ethenoadenosine triphosphate


Summary: 1,N-6-Ethenoadenosine triphosphate. A fluorescent analog of adenosine triphosphate.

Top Publications

  1. Ramos S, Moura J, Aureliano M. Recent advances into vanadyl, vanadate and decavanadate interactions with actin. Metallomics. 2012;4:16-22 pubmed publisher
    ..By affecting actin structure and function, vanadium can regulate many cellular processes of great physiological significance...
  2. Kardos R, Pozsonyi K, Nevalainen E, Lappalainen P, Nyitrai M, Hild G. The effects of ADF/cofilin and profilin on the conformation of the ATP-binding cleft of monomeric actin. Biophys J. 2009;96:2335-43 pubmed publisher
    ..The results of the fluorescence quenching experiments support a structural mechanism regarding the regulation of the nucleotide exchange on actin monomers by ADF/cofilin and profilin. ..
  3. Honzatko R, Lipscomb W. Interactions of phosphate ligands with Escherichia coli aspartate carbamoyltransferase in the crystalline state. J Mol Biol. 1982;160:265-86 pubmed
  4. Takács Kollár V, Nyitrai M, Hild G. The effect of mouse twinfilin-1 on the structure and dynamics of monomeric actin. Biochim Biophys Acta. 2016;1864:840-6 pubmed publisher
    ..The results suggest that the nucleotide binding cleft shifted into a more closed and stable conformational state of actin in the presence of twinfilin-1. ..
  5. Modzelewski R, Conner M. Disparate cytogenetic responses of peripheral blood and spleen lymphocytes to ethenoadenine nucleotides in vitro; maximal expression in splenic lymphocytes under conditions of enhanced membrane permeabilization. Carcinogenesis. 1990;11:571-6 pubmed
    Exogenously supplied 1,N6-ethenoadenosine triphosphate (epsilon-ATP) and 1,N6-ethenodeoxyadenosine triphosphate (epsilon-dATP) are potent inducers of sister chromatid exchanges (SCEs) in murine spleen lymphocytes but not in peripheral ..
  6. Kinosian H, Selden L, Gershman L, Estes J. Interdependence of profilin, cation, and nucleotide binding to vertebrate non-muscle actin. Biochemistry. 2000;39:13176-88 pubmed
    ..The data suggest that profilin binding to actin weakens nucleotide binding to actin by disrupting Mg(2+) coordination in the actin central cleft. ..
  7. Tesi C, Travers F, Barman T. Transient kinetics of the interaction of 1,N6-ethenoadenosine 5'-triphosphate with myosin subfragment 1 under normal and cryoenzymic conditions: a comparison with adenosine 5'-triphosphate. Biochemistry. 1988;27:4903-8 pubmed
    ..With ATP these values are 8 microM and 16 s-1, respectively. There is a large difference in the delta H for k2: 50 kJ.mol-1 for epsilon-ATP and 119 kJ.mol-1 for ATP.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  8. Harvey S, Cheung H. Fluorescence studies of 1,N6-ethenoadenosine triphosphate bound to G-actin: the nucleotide base is inaccessible to water. Biochem Biophys Res Commun. 1976;73:865-8 pubmed
    When 1,N6-ethenoadenosine triphosphate (epsilon-ATP) is free in solution, its fluorescence is collisionally quenched by iodide ion, by methionine, by tryptophan, and by cysteine...
  9. Palczewski K, Kochman M. Photoaffinity labeling of rabbit muscle fructose-1,6-bisphosphate aldolase with 8-azido-1,N6-ethenoadenosine 5'-triphosphate. Biochemistry. 1987;26:3466-71 pubmed
    ..Thr-265 was identified as the residue that was covalently modified by 8-N3-epsilon ATP. On the basis of these results and other data we propose a model for the mononucleotide binding site. ..

More Information


  1. Nowak E, Strzelecka Golaszewska H, Goody R. Kinetics of nucleotide and metal ion interaction with G-actin. Biochemistry. 1988;27:1785-92 pubmed
    ..abstract truncated at 250 words) ..
