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Chemical Compound Review

riboxine     [[(2R,3S,4R,5R)-3,4- dihydroxy-5-(6-oxo-3H...

Synonyms: Riboxin, AG-J-05225, CHEBI:17808, AC1L1NED, LS-84008, ...
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Disease relevance of Riboxin

  • IDP blocked the stimulatory effects of IFN in this bone resorption model [1].
  • Root conduction time (RCT), defined as the time difference between M-wave latency by cervical magnetic stimulation (CMS) and the total peripheral motor conduction time calculated from the shortest F-wave latency, was investigated in patients with inflammatory demyelinating neuropathies (IDP) and amyotrophic lateral sclerosis (ALS) [2].
  • For example, inflammatory demyelinating neuropathy (IDP) is often the first manifestation of HIV disease, when CD4 lymphocyte counts are relatively high [3].
  • During 22 years, we identified six patients who had clinical features of parkinsonism and dementia and who at autopsy had both IDP and AD and 20 parkinsonian patients without dementia who at autopsy had only IPD [4].
  • Using RT-PCR, we determined the expression of angiogenic regulators in DMBA-induced intraductal hyperplasia (IDP), carcinoma in situ (CIS), invasive tumors (INV), as well as normal tissue [5].

High impact information on Riboxin

  • Reverse-phase high-performance liquid chromatography analysis additionally shows that this enzyme has broad substrate specificity toward other nucleotides, UTP, UDP, ITP, and IDP [6].
  • Analysis of the relative rates of hydrolysis of nucleoside diphosphates (GDP = IDP > UDP > CDP >> ADP) suggests that soluble eNTPDase6 is a diphosphatase most likely not involved in regulation of ADP levels important for circulatory hemostasis [7].
  • Various fluorescence approaches also reveal an increased affinity of the catalytic site in mutant as compared with wild-type enzyme for GDP, IDP, and 2'(3')-N-methylanthraniloyl GDP [8].
  • Studies of in vitro assembly of isolated alpha-, beta-, and gamma- subunits into an active ATPase showed that ATP, GTP, and ITP all supported assembly, with half-maximal reconstitution of ATPase occurring at concentrations of 100-200 microM, whereas ADP, GDP, and IDP did not [9].
  • GDP is a competitive inhibitor of IDP exchange, a result predicted for the substituted enzyme mechanism but inconsistent with ternary complex mechanisms that involve an intermediate complex containing EF-Ts and both substrates [10].

Chemical compound and disease context of Riboxin


Biological context of Riboxin


Anatomical context of Riboxin

  • The apparent Km of inosine-5'-diphosphatase for IDP was unchanged when microsomes were treated with phospholipase C or at pH 10.3 after both these treatments approximately 85% of the enzyme remained bound to the membrane [15].
  • Both factors inhibit the activity of calf thymus DNA polymerase alpha in cell-free assays (termed inhibitor of DNA polymerase, IDP) [16].
  • The nucleosidediphosphatase of the Golgi differs from that present in rough endoplasmic reticulum in its absolute requirement for Ca2+ for activity and in its substrate specificity that is higher for UDP than for IDP [17].
  • Patients with IDP appear to exhibit a delay in maturation of both the adrenal cortex and the hypothalamo-pituitary gonadal axis usually with short stature and retardation of the bone age [18].
  • Samples were taken on days 1, 2, 3 and 7 after irradiation and subsequently at weekly intervals up to the end the of shelf-life (day 39 after irradiation) and were investigated for the K+ and Na+ content in the supernatant, for intracellular concentrations of ATP, ADP, ITP, IDP, GTP and GDP of erythrocytes, and for haemolysis [19].

Associations of Riboxin with other chemical compounds

  • In contrast, when microsomes were treated with sodium deoxycholate or subjected to nitrogen cavitation, approximately 75% of the inosine-5'-diphosphatase activity was released from the membrane, and the apparent Km of the enzyme for IDP increased 4- and 2-fold, respectively [15].
  • Specifically, we observed significant frequency shifts in the vibrational modes associated with the 6-keto and 2-amino positions of the guanine group of GDP and IDP that result from hydrogen bonding interactions between these groups and the two proteins [20].
  • It could be shown that under the present incubation conditions, formation of glucose 6-phosphate was closely linked to the ratio of (ATP + ITP)/(ADP + IDP) whereas changing redox ratios had little influence on the gluconeogenic rate [21].
  • The systolic blood pressure of SHRs injected with indapamide (IDP group) was statistically lower than that of SHRs injected with 2% gum Arabic solution (control group) [22].
  • 3. The binding of ADP to CF1 induced by tentoxin is inhibited by ATP and adenylyl imidodiphosphate but is not inhibited by other nucleotides including AMP, GDP, CDP, IDP, or beta, gamma-methylene ATP [23].

