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Chemical Compound Review

AC1LAD1Q     phenyl3-[(8-benzyl-7,9,9- trioxo-9$l^{6}...

Synonyms: Acyclonucleoside, phenyl 3-[(3-benzyl-2,2,4-trioxo-2
 
 
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Disease relevance of AIDS-045658

 

High impact information on AIDS-045658

 

Biological context of AIDS-045658

  • Hydroxylation of the allyl group gave a glycerol-1-yl acyclonucleoside which can be alternatively obtained by a displacement reaction of the tosyloxy group in 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)glycerol (14), followed by deisopropylidenation [8].
  • While acyclonucleosides undergo phosphorylation in the cytosol by cellular kinases, with their triphosphates being active acyclonucleoside metabolites, active 1,3,4,5-tetrahydroisoquinoline derivatives (compounds not containing a deoxyribose moiety), cannot be phosphorylated [9].
 

Associations of AIDS-045658 with other chemical compounds

 

Gene context of AIDS-045658

  • Acyclonucleoside analogues consisting of 5- and 5,6-substituted uracils and different acyclic chains: inhibitory properties vs purified E. coli uridine phosphorylase [12].
 

Analytical, diagnostic and therapeutic context of AIDS-045658

  • Therefore, the iron binding and removal properties of the acyclonucleoside iron chelators should remain similar to the ribonucleoside iron chelators, which is confirmed by the titration and competition reaction of the acyclonucleoside chelators with iron and ferritin, respectively [13].

References

  1. Enhancement of 5-fluoro-2'-deoxyuridine antineoplastic activity by 5-benzyloxybenzyloxybenzylacyclouridine in a human colon carcinoma cell line. Chu, E., Chu, M.Y., Darnowski, J.W., Chen, Z.H., Pan, B.C., Chu, S.H. Cancer Res. (1992) [Pubmed]
  2. Activity of acyclic 6-(phenylselenenyl)pyrimidine nucleosides against human immunodeficiency viruses in primary lymphocytes. Goudgaon, N.M., Schinazi, R.F. J. Med. Chem. (1991) [Pubmed]
  3. GR-891: a novel 5-fluorouracil acyclonucleoside prodrug for differentiation therapy in rhabdomyosarcoma cells. Marchal, J.A., Prados, J., Melguizo, C., Gómez, J.A., Campos, J., Gallo, M.A., Espinosa, A., Arena, N., Aránega, A. Br. J. Cancer (1999) [Pubmed]
  4. Inhibitor properties of some 5-substituted uracil acyclonucleosides, and 2,2'-anhydrouridines versus uridine phosphorylase from E. coli and mammalian sources. Drabikowska, A.K., Lissowska, L., Veres, Z., Shugar, D. Biochem. Pharmacol. (1987) [Pubmed]
  5. Synthesis and biological studies of unsaturated acyclonucleoside analogues of S-adenosyl-L-homocysteine hydrolase inhibitors. Hasan, A., Srivastava, P.C. J. Med. Chem. (1992) [Pubmed]
  6. Prodrugs of the selective antiherpesvirus agent 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine (BRL 39123) with improved gastrointestinal absorption properties. Harnden, M.R., Jarvest, R.L., Boyd, M.R., Sutton, D., Vere Hodge, R.A. J. Med. Chem. (1989) [Pubmed]
  7. Acyclonucleoside analogue inhibitors of mammalian purine nucleoside phosphorylase. Bzowska, A., Kulikowska, E., Shugar, D., Chen, B.Y., Lindborg, B., Johansson, N.G. Biochem. Pharmacol. (1991) [Pubmed]
  8. A novel synthesis of acyclonucleosides via allylation of 3-[1-(phenylhydrazono)-L-threo-2,3,4-trihydroxybut-1-yl]quinoxalin-2(1H)one. Hamid, H.M. Carbohydr. Res. (2003) [Pubmed]
  9. A study of the influence of newly synthesized acyclonucleosides and 1,2,3,4-tetrahydroisoquinoline derivatives on deoxythymidine and deoxycytidine kinase activities in human neurofibrosarcoma and ovarian cancer. Modrzejewska, H., Brzezińska, E., Dramiński, M., Zgit-Wróblewska, A., Krzykowska, K., Rozpończyk, E., Greger, J. Acta Biochim. Pol. (2003) [Pubmed]
  10. Calf spleen purine nucleoside phosphorylase: structure of its ternary complex with an N(7)-acycloguanosine inhibitor and a phosphate anion. Luić, M., Koellner, G., Shugar, D., Saenger, W., Bzowska, A. Acta Crystallogr. D Biol. Crystallogr. (2001) [Pubmed]
  11. Synthesis of 2',5'-oligoadenylate analogs containing an adenine acyclonucleoside and their ability to activate human RNase L. Ueno, Y., Ishihara, S., Ito, Y., Kitade, Y. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  12. Acyclonucleoside analogues consisting of 5- and 5,6-substituted uracils and different acyclic chains: inhibitory properties vs purified E. coli uridine phosphorylase. Drabikowska, A.K., Lissowska, L., Draminski, M., Zgit-Wroblewska, A., Shugar, D. Z. Naturforsch., C, J. Biosci. (1987) [Pubmed]
  13. Acyclonucleoside iron chelators of 1-(2-hydroxyethoxy)methyl-2-alkyl-3-hydroxy-4-pyridinones: potential oral iron chelation therapeutics. Liu, G., Men, P., Kenner, G.H., Miller, S.C., Bruenger, F.W. Nucleosides Nucleotides Nucleic Acids (2004) [Pubmed]
 
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