  2. Todorov L, Mihaylova Todorova S, Westfall T, Sneddon P, Kennedy C, Bjur R, et al. Neuronal release of soluble nucleotidases and their role in neurotransmitter inactivation. Nature. 1997;387:76-9 pubmed
    ..This release of specific nucleotidases together with ATP represents a new mechanism for terminating the actions of a neurotransmitter. ..
  3. Korenbaum E, Nordberg P, Björkegren Sjögren C, Schutt C, Lindberg U, Karlsson R. The role of profilin in actin polymerization and nucleotide exchange. Biochemistry. 1998;37:9274-83 pubmed
  4. Schobert B. Enzymatic synthesis of ATP analogs and their purification by reverse-phase high-performance liquid chromatography. Anal Biochem. 1995;226:288-92 pubmed
    ..After freeze-drying of the pooled fractions, the yield of the synthesized nucleoside triphosphate was approximately 70%. The described procedures are applicable either for analytical investigations or for semi-preparative purposes. ..
  5. Diniz C, Fresco P, Goncalves J. Regional differences in extracellular purine degradation in the prostatic and epididymal portions of the rat vas deferens. Clin Exp Pharmacol Physiol. 2005;32:721-7 pubmed
  6. Pavlov D, Muhlrad A, Cooper J, Wear M, Reisler E. Severing of F-actin by yeast cofilin is pH-independent. Cell Motil Cytoskeleton. 2006;63:533-42 pubmed
    ..The pH-independent severing by cofilin was confirmed using actin labeled at Cys374 with Oregon Green 488 maleimide. The depolymerization of actin by cofilin was faster at high pH. ..
  7. Ohm T, Wegner A. Random copolymerization of ATP-actin and ADP-actin. Biochemistry. 1991;30:11193-7 pubmed
    ..According to the analysis of the critical concentrations, the equilibrium constants for incorporation of ATP-actin or ADP-actin into filaments were independent of the type of nucleotide bound to contiguous subunits. ..
  8. Lv X, Huang L, Chen W, Wang X, Huang Y, Deng C, et al. Molecular characterization and serological reactivity of a vacuolar ATP synthase subunit ?-like protein from Clonorchis sinensis. Parasitol Res. 2014;113:1545-54 pubmed publisher
    ..This fundamental study would contribute to further researches that are related to growth and development and immunomodulation of C. sinensis. ..
  9. Pate E, Franks Skiba K, White H, Cooke R. The use of differing nucleotides to investigate cross-bridge kinetics. J Biol Chem. 1993;268:10046-53 pubmed
    ..D., Belknap, B., and Jiang, W. (1993) J. Biol. Chem. 268, 10039-10045) is used to better define the actomyosin interaction in fibers. ..
  10. Gualix J, Alvarez A, Pintor J, Miras Portugal M. Studies of chromaffin granule functioning by flow cytometry: transport of fluorescent epsilon-ATP and granular size increase induced by ATP. Receptors Channels. 1999;6:449-61 pubmed
    ..Moreover, no increase occurred in the presence of F- or acetate. The Cl- channel blockers were poorly effective, and only 2-(phenylamino)-benzoic acid (DPC) exhibited an effect on the ATP-induced granular size increase. ..
  11. Ooi A, Mihashi K. Effects of subtilisin cleavage of monomeric actin on its nucleotide binding. J Biochem. 1996;120:1104-10 pubmed
    ..Furthermore, the kinetic analysis of ATP exchange revealed that the binding equilibrium between ATP and divalent cation-free cleaved G-actin was much slower than that in the case of intact G-actin. ..
  12. Fenton R, Dobson J. Fluorometric quantitation of adenosine concentration in small samples of extracellular fluid. Anal Biochem. 1992;207:134-41 pubmed
    ..Thus, this assay is useful for determining the adenosine concentration in microliter samples of extracellular fluid and should facilitate investigations dealing with the functions of adenosine. ..
  13. Goldschmidt Clermont P, Machesky L, Doberstein S, Pollard T. Mechanism of the interaction of human platelet profilin with actin. J Cell Biol. 1991;113:1081-9 pubmed
    ..Lindberg (1985. Nature [Lond.] 318:472-474) that polyphosphoinositides inhibit the effects of profilin on actin polymerization, so lipid metabolism must also be taken into account when considering the functions of profilin in a cell. ..
