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Chemical Compound Review

Acridinamine     acridin-1-amine

Synonyms: CHEMBL146525, CCRIS 2105, AG-G-04304, NSC-170666, LS-14180, ...
 
 
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Disease relevance of Aminoacridine

  • Membrane preparations isolated from the photosynthetic lamellae of the cyanobacterium Plectonema boryanum generate upon illumination a transmembrane pH gradient of approximately 2 to 3 pH units (acid inside), as determined from the distribution of either fluorescent or radioactive amines (9 aminoacridine and [14C]methylamine, respectively) [1].
  • Both the electronic and steric properties of the side chain are shown to be important in determining the hypoxia selectivity of the compounds, by controlling the degree of aminoacridine/iminoacridan tautomerism [2].
  • The main disadvantages of the cholinesterase inhibitors used in clinical trials are the short duration of action in the case of physostigmine and the potential for liver toxicity seen with the aminoacridine derivatives [3].
  • Could an aminoacridine interfere with the cellular mechanisms involved in the process of human immunodeficiency virus infection [4]?
  • The response to nitracrine, 1-nitro-9-[3'(N,N-dimethyl)aminopropyl] aminoacridine, an anticancer agent, was examined in two strains of murine lymphoma L5178Y inversely cross-sensitive to X-rays and UV light [5].
 

High impact information on Aminoacridine

 

Biological context of Aminoacridine

  • Results from these studies indicate that oxidative stress and GSH depletion may enhance Alzheimer patients' susceptibility to the hepatotoxic potential of aminoacridine drugs [11].
 

Anatomical context of Aminoacridine

 

Associations of Aminoacridine with other chemical compounds

  • The probes used were a membrane-bound fluorescent aminoacridine, which monitors surface charge-density changes, the native carotenoids and added oxonol VI for monitoring electrical potential in the membrane and the pH indicators neutral red and cresol red [15].
 

Gene context of Aminoacridine

  • Inhibition of the U1A-RNA complex by an aminoacridine derivative [16].
  • The addition of the aminoacridine derivative to stem loop 2 RNA increases the susceptibility of other portions of the loop to digestion by RNase A, which implies that binding of the ligand changes the conformation or dynamics of the stem loop target site [16].
 

Analytical, diagnostic and therapeutic context of Aminoacridine

  • Single cell uptake and metabolism of DACA and the related but more basic aminoacridine 9-[3-(dimethylamino)propylamino]acridine (DAPA), and penetration through V79 and EMT6 MCL, were investigated by high-performance liquid chromatography [17].

References

  1. Energy transduction in the photosynthetic membranes of the cyanobacterium (blue-green alga) P-lectonema boryanum. Padan, E., Schuldiner, S. J. Biol. Chem. (1978) [Pubmed]
  2. Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "iminoacridan hypothesis". Denny, W.A., Atwell, G.J., Anderson, R.F., Wilson, W.R. J. Med. Chem. (1990) [Pubmed]
  3. Brain selective inhibition of acetylcholinesterase: a novel approach to therapy for Alzheimer's disease. Enz, A., Amstutz, R., Boddeke, H., Gmelin, G., Malanowski, J. Prog. Brain Res. (1993) [Pubmed]
  4. Could an aminoacridine interfere with the cellular mechanisms involved in the process of human immunodeficiency virus infection? Sotelo, J. Med. Hypotheses (1996) [Pubmed]
  5. Cytotoxicity and the effect of combined treatment with X-rays of an anticancer 1-nitro-9-aminoacridine derivative in L5178Y-R and L5178Y-S cells. Szumiel, I., Walicka, M. Neoplasma (1980) [Pubmed]
  6. Physicochemical properties correlated with drug resistance and the reversal of drug resistance in Plasmodium falciparum. Bray, P.G., Hawley, S.R., Mungthin, M., Ward, S.A. Mol. Pharmacol. (1996) [Pubmed]
  7. Zona pellucida-mediated acrosomal exocytosis in mouse spermatozoa: characterization of an intermediate stage prior to the completion of the acrosome reaction. Kligman, I., Glassner, M., Storey, B.T., Kopf, G.S. Dev. Biol. (1991) [Pubmed]
  8. NMR studies of configuration and tautomeric equilibria in nitroacridine antitumor agents. Boyd, M., Denny, W.A. J. Med. Chem. (1990) [Pubmed]
  9. Evidence for plasma membrane impermeability to small ions in acrosome-intact mouse spermatozoa bound to mouse zonae pellucidae, using an aminoacridine fluorescent pH probe: time course of the zona-induced acrosome reaction monitored by both chlortetracycline and pH probe fluorescence. Lee, M.A., Storey, B.T. Biol. Reprod. (1985) [Pubmed]
  10. Effects of anthrapyrazole antineoplastic agents on lipid peroxidation. Frank, P., Novak, R.F. Biochem. Biophys. Res. Commun. (1986) [Pubmed]
  11. Effect of glutathione depletion and oxidative stress on the in vitro cytotoxicity of velnacrine maleate. al Casey, S., Brewster, D., Viau, C., Acosta, D. Toxicol. Lett. (1995) [Pubmed]
  12. Quantitation of secretion by rat basophilic leukemia cells by measurements of quinacrine uptake. Kolber, M.A., Henkart, P.A. Biochim. Biophys. Acta (1988) [Pubmed]
  13. The potassium permeability of pancreatic islet cells: mechanisms of control and influence on insulin release. Henquin, J.C. Horm. Metab. Res. Suppl. (1980) [Pubmed]
  14. A fluorescence phase contrast study of the interaction between Toxoplasma gondii and lysosomes in living cells. Khavkin, T.N., Freidlin, I.S. Zeitschrift für Parasitenkunde (Berlin, Germany) (1977) [Pubmed]
  15. Characterization of reconstituted ATPase complex proteoliposomes prepared from the thermophilic cyanobacterium Synechococcus 6716. van Walraven, H.S., Lubberding, H.J., Marvin, H.J., Kraayenhof, R. Eur. J. Biochem. (1983) [Pubmed]
  16. Inhibition of the U1A-RNA complex by an aminoacridine derivative. Gayle, A.Y., Baranger, A.M. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  17. Extravascular transport of the DNA intercalator and topoisomerase poison N-[2-(Dimethylamino)ethyl]acridine-4-carboxamide (DACA): diffusion and metabolism in multicellular layers of tumor cells. Hicks, K.O., Pruijn, F.B., Baguley, B.C., Wilson, W.R. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
 
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