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Chemical Compound Review

Ara-HX     9-[3,4-dihydroxy-5- (hydroxymethyl)oxolan-2...

Synonyms: Inosine-8-14C, ACMC-209m62, H1383_SIGMA, I7637_SIGMA, NSC-20262, ...
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Disease relevance of riboxine

  • Inosine pranobex for preventing AIDS in patients with HIV infection [1].
  • During low flow ischemia, there was a substantial decrease in phosphocreatine in the uremic hearts and an accompanying marked increase in release of inosine into the coronary effluent (14.9 vs 6.1 microM, P < 0.01) [2].
  • Lactate dehydrogenase (LDH) release after 40 min of anoxia is 30-40% under control conditions, only 10-15% when adenine nucleotides or ADO are added during anoxia, and 20% when INO is added, suggesting that these additions may stabilize the plasma membrane during anoxia and help preserve cellular integrity [3].
  • The incremental areas of inosine and hypoxanthine were also greater in the glycogen storage disease group (29.2 +/- 7.2 vs. 0.4 +/- 0.1 and 134.6 +/- 23.1 vs. 14.9 +/- 3.2 mumol X min/liter, respectively) [4].
  • 77 patients with a first attack of genital herpes were entered into a double-blind trial to compare the efficacy of acyclovir with that of inosine pranobex [5].

Psychiatry related information on riboxine

  • Electroshock seizures resulted in a marked and prolonged rise in inosine, with maximal values at 5 min [6].
  • Inosine did not increase social interaction [7].
  • The linkage group identification numbers correspond to those for maps published by the Arús group in Spain and the Dirlewanger group in France. Forty-five percent of the loci showed segregation distortion most likely owing to the interspecific nature of the cross and mating system differences between almond (obligate outcrosser) and peach (selfer) [8].
  • RESULTS: Stroke animals receiving inosine pretreatment demonstrated a higher level of locomotor activity and less cerebral infarction [9].
  • Using the purified enzyme, 32.6 mM 5'-IMP was synthesized from inosine with a 41% molar yield, but the synthesized 5'-IMP was hydrolyzed back to inosine and phosphate as the reaction time was extended [10].

High impact information on riboxine

  • This complex contains the inosine-specific RNA binding protein p54(nrb), the splicing factor PSF, and the inner nuclear matrix structural protein matrin 3 [11].
  • We have developed a Xenopus oocyte model system which shows that a variety of hyperedited, inosine-containing RNAs are specifically retained in the nucleus [11].
  • To uncover the mechanism of inosine-induced retention, HeLa cell nuclear extracts were used to isolate a multiprotein complex that binds specifically and cooperatively to inosine-containing RNAs [11].
  • The patients were stratified in three groups according to their CD4+ cell count and randomly assigned to receive either inosine pranobex (1 g three times a day) (n = 429) or matching placebo (n = 437) for 24 weeks [12].
  • We demonstrate that during the reaction many, but not all, of the adenosine residues are converted to inosine residues, and we propose that the covalent modification is responsible for the irreversible change in base pairing properties [13].

Chemical compound and disease context of riboxine


Biological context of riboxine

  • In addition, we directly demonstrate that editing results from the conversion of adenosine to inosine by enzymatic deamination [19].
  • The structure also reveals previously unobserved interactions with the nucleotide that accounts for the specificity of the nucleotide binding site for AMP in preference to inosine monophosphate [20].
  • GPI-deficient erythrocytes incubated with glucose in the medium showed an accentuation of membrane protein aggregate formation; however, this was almost completely reversed by the addition of adenine and inosine to the incubation medium or by the use of fructose, the intermediate just distal to the "block" in glycolysis, as the sole substrate [21].
  • Together these results support a model in which adenosine and inosine induce changes in vascular permeability indirectly by activating mast cells, which in turn release vasoactive substances [22].
  • Patients treated with acyclovir or both drugs healed more quickly and had a shorter duration of viral shedding than those treated with inosine pranobex [5].

Anatomical context of riboxine


Associations of riboxine with other chemical compounds


Gene context of riboxine

  • Prolonged exposure of Huh-7 cells to a TLR7 ligand [SM360320 (9-benzyl-8-hydroxy-2-(2-methoxyethoxy)adenine)], alone or in combination with an inosine monophosphate dehydrogenase inhibitor, reduced HCV levels dose dependently [31].
  • Inosine-containing oligonucleotides based on the partial protein sequence were used to isolate a 679-bp cDNA for LTC4S from THP-1 cells [32].
  • A screen of retinal transcripts comparing retinas from normal mice to retinas from crx-/crx- knockout mice (with poorly differentiated photoreceptors) demonstrated a 6-fold reduction in one candidate, inosine monophosphate dehydrogenase 1 (IMPDH1; EC [33].
  • These results do not confirm the hypothesis that inosine accumulation in purine nucleoside phosphorylase deficiency causes adenosine deaminase inhibition, resulting in a common mechanism for the immune defects related to these two enzyme deficiencies [34].
  • RNA editing by members of the ADAR (adenosine deaminase that acts on RNA) enzyme family involves hydrolytic deamination of adenosine to inosine within the context of a double-stranded pre-mRNA substrate [35].