  14. Janmey P, Hvidt S, Oster G, Lamb J, Stossel T, Hartwig J. Effect of ATP on actin filament stiffness. Nature. 1990;347:95-9 pubmed
    ..These data support earlier proposals that actin is not merely a passive cable, but has an active mechanochemical role in cell function. ..
  15. Obsil T, Merola F, Lewit Bentley A, Amler E. The isolated H4-H5 cytoplasmic loop of Na,K-ATPase overexpressed in Escherichia coli retains its ability to bind ATP. FEBS Lett. 1998;426:297-300 pubmed
    ..Isolation of a soluble H4-H5 loop with the native ATP binding site is a crucial step for detailed studies of the molecular mechanism of ATP binding and utilisation. ..
  16. Franks Skiba K, Hwang T, Cooke R. Quenching of fluorescent nucleotides bound to myosin: a probe of the active-site conformation. Biochemistry. 1994;33:12720-8 pubmed
    ..Thus nucleotides in the myosin pocket do not become more accessible to the solvent when myosin binds to actin in either rigor-ADP or active complexes.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  17. Eads J, Mahoney N, Vorobiev S, Bresnick A, Wen K, Rubenstein P, et al. Structure determination and characterization of Saccharomyces cerevisiae profilin. Biochemistry. 1998;37:11171-81 pubmed
    ..The in vivo and in vitro properties of yeast profilin mutants with altered poly-L-proline and actin binding sites are discussed in the context of the crystal structure. ..
  18. Virta P, Holmström T, Munter T, Nyholm T, Kronberg L, Sjöholm R. Fluorescent 7- and 8-methyl etheno derivatives of adenosine and 6-amino-9-ethylpurine: syntheses and fluorescence properties. Nucleosides Nucleotides Nucleic Acids. 2003;22:85-98 pubmed
    ..Also, the stabilites of 5 and 7 in aqueous solutions were determined and found to be higher than that of the etheno derivative of adenosine. ..
  19. Sharon E, Zündorf G, Lévesque S, Beaudoin A, Reiser G, Fischer B. Fluorescent epsilon-ATP analogues for probing physicochemical properties of proteins. Synthesis, biochemical evaluation, and sensitivity to properties of the medium. Bioorg Med Chem. 2004;12:6119-35 pubmed
    ..An inverse relationship and a linear relationship were found between the pK(a) values of 3b and the medium dielectricity and viscosity, respectively. These correlations help the calibration of properties of a protein ATP-binding site. ..
  20. Mayernik J, Conner M, Giam C. Methods for the isolation and detection of etheno adducts in nucleotide pools in vivo following exposure to ethyl carbamate. J Chromatogr. 1990;526:407-22 pubmed
    ..Several etheno adducts (i.e. ethenoadenine, etheno-AMP, etheno-ADP and etheno-ATP) were also detected in total spleen cell nucleotide pools of trout following acute ethyl carbamate exposure. ..
  21. Miki M, Kouyama T. Domain motion in actin observed by fluorescence resonance energy transfer. Biochemistry. 1994;33:10171-7 pubmed
    ..In G-actin, the mean distance between probes was 2.79 nm with a full width at half-maximum of 3.91 nm, indicating a large number of conformational substates in solution.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  22. Conner M, Modzelewski R, Kawatani N. Sister chromatid exchange induced by etheno-ATP derivatives in vitro. Cancer Res. 1989;49:3839-43 pubmed
  23. Gualix J, Pintor J, Miras Portugal M. Characterization of nucleotide transport into rat brain synaptic vesicles. J Neurochem. 1999;73:1098-104 pubmed
    ..The mitochondrial ATP/ADP exchange inhibitor atractyloside, N-ethylmaleimide, and polysulfonic aromatic compounds such as Evans blue and 4,4'-diisothiocyanostilbene-2,2'-disulfonic acid also inhibit epsilon-ATP vesicular transport. ..
