Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H13N5O4 |
| Molecular Weight | 267.2413 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(N=CN2[C@H]3C[C@H](O)[C@@H](CO)O3)C(=O)N1
InChI
InChIKey=YKBGVTZYEHREMT-KVQBGUIXSA-N
InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1
Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. It is like guanosine, but with one oxygen atom removed. It is a nucleoside component of DNA. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-OHdG is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion. Deoxyguanosine has long been recognized as a potent cytotoxic agent to cultured mammalian cells. This toxicity or inhibition of DNA synthesis by deoxyguanosine appears to be mediated by deoxyguanosine triphosphate-mediated inhibition of the enzyme ribonucleotide reductase. Purine nucleoside phosphorylase deficiency is thought to cause T-lymphocyte depletion by accumulation of deoxyguanosine and deoxyguanosine triphosphate, resulting in feedback inhibition of ribonucleotide reductase and hence DNA synthesis. Deoxyguanosine nucleoside analogs are potent antiviral agents.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Apoptosis induces efflux of the mitochondrial matrix enzyme deoxyguanosine kinase. | 2001-06-29 |
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| Benzo(a)pyrene-coated onto Fe(2)O(3) particles-induced lung tissue injury: role of free radicals. | 2001-06-10 |
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| Enhancement of OGG1 protein AP lyase activity by increase of APEX protein. | 2001-06-05 |
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| Bioactivation of tamoxifen to metabolite E quinone methide: reaction with glutathione and DNA. | 2001-06 |
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| Effects of a Brussels sprouts extract on oxidative DNA damage and metabolising enzymes in rat liver. | 2001-06 |
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| The C(8)-(2'-deoxy-beta-D-ribofuranoside) of 7-deazaguanine: synthesis and base pairing of oligonucleotides with unusually linked nucleobases. | 2001-05-18 |
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| Mechanism of lower genotoxicity of toremifene compared with tamoxifen. | 2001-05-15 |
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| A new murine oxidative stress model associated with senescence. | 2001-05-15 |
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| Oxidation of thymine to 5-formyluracil in DNA promotes misincorporation of dGMP and subsequent elongation of a mismatched primer terminus by DNA polymerase. | 2001-05-11 |
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| Observation and elimination of N-acetylation of oligonucleotides prepared using fast-deprotecting phosphoramidites and ultra-mild deprotection. | 2001-05-07 |
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| Hepatocellular oxidative DNA injury induced by macrophage-derived nitric oxide. | 2001-05-01 |
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| Catechol estrogens induce oxidative DNA damage and estradiol enhances cell proliferation. | 2001-05-01 |
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| Acute hypoxia and hypoxic exercise induce DNA strand breaks and oxidative DNA damage in humans. | 2001-05 |
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| Hydrogen peroxide: effects on DNA, chromosomes, cell cycle and apoptosis induction in Fanconi's anemia cell lines. | 2001-05 |
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| Oxidative stress is reduced by the long-term use of vitamin E-coated dialysis filters. | 2001-05 |
|
| Superoxide dismutases enhance H2O2-induced DNA damage and alter its site specificity. | 2001-04-27 |
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| Maternal genetic effects on neonatal susceptibility to oxidative damage from environmental tobacco smoke. | 2001-04-18 |
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| Efficient methods for the synthesis of [2-15N]guanosine and 2'-deoxy[2-15N]guanosine derivatives. | 2001-04-17 |
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| Enhanced nucleophilicity and depressed electrophilicity of peroxide by zinc(II), aluminum(III) and lanthanum(III) ions. | 2001-04-17 |
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| Site-specific DNA damage at the GGG sequence by UVA involves acceleration of telomere shortening. | 2001-04-17 |
|
| DNA repair and aging in mouse liver: 8-oxodG glycosylase activity increase in mitochondrial but not in nuclear extracts. | 2001-04-15 |
|
| Analysis of enzyme kinetics using electrospray ionization mass spectrometry and multiple reaction monitoring: fucosyltransferase V. | 2001-04-03 |
|
| Urinary 8-oxo-7, 8-dihydro-2'-deoxyguanosine and biopyrrins levels among construction workers with asbestos exposure history. | 2001-04 |
|
| Docosahexaenoic acid supplementation-increased oxidative damage in bone marrow DNA in aged rats and its relation to antioxidant vitamins. | 2001-04 |
|
| Possible cause of G-C-->C-G transversion mutation by guanine oxidation product, imidazolone. | 2001-04 |
|
| Levels of malondialdehyde-deoxyguanosine in the gastric mucosa: relationship with lipid peroxidation, ascorbic acid, and Helicobacter pylori. | 2001-04 |
|
| Analysis of peroxynitrite reactions with guanine, xanthine, and adenine nucleosides by high-pressure liquid chromatography with electrochemical detection: C8-nitration and -oxidation. | 2001-04 |
