashiro, K., Yoshida, H., Nakai, S., Kawai, K., Adachi, M. Cancer Lett. (1995) [Pubmed]
  24. Biosynthesis of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and derivatives in in vitro grown strawberries. Pérez, A.G., Olías, R., Olías, J.M., Sanz, C. J. Agric. Food Chem. (1999) [Pubmed]
  25. Lanthanide 8-hydroxyquinoline-based podates with efficient emission in the NIR range. Imbert, D., Comby, S., Chauvin, A.S., Bünzli, J.C. Chem. Commun. (Camb.) (2005) [Pubmed]
  26. Structure-affinity profile of 8-hydroxycarbostyril-based agonists that dissociate slowly from the beta2-adrenoceptor. Deyrup, M.D., Nowicki, S.T., Richards, N.G., Otero, D.H., Harrison, J.K., Baker, S.P. Naunyn Schmiedebergs Arch. Pharmacol. (1999) [Pubmed]
  27. Evaluation of a new dipslide with a selective medium for the rapid detection of beta-glucuronidase-positive Escherichia coli. Larinkari, U., Rautio, M. Eur. J. Clin. Microbiol. Infect. Dis. (1995) [Pubmed]
  28. Synthesis of 3-ureido derivatives of coumarin and 2-quinolone as potent acyl-CoA: cholesterol acyltransferase inhibitors. Tawada, H., Natsugari, H., Ishikawa, E., Sugiyama, Y., Ikeda, H., Meguro, K. Chem. Pharm. Bull. (1995) [Pubmed]
  29. The significance of the hairpin counter-current principle in the pathogenesis of toxic kidney lesions. An investigation of the influence of antidiuretic hormone and papaverine on hydroxyquinoline nephropathy of the rat. Büchner, S.A., Meier-Ruge, W. Beiträge zur Pathologie. (1977) [Pubmed]
  30. Hydroxyquinoline overcomes PCR inhibition by UV-damaged mineral oil. Gilgen, M., Höfelein, C., Lüthy, J., Hübner, P. Nucleic Acids Res. (1995) [Pubmed]
  31. Transferrin receptor expression of the hyperplastic lesions of hepatocyte in experimental hepatocarcinogenesis. Park, C.I., Park, Y.N., Jung, W.H. J. Korean Med. Sci. (1995) [Pubmed]
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