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Chemical Compound Review

NSC-13286     4-[(E)-2-quinolin-4- ylethenyl]quinoline

Synonyms: NSC-631618, AC1NZJ1X, NSC13286, NSC631618, AR-1F8009, ...
 
 
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Disease relevance of Codeinone

 

Psychiatry related information on Codeinone

  • We studied the effects of transauricular electroshock (ECS) on EEG and EMG patterns, and overt behaviors (wet-dog shaking and excessive grooming), caused by RX 336-M (7,8-dihydro-5',6'-dimethylcyclohex-5'-eno-1',2', 8',14 codeinone) in rats [6].
 

High impact information on Codeinone

  • After gene silencing, the precursor alkaloid (S)-reticuline-seven enzymatic steps upstream of codeinone-accumulated in transgenic plants at the expense of morphine, codeine, oripavine and thebaine [7].
  • Mutagenesis studies have established that Cys-191 does not act as a crucial acid in the mechanism of reduction of the olefinic bond found in 2-cyclohexenone and codeinone [8].
  • Seven benzylisoquinoline alkaloid biosynthetic enzymes, (S)-N-methylcoclaurine 3'-hydroxylase (CYP80B1), berberine bridge enzyme, codeinone reductase, 6OMT, CNMT, 4'OMT and SAT were localized by immunofluorescence labeling to the sieve elements in the root and hypocotyl of opium poppy seedlings [9].
  • Along the morphine biosynthetic pathway in opium poppy, codeinone reductase catalyzes the NADPH-dependent reduction of codeinone to codeine [1].
  • A comparison of the translations of the nucleotide sequences indicate that the codeinone reductase isoforms are 53% identical to 6'-deoxychalcone synthase from soybean suggesting an evolutionary although not a functional link between enzymes of phenylpropanoid and alkaloid biosynthesis [1].
 

Chemical compound and disease context of Codeinone

 

Biological context of Codeinone

 

Anatomical context of Codeinone

  • The authors previously found that codeinone, an oxidation metabolite of codeine, among 10 opioids, showed the highest cytotoxic activity (DNA fragmentation-inducing activity) against human promyelocytic leukemic cell lines (HL-60) [11].
  • METHODS: Apoptosis was induced by treating HL-60 cells for 1-6 h with codeine or codeinone [11].
  • Fluorometric assay showed that codeinone time-dependently activated caspase 3 and caspase 9, but not caspase 8, suggesting the activation of intrinsic apoptotic signaling pathway via mitochondria [12].
  • These data suggest that codeinone induces cytotoxicity in oral tumor cell lines, possibly by a Michael-like addition of a protein SH or of an amino group to the bouble bond of codeinone [5].
  • Human oral gingival fibroblasts (HGF) were relatively resistant to codeinone, as judged by higher SI ratio (3.7) suggesting the tumor-selective cytotoxicity of codeinone [5].
 

Associations of Codeinone with other chemical compounds

 

Gene context of Codeinone

  • The reaction of morphinone reductase (MR) with the physiological reductant NADH and the oxidizing substrate codeinone has been studied by multiple and single wavelength stopped-flow spectroscopy [15].
  • Codeinone stimulated the release of both cytochrome c and cytochrome oxidase, and cleavage of procaspase 3 without significant changes in both the activity and expression of MnSOD [11].
  • According to the MS/MS fragmentation pathway, the investigated compounds can be grouped into 4 subsets: (1) morphine and codeine, (2) morphinone, codeinone, and neopinone, (3) thebaine and oripavine, (4) salutaridine and salutaridinol [16].
  • In screening cytotoxic agents in morphine alkaloids [TE1-10], codeinone [TE8] was cytotoxic against two human oral tumor cells lines (HSC-2 and HSG) [5].
 

Analytical, diagnostic and therapeutic context of Codeinone

  • Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum [1].
  • These isoenzymes could not be separated for characterization and showed slightly different kinetic features (Km values: codeinone 9 microM; NADPH 81 microM) compared with the cell culture enzyme [17].
  • Western blot analysis demonstrated that codeinone enhanced the Pro-apoptotic Bax protein expression, but reduced the anti-apoptotic Bcl-2 protein expression [12].
  • The structures of all new compounds were assigned by the spectral data, that of the cycloadduct of codeinone was additionally verified by X-ray crystallography [18].

