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Chemical Compound Review

canavanine     2-amino-4- (diaminomethylideneamino) oxy...

Synonyms: DL-Canavanine, C1625_SIGMA, HSDB 3471, LS-47817, AR-1K8743, ...
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Disease relevance of canavanine

  • Cumulative toxicity was reduced greatly when canavanine was administered at a dose level of 2.0 g/kg for 5 days (weight loss of 13%) [1].
  • Analysis of the relationship of caloric deprivation to tumor growth reduction established that canavanine-mediated curtailment of tumor growth was not caused by reduced food intake and its associated loss in body weight [1].
  • In Escherichia coli, Lon protease is responsible for the rate-limiting step in degradation of highly unstable proteins such as SulA, RcsA, and lambdaN protein, as well as for about 50% of the rapid degradation of abnormal proteins such as canavanine-containing proteins [2].
  • The function of ScRheb is dependent on having an intact effector domain since mutations in the effector domain of ScRheb are incapable of complementing canavanine hypersensitivity of scrheb disruptant cells [3].
  • Adeno-associated virus replication. The effect of L-canavanine or a helper virus mutation on accumulation of viral capsids and progeny single-stranded DNA [4].

Psychiatry related information on canavanine


High impact information on canavanine

  • Pro-opiomelanocortin that accumulated in the presence of canavanine was also sulfated [7].
  • The arginyl-tRNA synthetase of the bruchid beetle larvae discriminates between L-arginine and L-canavanine, and canavanyl proteins are not synthesized [8].
  • Such hypothesis is confirmed by our in vivo experiments, showing that the administration of the NOS inhibitor L-canavanine to endothelioma-bearing mice significantly reduced both the volume and the relapse time of the tumor [9].
  • Strains selectively mutagenized in this site display a mutator phenotype detected as a drastically increased spontaneous forward mutation rate to canavanine resistance or as an elevated reversion rate to lysine prototrophy [10].
  • Both the size and the structure of the PP precursor was supported by the results of peptide analysis of biosynthetically labeled pro-PP isolated from canine PP cells in which processing was prevented by the arginine analogue canavanine [11].

Chemical compound and disease context of canavanine


Biological context of canavanine


Anatomical context of canavanine

  • Canavanine inhibits vimentin assembly but not its synthesis in chicken embryo erythroid cells [21].
  • Continued exposure of the fat body to canavanine decreases in vitro protein secretion but the proportion of canavanyl vitellogenin to native vitellogenin increases [22].
  • Double-label protein-turnover experiments with larvae injected with [14C]canavanine- and [3H]arginine-containing hemolymph proteins showed that canavanine-containing proteins were degraded preferentially [23].
  • Furthermore, cloned canavanine-resistant variant cells having integrated copies of the CAT minigenes expressed CAT at similar levels as compared to the parental cell lines [16].
  • Using the human colonic tumor cell line, HT-29, time-dose studies were performed with log-phase cultures in order to determine conditions which maximize the incorporation of L-canavanine into cellular proteins while leaving a large fraction of the cells viable for subsequent gamma-ray survival measurements [18].

Associations of canavanine with other chemical compounds


Gene context of canavanine

  • APOBEC3G expression caused a 20-fold increase in frequency of mutation to canavanine-resistance, which was further elevated in a uracil DNA glycosylase-deficient background [28].
  • This gene, which we have designated STI1, for stress inducible, was also induced by the amino acid analog canavanine and showed a slight increase in expression as cells moved into stationary phase [29].
  • Disruption of the MLH1 gene results in elevated spontaneous mutation rates during vegetative growth as measured by forward mutation to canavanine resistance and reversion of the hom3-10 allele [30].
  • Genetic analysis of Saccharomyces cerevisiae also has identified a role for Rad27p in mutation avoidance. rad27Delta mutants display both a repeat tract instability phenotype and a high rate of forward mutations to canavanine resistance that result primarily from duplications of DNA sequences that are flanked by direct repeats [31].
  • Although rad23Delta rpn10Delta displays similar sensitivity to DNA damage as a rad23Delta single mutant, deletion of RAD23 in rpn10Delta significantly increased sensitivity to canavanine, a phenotype associated with an rpn10Delta single mutant [32].