|
| Accumulation of 8-oxo-2'-deoxyguanosine and increased expression of hMTH1 protein in brain tumors. | 2001-04 |
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| Oxidative stress in chemoprevention trials. | 2001-04 |
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| Nucleotide synthesis via methods without nucleoside-base protection. | 2001-04 |
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| Induction of direct adducts, apurinic/apyrimidinic sites and oxidized bases in nuclear DNA of human HeLa S3 tumor cells by tetrachlorohydroquinone. | 2001-04 |
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| Oxidative damage and direct adducts in calf thymus DNA induced by the pentachlorophenol metabolites, tetrachlorohydroquinone and tetrachloro-1,4-benzoquinone. | 2001-04 |
|
| Influence of flanking sequence context on the mutagenicity of acetylaminofluorene-derived DNA adducts in mammalian cells. | 2001-03-27 |
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| Protein and DNA oxidation in spinal injury: neurofilaments--an oxidation target. | 2001-03-15 |
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| 1,N(2)-propanodeoxyguanosine adduct formation in aortic DNA following inhalation of acrolein. | 2001-03 |
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| The relation of oxidative DNA damage to hypertension and other cardiovascular risk factors in Tanzania. | 2001-03 |
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| Relationships between perceived workload, stress and oxidative DNA damage. | 2001-03 |
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| Pulmonary carcinogenesis induced by ferric nitrilotriacetate in mice and protection from it by Brazilian propolis and artepillin C. | 2001-03 |
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| Active intestinal absorption of nucleosides by Na+-dependent transport across the brush border membrane in cows. | 2001-03 |
|
| Analysis of fluoroquinolone-mediated photosensitization of 2'-deoxyguanosine, calf thymus and cellular DNA: determination of type-I, type-II and triplet-triplet energy transfer mechanism contribution. | 2001-03 |
|
| HU binding to DNA: evidence for multiple complex formation and DNA bending. | 2001-02-27 |
|
| Effects of benzo[a]pyrene DNA adducts on Escherichia coli DNA polymerase I (Klenow fragment) primer-template interactions: evidence for inhibition of the catalytically active ternary complex formation. | 2001-02-20 |
|
| Eosinophil peroxidase catalyzes bromination of free nucleosides and double-stranded DNA. | 2001-02-20 |
|
| The effect of dietary carotenoids on lung tumorigenesis induced by intratracheally instillated diesel exhaust particles. | 2001-02 |
|
| Melatonin prevents delta-aminolevulinic acid-induced oxidative DNA damage in the presence of Fe2+. | 2001-02 |
|
| Interaction of Escherichia coli purine nucleoside phosphorylase (PNP) with the cationic and zwitterionic forms of the fluorescent substrate N(7)-methylguanosine. | 2001-01-12 |
|
| Antitumor efficacy of SarCNU in a human glioma xenograft model expressing both MGMT and extraneuronal monoamine transporter. | 2001-01 |
|
| The role of duck hepatitis B virus and aflatoxin B1 in the induction of oxidative stress in the liver. | 2001 |
|
| Gene- and tissue-specificity of mutation in Big Blue rats treated with the hepatocarcinogen N-hydroxy-2-acetylaminofluorene. | 2001 |
|
| Comparison of iron-catalyzed DNA and lipid oxidation. | 2001 |
Sample Use Guides
2'-deoxyguanosine toxicity for T lymphoblasts is markedly potentiated by 8-aminoguanosine and is mediated by the accumulation of deoxyguanosine triphosphate. In contrast, the growth of T4+ mature T cell lines and B lymphoblast cell lines is inhibited by somewhat higher concentrations of 2'-deoxyguanosine (ID50 20 and 18 microM, respectively) in the presence of 8-aminoguanosine without an increase in deoxyguanosine triphosphate levels. Cytotoxicity correlates instead with a three- to fivefold increase in guanosine triphosphate (GTP) levels after 24 h. Accumulation of GTP and growth inhibition also result from exposure to guanosine, but not to guanine at equimolar concentrations. B lymphoblasts which are deficient in the purine salvage enzyme hypoxanthine guanine phosphoribosyltransferase are completely resistant to 2'-deoxyguanosine or guanosine concentrations up to 800 microM and do not demonstrate an increase in GTP levels.
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C707
Created by
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LOINC |
75149-5
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LOINC |
59201-4
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LOINC |
75134-7
Created by
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135398592
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Deoxyguanosine
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961-07-9
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C421
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22837
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SUB197050
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213-505-8
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100000182770
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17172
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G9481N71RO
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DTXSID30883626
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SUBSTANCE RECORD
