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Chemical Compound Review

AG-G-53443     2-[methyl-(N'- phosphonocarbamimidoyl) amino...

Synonyms: CTK5C5695, AC1L19KA, 67-07-2, 143905-EP2287165A2, 143905-EP2287166A2, ...
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Disease relevance of phosphocreatine

  • Ten minutes of ischemia caused quiescence, a fall in interstitial pH (from 7.2 +/- 0.01 to 6.1 +/- 0.8), creatine phosphate (CP), and ATP (from 54.5 +/- 5.0 and 25.0 +/- 1.9 to 5.0 +/- 1.1 and 15.3 +/- 2.5 mumol/g dry wt, P < .01) [1].
  • Formation and utilization of novel high energy phosphate reservoirs in Ehrlich ascites tumor cells. Cyclocreatine-3-P and creatine-P [2].
  • The results can be summarized as follow: (a) In the normoxic brain, the ratio between PCr and Pi was greater than 1 (1.2-1.4), while under hypoxia or asphyxia a significant decrease that was correlated to the FiO2 levels was recorded [3].
  • Using results from both methods, at 20 degrees C the ratio of phosphorylcreatine split during a tetanus to O2 consumption during recovery ranged from 5.2 to 6.2 mumol/mumol, and postcontractile ATP hydrolysis was estimated to be 13.6 +/- 4.1 (n = 3) nmol/mumol total creatine [4].
  • Finally, in the presence of 100 microM MgATP and 250 microM MgADP, a decrease in PCr resulted in rigor; the half-maximal contracture being recorded at 1 mM PCr [5].

High impact information on phosphocreatine

  • We have blocked creatine kinase (CK)-mediated phosphocreatine (PCr) -->/<-- ATP transphosphorylation in skeletal muscle by combining targeted mutations in the genes encoding mitochondrial and cytosolic CK in mice [6].
  • Metabolite channeling: a phosphorylcreatine shuttle to mediate high energy phosphate transport between sperm mitochondrion and tail [7].
  • The finding of an isoenzyme of creatine phosphokinase attached to the M-line region of the myofibril revealed the peripheral receptor for the mitochondrially generated phosphorylcreatine [8].
  • In group 4, hypoperfusion resulted in progressive damage. pH fell to 6.2 +/- 0.7, diastolic pressure increased to 34 +/- 5.6 mm Hg, CP and ATP became depressed, and oxidative stress occurred [1].
  • After 45 min of reperfusion PCr recovered to 65 +/- 5% of control in untreated (group I) hearts compared with 89 +/- 8% in h-SOD-treated (group II) hearts (p less than .01 vs group I) and with 83 +/- 6% of control in h-SOD/catalase-treated (group III) hearts (p less than .05 vs group I) [9].

Chemical compound and disease context of phosphocreatine


Biological context of phosphocreatine

  • Doubling of the heart rate resulted in a significant decrease in phosphocreatine (PCr) content (11% at 28 degrees C, 8% at 37 degrees C), which was matched by an increase in inorganic phosphate (P(i)) content, although oxygen supply was shown to be nonlimiting [14].
  • Because a possible involvement of energy metabolism in the action of ADM was suggested previously, the adenylate energy charge and phosphorylcreatine mol fraction were determined in the ADM-treated cells [15].
  • A biochemical pathway for a cellular behaviour: pHi, phosphorylcreatine shuttles, and sperm motility [16].
  • These properties enable cyclocreatine-P to continue to thermodynamically buffer the adenylate system and transport high energy phosphate throughout the long muscle fibers at cytosolic pH values and phosphorylation potentials well below the range where the creatine-P system can function effectively [17].
  • Neither gestational age nor maternal diabetes affected the tissue's energy potential (ATP-to-ADP and PCr-to-Cr ratios) [18].