References

  1. Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum. Unterlinner, B., Lenz, R., Kutchan, T.M. Plant J. (1999) [Pubmed]
  2. Mechanistic studies of morphine dehydrogenase and stabilization against covalent inactivation. Walker, E.H., French, C.E., Rathbone, D.A., Bruce, N.C. Biochem. J. (2000) [Pubmed]
  3. Effects of glutathione and phenobarbital on the toxicity of codeinone. Nagamatsu, K., Inoue, K., Terao, T., Toki, S. Biochem. Pharmacol. (1986) [Pubmed]
  4. Effect of anticancer agents on codeinone-induced apoptosis in human cancer cell lines. Takeuchi, R., Hoshijima, H., Onuki, N., Nagasaka, H., Chowdhury, S.A., Kawase, M., Sakagami, H. Anticancer Res. (2005) [Pubmed]
  5. Cell death-inducing activity of opiates in human oral tumor cell lines. Kawase, M., Sakagami, H., Furuya, K., Kikuchi, H., Nishikawa, H., Motohashi, N., Morimoto, Y., Varga, A., Molnár, J. Anticancer Res. (2002) [Pubmed]
  6. EEG, EMG and behavioral evidence for the involvement of endorphin systems in postictal events after electroconvulsive shock in rats. Tortella, F.C., Cowan, A. Life Sci. (1982) [Pubmed]
  7. RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy. Allen, R.S., Millgate, A.G., Chitty, J.A., Thisleton, J., Miller, J.A., Fist, A.J., Gerlach, W.L., Larkin, P.J. Nat. Biotechnol. (2004) [Pubmed]
  8. Crystal structure of bacterial morphinone reductase and properties of the C191A mutant enzyme. Barna, T., Messiha, H.L., Petosa, C., Bruce, N.C., Scrutton, N.S., Moody, P.C. J. Biol. Chem. (2002) [Pubmed]
  9. The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy. Samanani, N., Alcantara, J., Bourgault, R., Zulak, K.G., Facchini, P.J. Plant J. (2006) [Pubmed]
  10. A practical synthesis of codeine from dihydrothebainone. Weller, D.D., Rapoport, H. J. Med. Chem. (1976) [Pubmed]
  11. Comparative analysis of apoptosis-inducing activity of codeine and codeinone. Hitosugi, N., Hatsukari, I., Ohno, R., Hashimoto, K., Mihara, S., Mizukami, S., Nakamura, S., Sakagami, H., Nagasaka, H., Matsumoto, I., Kawase, M. Anesthesiology (2003) [Pubmed]
  12. Analysis of apoptosis signaling pathway in human cancer cells by codeinone, a synthetic derivative of codeine. Hitosugi, N., Nagasaka, H., Sakagami, H., Matsumoto, I., Kawase, M. Anticancer Res. (2003) [Pubmed]
  13. In vitro formation of codeinone from codeine by rat or guinea pig liver homogenate and its acute toxicity in mice. Nagamatsu, K., Terao, T., Toki, S. Biochem. Pharmacol. (1985) [Pubmed]
  14. Induction of non-apoptotic cell death by morphinone in human promyelocytic leukemia HL-60 cells. Takeuchi, R., Hoshijima, H., Nagasaka, H., Chowdhury, S.A., Kikuchi, H., Kanda, Y., Kunii, S., Kawase, M., Sakagami, H. Anticancer Res. (2006) [Pubmed]
  15. Reductive and oxidative half-reactions of morphinone reductase from Pseudomonas putida M10: a kinetic and thermodynamic analysis. Craig, D.H., Moody, P.C., Bruce, N.C., Scrutton, N.S. Biochemistry (1998) [Pubmed]
  16. Electrospray tandem mass spectrometric investigations of morphinans. Raith, K., Neubert, R., Poeaknapo, C., Boettcher, C., Zenk, M.H., Schmidt, J. J. Am. Soc. Mass Spectrom. (2003) [Pubmed]
  17. Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures and differentiated plants. Lenz, R., Zenk, M.H. Eur. J. Biochem. (1995) [Pubmed]
  18. Syntheses of novel pyridazinomorphinans by inverse electron demand cycloaddition and their binding to mu and kappa receptors. Klindert, T., Stroetmann, I., Seitz, G., Höfner, G., Wanner, K.T., Frenzen, G., Eckhoff, B. Arch. Pharm. (Weinheim) (1997) [Pubmed]
 
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