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Chemical Compound Review

Quinacrine hydrochloride     N'-(6-chloro-2-methoxy- acridin-9-yl)-N,N...

Synonyms: Atebrine, Italchin, Metochin, Metoquin, Palacrin, ...
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Disease relevance of quinacrine


High impact information on quinacrine

  • The transcription signal from the promoter for the 7.5-kilobase rRNA precursor (the gene promoter) is unaffected over a large range of intercalating agent concentrations regardless of whether the template is injected plasmid DNA in oocytes, the amplified endogenous nucleoli of oocytes, or the endogenous chromosomes of cultured Xenopus kidney cells [6].
  • Conversely, daunorubicin, an intercalating agent and topoisomerase II inhibitor, induced apoptosis of both resting and activated lymphocytes [7].
  • Complexes of the intercalating agent, acridine orange, with double-stranded DNA in situ, emit green fluorescence upon excitation with blue laser light [8].
  • By agarose gel electrophoresis, we verified that nafidimide is an intercalating agent, through its alteration of the electrophoretic migration of DNA products produced by the relaxing action of DNA topoisomerase I. Concentrations of up to 100 microM of nafidimide did not produce topoisomerase I-mediated DNA cleavage [9].
  • ADR, an intercalating agent and membrane inhibitor, showed a significant depression of PMN degranulation and lysozyme release at 10(-4) and 10(-3) mol/L (15.3% +/- 1.7% v 24% +/- 7%, P less than .01; and 15.0% +/- 2.5% v 24% +/- 7%, P less than or equal to .025) [10].

Chemical compound and disease context of quinacrine


Biological context of quinacrine

  • We have studied the kinetics of breakage of apurinic (AP) sites by the intercalating agent 9-aminoellipticine using fluorimetric methods with single (ss)- and double (ds)-stranded apurinic DNA [14].
  • This was ascribed to stacking interactions of the intercalating agent with base pairs which provide an additional stabilization of the [mRNA/DNA] hybrid [15].
  • In particular, EBE-A22 unwinds supercoiled plasmid, stabilizes duplex DNA against heat denaturation, and produces negative CD and ELD signals, as expected for an intercalating agent [16].
  • The design of oligonucleotides with an internal intercalating agent might be of interest to control gene expression through recognition of secondary structures in single-stranded targets [17].
  • Site-specific cleavage of single-stranded and double-stranded DNA sequences by oligodeoxyribonucleotides covalently linked to an intercalating agent and an EDTA-Fe chelate [18].

Anatomical context of quinacrine


Associations of quinacrine with other chemical compounds


Gene context of quinacrine

  • The prognostic value of BCRP and Pgp were analyzed in the whole population and according to intercalating agent [27].
  • alpha-DNA X: alpha and beta tetrathymidilates covalently linked to oxazolopyridocarbazolium (OPC): comparative stabilization of oligo beta-[dT]:oligo beta-[dA] and oligo alpha-[dT]:oligo beta-[dA] duplexes by the intercalating agent [28].

