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Chemical Compound Review

Decamine     1-[10-(4-amino-2-methyl- quinolin-1...

Synonyms: Dequadin, Dequavet, Labosept, Dekadin, Solvidont, ...
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Disease relevance of Labosept


High impact information on Labosept

  • Dequalinium has previously been shown to be an anticarcinoma agent (M. J. Weiss et al., Proc. Natl. Acad. Sci. USA, 84: 5444-5448, 1987) [6].
  • Dequalinium belongs to a group of cationic lipophilic drugs believed to be selectively cytotoxic to malignant cells of epithelial origin by virtue of their accumulation in mitochondria [7].
  • We found that multidrug-resistant lines were less sensitive than parental cell lines to the intrinsic growth inhibitory effects of dequalinium (IC50, 4.4 versus 0.3 microM in multidrug-resistant and sensitive P388 cells, respectively), whereas they were equally sensitive as the parental line to the effects of trifluoperazine [7].
  • Studies conducted with types I, II, and III rat brain isozymes, resolved by hydroxylapatite chromatography, demonstrate that dequalinium inhibits each of them with similar potency (50% inhibitory concentration of 11 microM) and imply that the site of contact on the enzyme is a highly conserved region [6].
  • Related studies show that the analogues display the same rank order of inhibitory potency when tested with the trypsin-generated catalytic fragment of the enzyme, indicating that dequalinium inhibits kinase activity through an interaction with the catalytic subunit [6].

Chemical compound and disease context of Labosept

  • Dequalinium was able to inhibit both processes in vitro with close correlation to a murine malaria model, reducing parasitemia levels, prolonging the survival time post-infection and curing 40% of infected mice using a combination therapy with a loading dose of chloroquine [8].

Biological context of Labosept


Anatomical context of Labosept

  • The trypanocidal drug crystal violet, as well as other cationic drugs such as dequalinium, induced a rapid dose-related collapse of the inner mitochondrial membrane potential [14].
  • Affinity labeling was abolished on both liver and brain membranes by apamin, scyllatoxin, dequalinium, gallamine, and d-tubocurarine [15].
  • When applied to the intracellular side of inside-out excised patches from Xenopus oocytes, dequalinium blocks CNGA1 channels with a K(1/2) approximately 190 nM and CNGA1+CNGB1 channels with a K(1/2) approximately 385 nM, at 0 mV [11].
  • 7. Direct activation of SKCa channels by raising cytosolic Ca2+ in hepatocytes evoked an outward current which was reduced by the three blockers, with dequalinium being the most potent [16].
  • 1. Nine bis-quinolinyl and bis-quinolinium compounds related to dequalinium, and previously shown to block apamin-sensitive small conductance Ca(2+)-activated K(+) channels (SK(Ca)), have been tested for their inhibitory effects on actions mediated by intermediate conductance Ca(2+)-activated K(+) channels (IK(Ca)) in rabbit blood cells [17].

Associations of Labosept with other chemical compounds


Gene context of Labosept

  • Dequalinium has recently been reported to block CNGA1 and CNGA2 channels expressed in Xenopus laevis [22].
  • Peptide toxins such as apamin and scyllatoxin, as well as organic compounds such as quaternary salts of bicuculline, dequalinium, UCL 1684 and UCL 1848 serve as non-specific SK channel blockers [23].
  • Photoinduced inactivation of protein kinase C by dequalinium identifies the RACK-1-binding domain as a recognition site [24].
  • We previously noted that dequalinium is a high-affinity blocker of CNGA1 channels from the intracellular side, with little or no state dependence at 0 mV [25].
  • Therefore, it is pertinent to consider that dequalinium could be used as a molecular probe to assess toxic mechanisms related to the amyloid formation of alpha-synuclein [9].

