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Chemical Compound Review

imido-diP     (phosphonoamino)phosphonic acid

Synonyms: imido-di-P, CHEMBL265450, AG-L-18751, AC1Q6RRY, CTK1A4164, ...
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Disease relevance of Imidodiphosphonic acid

  • Herein, a distinct protein-tyrosine phosphatase (PTPase) in membrane preparations from v-Ras transformed NIH 3T3 cells was found to be activated by guanyl-5'-yl imidodiphosphate (GMPPNP) and was identified as an effector for pertussis toxin (PTx)-sensitive G-protein alpha subunits [1].
  • The synthesis of the 536-nucleotide long run-off transcript resulting from initiation at the adenovirus major late promoter was found to be dependent upon the presence of either ATP or dATP (with the imido derivative adenyl-5'-yl imidodiphosphate being used as the substrate for the RNA polymerase elongation reaction) [2].
  • It is not activated by free Mg (2+), in contrast to the cytoplasmic pyrophosphatase from Rhodospirillum rubrum, and it is not inhibited by NaF, methylendiphosphate, or imidodiphosphate [3].
  • In a purified system from Escherichia coli containing ribosomes complexed with poly(uridylic acid) and N-acetyl-phenylalanyl-tRNA, the nonhydrolyzable analog of GTP, guanyl-5'-yl imidodiphosphate (Guo-5'-P2-NH-P), promotes polypeptide synthesis at a rate several times slower than GTP [4].

High impact information on Imidodiphosphonic acid

  • Uncapped U- or G-initiated transcripts were obtained in the presence of UMP-PNP or GMP-PNP, the respective imidodiphosphate analogs [5].
  • We have compared the working stroke on the binding of four myosin complexes (myosin, myosin-ADP, myosin-pyrophosphate, and myosin-adenyl-5'yl imidodiphosphate) with that observed while hydrolyzing ATP [6].
  • Moreover, NaF (in the presence of Al3+) and guanyl-5'-yl imidodiphosphate mediate strong activation of cyc- adenylyl cyclase provided the cholate extracts of brush border membranes are also present [7].
  • The kinetics of turkey erythrocyte membrane adenylate cyclase activation by beta-agonists and guanyl-5'-yl imidodiphosphate is explored as a function of the concentration of the GTP regulatory protein and of the catalytic unit [8].
  • An adenylate cyclase [ATP pyrophosphatelyase (cyclizing), EC] preparation that is not stimulated by NaF,5'-guanylyl imidodiphosphate, or Ca2+.calmodulin has been isolated from bovine cerebral cortex by Affi-Gel Blue chromatography and calmodulin-Sepharose chromatography [9].

Chemical compound and disease context of Imidodiphosphonic acid


Biological context of Imidodiphosphonic acid


Anatomical context of Imidodiphosphonic acid


Associations of Imidodiphosphonic acid with other chemical compounds

  • The initial rates of tryptic digestion at the 50/20-kDa junction in myosin subfragment 1 (S-1) were determined for free S-1, acto-S-1, and acto-S-1 in the presence of magnesium adenyl-5'-yl imidodiphosphate (Mg AMP-PNP) and MgATP under ionic strength conditions ranging from 30 to 124 mM [21].
  • Treatment of brain membranes with the guanine nucleotide guanyl-5'-yl imidodiphosphate prior to solubilization prevented the retention of [3H]dopamine but not [3H]SCH 23390-labeled soluble receptors [22].
  • Among other nucleotides tested (CTP, GTP, ITP, TTP, XTP, adenosine 5'-(beta,gamma-methylene)triphosphate (AMP-PCP), adenyl-5'-yl imidodiphosphate (AMP-P(NH)P), ADP, adenosine 5'-O-(3-thiotriphosphate) (ATP gamma S), and UTP), only UTP and ATP gamma S displayed biphasic effects with potencies and efficacies almost identical to those of ATP [23].
  • The hydrolysis-resistant analogs of GTP, such as guanosine 5'-3-O-(thio)triphosphate and guanyl-5'-yl imidodiphosphate, greatly potentiated the stimulatory effects of ATP and ADP on PtdEtn hydrolysis [24].
  • The affinity of binding sites for [3H]prazosin or for alpha-receptor agonists was the same in the three groups of rats and affinity for epinephrine was unaffected by the presence of guanyl-5'-yl imidodiphosphate (30-100 microM) [25].