Analytical, diagnostic and therapeutic context of canavanine

  • The reduction in tumor volume, expressed as the percentage of regression, was 22% in animals receiving canavanine, 3.0 g/kg daily for 5 days and 60% in the 3.0-g/kg-daily-for-9-days treatment group [1].
  • Both the intracellular and secreted albumin produced by canavanine-treated cells were analyzed by DEAE-cellulose chromatography and were found to be more acidic than normal proalbumin and albumin [33].
  • In the present study, we evaluated the effects of L-canavanine, a selective iNOS inhibitor, in an animal model of septic shock, with a particular focus on tissue oxidative metabolism and organ functions [34].
  • The relation was restored by dexamethasone (which also restored in vivo blood pressure and flow), but not by L-canavanine (which restored perfusion pressure by further mobilization of intracellular Ca2+) [14].
  • Synchronized cell cultures were infected with 32P-labelled or unlabelled BPV in the presence or absence of aphidicolin and L-canavanine [35].


  1. Growth inhibition of a rat colon tumor by L-canavanine. Thomas, D.A., Rosenthal, G.A., Gold, D.V., Dickey, K. Cancer Res. (1986) [Pubmed]
  2. Role of the heat shock protein DnaJ in the lon-dependent degradation of naturally unstable proteins. Jubete, Y., Maurizi, M.R., Gottesman, S. J. Biol. Chem. (1996) [Pubmed]
  3. The Saccharomyces cerevisiae Rheb G-protein is involved in regulating canavanine resistance and arginine uptake. Urano, J., Tabancay, A.P., Yang, W., Tamanoi, F. J. Biol. Chem. (2000) [Pubmed]
  4. Adeno-associated virus replication. The effect of L-canavanine or a helper virus mutation on accumulation of viral capsids and progeny single-stranded DNA. Myers, M.W., Carter, B.J. J. Biol. Chem. (1981) [Pubmed]
  5. Comparison of the effects of specific and nonspecific inhibition of nitric oxide synthase on morphine analgesia, tolerance and dependence in mice. Ozek, M., Uresin, Y., Güngör, M. Life Sci. (2003) [Pubmed]
  6. Detrimental effects of nitric oxide inhibition on hepatic encephalopathy in rats with thioacetamide-induced fulminant hepatic failure: role of nitric oxide synthase isoforms. Chu, C.J., Chang, C.C., Wang, T.F., Lee, F.Y., Chang, F.Y., Chen, Y.C., Chan, C.C., Huang, H.C., Wang, S.S., Lee, S.D. J. Gastroenterol. Hepatol. (2006) [Pubmed]
  7. Rat pro-opiomelanocortin contains sulfate. Hoshina, H., Hortin, G., Boime, I. Science (1982) [Pubmed]
  8. A novel means for dealing with L-canavanine, a toxic metabolite. Rosenthal, G.A., Dahlman, D.L., Janzen, D.H. Science (1976) [Pubmed]
  9. Middle T antigen-transformed endothelial cells exhibit an increased activity of nitric oxide synthase. Ghigo, D., Arese, M., Todde, R., Vecchi, A., Silvagno, F., Costamagna, C., Dong, Q.G., Alessio, M., Heller, R., Soldi, R., Trucco, F., Garbarino, G., Pescarmona, G., Mantovani, A., Bussolino, F., Bosia, A. J. Exp. Med. (1995) [Pubmed]
  10. The 3' to 5' exonuclease activity located in the DNA polymerase delta subunit of Saccharomyces cerevisiae is required for accurate replication. Simon, M., Giot, L., Faye, G. EMBO J. (1991) [Pubmed]
  11. A cDNA encoding a small common precursor for human pancreatic polypeptide and pancreatic icosapeptide. Boel, E., Schwartz, T.W., Norris, K.E., Fiil, N.P. EMBO J. (1984) [Pubmed]
  12. L-canavanine incorporation into vitellogenin and macromolecular conformation. Rosenthal, G.A., Reichhart, J.M., Hoffmann, J.A. J. Biol. Chem. (1989) [Pubmed]
  13. Induction of brain ornithine decarboxylase during recovery from metabolic, mechanical, thermal, or chemical injury. Dienel, G.A., Cruz, N.F. J. Neurochem. (1984) [Pubmed]
  14. Effects of dexamethasone and L-canavanine on the intracellular calcium-contraction relation of the rat tail artery during septic shock. Mansart, A., Bollaert, P.E., Giummelly, P., Capdeville-Atkinson, C., Atkinson, J. Am. J. Physiol. Heart Circ. Physiol. (2006) [Pubmed]