Analytical, diagnostic and therapeutic context of quinacrine


  1. Physicochemical and pharmacological properties of the antitumor ellipticine derivative 2-(diethylamino-2-ethyl)9-hydroxy ellipticinium-chloride, HCl. Auclair, C., Pierre, A., Voisin, E., Pepin, O., Cros, S., Colas, C., Saucier, J.M., Verschuere, B., Gros, P., Paoletti, C. Cancer Res. (1987) [Pubmed]
  2. A mutation in yeast topoisomerase II that confers hypersensitivity to multiple classes of topoisomerase II poisons. Dong, J., Walker, J., Nitiss, J.L. J. Biol. Chem. (2000) [Pubmed]
  3. Selective inhibition of the cytopathic effect of type A influenza viruses by oligodeoxynucleotides covalently linked to an intercalating agent. Zerial, A., Thuong, N.T., Hélène, C. Nucleic Acids Res. (1987) [Pubmed]
  4. Inhibition of simian virus 40 DNA replication in CV-1 cells by an oligodeoxynucleotide covalently linked to an intercalating agent. Birg, F., Praseuth, D., Zerial, A., Thuong, N.T., Asseline, U., Le Doan, T., Hélène, C. Nucleic Acids Res. (1990) [Pubmed]
  5. Fate of input oncornavirion RNA--biological studies. Sveda, M.M., Fields, B.N., Soeiro, R. J. Virol. (1976) [Pubmed]
  6. Effect of intercalating agents on RNA polymerase I promoter selection in Xenopus laevis. Pruitt, S.C., Reeder, R.H. Mol. Cell. Biol. (1984) [Pubmed]
  7. The topoisomerase inhibitors camptothecin and etoposide induce a CD95-independent apoptosis of activated peripheral lymphocytes. Ferraro, C., Quemeneur, L., Fournel, S., Prigent, A.F., Revillard, J.P., Bonnefoy-Berard, N. Cell Death Differ. (2000) [Pubmed]
  8. Binding of acridine orange to DNA in situ of cells from patients with acute leukemia. Walle, A.J., Wong, G.Y. Cancer Res. (1989) [Pubmed]
  9. In vitro toxicity and DNA cleaving capacity of benzisoquinolinedione (nafidimide; NSC 308847) in human leukemia. Andersson, B.S., Beran, M., Bakic, M., Silberman, L.E., Newman, R.A., Zwelling, L.A. Cancer Res. (1987) [Pubmed]
  10. Impaired in vitro polymorphonuclear function secondary to the chemotherapeutic effects of vincristine, adriamycin, cyclophosphamide, and actinomycin D. Cairo, M.S., Mallett, C., VandeVen, C., Kempert, P., Bennetts, G.A., Katz, J. J. Clin. Oncol. (1986) [Pubmed]
  11. Phase II trial of echinomycin in patients with advanced or recurrent colorectal cancer. Wadler, S., Tenteromano, L., Cazenave, L., Sparano, J.A., Greenwald, E.S., Rozenblit, A., Kaleya, R., Wiernik, P.H. Cancer Chemother. Pharmacol. (1994) [Pubmed]
  12. Efficacy and toxicity of the novel chemotherapeutic agent KW-2170 in recurrent epithelial ovarian cancer. Estes, J.M., Leath, C.A., Williams, S., Modiano, M.R., Sawyer, M., Cohn, D., Straughn, J.M., Barnes, M.N., Alvarez, R.D. Gynecol. Oncol. (2006) [Pubmed]
  13. Bacterial and mammalian cell mutagenesis, sister-chromatid exchange, and mouse lung adenoma bioassay with the antineoplastic acridine derivative amsacrine. de la Iglesia, F.A., Fitzgerald, J.E., McGuire, E.J., Kim, S.N., Heifetz, C.L., Stoner, G.D. Journal of toxicology and environmental health. (1984) [Pubmed]
  14. Mechanism of cleavage of apurinic sites by 9-aminoellipticine. Bertrand, J.R., Vasseur, J.J., Gouyette, A., Rayner, B., Imbach, J.L., Paoletti, C., Malvy, C. J. Biol. Chem. (1989) [Pubmed]
  15. Enzymatic amplification of translation inhibition of rabbit beta-globin mRNA mediated by anti-messenger oligodeoxynucleotides covalently linked to intercalating agents. Cazenave, C., Loreau, N., Thuong, N.T., Toulmé, J.J., Hélène, C. Nucleic Acids Res. (1987) [Pubmed]