Gene context of Riboxin

  • Consistent with the enzyme expressed in mammalian cells, this recombinant NTPDase6 efficiently hydrolyzes GDP, IDP, and UDP (specific activity of approximately 50000 micromol mg(-1) h(-1)), with slower hydrolysis of CDP, ITP, GTP, CTP, ADP, and UTP and virtually no hydrolysis of ATP [24].
  • In general, the spectral shifts provide a rationale for the stronger binding of GDP and IDP with p21 compared to EF-Tu [20].
  • The rank order of potency of various diphosphonucleotides at the P2Y6 receptor was: UDP > TDP > IDP > GDP > ADP >> CDP [25].
  • Genotype of Xba I RFLP at CYP2D6 locus was analyzed in 43 healthy individuals and 51 patients with IDP [26].
  • A new genetic map of maize, ISU-IBM Map4, that integrates 2029 existing markers with 1329 new indel polymorphism (IDP) markers has been developed using intermated recombinant inbred lines (IRILs) from the intermated B73 x Mo17 (IBM) population [27].

Analytical, diagnostic and therapeutic context of Riboxin

  • However, an analysis of titration curves for a number of nucleoside diphosphates (ADP, IDP, GDP) showed that there is a substantial synergism in binding of the metal ion and nucleotide to the enzyme in the ternary complex [28].
  • The website provides access to IDP primer sequences, sequences from which IDP primers were designed, optimized marker-specific PCR conditions, and polymorphism data for all IDP markers [27].
  • Computerized mass spectrometry of clastogenic fractions obtained by HPLC of plasma ultrafiltrates detected molecular peaks compatible with inosine triphosphate and inosine diphosphate (ITP and IDP) [29].
  • In all 3 patients, the DPD/IDP ratio was greater than 1 before transplantation [30].
  • A method has been developed where quantitative evaluation of intragastric (IGP), intraduodenal (IDP), and intracolonic (ICP) pressures (cm H2O) can be obtained in the bilaterally vagotomized spinal rat [31].