Analytical, diagnostic and therapeutic context of riboxine


  1. Inosine pranobex for preventing AIDS in patients with HIV infection. Forthal, D.N. N. Engl. J. Med. (1991) [Pubmed]
  2. Impairment of cardiac function and energetics in experimental renal failure. Raine, A.E., Seymour, A.M., Roberts, A.F., Radda, G.K., Ledingham, J.G. J. Clin. Invest. (1993) [Pubmed]
  3. Mechanisms whereby exogenous adenine nucleotides improve rabbit renal proximal function during and after anoxia. Mandel, L.J., Takano, T., Soltoff, S.P., Murdaugh, S. J. Clin. Invest. (1988) [Pubmed]
  4. Excess purine degradation in exercising muscles of patients with glycogen storage disease types V and VII. Mineo, I., Kono, N., Shimizu, T., Hara, N., Yamada, Y., Sumi, S., Nonaka, K., Tarui, S. J. Clin. Invest. (1985) [Pubmed]
  5. Treatment of first-attack genital herpes--acyclovir versus inosine pranobex. Mindel, A., Kinghorn, G., Allason-Jones, E., Woolley, P., Barton, I., Faherty, A., Jeavons, M., Williams, P., Patou, G. Lancet (1987) [Pubmed]
  6. Electroshock seizures in mice: effect on brain adenosine and its metabolites. Lewin, E., Bleck, V. Epilepsia (1981) [Pubmed]
  7. Central effects of nicotinamide and inosine which are not mediated through benzodiazepine receptors. Bold, J.M., Gardner, C.R., Walker, R.J. Br. J. Pharmacol. (1985) [Pubmed]
  8. An expanded genetic linkage map of Prunus based on an interspecific cross between almond and peach. Bliss, F.A., Arulsekar, S., Foolad, M.R., Becerra, V., Gillen, A.M., Warburton, M.L., Dandekar, A.M., Kocsisne, G.M., Mydin, K.K. Genome (2002) [Pubmed]
  9. Inosine reduces ischemic brain injury in rats. Shen, H., Chen, G.J., Harvey, B.K., Bickford, P.C., Wang, Y. Stroke (2005) [Pubmed]
  10. A novel selective nucleoside phosphorylating enzyme from Morganella morganii. Asano, Y., Mihara, Y., Yamada, H. J. Biosci. Bioeng. (1999) [Pubmed]
  11. The fate of dsRNA in the nucleus: a p54(nrb)-containing complex mediates the nuclear retention of promiscuously A-to-I edited RNAs. Zhang, Z., Carmichael, G.G. Cell (2001) [Pubmed]
  12. The efficacy of inosine pranobex in preventing the acquired immunodeficiency syndrome in patients with human immunodeficiency virus infection. The Scandinavian Isoprinosine Study Group. Pedersen, C., Sandström, E., Petersen, C.S., Norkrans, G., Gerstoft, J., Karlsson, A., Christensen, K.C., Håkansson, C., Pehrson, P.O., Nielsen, J.O. N. Engl. J. Med. (1990) [Pubmed]
  13. An unwinding activity that covalently modifies its double-stranded RNA substrate. Bass, B.L., Weintraub, H. Cell (1988) [Pubmed]
  14. In-vitro inhibition of LAV/HTLV-III infected lymphocytes by dithiocarb and inosine pranobex. Pompidou, A., Zagury, D., Gallo, R.C., Sun, D., Thornton, A., Sarin, P.S. Lancet (1985) [Pubmed]
  15. Myocardial lactate and adenosine metabolite production as indicators of exercise-induced myocardial ischemia in the dog. Vrobel, T.R., Jorgensen, C.R., Bache, R.J. Circulation (1982) [Pubmed]
  16. Molecular transformation of tumor adenylosuccinate synthetase and characteristics of its converting factor. Matsuda, Y., Shiraki, H., Nakagawa, H. Cancer Res. (1982) [Pubmed]
  17. The reversal of methotrexate cytotoxicity to mouse bone marrow cells by leucovorin and nucleosides. Pinedo, H.M., Zaharko, D.S., Bull, J.M., Chabner, B.A. Cancer Res. (1976) [Pubmed]
  18. Future therapy of hepatitis C. McHutchison, J.G., Patel, K. Hepatology (2002) [Pubmed]
  19. Editing of glutamate receptor subunit B pre-mRNA in vitro by site-specific deamination of adenosine. Yang, J.H., Sklar, P., Axel, R., Maniatis, T. Nature (1995) [Pubmed]
  20. Structural basis for the activation of glycogen phosphorylase b by adenosine monophosphate. Sprang, S.R., Withers, S.G., Goldsmith, E.J., Fletterick, R.J., Madsen, N.B. Science (1991) [Pubmed]
  21. Erythrocyte membrane proteins in hereditary glucosephosphate isomerase deficiency. Coetzer, T., Zail, S.S. J. Clin. Invest. (1979) [Pubmed]
