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Chemical Compound Review

ACMC-209qyj     9-[4-hydroxy-5- (hydroxymethyl)oxolan-2- yl]...

Synonyms: SureCN12222465, CHEBI:106032, Oprea1_655959, AC1L19OM, LT00138048, ...
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Disease relevance of deoxyinosine


High impact information on deoxyinosine


Chemical compound and disease context of deoxyinosine


Biological context of deoxyinosine


Anatomical context of deoxyinosine

  • Furthermore, the presence of deoxyinosine potentiates FUra action in HuTu 80 cells, while having no effect on growth inhibition by FUra in HT 29 cells [10].
  • 1. Concave-downward double-reciprocal plots were obtained for rabbit erythrocyte purine nucleoside phosphorylase when the concentration of Pi was varied over a wide range at a fixed saturating concentration of either inosine or deoxyinosine [19].
  • A nucleotidase (EC isolated previously from rat liver cytosol was specifically measured in 14 different rat tissues and in subcellular fractions of liver and spleen, taking advantage of the stimulation exerted on it by deoxyinosine [20].
  • By screening of a rat liver cDNA library with complex and deoxyinosine containing oligonucleotide probes a cDNA clone was isolated and shown by sequencing to code for the amino-terminal half of the rat liver 28 kDa gap junction protein [21].
  • Initially, samples of peripheral blood mononuclear cells (PBMC), spleens, lungs, kidneys and livers of pigs from Germany and Spain were tested with a PCR assay which targets conserved regions of the herpesvirus DNA polymerase gene with degenerate and deoxyinosine-substituted primers [22].

Associations of deoxyinosine with other chemical compounds

  • Under optimal cleavage conditions, endonuclease V forms two stable complexes with DNA containing deoxyinosine, but not with DNA containing base mismatches or deoxynebularine, suggesting that the 6-keto group of hypoxanthine in DNA is critical for stable interactions with the protein [13].
  • Here we show that RdgB protein and RdgB homologs from Saccharomyces cerevisiae, mouse, and human all possess deoxyribonucleoside triphosphate pyrophosphohydrolase activity and that all four RdgB homologs have high specificity for dHAPTP and deoxyinosine triphosphate compared with the four canonical dNTPs and several other noncanonical (d)NTPs [23].
  • Equitoxic doses of gamma radiation, cisplatin or the antimetabolite deoxyinosine had little effect on pRB levels [24].
  • N1 deoxyadenosine adducts are unstable and can undergo either hydrolytic deamination to yield N1 deoxyinosine adducts or Dimroth rearrangement to yield N(6) adducts [25].
  • These results suggest that endonuclease V has a significant role in the repair of deaminated deoxyadenosine (deoxyinosine) and abasic sites in DNA, but there was no evidence for its cleavage in vivo of single-stranded or uracil-containing DNA [26].

Gene context of deoxyinosine

  • A polymerase chain reaction (PCR)-based cloning strategy was applied using: (1) an initial PCR with deoxyinosine-containing primers designed to target conserved regions in CCK receptors, followed by (2) rapid amplification of cDNA ends (RACE), and (3) full-length PCR of the CCK-CHR cDNA [27].
  • Human neutrophil lipocalin (HNL) cDNA was amplified by PCR technology in combination with deoxyinosine containing oligonucleotides for cloning, sequencing and production of the recombinant protein in E. coli [28].
  • Polymerase chain reaction (PCR) primers were designed to regions conserved in both TAG-1 and axonin-1 using deoxyinosine at ambiguous positions [29].
  • Using enzyme purified from an overproducing strain, the deoxyinosine- and mismatch-specific activities of endonuclease V was found to have different divalent metal requirements [13].
  • In addition, the enzyme also cleaved the 5'-single-stranded tails of flap and pseudo-Y DNA structures, suggesting that deoxyinosine 3'-endonuclease is a bacterial functional homologue of human FEN1 and yeast RTH1 nucleases [1].

Analytical, diagnostic and therapeutic context of deoxyinosine

  • One of these coeluted with deoxyinosine on HPLC, while the second was tentatively identified as the positional isomer, 7-(beta-D-2'-deoxyribofuranosyl)hypoxanthine [30].


