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Chemical Compound Review

Isochinolin     isoquinoline

Synonyms: ISOQUINOLINE, beta-Quinoline, PubChem7536, SureCN2491, SureCN9654, ...
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Disease relevance of isoquinoline


Psychiatry related information on isoquinoline

  • The results of the present study suggest that isoquinoline alkaloids may be potential agents in the treatment of drug abuse [6].
  • Evidence is reviewed that points out possible common features of alcohol and opiate dependence leading to the speculation for a common mode of treatment may reside in plants rich in isoquinoline alkaloids [7].

High impact information on isoquinoline

  • The results also demonstrate that the induction of Na+ influx by CSF-1 is inhibited by the protein kinase C inhibitors staurosporine and the isoquinoline derivative H7, but not by HA1004.(ABSTRACT TRUNCATED AT 250 WORDS)[8]
  • The mitochrondrial benzodiazepine receptor (mBzR) binds a subset of benzodiazepines and isoquinoline carboxamides with nanomolar affinity and consists of the voltage-dependent anion channel, the adenine nucleotide translocator, and an 18-kDa protein [9].
  • The 18-kDa protein is labeled by the isoquinoline carboxamide mBzR ligand [3H]PK14105, whereas the 30- and 32-kDa subunits are labeled by the benzodiazepine (Bz) ligands [3H]flunitrazepam and [3H]AHN-086 [10].
  • Recently, an endogenous catechol isoquinoline, 1(R),2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline [N-methyl(R)salsolinol], was proved to be a neurotoxin specific for dopamine neurons by in vivo and in vitro experiments [11].
  • In vitro reconstitution experiments suggested that the PBR was a multimeric complex in which the isoquinoline binding site was on the Mr 18,000 subunit, denoted pk18, whereas the benzodiazepine binding site required the association of this subunit with VDAC to be expressed [12].

Chemical compound and disease context of isoquinoline


Biological context of isoquinoline


Anatomical context of isoquinoline


Associations of isoquinoline with other chemical compounds


Gene context of isoquinoline

  • Thus, THI 52, a new synthetic isoquinoline alkaloid, may be beneficial in inflammatory disorders where the overproduction of NO and TNF-alpha is a matter of concern [28].
  • Isoindoline derivatives were found to be more potent DPP8 inhibitors than isoquinoline derivatives [29].
  • Here we report the discovery of several isoquinoline analogues, exemplified by 1 and 2, which bind IGFBP-3 as well as other IGFBPs at low nanomolar concentrations [30].
  • The isoquinoline sulfonyl piperazine compound H7 at concentrations that inhibit PDGF-stimulated PKC activity had no effect on PDGF-stimulated PI 3 kinase activity in antiphospotyrosine immunoprecipitates [31].
  • In attempting to characterize the role of protein kinase A (PKA) in regulating the beta-2 adrenergic receptor (AR) in human airway cells, we observed a seemingly profound capacity of the isoquinoline H-89, a potent and widely used PKA inhibitor, to attenuate agonist-mediated desensitization of the beta-2 AR [32].

Analytical, diagnostic and therapeutic context of isoquinoline

  • Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis [33].
  • An additional PKA/PKB mutation, Q181K, corrects the defect, as shown both by the crystal structure of triple mutant PKAB3 (PKAalpha V123A, L173M, Q181K) and by surface plasmon resonance spectroscopy binding studies with ATP and three isoquinoline inhibitors [34].
  • The technique of capillary electrophoresis - mass spectrometry (CE-MS) was applied for determination of isoquinoline alkaloids in crude methanolic extracts of medicinal plants [35].
  • The axial 8-methyl-6-exocyclic methylene isoquinoline (20) is the most potent compound in the mouse abdominal constriction assay (ED50 = 0.05 mg/kg sc), whereas the equatorial 8-methyl isomer (16) was significantly less potent (ED50 = 3.3 mg/kg sc) [36].
  • Using post-embedding immunogold techniques the cytological localization of the two branchpoint enzymes of isoquinoline biosynthesis, berberine bridge enzyme (BBE) and (S)-tetrahydroprotoberberine oxidase (STOX), was demonstrated [37].