  22. Adenosine and inosine increase cutaneous vasopermeability by activating A(3) receptors on mast cells. Tilley, S.L., Wagoner, V.A., Salvatore, C.A., Jacobson, M.A., Koller, B.H. J. Clin. Invest. (2000) [Pubmed]
  23. Abnormal purine metabolism and purine overproduction in a patient deficient in purine nucleoside phosphorylase. Cohen, A., Doyle, D., Martin, D.W., Ammann, A.J. N. Engl. J. Med. (1976) [Pubmed]
  24. An antisense mRNA directs the covalent modification of the transcript encoding fibroblast growth factor in Xenopus oocytes. Kimelman, D., Kirschner, M.W. Cell (1989) [Pubmed]
  25. Probing the function of the eucaryotic 5' cap structure by using a monoclonal antibody directed against cap-binding proteins. Sonenberg, N., Guertin, D., Cleveland, D., Trachsel, H. Cell (1981) [Pubmed]
  26. Adenosine: a physiological modulator of superoxide anion generation by human neutrophils. Cronstein, B.N., Kramer, S.B., Weissmann, G., Hirschhorn, R. J. Exp. Med. (1983) [Pubmed]
  27. Oxypurine cycle in human erythrocytes regulated by pH, inorganic phosphate, and oxygen. Berman, P.A., Black, D.A., Human, L., Harley, E.H. J. Clin. Invest. (1988) [Pubmed]
  28. Proposed explanation for S-adenosylhomocysteine hydrolase deficiency in purine nucleoside phosphorylase and hypoxanthine-guanine phosphoribosyltransferase-deficient patients. Hershfield, M.S. J. Clin. Invest. (1981) [Pubmed]
  29. The purine nucleotide cycle. A pathway for ammonia production in the rat kidney. Bogusky, R.T., Lowenstein, L.M., Lowenstein, J.M. J. Clin. Invest. (1976) [Pubmed]
  30. Sodium-dependent nucleoside transport in rabbit intestinal epithelium. Roden, M., Paterson, A.R., Turnheim, K. Gastroenterology (1991) [Pubmed]
  31. Activation of anti-hepatitis C virus responses via Toll-like receptor 7. Lee, J., Wu, C.C., Lee, K.J., Chuang, T.H., Katakura, K., Liu, Y.T., Chan, M., Tawatao, R., Chung, M., Shen, C., Cottam, H.B., Lai, M.M., Raz, E., Carson, D.A. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  32. Molecular cloning and expression of human leukotriene-C4 synthase. Welsch, D.J., Creely, D.P., Hauser, S.D., Mathis, K.J., Krivi, G.G., Isakson, P.C. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  33. Mutations in the inosine monophosphate dehydrogenase 1 gene (IMPDH1) cause the RP10 form of autosomal dominant retinitis pigmentosa. Bowne, S.J., Sullivan, L.S., Blanton, S.H., Cepko, C.L., Blackshaw, S., Birch, D.G., Hughbanks-Wheaton, D., Heckenlively, J.R., Daiger, S.P. Hum. Mol. Genet. (2002) [Pubmed]
  34. Use of the integrated steady state rate equation to investigate product inhibition of human red cell adenosine deaminase and its relevance to immune dysfunction. Osborne, W.R., Chen, S.H., Scott, C.R. J. Biol. Chem. (1978) [Pubmed]
  35. Adenosine to inosine editing by ADAR2 requires formation of a ternary complex on the GluR-B R/G site. Jaikaran, D.C., Collins, C.H., MacMillan, A.M. J. Biol. Chem. (2002) [Pubmed]
  36. Inosine-containing primers for mRNA differential display. Rohrwild, M., Alpan, R.S., Liang, P., Pardee, A.B. Trends Genet. (1995) [Pubmed]
  37. Efficacy of recombinant-derived human superoxide dismutase on porcine left ventricular contractility after normothermic global myocardial ischemia and hypothermic cardioplegic arrest. Dworkin, G.H., Abd-Elfattah, A.S., Yeh, T., Wechsler, A.S. Circulation (1990) [Pubmed]
  38. A double-stranded RNA unwinding activity introduces structural alterations by means of adenosine to inosine conversions in mammalian cells and Xenopus eggs. Wagner, R.W., Smith, J.E., Cooperman, B.S., Nishikura, K. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  39. Protection of the stunned myocardium. Selective nucleoside transport blocker administered after 20 minutes of ischemia augments recovery of ventricular function. Abd-Elfattah, A.S., Ding, M., Dyke, C.M., Wechsler, A.S. Circulation (1993) [Pubmed]
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