Gene context of Imidodiphosphonic acid


Analytical, diagnostic and therapeutic context of Imidodiphosphonic acid


  1. Inactivation of raf-1 by a protein-tyrosine phosphatase stimulated by GTP and reconstituted by Galphai/o subunits. Dent, P., Reardon, D.B., Wood, S.L., Lindorfer, M.A., Graber, S.G., Garrison, J.C., Brautigan, D.L., Sturgill, T.W. J. Biol. Chem. (1996) [Pubmed]
  2. Energy requirement for specific transcription initiation by the human RNA polymerase II system. Sawadogo, M., Roeder, R.G. J. Biol. Chem. (1984) [Pubmed]
  3. Rhodobacter sphaeroides has a family II pyrophosphatase: comparison with other species of photosynthetic bacteria. Celis, H., Franco, B., Escobedo, S., Romero, I. Arch. Microbiol. (2003) [Pubmed]
  4. Polypeptide-chain elongation promoted by guanyl-5'-yl imidodiphosphate. Girbes, T., Vazquez, D., Modolell, J. Eur. J. Biochem. (1976) [Pubmed]
  5. Mechanism of RNA polymerase II--specific initiation of transcription in vitro: ATP requirement and uncapped runoff transcripts. Bunick, D., Zandomeni, R., Ackerman, S., Weinmann, R. Cell (1982) [Pubmed]
  6. The working stroke upon myosin-nucleotide complexes binding to actin. Steffen, W., Smith, D., Sleep, J. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  7. Intestinal brush border membranes contain regulatory subunits of adenylyl cyclase. Domínguez, P., Velasco, G., Barros, F., Lazo, P.S. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  8. Kinetics of interaction between beta-receptors, GTP protein, and the catalytic unit of turkey erythrocyte adenylate cyclase. Tolkovsky, A.M., Braun, S., Levitzki, A. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  9. Evidence for a dissociable protein subunit required for calmodulin stimulation of brain adenylate cyclase. Toscano, W.A., Westcott, K.R., LaPorte, D.C., Storm, D.R. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  10. Pertussis toxin reverses Gpp(NH)p inhibition of basal and forskolin activated adipocyte adenylate cyclase. Fain, J.N., O'Donnell, C.J., Mills, I., Gárciá-Sáinz, J.A. Biochem. Biophys. Res. Commun. (1983) [Pubmed]
  11. Hydrolysis of adenyl-5-yl imidodiphosphate by beef heart mitochondrial ATPase. Tomaszek, T.A., Schuster, S.M. J. Biol. Chem. (1986) [Pubmed]
  12. Modulation of dimer stability in yeast pyrophosphatase by mutations at the subunit interface and ligand binding to the active site. Salminen, A., Parfenyev, A.N., Salli, K., Efimova, I.S., Magretova, N.N., Goldman, A., Baykov, A.A., Lahti, R. J. Biol. Chem. (2002) [Pubmed]
  13. The role of calcium in the control of adrenal adenylate cyclase. Enhancement of enzyme activation by guanyl-5'-yl imidodiphosphate. Mahaffee, D.D., Ontjes, D.A. J. Biol. Chem. (1980) [Pubmed]
  14. Guanine nucleotide inhibition of cyc- S49 mouse lymphoma cell membrane adenylyl cyclase. Hildebrandt, J.D., Hanoune, J., Birnbaumer, L. J. Biol. Chem. (1982) [Pubmed]
  15. Hormone-stimulated desensitization of hormone-dependent adenylyl cyclase. Dual action of luteninizing hormone on pig graafian follicle membranes. Bockaert, J., Hunzicker-Dunn, M., Birnbaumer, L. J. Biol. Chem. (1976) [Pubmed]
  16. A minor component of the binding of [3H]guanyl-5'-yl imidodiphosphate to cardiac membranes associated with the activation of adenylate cyclase. Baker, S.P., Potter, L.T. J. Biol. Chem. (1981) [Pubmed]
  17. Effect of ethylene glycol and Ca2+ on the binding of Mg2+ x adenyl-5'-yl imidodiphosphate to rabbit skeletal myofibrils. Johnson, R.E. J. Biol. Chem. (1986) [Pubmed]