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  2. Molecular cloning of the isoquinoline 1-oxidoreductase genes from Pseudomonas diminuta 7, structural analysis of iorA and iorB, and sequence comparisons with other molybdenum-containing hydroxylases. Lehmann, M., Tshisuaka, B., Fetzner, S., Lingens, F. J. Biol. Chem. (1995) [Pubmed]
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  4. Berberine inhibits growth, induces G1 arrest and apoptosis in human epidermoid carcinoma A431 cells by regulating Cdki-Cdk-cyclin cascade, disruption of mitochondrial membrane potential and cleavage of caspase 3 and PARP. Mantena, S.K., Sharma, S.D., Katiyar, S.K. Carcinogenesis (2006) [Pubmed]
  5. Isoquinoline derivatives as endogenous neurotoxins in the aetiology of Parkinson's disease. McNaught, K.S., Carrupt, P.A., Altomare, C., Cellamare, S., Carotti, A., Testa, B., Jenner, P., Marsden, C.D. Biochem. Pharmacol. (1998) [Pubmed]
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  8. Colony-stimulating factor 1 activates protein kinase C in human monocytes. Imamura, K., Dianoux, A., Nakamura, T., Kufe, D. EMBO J. (1990) [Pubmed]
  9. Mitochondrial benzodiazepine receptor linked to inner membrane ion channels by nanomolar actions of ligands. Kinnally, K.W., Zorov, D.B., Antonenko, Y.N., Snyder, S.H., McEnery, M.W., Tedeschi, H. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  10. Isolation of the mitochondrial benzodiazepine receptor: association with the voltage-dependent anion channel and the adenine nucleotide carrier. McEnery, M.W., Snowman, A.M., Trifiletti, R.R., Snyder, S.H. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  11. (R)salsolinol N-methyltransferase activity increases in parkinsonian lymphocytes. Naoi, M., Maruyama, W., Nakao, N., Ibi, T., Sahashi, K., Benedetti, M.S. Ann. Neurol. (1998) [Pubmed]
  12. The Mr 18,000 subunit of the peripheral-type benzodiazepine receptor exhibits both benzodiazepine and isoquinoline carboxamide binding sites in the absence of the voltage-dependent anion channel or of the adenine nucleotide carrier. Joseph-Liauzun, E., Farges, R., Delmas, P., Ferrara, P., Loison, G. J. Biol. Chem. (1997) [Pubmed]
  13. Selective dopaminergic neurotoxicity of isoquinoline derivatives related to Parkinson's disease: studies using heterologous expression systems of the dopamine transporter. Storch, A., Ott, S., Hwang, Y.I., Ortmann, R., Hein, A., Frenzel, S., Matsubara, K., Ohta, S., Wolf, H.U., Schwarz, J. Biochem. Pharmacol. (2002) [Pubmed]
  14. Increased density of peripheral benzodiazepine-binding sites in ovarian carcinomas as compared with benign ovarian tumours and normal ovaries. Katz, Y., Ben-Baruch, G., Kloog, Y., Menczer, J., Gavish, M. Clin. Sci. (1990) [Pubmed]
  15. Effect of 6(5H)-phenanthridinone, an inhibitor of poly(ADP-ribose) polymerase, on cultured tumor cells. Weltin, D., Marchal, J., Dufour, P., Potworowski, E., Oth, D., Bischoff, P. Oncol. Res. (1994) [Pubmed]
  16. Synthesis and assay of isoquinoline derivatives as HIV-1 Tat-TAR interaction inhibitors. He, M., Yuan, D., Lin, W., Pang, R., Yu, X., Yang, M. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  17. Cloning and expression of a pharmacologically unique bovine peripheral-type benzodiazepine receptor isoquinoline binding protein. Parola, A.L., Stump, D.G., Pepperl, D.J., Krueger, K.E., Regan, J.W., Laird, H.E. J. Biol. Chem. (1991) [Pubmed]
  18. Purification and characterization of isoquinoline 1-oxidoreductase from Pseudomonas diminuta 7, a novel molybdenum-containing hydroxylase. Lehmann, M., Tshisuaka, B., Fetzner, S., Röger, P., Lingens, F. J. Biol. Chem. (1994) [Pubmed]
  19. Inhibition of cytotoxic T lymphocyte-mediated lysis and cellular proliferation by isoquinoline sulfonamide protein kinase inhibitors. Evidence for the involvement of protein kinase C in lymphocyte function. Juszczak, R.J., Russell, J.H. J. Biol. Chem. (1989) [Pubmed]