Analytical, diagnostic and therapeutic context of Labosept


  1. Photo-induced inactivation of protein kinase calpha by dequalinium inhibits motility of murine melanoma cells. Sullivan, R.M., Stone, M., Marshall, J.F., Uberall, F., Rotenberg, S.A. Mol. Pharmacol. (2000) [Pubmed]
  2. Expression of Escherichia coli TehA gives resistance to antiseptics and disinfectants similar to that conferred by multidrug resistance efflux pumps. Turner, R.J., Taylor, D.E., Weiner, J.H. Antimicrob. Agents Chemother. (1997) [Pubmed]
  3. Ganglion-blocking activity of dequalinium in frog and rat sympathetic ganglia in vitro. Dunn, P.M. Eur. J. Pharmacol. (1993) [Pubmed]
  4. Toxicity of the mitochondrial poison dequalinium chloride in a murine model system. Gamboa-Vujicic, G., Emma, D.A., Liao, S.Y., Fuchtner, C., Manetta, A. Journal of pharmaceutical sciences. (1993) [Pubmed]
  5. Study of the selective cytotoxic properties of cationic, lipophilic mitochondrial-specific compounds in gynecologic malignancies. Christman, J.E., Miller, D.S., Coward, P., Smith, L.H., Teng, N.N. Gynecol. Oncol. (1990) [Pubmed]
  6. Inhibition of rodent protein kinase C by the anticarcinoma agent dequalinium. Rotenberg, S.A., Smiley, S., Ueffing, M., Krauss, R.S., Chen, L.B., Weinstein, I.B. Cancer Res. (1990) [Pubmed]
  7. Comparison of the efficacy of a phenothiazine and a bisquinaldinium calmodulin antagonist against multidrug-resistant P388 cell lines. Hait, W.N., Pierson, N.R. Cancer Res. (1990) [Pubmed]
  8. Plasmodium berghei: in vitro and in vivo activity of dequalinium. Rodrigues, J.R., Gamboa de Dom??nguez, N. Exp. Parasitol. (2007) [Pubmed]
  9. Dequalinium-induced protofibril formation of alpha-synuclein. Lee, C.H., Kim, H.J., Lee, J.H., Cho, H.J., Kim, J., Chung, K.C., Jung, S., Paik, S.R. J. Biol. Chem. (2006) [Pubmed]
  10. Dequalinium induces a selective depletion of mitochondrial DNA from HeLa human cervical carcinoma cells. Schneider Berlin, K.R., Ammini, C.V., Rowe, T.C. Exp. Cell Res. (1998) [Pubmed]
  11. Dequalinium: a novel, high-affinity blocker of CNGA1 channels. Rosenbaum, T., Islas, L.D., Carlson, A.E., Gordon, S.E. J. Gen. Physiol. (2003) [Pubmed]
  12. Synthesis and quantitative structure-activity relationship of a novel series of small conductance Ca(2+)-activated K+ channel blockers related to dequalinium. Galanakis, D., Davis, C.A., Ganellin, C.R., Dunn, P.M. J. Med. Chem. (1996) [Pubmed]
  13. Synthesis and structure-activity relationships of dequalinium analogues as K+ channel blockers. Investigations on the role of the charged heterocycle. Galanakis, D., Davis, C.A., Del Rey Herrero, B., Ganellin, C.R., Dunn, P.M., Jenkinson, D.H. J. Med. Chem. (1995) [Pubmed]
  14. Digitonin permeabilization does not affect mitochondrial function and allows the determination of the mitochondrial membrane potential of Trypanosoma cruzi in situ. Vercesi, A.E., Bernardes, C.F., Hoffmann, M.E., Gadelha, F.R., Docampo, R. J. Biol. Chem. (1991) [Pubmed]
  15. Comparable 30-kDa apamin binding polypeptides may fulfill equivalent roles within putative subtypes of small conductance Ca(2+)-activated K+ channels. Wadsworth, J.D., Doorty, K.B., Strong, P.N. J. Biol. Chem. (1994) [Pubmed]
  16. Discrimination between subtypes of apamin-sensitive Ca(2+)-activated K+ channels by gallamine and a novel bis-quaternary quinolinium cyclophane, UCL 1530. Dunn, P.M., Benton, D.C., Campos Rosa, J., Ganellin, C.R., Jenkinson, D.H. Br. J. Pharmacol. (1996) [Pubmed]
  17. Compounds that block both intermediate-conductance (IK(Ca)) and small-conductance (SK(Ca)) calcium-activated potassium channels. Malik-Hall, M., Ganellin, C.R., Galanakis, D., Jenkinson, D.H. Br. J. Pharmacol. (2000) [Pubmed]
  18. Photoinactivation of the F1-ATPase from spinach chloroplasts by dequalinium is accompanied by derivatization of methionine beta183. Ren, H.M., Allison, W.S. J. Biol. Chem. (1997) [Pubmed]
  19. Anticarcinoma activity of a novel drug, 3-ethyl-3'-methyl-thiatelluracarbocyanine iodide (Te), a tellurium-containing cyanine targeted at mitochondria. Sun, X., Wong, J.R., Song, K., Chen, L.B. Clin. Cancer Res. (1996) [Pubmed]
  20. Cloning and expression of a small-conductance Ca(2+)-activated K+ channel from the mouse cochlea: coexpression with alpha9/alpha10 acetylcholine receptors. Nie, L., Song, H., Chen, M.F., Chiamvimonvat, N., Beisel, K.W., Yamoah, E.N., Vázquez, A.E. J. Neurophysiol. (2004) [Pubmed]
  21. Suramin prevents cerebellar granule cell-death induced by dequalinium. Chan, C.F., Lin-Shiau, S.Y. Neurochem. Int. (2001) [Pubmed]
  22. Mutation of the pore glutamate affects both cytoplasmic and external dequalinium block in the rat olfactory CNGA2 channel. Qu, W., Moorhouse, A.J., Lewis, T.M., Pierce, K.D., Barry, P.H. Eur. Biophys. J. (2005) [Pubmed]
  23. Small conductance Ca2+-activated K+ channels as targets of CNS drug development. Blank, T., Nijholt, I., Kye, M.J., Spiess, J. Current drug targets. CNS and neurological disorders. (2004) [Pubmed]
  24. Photoinduced inactivation of protein kinase C by dequalinium identifies the RACK-1-binding domain as a recognition site. Rotenberg, S.A., Sun, X.G. J. Biol. Chem. (1998) [Pubmed]
  25. State-dependent block of CNG channels by dequalinium. Rosenbaum, T., Gordon-Shaag, A., Islas, L.D., Cooper, J., Munari, M., Gordon, S.E. J. Gen. Physiol. (2004) [Pubmed]
  26. Inhibition of rat colon tumor isograft growth with dequalinium chloride. Bleday, R., Weiss, M.J., Salem, R.R., Wilson, R.E., Chen, L.B., Steele, G. Archives of surgery (Chicago, Ill. : 1960) (1986) [Pubmed]
  27. Dequalinium vesicles form stable complexes with plasmid DNA which are protected from DNase attack. Lasch, J., Meye, A., Taubert, H., Koelsch, R., Mansa-ard, J., Weissig, V. Biol. Chem. (1999) [Pubmed]
  28. Determination of the quaternary ammonium compounds dequalinium and cetylpyridinium chlorides in candy-based lozenges by high-performance liquid chromatography. Taylor, R.B., Toasaksiri, S., Reid, R.G., Wood, D. The Analyst. (1997) [Pubmed]
  29. Comparative in vitro evaluation of dequalinium B, a new boron carrier for neutron capture therapy (NCT). Adams, D.M., Ji, W., Barth, R.F., Tjarks, W. Anticancer Res. (2000) [Pubmed]
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