  1. Cleavage of insertion/deletion mismatches, flap and pseudo-Y DNA structures by deoxyinosine 3'-endonuclease from Escherichia coli. Yao, M., Kow, Y.W. J. Biol. Chem. (1996) [Pubmed]
  2. Alpha-deoxyadenosine, a major anoxic radiolysis product of adenine in DNA, is a substrate for Escherichia coli endonuclease IV. Ide, H., Tedzuka, K., Shimzu, H., Kimura, Y., Purmal, A.A., Wallace, S.S., Kow, Y.W. Biochemistry (1994) [Pubmed]
  3. Dual roles of glycosyl torsion angle conformation and stereochemical configuration in butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adducts: a structural perspective. Merritt, W.K., Kowalczyk, A., Scholdberg, T.A., Dean, S.M., Harris, T.M., Harris, C.M., Lloyd, R.S., Stone, M.P. Chem. Res. Toxicol. (2005) [Pubmed]
  4. Type-specific detection of echovirus 30 isolates using degenerate reverse transcriptase PCR primers. Kilpatrick, D.R., Quay, J., Pallansch, M.A., Oberste, M.S. J. Clin. Microbiol. (2001) [Pubmed]
  5. Cloning and expression of the metallo-proteinase inhibitor (S-MPI) gene from Streptomyces nigrescens. Tanaka, K., Saito, H., Oda, K., Murao, S., Takahashi, H. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  6. Purinergic regulation of food intake. Levine, A.S., Morley, J.E. Science (1982) [Pubmed]
  7. Nucleic acid specificity of a vertebrate telomere-binding protein: evidence for G-G base pair recognition at the core-binding site. Gualberto, A., Patrick, R.M., Walsh, K. Genes Dev. (1992) [Pubmed]
  8. Selective amplification of an mRNA and related pseudogene for a human ADP-ribosylation factor, a guanine nucleotide-dependent protein activator of cholera toxin. Monaco, L., Murtagh, J.J., Newman, K.B., Tsai, S.C., Moss, J., Vaughan, M. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  9. Molecular cloning of the human cholecystokinin gene by use of a synthetic probe containing deoxyinosine. Takahashi, Y., Kato, K., Hayashizaki, Y., Wakabayashi, T., Ohtsuka, E., Matsuki, S., Ikehara, M., Matsubara, K. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  10. Comparison of 5-fluorouracil metabolism in two human gastrointestinal tumor cell lines. Washtien, W.L. Cancer Res. (1984) [Pubmed]
  11. Purification and characterization of a novel deoxyinosine-specific enzyme, deoxyinosine 3' endonuclease, from Escherichia coli. Yao, M., Hatahet, Z., Melamede, R.J., Kow, Y.W. J. Biol. Chem. (1994) [Pubmed]
  12. Interaction of deoxyinosine 3'-endonuclease from Escherichia coli with DNA containing deoxyinosine. Yao, M., Kow, Y.W. J. Biol. Chem. (1995) [Pubmed]
  13. Further characterization of Escherichia coli endonuclease V. Mechanism of recognition for deoxyinosine, deoxyuridine, and base mismatches in DNA. Yao, M., Kow, Y.W. J. Biol. Chem. (1997) [Pubmed]
  14. A deoxyinosine specific endonuclease from hyperthermophile, Archaeoglobus fulgidus: a homolog of Escherichia coli endonuclease V. Liu, J., He, B., Qing, H., Kow, Y.W. Mutat. Res. (2000) [Pubmed]
  15. Identification of I:A mismatch base-pairing structure in DNA. Uesugi, S., Oda, Y., Ikehara, M., Kawase, Y., Ohtsuka, E. J. Biol. Chem. (1987) [Pubmed]
  16. Base pairing involving deoxyinosine: implications for probe design. Martin, F.H., Castro, M.M., Aboul-ela, F., Tinoco, I. Nucleic Acids Res. (1985) [Pubmed]
  17. Preferential recognition of I.T base-pairs in the initiation of excision-repair by hypoxanthine-DNA glycosylase. Dianov, G., Lindahl, T. Nucleic Acids Res. (1991) [Pubmed]
  18. Purine nucleoside phosphorylase. Microheterogeneity and comparison of kinetic behavior of the enzyme from several tissues and species. Agarwal, K.C., Agarwal, R.P., Stoeckler, J.D., Parks, R.E. Biochemistry (1975) [Pubmed]
  19. Rabbit erythrocyte purine nucleoside phosphorylase. Initial-velocity studies. Savage, B., Spencer, N. Biochem. J. (1979) [Pubmed]
  20. Subcellular distribution and activity in different rat tissues of a deoxyinosine-activated nucleotidase. Tjernshaugen, H., Fritzson, P. Biochem. J. (1976) [Pubmed]
  21. Identification of a rat liver cDNA and mRNA coding for the 28 kDa gap junction protein. Heynkes, R., Kozjek, G., Traub, O., Willecke, K. FEBS Lett. (1986) [Pubmed]
  22. Detection of two novel porcine herpesviruses with high similarity to gammaherpesviruses. Ehlers, B., Ulrich, S., Goltz, M. J. Gen. Virol. (1999) [Pubmed]
  23. Substrate Specificity of RdgB Protein, a Deoxyribonucleoside Triphosphate Pyrophosphohydrolase. Burgis, N.E., Cunningham, R.P. J. Biol. Chem. (2007) [Pubmed]
  24. Inhibition of retinoblastoma protein translation by UVB in human melanocytic cells and reduced cell cycle arrest following repeated irradiation. Pedley, J., Ablett, E.M., Pettit, A., Meyer, J., Dunn, I.S., Sturm, R.A., Parsons, P.G. Oncogene (1996) [Pubmed]
  25. Mutagenic spectrum of butadiene-derived N1-deoxyinosine adducts and N6,N6-deoxyadenosine intrastrand cross-links in mammalian cells. Kanuri, M., Nechev, L.V., Tamura, P.J., Harris, C.M., Harris, T.M., Lloyd, R.S. Chem. Res. Toxicol. (2002) [Pubmed]
  26. Endonuclease V (nfi) mutant of Escherichia coli K-12. Guo, G., Weiss, B. J. Bacteriol. (1998) [Pubmed]
  27. Molecular cloning of an unusual bicistronic cholecystokinin receptor mRNA expressed in chicken brain: a structural and functional expression study. Nilsson, I.B., Svensson, S.P., Monstein, H.J. Regul. Pept. (2003) [Pubmed]
  28. Cloning and expression of human neutrophil lipocalin cDNA derived from bone marrow and ovarian cancer cells. Bartsch, S., Tschesche, H. FEBS Lett. (1995) [Pubmed]
  29. cDNA cloning, structural features, and eucaryotic expression of human TAG-1/axonin-1. Hasler, T.H., Rader, C., Stoeckli, E.T., Zuellig, R.A., Sonderegger, P. Eur. J. Biochem. (1993) [Pubmed]
  30. The purine-2-deoxyribonucleosidase from Crithidia luciliae. Purification and trans-N-deoxyribosylase activity. Steenkamp, D.J. Eur. J. Biochem. (1991) [Pubmed]
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