Anatomical context of phosphocreatine


Associations of phosphocreatine with other chemical compounds

  • Acetyl-P, ATP, enolpyruvate-P, creatine-P, and fructose-1,6-P2 are not phosphoryl donors [24].
  • (b) A clear correlation was found between the decrease in PCr/Pi values and the increased NADH redox state developed under decreased O2 supply to the brain [3].
  • In contrast with the untreated hearts, the nifedipine-treated hearts showed a rapid recovery of CP content during reperfusion [10].
  • The in vivo redox status of cytochromes at different FiO2 was directly compared with in vitro measured changes in cortical metabolites known to reflect energy production, i.e., glucose, pyruvate, lactate, phosphocreatine (PCr), ADP, and ATP [25].
  • This explanation is based on the slow diffusion of Mg2+ within the myofibril and on the contrast of PCr with both ATP and phosphoenolpyruvate, in that PCr does not bind Mg2+ under physiological conditions, whereas both the other two bind it more tightly than the products of their hydrolysis do [26].

Gene context of phosphocreatine

  • CONCLUSION: PCr accumulation may prevent TNFalpha-induced apoptosis in murine hepatocytes by suppression of truncated Bid targeting to mitochondria [27].
  • In M-CK-deficient muscles there was respective depletion of PCr, Cr and ATP levels to 31, 41 and 83% of normal [28].
  • The effects of La infusion on intracellular [PCr], [Pi], [phosphomonoester], [ADP], and [NH3] in PFK-deficient patients are consistent with the hypothesis that exogenous La augments the rate of oxidative phosphorylation in active muscle by bypassing the enzymatic block at PFK [29].
  • In contrast, the P-creatine and ATP decreased in the CA1 region at 48 and 96 hr of reflow, respectively [30].
  • To determine if this reduction was merely the result of an ATP maintenance system, ATP was regenerated using either phosphoenolpyruvate and pyruvate kinase (PEP-PK), or PCr and soluble bovine cardiac CK [31].

Analytical, diagnostic and therapeutic context of phosphocreatine

  • In contrast, denervation for as long as 6 weeks did not have a significant effect on the levels of creatine-P kinase molecules in this muscle type [20].
  • The best correlations were found between EEG activity and pH and PCr; correlation coefficients ranged from 0.93 to 0.95 [32].
  • Cr uptake was assessed by skeletal muscle (14)C-Cr accumulation to Cr and PCr by using hindlimb perfusion, and CrT protein content was assessed by Western blot [33].
  • ATP, ADP, AMP, IMP, and PCr were determined by HPLC with UV detection in controls after maximal and endurance training for 6 weeks with or without a respective final test and also after final exhaustive or endurance test without preceding training [34].
  • The levels of ATP and creatine phosphate (CP) at the site of MBF determination were measured 60 min after ligation, and mitochondrial function (RCI, QO2) in the ischemic and non-ischemic areas was determined [35].