  20. CD44 ligation induces caspase-independent cell death via a novel calpain/AIF pathway in human erythroleukemia cells. Artus, C., Maquarre, E., Moubarak, R.S., Delettre, C., Jasmin, C., Susin, S.A., Robert-Lézénès, J. Oncogene (2006) [Pubmed]
  21. Characterization of p18, a component of the lamin B receptor complex and a new integral membrane protein of the avian erythrocyte nuclear envelope. Simos, G., Maison, C., Georgatos, S.D. J. Biol. Chem. (1996) [Pubmed]
  22. Identification and molecular characterization of the isoquinoline rat intestinal binding site using 6,7-dimethoxy-4-(4'-amino-3'-[125I]iodobenzyl) isoquinoline. Servin, A.L., Christinaki, H., Viel, C. Mol. Pharmacol. (1986) [Pubmed]
  23. The effect of isoquinoline alkaloids on opiate withdrawal. Capasso, A., Piacente, S., De Tommasi, N., Rastrelli, L., Pizza, C. Current medicinal chemistry. (2006) [Pubmed]
  24. Development of ligands for the peripheral benzodiazepine receptor. James, M.L., Selleri, S., Kassiou, M. Current medicinal chemistry. (2006) [Pubmed]
  25. Isolation and characterization of a rat brain triakontatetraneuropeptide, a posttranslational product of diazepam binding inhibitor: specific action at the Ro 5-4864 recognition site. Slobodyansky, E., Guidotti, A., Wambebe, C., Berkovich, A., Costa, E. J. Neurochem. (1989) [Pubmed]
  26. Comparative EPR and redox studies of three prokaryotic enzymes of the xanthine oxidase family: quinoline 2-oxidoreductase, quinaldine 4-oxidase, and isoquinoline 1-oxidoreductase. Canne, C., Stephan, I., Finsterbusch, J., Lingens, F., Kappl, R., Fetzner, S., Hüttermann, J. Biochemistry (1997) [Pubmed]
  27. PK 11195 attenuates kainic acid-induced seizures and alterations in peripheral-type benzodiazepine receptor (PBR) protein components in the rat brain. Veenman, L., Leschiner, S., Spanier, I., Weisinger, G., Weizman, A., Gavish, M. J. Neurochem. (2002) [Pubmed]
  28. Suppression of tumor necrosis factor-alpha and inducible nitric oxide synthase gene expression by THI 52, a new synthetic naphthyl-benzylisoquinoline alkaloid. Kang, Y.J., Lee, B.K., Lee, Y.S., Seo, H.G., Park, M.K., Kim, H.J., Pyo, H.S., Chong, W.S., Jung, H.J., Yun-Choi, H.S., Lee, D.H., Chang, K.C. Biochem. Pharmacol. (2003) [Pubmed]
  29. Novel isoindoline compounds for potent and selective inhibition of prolyl dipeptidase DPP8. Jiaang, W.T., Chen, Y.S., Hsu, T., Wu, S.H., Chien, C.H., Chang, C.N., Chang, S.P., Lee, S.J., Chen, X. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  30. Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins. Chen, C., Zhu, Y.F., Liu, X.J., Lu, Z.X., Xie, Q., Ling, N. J. Med. Chem. (2001) [Pubmed]
  31. PDGF-mediated activation of phosphatidylinositol 3 kinase in human mesangial cells. Choudhury, G.G., Biswas, P., Grandaliano, G., Fouqueray, B., Harvey, S.A., Abboud, H.E. Kidney Int. (1994) [Pubmed]
  32. Pharmacological inhibition of protein kinases in intact cells: antagonism of beta adrenergic receptor ligand binding by H-89 reveals limitations of usefulness. Penn, R.B., Parent, J.L., Pronin, A.N., Panettieri, R.A., Benovic, J.L. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  33. Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Frick, S., Kutchan, T.M. Plant J. (1999) [Pubmed]
  34. Mutants of protein kinase A that mimic the ATP-binding site of protein kinase B (AKT). Gassel, M., Breitenlechner, C.B., Rüger, P., Jucknischke, U., Schneider, T., Huber, R., Bossemeyer, D., Engh, R.A. J. Mol. Biol. (2003) [Pubmed]
  35. Analysis of isoquinoline alkaloids in medicinal plants by capillary electrophoresis-mass spectrometry. Sturm, S., Stuppner, H. Electrophoresis (1998) [Pubmed]
  36. Synthesis, antinociceptive activity, and opioid receptor profiles of substituted trans-3-(decahydro- and octahydro-4a-isoquinolinyl)phenols. Judd, D.B., Brown, D.S., Lloyd, J.E., McElroy, A.B., Scopes, D.I., Birch, P.J., Hayes, A.G., Sheehan, M.J. J. Med. Chem. (1992) [Pubmed]
  37. Immunocytological localization of two enzymes involved in berberine biosynthesis. Bock, A., Wanner, G., Zenk, M.H. Planta (2002) [Pubmed]
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