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  2. Electrophysiological evaluation of conduction in the most proximal motor root segment. Inaba, A., Yokota, T., Otagiri, A., Nishimura, T., Saito, Y., Ichikawa, T., Mizusawa, H. Muscle Nerve (2002) [Pubmed]
  3. Selected peripheral neuropathies associated with human immunodeficiency virus infection and antiretroviral therapy. Simpson, D.M. J. Neurovirol. (2002) [Pubmed]
  4. Alzheimer's disease and idiopathic Parkinson's disease coexistence. Rajput, A.H., Rozdilsky, B., Rajput, A. Journal of geriatric psychiatry and neurology. (1993) [Pubmed]
  5. Expression of angiogenic factors is upregulated in DMBA-induced rat mammary pathologies. Yan, M., Schneider, J., Gear, R., Lu, F., LaDow, K., Warshawsky, D., Heffelfinger, S.C. Pathobiology (2004) [Pubmed]
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  8. Glutamine 170 to tyrosine substitution in yeast mitochondrial F1 beta-subunit increases catalytic site interaction with GDP and IDP and produces negative cooperativity of GTP and ITP hydrolysis. Jault, J.M., Divita, G., Allison, W.S., Di Pietro, A. J. Biol. Chem. (1993) [Pubmed]
  9. Trinitrophenyl-ATP and -ADP bind to a single nucleotide site on isolated beta-subunit of Escherichia coli F1-ATPase. In vitro assembly of F1-subunits requires occupancy of the nucleotide-binding site on beta-subunit by nucleoside triphosphate. Rao, R., Al-Shawi, M.K., Senior, A.E. J. Biol. Chem. (1988) [Pubmed]
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  13. Preparation, characterization and crystallization of an antibody Fab fragment that recognizes RNA. Crystal structures of native Fab and three Fab-mononucleotide complexes. Pokkuluri, P.R., Bouthillier, F., Li, Y., Kuderova, A., Lee, J., Cygler, M. J. Mol. Biol. (1994) [Pubmed]
  14. Plasmalemma-bound nucleoside diphosphatase as a cytochemical marker of central nervous system (CNS) mesodermal cells. Vorbrodt, A.W., Wisniewski, H.M. J. Histochem. Cytochem. (1982) [Pubmed]
  15. Latency of inosine-5'-diphosphatase in microsomes isolated from rat liver. LIttle, J.S., Thiers, D.R., Widnell, C.C. J. Biol. Chem. (1976) [Pubmed]
  16. Regulatory factors produced by lymphocytes. II. Inhibition of cellular DNA synthesis associated with a factor inhibiting DNA polymerase alpha activity. Lee, S.C., Lucas, Z.J. J. Immunol. (1977) [Pubmed]
  17. Orientation and role of nucleosidediphosphatase and 5'-nucleotidase in Golgi vesicles from rat liver. Brandan, E., Fleischer, B. Biochemistry (1982) [Pubmed]
  18. The secretion of adrenal androgens and growth patterns of patients with hypogonadotropic hypogonadism and isiopathic delayed puberty. Copeland, K.C., Paunier, L., Sizonenko, P.C. J. Pediatr. (1977) [Pubmed]
  19. Altered intracellular purine nucleotides in gamma-irradiated red blood cell concentrates. Leitner, G.C., Neuhauser, M., Weigel, G., Kurze, S., Fischer, M.B., Höcker, P. Vox Sang. (2001) [Pubmed]
  20. Hydrogen bond interactions of G proteins with the guanine ring moiety of guanine nucleotides. Weng, G., Chen, C.X., Balogh-Nair, V., Callender, R., Manor, D. Protein Sci. (1994) [Pubmed]
  21. Gluconeogenesis in vitro. Formation of glucose 6-phosphate from malate by a cell-free rat-liver system consisting of cytosol and mitochondria. Mörikofer-Zwez, S., Stoecklin, F.B., Walter, P. Eur. J. Biochem. (1982) [Pubmed]
  22. Effect of indapamide on atrial natriuretic polypeptide receptor in spontaneously hypertensive rat kidney. Ogura, T., Mitsui, T., Yamamoto, I., Katayama, E., Ota, Z., Ogawa, N. Res. Commun. Chem. Pathol. Pharmacol. (1986) [Pubmed]
  23. Tentoxin-induced binding of adenine nucleotides to soluble spinach chloroplast coupling factor 1. Reimer, S., Selman, B.R. Biochim. Biophys. Acta (1979) [Pubmed]
  24. Bacterial expression, characterization, and disulfide bond determination of soluble human NTPDase6 (CD39L2) nucleotidase: implications for structure and function. Ivanenkov, V.V., Murphy-Piedmonte, D.M., Kirley, T.L. Biochemistry (2003) [Pubmed]
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  28. Magnetic resonance studies on manganese-nucleotide complexes of phosphoglycerate kinase. Chapman, B.E., O'Sullivan, W.J., Scopes, R.K., Reed, G.H. Biochemistry (1977) [Pubmed]
  29. Clastogenic inosine nucleotide as components of the chromosome breakage factor in scleroderma patients. Auclair, C., Gouyette, A., Levy, A., Emerit, I. Arch. Biochem. Biophys. (1990) [Pubmed]
  30. Reversal of digital clubbing after lung transplantation in cystic fibrosis patients: a clue to the pathogenesis of clubbing. Augarten, A., Goldman, R., Laufer, J., Szeinberg, A., Efrati, O., Barak, A., Miller, M.S., Yahav, Y. Pediatr. Pulmonol. (2002) [Pubmed]
  31. A method for simultaneous measurement of intragastric, intraduodenal, and intracolonic pressures in the bilaterally vagotomized spinal rat. Zhu, Y.N., Dhasmana, K.M., Erdmann, W. Journal of pharmacological and toxicological methods. (1994) [Pubmed]
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