  1. Metabolic adaptation during a sequence of no-flow and low-flow ischemia. A possible trigger for hibernation. Ferrari, R., Cargnoni, A., Bernocchi, P., Pasini, E., Curello, S., Ceconi, C., Ruigrok, T.J. Circulation (1996) [Pubmed]
  2. Formation and utilization of novel high energy phosphate reservoirs in Ehrlich ascites tumor cells. Cyclocreatine-3-P and creatine-P. Annesley, T.M., Walker, J.B. J. Biol. Chem. (1978) [Pubmed]
  3. Brain oxidative metabolism of the newborn dog: correlation between 31P NMR spectroscopy and pyridine nucleotide redox state. Mayevsky, A., Nioka, S., Subramanian, V.H., Chance, B. J. Cereb. Blood Flow Metab. (1988) [Pubmed]
  4. Reappraisal of diffusion, solubility, and consumption of oxygen in frog skeletal muscle, with applications to muscle energy balance. Mahler, M., Louy, C., Homsher, E., Peskoff, A. J. Gen. Physiol. (1985) [Pubmed]
  5. Rigor tension in single skinned rat cardiac cell: role of myofibrillar creatine kinase. Veksler, V.I., Lechene, P., Matrougui, K., Ventura-Clapier, R. Cardiovasc. Res. (1997) [Pubmed]
  6. Altered Ca2+ responses in muscles with combined mitochondrial and cytosolic creatine kinase deficiencies. Steeghs, K., Benders, A., Oerlemans, F., de Haan, A., Heerschap, A., Ruitenbeek, W., Jost, C., van Deursen, J., Perryman, B., Pette, D., Brückwilder, M., Koudijs, J., Jap, P., Veerkamp, J., Wieringa, B. Cell (1997) [Pubmed]
  7. Metabolite channeling: a phosphorylcreatine shuttle to mediate high energy phosphate transport between sperm mitochondrion and tail. Tombes, R.M., Shapiro, B.M. Cell (1985) [Pubmed]
  8. Transport of energy in muscle: the phosphorylcreatine shuttle. Bessman, S.P., Geiger, P.J. Science (1981) [Pubmed]
  9. Evidence for a reversible oxygen radical-mediated component of reperfusion injury: reduction by recombinant human superoxide dismutase administered at the time of reflow. Ambrosio, G., Weisfeldt, M.L., Jacobus, W.E., Flaherty, J.T. Circulation (1987) [Pubmed]
  10. Protective effect of nifedipine in myocardial ischemia assessed by phosphorus-31 nuclear magnetic resonance. Ruigrok, T.J., van Echteld, C.J., de Kruijff, B., Borst, C., Meijler, F.L. Eur. Heart J. (1983) [Pubmed]
  11. 3-Hydroxybutyrate aids the recovery of the energy state from aglycaemic hypoxia of adult but not neonatal rat brain slices. Brooks, K.J., Clark, J.B., Bates, T.E. J. Neurochem. (1998) [Pubmed]
  12. Effects of accumulation of phosphocreatine on utilization and restoration of high-energy phosphates during anoxia and recovery in thin hippocampal slices from the guinea pig. Yoneda, K., Arakawa, T., Asaoka, Y., Fukuoka, Y., Kinugasa, K., Takimoto, K., Okada, Y. Exp. Neurol. (1983) [Pubmed]
  13. Relative abilities of phosphagens with different thermodynamic or kinetic properties to help sustain ATP and total adenylate pools in heart during ischemia. Turner, D.M., Walker, J.B. Arch. Biochem. Biophys. (1985) [Pubmed]
  14. Cardiac high-energy phosphates adapt faster than oxygen consumption to changes in heart rate. Eijgelshoven, M.H., van Beek, J.H., Mottet, I., Nederhoff, M.G., van Echteld, C.J., Westerhof, N. Circ. Res. (1994) [Pubmed]
  15. Modification by adenosine of the effect of adriamycin on myocardial cells in culture. Seraydarian, M.W., Artaza, L. Cancer Res. (1979) [Pubmed]
  16. A biochemical pathway for a cellular behaviour: pHi, phosphorylcreatine shuttles, and sperm motility. Shapiro, B.M., Tombes, R.M. Bioessays (1985) [Pubmed]
  17. 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]
  18. Diabetes affects sorbitol and myo-inositol levels of neuroectodermal tissue during embryogenesis in rat. Sussman, I., Matschinsky, F.M. Diabetes (1988) [Pubmed]
