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Chemical Compound Review

deoxyinosine     9-[(2R,4S,5R)-4-hydroxy-5...

Synonyms: delta-Ino, d-Ino, SureCN24307, SureCN24308, AG-H-60709, ...
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Disease relevance of deoxyinosine


High impact information on deoxyinosine

  • The differences between the normal and HPR transferase-deficient cells were lost when ribose reutilization from endogenous nucleotide breakdown was impaired in the HPR transferase-deficient cells by incubation with 2'-deoxyinosine [3].
  • In this study, we demonstrated the artifactual formation of these two deamination products during acid hydrolysis and hence developed a method for detecting and measuring 2'-deoxyinosine, the nucleoside of hypoxanthine [4].
  • This assay detected an increase in the levels of 2'-deoxyinosine in DNA when commercial salmon testis DNA was treated with nitrous acid [4].
  • Instead, the results show a very small shift (1.3 ppm), indicating that C-6 of 2'-deoxyinosine retains its sp2 hybridization after binding by calf intestinal adenosine deaminase [5].
  • We show that dI-substituted molecules that cannot form the G-strand structure nonetheless function as substrates for telomere repeat addition in vitro by the telomere lengthening enzyme, telomerase [6].

Biological context of deoxyinosine

  • PURPOSE: The aims of this study were to develop a stealth, pegylated liposomal formulation of 2'-deoxyinosine (d-Ino), a 5-fluorouracil (5-FU) modulator, to evaluate its efficacy in vitro and in tumor-bearing mice, and to study its pharmacokinetics in rats [7].
  • The sensitivity was also increased by a factor of 10 by using in addition to the deoxyinosine (dI)-containing primers, respective homologous primers in which dI was substituted by dG in the region of sequence homology [8].
  • The inhibitory potency of this siHybrid was increased (IC50 value of 7.8 nM) using a homologous chemically modified siHybrid (mH) in which the 19-mer sense strand had the following pattern of 2 '-deoxyinosine (dI) and 2 '-O-methylribonucleotide (2 '-OMe) residues: 5'-d(TITIT)-2'OMe(GCGGUGGUU)-d(GICIT) [9].

Associations of deoxyinosine with other chemical compounds


Gene context of deoxyinosine


Analytical, diagnostic and therapeutic context of deoxyinosine

  • Our assay for 2'-deoxyinosine employs nuclease P1 and alkaline phosphatase to achieve release of the nucleosides from DNA, followed by HPLC prepurification with subsequent GC-MS analysis of the nucleosides [4].


  1. Incorporation of oxidatively modified 2'-deoxynucleotide triphosphates by HIV-1 RT on RNA and DNA templates. Wuenschell, G.E., Valentine, M.R., Termini, J. Chem. Res. Toxicol. (2002) [Pubmed]
  2. One-pot Microbial Synthesis of 2'-deoxyribonucleoside from Glucose, Acetaldehyde, and a Nucleobase. Horinouchi, N., Ogawa, J., Kawano, T., Sakai, T., Saito, K., Matsumoto, S., Sasaki, M., Mikami, Y., Shimizu, S. Biotechnol. Lett. (2006) [Pubmed]
  3. The influence of ribose 5-phosphate availability on purine synthesis of cultured human lymphoblasts and mitogen-stimulated lymphocytes. Pilz, R.B., Willis, R.C., Boss, G.R. J. Biol. Chem. (1984) [Pubmed]
  4. Potential artifacts in the measurement of DNA deamination. Lim, K.S., Huang, S.H., Jenner, A., Wang, H., Tang, S.Y., Halliwell, B. Free Radic. Biol. Med. (2006) [Pubmed]
  5. Enzyme-substrate complexes of adenosine and cytidine deaminases: absence of accumulation of water adducts. Shih, P., Wolfenden, R. Biochemistry (1996) [Pubmed]
  6. Telomere G-strand structure and function analyzed by chemical protection, base analogue substitution, and utilization by telomerase in vitro. Henderson, E.R., Moore, M., Malcolm, B.A. Biochemistry (1990) [Pubmed]
  7. Development of stealth liposome formulation of 2'-deoxyinosine as 5-fluorouracil modulator: in vitro and in vivo study. Fanciullino, R., Giacometti, S., Aubert, C., Fina, F., Martin, P.M., Piccerelle, P., Ciccolini, J. Pharm. Res. (2005) [Pubmed]
  8. A spot multiplex nested RT-PCR for the simultaneous and generic detection of viruses involved in the aetiology of grapevine leafroll and rugose wood of grapevine. Dovas, C.I., Katis, N.I. J. Virol. Methods (2003) [Pubmed]
  9. Chemically modified short interfering hybrids (siHYBRIDS): nanoimmunoliposome delivery in vitro and in vivo for RNAi of HER-2. Hogrefe, R.I., Lebedev, A.V., Zon, G., Pirollo, K.F., Rait, A., Zhou, Q., Yu, W., Chang, E.H. Nucleosides Nucleotides Nucleic Acids (2006) [Pubmed]
  10. Inosine and 2'-deoxyinosine and their synthetic analogues: lipophilicity in the relation to their retention in reversed-phase liquid chromatography and the stability characteristics. Novotny, L., Abdel-Hamid, M., Hamza, H. Journal of pharmaceutical and biomedical analysis. (2000) [Pubmed]
  11. Reduced activity of anabolizing enzymes in 5-fluorouracil-resistant human stomach cancer cells. Inaba, M., Mitsuhashi, J., Sawada, H., Miike, N., Naoe, Y., Daimon, A., Koizumi, K., Tsujimoto, H., Fukushima, M. Jpn. J. Cancer Res. (1996) [Pubmed]
  12. Early postimplantation embryolethality in mice following in utero inhibition of adenosine deaminase with 2'-deoxycoformycin. Knudsen, T.B., Gray, M.K., Church, J.K., Blackburn, M.R., Airhart, M.J., Kellems, R.E., Skalko, R.G. Teratology (1989) [Pubmed]
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