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Chemical Compound Review

cyclocreatine     2-(2-amino-4,5- dihydroimidazol-1...

Synonyms: CHEMBL179900, SureCN450343, SureCN673051, AG-K-68340, BSPBio_003151, ...
 
 
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Disease relevance of NSC707961

 

Psychiatry related information on NSC707961

 

High impact information on NSC707961

  • Growth rate inhibition of subcutaneously implanted tumors results from feeding rats and athymic nude mice diets containing 1% cyclocreatine or 1%, 2%, 5%, or 10% creatine [6].
  • Cell cycle studies of cyclocreatine, a new anticancer agent [7].
  • We used the creatine analogs cyclocreatine (cCr) or beta-guanidopropionate (beta GPA) to test if mass action ratios (gamma) for CK in muscle could be predicted from combined equilibrium constants (Kcomb) measured in solutions mimicking the intracellular environment [8].
  • We tested the hypothesis that if ischemia is important for the formation of NCF from the myocardium, then blocking (or delaying) ischemic changes with cyclocreatine should inhibit the release of NCF [9].
  • Next the effect of cyclocreatine on neutrophils in the Boyden chamber was determined and it was found that it did not alter neutrophil migration, which excludes a direct inhibitory effect on the cells [9].
 

Chemical compound and disease context of NSC707961

  • ATP levels were sustained at high values substantially longer in breast muscle of cyclocreatine-fed chicks, compared to control-fed chicks, during total ischemia initiated 2 h after injection of both groups with the beta-adrenergic agonist isoproterenol (5 mg/kg subcutaneous) [2].
  • Cyclocreatine 0.5% did not increase survival time during hypoxia (5% O2) [4].
  • The growth-inhibitory effect of cyclocreatine (CCr) and the kinetics of CCr and Na(+) cotransport were investigated in MCF7 human breast cancer cells and its adriamycin-resistant subline with use of (31)P- and (23)Na-NMR spectroscopy [10].
 

Biological context of NSC707961

 

Anatomical context of NSC707961

  • Cyclocreatine inhibits the production of neutrophil chemotactic factors from isolated hearts [9].
  • Cyclocreatine (cCr), whose phosphorylated form is a very poor substrate for CK, inhibited proliferation of the L1236 cell line nearly entirely [11].
  • Suspensions of chopped whole brain from 11- to 14-day-old chick embryos were incubated with 30 mM cyclocreatine for 90 min, resulting in accumulation of 100 mumol/g dry weight of cyclocreatine-P, and then incubated for up to 1 h with a series of excitatory amino acids of widely differing potencies [15].
  • Further experiments utilizing type IV collagen as attractant demonstrated that cyclocreatine inhibited the chemokinetic (91%) and the haptotactic (73%) responses and the in vitro invasion of A2058-055 cells through Matrigel-coated membranes (88%) [16].
  • Cyclocreatine-treated dogs (n = 6) were injected intravenously with cyclocreatine solution (600 mg/kg) 1 h before the experiment and during ligation of the coronary artery [17].
 

Associations of NSC707961 with other chemical compounds

  • After 2 weeks, cyclocreatine-fed (n = 8) and control (n = 7) rats were anesthetized, the heart was excised and retrograde perfusion was begun at 10 ml/min per g with 37 degrees C, phosphate-free buffer containing glucose and oxygen [3].
  • Creatine and cyclocreatine attenuate MPTP neurotoxicity [18].
  • Porcine carotid arteries were superfused for 12 h with Krebs-Henseleit buffer at 22 degrees C, containing 11 mM glucose as substrate, and supplemented with either 20 mM beta-guanidinopropionic acid (beta-GPA), methyl-guanidinopropionic acid (m-GPA), guanidinoacetic acid (GA) or cyclocreatine (cCr) [19].
 

Gene context of NSC707961

  • In addition, motility stimulation of A2058-055 cells by either autotaxin or fibronectin was markedly inhibited by cyclocreatine [16].
  • Moreover, the data suggest a possible interplay between p53 mutations, HCC, CK expression, and the growth-inhibitory effects of cyclocreatine in HCC [20].
 

