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Chemical Compound Review

Adenophostin     [(2R,3R,4R,5R)-2-(6- aminopurin-9-yl)-4...

Synonyms: adenophostin a, CHEMBL204385, CHEBI:440381, DNC014777, LS-173343, ...
 
 
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High impact information on C13727

 

Biological context of C13727

 

Anatomical context of C13727

  • At pH 8.3, a synthetic analog of adenophostin A (which we named acyclophostin), in which most elements of the ribose ring have been removed, bound with substantially higher affinity (Kd = 2.76 +/- 0.26 nM) than Ins(1,4,5)P3 (Kd = 7.96 +/- 1.02 nM) to the 3H-Ins(1,4,5)P3-binding sites of hepatic membranes [9].
  • Here we report that activation of IP(3)R by adenophostin-A (AP) yields non-quantal Ca(2+)mobilization in mast cells [10].
  • Known agonists of the cerebellar InsP(3)receptor such as 3-deoxy InsP(3)and adenophostin A were also able to mobilize Ca(2+)from aorta microsomes [11].
  • These measurements, made at the single nuclear pore level, reveal a displacement of the central mass towards the nuclear side of the membrane following treatments with adenophostin A, a specific agonist of calcium channels (inositol 1,4,5-trisphosphate (IP(3)) receptors) located in the nuclear envelope [12].
 

Associations of C13727 with other chemical compounds

 

Gene context of C13727

  • We conclude that the IP(3)-binding domains of the various IP(3)R isoforms differ in binding characteristics for IP(3) and adenophostin A, and are differentially modulated by Ca(2+) and calmodulin, suggesting that the various IP(3)R isoforms can have different intracellular functions [17].
  • Cellular dialysis with phorbol 12-myristate 13-acetate, an activator of PKC, significantly reduced peak sodium current amplitude, while adenophostin A, an activator of IP(3) receptors, significantly increased peak sodium current amplitude [18].
 

Analytical, diagnostic and therapeutic context of C13727

References

  1. Functional properties of recombinant type I and type III inositol 1, 4,5-trisphosphate receptor isoforms expressed in COS-7 cells. Boehning, D., Joseph, S.K. J. Biol. Chem. (2000) [Pubmed]
  2. Adenophostin A induces spatially restricted calcium signaling in Xenopus laevis oocytes. Bird, G.S., Takahashi, M., Tanzawa, K., Putney, J.W. J. Biol. Chem. (1999) [Pubmed]
  3. Adenophostins, newly discovered metabolites of Penicillium brevicompactum, act as potent agonists of the inositol 1,4,5-trisphosphate receptor. Takahashi, M., Tanzawa, K., Takahashi, S. J. Biol. Chem. (1994) [Pubmed]
  4. Structural determinants of adenophostin A activity at inositol trisphosphate receptors. Correa, V., Riley, A.M., Shuto, S., Horne, G., Nerou, E.P., Marwood, R.D., Potter, B.V., Taylor, C.W. Mol. Pharmacol. (2001) [Pubmed]
  5. Down-regulation of the inositol 1,4,5-trisphosphate receptor in mouse eggs following fertilization or parthenogenetic activation. Jellerette, T., He, C.L., Wu, H., Parys, J.B., Fissore, R.A. Dev. Biol. (2000) [Pubmed]
  6. Molecular recognition of adenophostin, a very potent Ca2+ inducer, at the D-myo-inositol 1,4,5-trisphosphate receptor. Hotoda, H., Murayama, K., Miyamoto, S., Iwata, Y., Takahashi, M., Kawase, Y., Tanzawa, K., Kaneko, M. Biochemistry (1999) [Pubmed]
  7. Adenophostin-medicated quantal Ca2+ release in the purified and reconstituted inositol 1,4,5-trisphosphate receptor type 1. Hirota, J., Michikawa, T., Miyawaki, A., Takahashi, M., Tanzawa, K., Okura, I., Furuichi, T., Mikoshiba, K. FEBS Lett. (1995) [Pubmed]
  8. Intracellular calcium oscillations signal apoptosis rather than activation in in vitro aged mouse eggs. Gordo, A.C., Rodrigues, P., Kurokawa, M., Jellerette, T., Exley, G.E., Warner, C., Fissore, R. Biol. Reprod. (2002) [Pubmed]
  9. Acyclophostin: a ribose-modified analog of adenophostin A with high affinity for inositol 1,4,5-trisphosphate receptors and pH-dependent efficacy. Beecroft, M.D., Marchant, J.S., Riley, A.M., Van Straten, N.C., Van der Marel, G.A., Van Boom, J.H., Potter, B.V., Taylor, C.W. Mol. Pharmacol. (1999) [Pubmed]
  10. Sorting of calcium signals at the junctions of endoplasmic reticulum and mitochondria. Csordás, G., Hajnóczky, G. Cell Calcium (2001) [Pubmed]
  11. Subtype identification and functional properties of inositol 1,4, 5-trisphosphate receptors in heart and aorta. Tovey, S.C., Dyer, J.L., Godfrey, R.E., Khan, S.Z., Bilmen, J.G., Mezna, M., Michelangeli, F. Pharmacol. Res. (2000) [Pubmed]
  12. Nuclear side conformational changes in the nuclear pore complex following calcium release from the nuclear membrane. Mooren, O.L., Erickson, E.S., Moore-Nichols, D., Dunn, R.C. Physical biology. (2004) [Pubmed]
  13. Adenophostin A and inositol 1,4,5-trisphosphate differentially activate Cl- currents in Xenopus oocytes because of disparate Ca2+ release kinetics. Machaca, K., Hartzell, H.C. J. Biol. Chem. (1999) [Pubmed]
  14. Inframolecular studies of the protonation of adenophostin A: comparison with 1-D-myo-inositol 1,4,5-trisphosphate. Felemez, M., Marwood, R.D., Potter, B.V., Spiess, B. Biochem. Biophys. Res. Commun. (1999) [Pubmed]
  15. Association of the inositol (1,4,5)-trisphosphate receptor ligand binding site with phosphatidylinositol (4,5)-bisphosphate and adenophostin A. Glouchankova, L., Krishna, U.M., Potter, B.V., Falck, J.R., Bezprozvanny, I. Mol. Cell Biol. Res. Commun. (2000) [Pubmed]
  16. Conformational analysis of cyclophostin and designed analogs in comparison with the potent IP3 receptor agonist adenophostin A. Iwata, Y., de Kort, M., Challiss, R.A., van der Marel, G.A., van Boom, J.H., Miyamoto, S. Drug design and discovery. (2001) [Pubmed]
  17. Ca2+ and calmodulin differentially modulate myo-inositol 1,4, 5-trisphosphate (IP3)-binding to the recombinant ligand-binding domains of the various IP3 receptor isoforms. Vanlingen, S., Sipma, H., De Smet, P., Callewaert, G., Missiaen, L., De Smedt, H., Parys, J.B. Biochem. J. (2000) [Pubmed]
  18. Activation of protein kinase C and inositol 1,4,5-triphosphate receptors antagonistically modulate voltage-gated sodium channels in striatal neurons. Hourez, R., Azdad, K., Vanwalleghem, G., Roussel, C., Gall, D., Schiffmann, S.N. Brain Res. (2005) [Pubmed]
  19. Inositol 1,4,5-trisphosphate receptors are downregulated in mouse oocytes in response to sperm or adenophostin A but not to increases in intracellular Ca(2+) or egg activation. Brind, S., Swann, K., Carroll, J. Dev. Biol. (2000) [Pubmed]
 
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