  19. 31P NMR detection of subcellular creatine kinase fluxes in the perfused rat heart: contractility modifies energy transfer pathways. Joubert, F., Mazet, J.L., Mateo, P., Hoerter, J.A. J. Biol. Chem. (2002) [Pubmed]
  20. Effect of denervation on the levels and rates of synthesis of specific enzymes in "fast-twitch" (breast) muscle fibers of the chicken. Shackelford, J.E., Lebherz, H.G. J. Biol. Chem. (1981) [Pubmed]
  21. Light-induced changes in energy metabolites, guanine nucleotides, and guanylate cyclase within frog retinal layers. de Azeredo, F.A., Lust, W.D., Passonneau, J.V. J. Biol. Chem. (1981) [Pubmed]
  22. Effects of focal cortical freezing lesion on regional energy metabolism. Buczek, M., Ratcheson, R.A., Lust, W.D., McHugh, M., Pappius, H.M. J. Cereb. Blood Flow Metab. (1991) [Pubmed]
  23. The role of phosphorylcreatine and creatine in the regulation of mitochondrial respiration in human skeletal muscle. Walsh, B., Tonkonogi, M., Söderlund, K., Hultman, E., Saks, V., Sahlin, K. J. Physiol. (Lond.) (2001) [Pubmed]
  24. A specific enzyme for glucose 1,6-bisphosphate synthesis. Rose, I.A., Warms, J.V., Kaklij, G. J. Biol. Chem. (1975) [Pubmed]
  25. O2 dependence of in vivo brain cytochrome redox responses and energy metabolism in bloodless rats. Sylvia, A.L., Piantadosi, C.A. J. Cereb. Blood Flow Metab. (1988) [Pubmed]
  26. The effect of Mg2+ on cardiac muscle function: Is CaATP the substrate for priming myofibril cross-bridge formation and Ca2+ reuptake by the sarcoplasmic reticulum? Smith, G.A., Vandenberg, J.I., Freestone, N.S., Dixon, H.B. Biochem. J. (2001) [Pubmed]
  27. Relocation of truncated bid plays an important role in suppression of tumor necrosis factor alpha induced apoptosis in hepatocytes isolated from transgenic mouse. Shiotani, T., Yamanokuchi, S., Hatano, E., Ikai, I. J. Surg. Res. (2005) [Pubmed]
  28. Effects of the creatine analogue beta-guanidinopropionic acid on skeletal muscles of mice deficient in muscle creatine kinase. van Deursen, J., Jap, P., Heerschap, A., ter Laak, H., Ruitenbeek, W., Wieringa, B. Biochim. Biophys. Acta (1994) [Pubmed]
  29. Muscle metabolism during lactate infusion in human phosphofructokinase deficiency. Bertocci, L.A., Haller, R.G., Lewis, S.F. J. Appl. Physiol. (1993) [Pubmed]
  30. Energy metabolism in delayed neuronal death of CA1 neurons of the hippocampus following transient ischemia in the gerbil. Arai, H., Passonneau, J.V., Lust, W.D. Metabolic brain disease. (1986) [Pubmed]
  31. Specific enhancement of the cardiac myofibrillar ATPase by bound creatine kinase. Krause, S.M., Jacobus, W.E. J. Biol. Chem. (1992) [Pubmed]
  32. Concomitant EEG, lactate, and phosphorus changes by 1H and 31P NMR spectroscopy during repeated brief cerebral ischemia. Conger, K.A., Halsey, J.H., Luo, K.L., Tan, M.J., Pohost, G.M., Hetherington, H.P. J. Cereb. Blood Flow Metab. (1995) [Pubmed]
  33. Muscle creatine uptake and creatine transporter expression in response to creatine supplementation and depletion. Brault, J.J., Abraham, K.A., Terjung, R.L. J. Appl. Physiol. (2003) [Pubmed]
  34. Purine nucleotides and AMP deamination during maximal and endurance swimming exercise in heart and skeletal muscle of rats. Weicker, H., Hageloch, W., Luo, J., Müller, D., Werle, E., Sehling, K.M. International journal of sports medicine. (1990) [Pubmed]
  35. Beneficial effect of nipradilol (K-351) on acute myocardial ischemia. Study of the relationship between regional myocardial blood flow and energy metabolism. Okamoto, Y., Matsubara, T., Iyeda, N., Miyajima, K., Iida, K., Nishida, T., Kobayashi, S., Kakinuma, Y., Itoh, K., Hibi, N. Jpn. J. Pharmacol. (1990) [Pubmed]
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