Analytical, diagnostic and therapeutic context of NSC707961

References

  1. Cyclocreatine accumulation leads to cellular swelling in C6 glioma multicellular spheroids: diffusion and one-dimensional chemical shift nuclear magnetic resonance microscopy. Schiffenbauer, Y.S., Tempel, C., Abramovitch, R., Meir, G., Neeman, M. Cancer Res. (1995) [Pubmed]
  2. Enhanced ability of skeletal muscle containing cyclocreatine phosphate to sustain ATP levels during ischemia following beta-adrenergic stimulation. Turner, D.M., Walker, J.B. J. Biol. Chem. (1987) [Pubmed]
  3. Myocardial protection during ischemia by prior feeding with the creatine analog: cyclocreatine. Jacobstein, M.D., Gerken, T.A., Bhat, A.M., Carlier, P.G. J. Am. Coll. Cardiol. (1989) [Pubmed]
  4. Cyclocreatine phosphate, an analogue of creatine phosphate, does not improve hypoxic tolerance in mice. Artru, A.A., Michenfelder, J.D. J. Neurochem. (1982) [Pubmed]
  5. Neuroprotective effects of creatine and cyclocreatine in animal models of Huntington's disease. Matthews, R.T., Yang, L., Jenkins, B.G., Ferrante, R.J., Rosen, B.R., Kaddurah-Daouk, R., Beal, M.F. J. Neurosci. (1998) [Pubmed]
  6. Inhibition of rate of tumor growth by creatine and cyclocreatine. Miller, E.E., Evans, A.E., Cohn, M. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  7. Cell cycle studies of cyclocreatine, a new anticancer agent. Martin, K.J., Winslow, E.R., Kaddurah-Daouk, R. Cancer Res. (1994) [Pubmed]
  8. Creatine kinase equilibration follows solution thermodynamics in skeletal muscle. 31P NMR studies using creatine analogs. Wiseman, R.W., Kushmerick, M.J. J. Biol. Chem. (1995) [Pubmed]
  9. Cyclocreatine inhibits the production of neutrophil chemotactic factors from isolated hearts. Elgebaly, S.A., Allam, M.E., Rossomando, E.F., Cordis, G.A., Forouhar, F., Farghaly, A., Kreutzer, D.L. Am. J. Pathol. (1990) [Pubmed]
  10. Kinetics of cyclocreatine and Na(+) cotransport in human breast cancer cells: mechanism of activity. Maril, N., Degani, H., Rushkin, E., Sherry, A.D., Cohn, M. Am. J. Physiol. (1999) [Pubmed]
  11. Hodgkin disease-derived cell lines expressing ubiquitous mitochondrial creatine kinase show growth inhibition by cyclocreatine treatment independent of apoptosis. Kornacker, M., Schlattner, U., Wallimann, T., Verneris, M.R., Negrin, R.S., Kornacker, B., Staratschek-Jox, A., Diehl, V., Wolf, J. Int. J. Cancer (2001) [Pubmed]
  12. Creatine biosynthesis during embryonic development. False feedback suppression of liver amidinotransferase by N-acetimidoylsarcosine and 1-carboxymethyl-2-iminoimidazolidine (cyclocreatine). Walker, J.B., Hannan, J.K. Biochemistry (1976) [Pubmed]
  13. Enhancement of cardiac function by cyclocreatine in models of cardiopulmonary bypass. Houser, S.L., Elkerm, A.F., Wei, Z., Doyle, K., Houser, D., Liu, X.K., Tyles, E., Kaddurah-Daouk, R., Elgebaly, S.A. J. Mol. Cell. Cardiol. (1995) [Pubmed]
  14. Molecular characterization of the human CRT-1 creatine transporter expressed in Xenopus oocytes. Dai, W., Vinnakota, S., Qian, X., Kunze, D.L., Sarkar, H.K. Arch. Biochem. Biophys. (1999) [Pubmed]
  15. Utilization of the synthetic phosphagen cyclocreatine phosphate by a simple brain model during stimulation by neuroexcitatory amino acids. Woznicki, D.T., Walker, J.B. J. Neurochem. (1988) [Pubmed]
  16. Cyclocreatine inhibits stimulated motility in tumor cells possessing creatine kinase. Mulvaney, P.T., Stracke, M.L., Nam, S.W., Woodhouse, E., O'Keefe, M., Clair, T., Liotta, L.A., Khaddurah-Daouk, R., Schiffmann, E. Int. J. Cancer (1998) [Pubmed]
  17. Cyclocreatine inhibits neutrophil accumulation in the myocardium of a canine model of coronary artery occlusion and reperfusion. Elgebaly, S.A., Allam, M.E., Houser, S., Hashmi, F., Forouhar, F., Miano, D. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  18. Creatine and cyclocreatine attenuate MPTP neurotoxicity. Matthews, R.T., Ferrante, R.J., Klivenyi, P., Yang, L., Klein, A.M., Mueller, G., Kaddurah-Daouk, R., Beal, M.F. Exp. Neurol. (1999) [Pubmed]
  19. The utilisation of creatine and its analogues by cytosolic and mitochondrial creatine kinase. Boehm, E.A., Radda, G.K., Tomlin, H., Clark, J.F. Biochim. Biophys. Acta (1996) [Pubmed]
  20. Elevated creatine kinase activity in primary hepatocellular carcinoma. Meffert, G., Gellerich, F.N., Margreiter, R., Wyss, M. BMC gastroenterology [electronic resource]. (2005) [Pubmed]
  21. Creatine and cyclocreatine treatment of human colon adenocarcinoma xenografts: 31P and 1H magnetic resonance spectroscopic studies. Kristensen, C.A., Askenasy, N., Jain, R.K., Koretsky, A.P. Br. J. Cancer (1999) [Pubmed]
 
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