  24. White H, Belknap B, Jiang W. Kinetics of binding and hydrolysis of a series of nucleoside triphosphates by actomyosin-S1. Relationship between solution rate constants and properties of muscle fibers. J Biol Chem. 1993;268:10039-45 pubmed
    ..1993) to determine the average distance over which cross-bridges remain attached during unloaded shortening to be 5-12 nm. ..
  25. Kasprzak A. Myosin subfragment 1 activates ATP hydrolysis on Mg(2+)-G-actin. Biochemistry. 1994;33:12456-62 pubmed
    ..The effect of deoxyribonuclease I on the rates of nucleotide dissociation and hydrolysis was examined.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  26. Kim D, Churchich J. Active site modification of 4-aminobutyrate aminotransferase with ATP analogs. Biochim Biophys Acta. 1987;916:265-70 pubmed
    ..It is postulated that the catalytic domain of 4-aminobutyrate aminotransferase is accessible to bulky reagents of greater length than the substrates 4-aminobutyrate and alpha-ketoglutarate. ..
  27. Frieden C, Patane K. Mechanism for nucleotide exchange in monomeric actin. Biochemistry. 1988;27:3812-20 pubmed
    ..muscle G-actin has been treated to obtain ADP, 1,N6-ethenoadenosine diphosphate (epsilon-ADP), or 1,N6-ethenoadenosine triphosphate (epsilon-ATP) at the nucleotide binding site and either Mg2+ or Ca2+ at high- and moderate-affinity ..
  28. Xie L, Li W, Rhodes T, White H, Schoenberg M. Transient kinetic analysis of N-phenylmaleimide-reacted myosin subfragment-1. Biochemistry. 1999;38:5925-31 pubmed
    ..W. (1978) Biochemistry 17, 3432]. However, NPM-modified S1 exhibited virtually no fluorescence enhancement upon ATP binding. This provides further evidence that M.ATP is the predominant intermediate of NPM-S1-catalyzed ATP hydrolysis. ..
  29. Eldin P, Le Cunff M, Vosberg H, Mornet D, Leger J. Mapping of the actomyosin interfaces. Proc Natl Acad Sci U S A. 1994;91:2772-6 pubmed
    ..Rypnieski, R. W., Schmidt-Bäse, K., Smith, R., Tomchick, D. R., Benning, M. M., Winkelmann, D. A., Wesenberg, G. & Holden, H. M. (1993) Science 261, 50-58]. ..
  30. Kasprzak A. Myosin subfragment 1 inhibits dissociation of nucleotide and calcium from G-actin. J Biol Chem. 1993;268:13261-6 pubmed
    ..The removal of the last 3 amino acids from actin produced a derivative whose behavior in binding to S1, as well as in the kinetics of epsilon ATP and Ca2+ dissociation, was undistinguishable from the unmodified protein. ..
  31. De La Cruz E, Pollard T. Nucleotide-free actin: stabilization by sucrose and nucleotide binding kinetics. Biochemistry. 1995;34:5452-61 pubmed
    ..2 x 10(-9) M for Mg(2+)-ATP-actin, 4.4 x 10(-9) M for Mg(2+)-epsilon ATP-actin, and 1.2 x 10(-10) M for Ca(2+)-ATP-actin. ..
  32. Gualix J, Abal M, Pintor J, Miras Portugal M. Presence of epsilon-adenosine tetraphosphate in chromaffin granules after transport of epsilon-ATP. FEBS Lett. 1996;391:195-8 pubmed
    ..15 pmol/mg of granular protein). Intragranular concentrations of epsilon-ATP higher than 500 pmol/mg of protein (approximately to 175 microM intragranular) resulted in a non-saturable production of epsilon-Ap4. ..
  33. Root D, Reisler E. The accessibility of etheno-nucleotides to collisional quenchers and the nucleotide cleft in G- and F-actin. Protein Sci. 1992;1:1014-22 pubmed
    ..Thus, the binding of S-1 induces conformational changes in the cleft region of actin that are different from those caused by Mg2+ polymerization of actin.(ABSTRACT TRUNCATED AT 250 WORDS) ..