  15. Beneficial effects of L-canavanine, a selective inhibitor of inducible nitric oxide synthase, during rodent endotoxaemia. Liaudet, L., Feihl, F., Rosselet, A., Markert, M., Hurni, J.M., Perret, C. Clin. Sci. (1996) [Pubmed]
  16. Human argininosuccinate synthetase minigenes are subject to arginine-mediated repression but not to trans induction. Boyce, F.M., Anderson, G.M., Rusk, C.D., Freytag, S.O. Mol. Cell. Biol. (1986) [Pubmed]
  17. Antitumor activity of L-canavanine against L1210 murine leukemia. Green, M.H., Brooks, T.L., Mendelsohn, J., Howell, S.B. Cancer Res. (1980) [Pubmed]
  18. Enhancement of human tumor cell killing by L-canavanine in combination with gamma-radiation. Green, M.H., Ward, J.F. Cancer Res. (1983) [Pubmed]
  19. Lupus-inducing drugs alter the structure of supercoiled circular DNA domains. Zacharias, W., Koopman, W.J. Arthritis Rheum. (1990) [Pubmed]
  20. How an inhibitor of the HIV-I protease modulates proteasome activity. Schmidtke, G., Holzhütter, H.G., Bogyo, M., Kairies, N., Groll, M., de Giuli, R., Emch, S., Groettrup, M. J. Biol. Chem. (1999) [Pubmed]
  21. Canavanine inhibits vimentin assembly but not its synthesis in chicken embryo erythroid cells. Moon, R.T., Lazarides, E. J. Cell Biol. (1983) [Pubmed]
  22. In vitro incorporation of L-canavanine into vitellogenin of the fat body of the migratory locust Locusta migratoria migratorioides. Pines, M., Rosenthal, G.A., Applebaum, S.W. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  23. L-Canavanine and protein synthesis in the tobacco hornworm Manduca sexta. Rosenthal, G.A., Dahlman, D.L. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  24. Purification and characterization of the higher plant enzyme L-canaline reductase. Rosenthal, G.A. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  25. UVA radiation is highly mutagenic in cells that are unable to repair 7,8-dihydro-8-oxoguanine in Saccharomyces cerevisiae. Kozmin, S., Slezak, G., Reynaud-Angelin, A., Elie, C., de Rycke, Y., Boiteux, S., Sage, E. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  26. Sensitivity of mammalian cells expressing mutant ubiquitin to protein-damaging agents. Tsirigotis, M., Zhang, M., Chiu, R.K., Wouters, B.G., Gray, D.A. J. Biol. Chem. (2001) [Pubmed]
  27. Arginine deiminase from Mycoplasma arthritidis. Structure-activity relationships among substrates and competitive inhibitors. Smith, D.W., Ganaway, R.L., Fahrney, D.E. J. Biol. Chem. (1978) [Pubmed]
  28. APOBEC3G hypermutates genomic DNA and inhibits Ty1 retrotransposition in yeast. Schumacher, A.J., Nissley, D.V., Harris, R.S. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  29. Isolation and characterization of STI1, a stress-inducible gene from Saccharomyces cerevisiae. Nicolet, C.M., Craig, E.A. Mol. Cell. Biol. (1989) [Pubmed]
  30. Dual requirement in yeast DNA mismatch repair for MLH1 and PMS1, two homologs of the bacterial mutL gene. Prolla, T.A., Christie, D.M., Liskay, R.M. Mol. Cell. Biol. (1994) [Pubmed]
  31. Identification of rad27 mutations that confer differential defects in mutation avoidance, repeat tract instability, and flap cleavage. Xie, Y., Liu, Y., Argueso, J.L., Henricksen, L.A., Kao, H.I., Bambara, R.A., Alani, E. Mol. Cell. Biol. (2001) [Pubmed]
  32. Pleiotropic defects caused by loss of the proteasome-interacting factors Rad23 and Rpn10 of Saccharomyces cerevisiae. Lambertson, D., Chen, L., Madura, K. Genetics (1999) [Pubmed]
  33. Secretion of proalbumin by canavanine-treated Hep-G2 cells. Redman, C.M., Avellino, G., Yu, S. J. Biol. Chem. (1983) [Pubmed]
  34. L-canavanine improves organ function and tissue adenosine triphosphate levels in rodent endotoxemia. Liaudet, L., Fishman, D., Markert, M., Perret, C., Feihl, F. Am. J. Respir. Crit. Care Med. (1997) [Pubmed]
  35. Reversible inhibition of bovine parvovirus DNA replication by aphidicolin and L-canavanine. Robertson, A.T., Bates, R.C., Stout, E.R. J. Gen. Virol. (1984) [Pubmed]
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