  18. On the mechanism of activation of fat cell adenylate cyclase by guanine nucleotides. An explanation for the biphasic inhibitory and stimulatory effects of the nucleotides and the role of hormones. Rodbell, M. J. Biol. Chem. (1975) [Pubmed]
  19. Sarcoplasmic reticulum ATPase catalyzes hydrolysis of adenyl-5'-yl imidodiphosphate. Taylor, J.S. J. Biol. Chem. (1981) [Pubmed]
  20. Kinesin and cytoplasmic dynein binding to brain microsomes. Yu, H., Toyoshima, I., Steuer, E.R., Sheetz, M.P. J. Biol. Chem. (1992) [Pubmed]
  21. The binding of myosin subfragment 1 to actin can be measured by proteolytic rates method. Duong, A.M., Reisler, E. J. Biol. Chem. (1987) [Pubmed]
  22. Dopamine D1 receptors characterized with [3H]SCH 23390. Solubilization of a guanine nucleotide-sensitive form of the receptor. Niznik, H.B., Otsuka, N.Y., Dumbrille-Ross, A., Grigoriadis, D., Tirpak, A., Seeman, P. J. Biol. Chem. (1986) [Pubmed]
  23. Dual regulation of arachidonic acid release by P2U purinergic receptors in dibutyryl cyclic AMP-differentiated HL60 cells. Xing, M., Thévenod, F., Mattera, R. J. Biol. Chem. (1992) [Pubmed]
  24. ATP stimulates the hydrolysis of phosphatidylethanolamine in NIH 3T3 cells. Potentiating effects of guanosine triphosphates and sphingosine. Kiss, Z., Anderson, W.B. J. Biol. Chem. (1990) [Pubmed]
  25. Decreased alpha 1-adrenoceptor responsiveness and density in liver cells of thyroidectomized rats. Preiksaitis, H.G., Kan, W.H., Kunos, G. J. Biol. Chem. (1982) [Pubmed]
  26. Quantitative analysis of the complex between p21ras and the Ras-binding domain of the human Raf-1 protein kinase. Herrmann, C., Martin, G.A., Wittinghofer, A. J. Biol. Chem. (1995) [Pubmed]
  27. Coupling of glucagon receptor to adenylyl cyclase. Requirement of a receptor-related guanyl nucleotide binding site for coupling of receptor to the enzyme. Iyengar, R., Swartz, T.L., Birnbaumer, L. J. Biol. Chem. (1979) [Pubmed]
  28. Unliganded epidermal growth factor receptor dimerization induced by direct interaction of quinazolines with the ATP binding site. Arteaga, C.L., Ramsey, T.T., Shawver, L.K., Guyer, C.A. J. Biol. Chem. (1997) [Pubmed]
  29. Secretin stimulates cyclic AMP formation in the rat brain. Fremeau, R.T., Korman, L.Y., Moody, T.W. J. Neurochem. (1986) [Pubmed]
  30. Regional stimulatory and inhibitory effects of guanine nucleotides on [125I]galanin binding in rat brain: relationship with the rate of occupancy of galanin receptors by endogenous galanin. Lagny-Pourmir, I., Epelbaum, J. Neuroscience (1992) [Pubmed]
  31. Temperature-modulated binding of ADP and adenyl-5'-yl imidodiphosphate to myosin subfragment 1 studied by calorimetric titration. Kodama, T. J. Biol. Chem. (1981) [Pubmed]
  32. Identification of a gamma subunit associated with the adenylyl cyclase regulatory proteins Ns and Ni. Hildebrandt, J.D., Codina, J., Risinger, R., Birnbaumer, L. J. Biol. Chem. (1984) [Pubmed]
  33. ATP formation from adenyl-5'-yl imidodiphosphate, a nonhydrolyzable ATP analog. Penningroth, S.M., Olehnik, K., Cheung, A. J. Biol. Chem. (1980) [Pubmed]
  34. Single photon emission computed tomography in the diagnosis of inflammatory spondyloarthropathies. Hanly, J.G., Barnes, D.C., Mitchell, M.J., MacMillan, L., Docherty, P. J. Rheumatol. (1993) [Pubmed]
  35. Value of positive myocardial infarction imaging in coronary care units. Joseph, S.P., Pereira-Prestes, A.V., Ell, P.J., Donaldson, R., Somerville, W., Emanuel, R.W. British medical journal. (1979) [Pubmed]
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