  16. DNA interaction of the tyrosine protein kinase inhibitor PD153035 and its N-methyl analogue. Goossens, J.F., Bouey-Bencteux, E., Houssin, R., Hénichart, J.P., Colson, P., Houssier, C., Laine, W., Baldeyrou, B., Bailly, C. Biochemistry (2001) [Pubmed]
  17. Recognition of hairpin-containing single-stranded DNA by oligonucleotides containing internal acridine derivatives. François, J.C., Hélène, C. Bioconjug. Chem. (1999) [Pubmed]
  18. Site-specific cleavage of single-stranded and double-stranded DNA sequences by oligodeoxyribonucleotides covalently linked to an intercalating agent and an EDTA-Fe chelate. Boidot-Forget, M., Chassignol, M., Takasugi, M., Thuong, N.T., Hélène, C. Gene (1988) [Pubmed]
  19. Actinomycin D-associated lesions mimicking DNA-DNA interstrand crosslinks detected by alkaline elution in cultured mammalian cells. Fox, J.M., Byrne, T.D., Woods, W.G. Biochem. Pharmacol. (1985) [Pubmed]
  20. An acridine-linked oligodeoxynucleotide targeted to the common 5' end of trypanosome mRNAs kills cultured parasites. Verspieren, P., Cornelissen, A.W., Thuong, N.T., Hélène, C., Toulmé, J.J. Gene (1987) [Pubmed]
  21. Ectopic expression of toll-like receptor-3 (TLR-3) overcomes the double-stranded RNA (dsRNA) signaling defects of P2.1 cells. Sun, Y., Leaman, D.W. J. Interferon Cytokine Res. (2004) [Pubmed]
  22. Actinomycin D induces histone gamma-H2AX foci and complex formation of gamma-H2AX with Ku70 and nuclear DNA helicase II. Mischo, H.E., Hemmerich, P., Grosse, F., Zhang, S. J. Biol. Chem. (2005) [Pubmed]
  23. Studies on transcription termination and splicing of the rRNA precursor in vivo in the presence of proflavine. Nielsen, O.F., Carin, M., Westergaard, O. Nucleic Acids Res. (1984) [Pubmed]
  24. Internal Structure and Dynamics of Isolated Escherichia coli Nucleoids Assessed by Fluorescence Correlation Spectroscopy. Romantsov, T., Fishov, I., Krichevsky, O. Biophys. J. (2007) [Pubmed]
  25. Echinomycin: the first bifunctional intercalating agent in clinical trials. Foster, B.J., Clagett-Carr, K., Shoemaker, D.D., Suffness, M., Plowman, J., Trissel, L.A., Grieshaber, C.K., Leyland-Jones, B. Investigational new drugs. (1985) [Pubmed]
  26. The reaction between nitracrine and glutathione: implications for hypoxic cell radiosensitization and cytotoxicity. Wilson, W.R., Anderson, R.F. Int. J. Radiat. Oncol. Biol. Phys. (1989) [Pubmed]
  27. Breast cancer resistance protein and P-glycoprotein in 149 adult acute myeloid leukemias. Benderra, Z., Faussat, A.M., Sayada, L., Perrot, J.Y., Chaoui, D., Marie, J.P., Legrand, O. Clin. Cancer Res. (2004) [Pubmed]
  28. alpha-DNA X: alpha and beta tetrathymidilates covalently linked to oxazolopyridocarbazolium (OPC): comparative stabilization of oligo beta-[dT]:oligo beta-[dA] and oligo alpha-[dT]:oligo beta-[dA] duplexes by the intercalating agent. Bazile, D., Gautier, C., Rayner, B., Imbach, J.L., Paoletti, C., Paoletti, J. Nucleic Acids Res. (1989) [Pubmed]
  29. Phase II trial of piroxantrone in metastatic gastric adenocarcinoma. Pazdur, R., Bready, B., Scalzo, A.J., Brandof, J.E., Close, D.R., Kolbye, S., Winn, R.J. Investigational new drugs. (1994) [Pubmed]
  30. Oligo-alpha-thymidylates covalently linked to intercalating agents: circular dichroism studies of their interaction with complementary sequences. Durand, M., Maurizot, J.C., Asseline, U., Thuong, N.T., Hélène, C. Bioconjug. Chem. (1993) [Pubmed]
  31. Molecular analysis of mutations induced by the intercalating agent ellipticine at the hisD3052 allele of Salmonella typhimurium TA98. DeMarini, D.M., Abu-Shakra, A., Gupta, R., Hendee, L.J., Levine, J.G. Environ. Mol. Mutagen. (1992) [Pubmed]
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