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Chemical Compound Review

NEPLANOCIN     (1S,2S,3R)-3-(6-amino-2H- purin-9-yl)-5...

Synonyms: AC1NRCKA
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Disease relevance of NEPLANOCIN

  • Strikingly, in comparing the therapeutic indices between the paired pre- and post-3'-azido-3'-deoxythymidine (AZT) treatment HIV-1 isolates, DZNep and neplanocin A showed an increase of 3- to 18-fold in their potency against AZT-resistant HIV-1 isolates [1].
  • In addition, we show that neplanocin A is a potent inhibitor of vaccinia virus (WR) multiplication in monolayer cultures of mouse L-cells [2].
  • We have compared the metabolism and some of the metabolic effects of neplanocin A and synthetic (+/-)-aristeromycin (C-Ado) in murine leukemia L1210 cells in culture [3].
  • In vivo, neplanocin A afforded only marginal protection against a lethal infection of mice with vesicular stomatitis virus [4].
  • Depending on the cells used, the MIC of neplanocin A for these viruses ranged from 0.01 to 4 micrograms/ml, and depending on the parameter used to assess toxicity for the host cell, the specificity index of neplanocin A ranged from 50 to 4,000 [4].

High impact information on NEPLANOCIN


Chemical compound and disease context of NEPLANOCIN


Biological context of NEPLANOCIN


Anatomical context of NEPLANOCIN


Associations of NEPLANOCIN with other chemical compounds


Gene context of NEPLANOCIN

  • This selection yielded several variants that were nonresponsive to both TRH- and EGF-induced stretching but were still responsive to stretching induced by several other agents (tetradecanoylphorbol acetate [TPA], butyrate, and Neplanocin A) [23].
  • However, by removing the 4'-hydroxymethyl group from neplanocin A, analogs 1 and 2 are no longer substrates for adenosine deaminase and adenosine kinase [20].
  • Neplanocin A. A potent inhibitor of S-adenosylhomocysteine hydrolase and of vaccinia virus multiplication in mouse L929 cells [2].
  • Fluoroneplanocin A exhibited 2-fold more potent SAH inhibitory activity than the parent neplanocin A [24].
  • These results confirm that S-adenosylhomocysteine hydrolase is the molecular target which mediates the antiviral effects of neplanocin A and that transformation by cellular adenosine kinase mediates its cytotoxic properties [16].

Analytical, diagnostic and therapeutic context of NEPLANOCIN


  1. Anti-human immunodeficiency virus 1 (HIV-1) activities of 3-deazaadenosine analogs: increased potency against 3'-azido-3'-deoxythymidine-resistant HIV-1 strains. Mayers, D.L., Mikovits, J.A., Joshi, B., Hewlett, I.K., Estrada, J.S., Wolfe, A.D., Garcia, G.E., Doctor, B.P., Burke, D.S., Gordon, R.K. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  2. Neplanocin A. A potent inhibitor of S-adenosylhomocysteine hydrolase and of vaccinia virus multiplication in mouse L929 cells. Borchardt, R.T., Keller, B.T., Patel-Thombre, U. J. Biol. Chem. (1984) [Pubmed]
  3. Differences in the metabolism and metabolic effects of the carbocyclic adenosine analogs, neplanocin A and aristeromycin. Bennett, L.L., Allan, P.W., Rose, L.M., Comber, R.N., Secrist, J.A. Mol. Pharmacol. (1986) [Pubmed]
  4. Antiviral and antimetabolic activities of neplanocins. De Clercq, E. Antimicrob. Agents Chemother. (1985) [Pubmed]
  5. N6-methyladenosine residues in an intron-specific region of prolactin pre-mRNA. Carroll, S.M., Narayan, P., Rottman, F.M. Mol. Cell. Biol. (1990) [Pubmed]
  6. Biochemical mode of cytotoxic action of neplanocin A in L1210 leukemic cells. Inaba, M., Nagashima, K., Tsukagoshi, S., Sakurai, Y. Cancer Res. (1986) [Pubmed]
  7. The role of nicotinamide adenine dinucleotide in the inhibition of bovine liver S-adenosylhomocysteine hydrolase by neplanocin A. Matuszewska, B., Borchardt, R.T. J. Biol. Chem. (1987) [Pubmed]
  8. Neplanocin A. Actions on S-adenosylhomocysteine hydrolase and on hormone synthesis by GH4C1 cells. Wolfson, G., Chisholm, J., Tashjian, A.H., Fish, S., Abeles, R.H. J. Biol. Chem. (1986) [Pubmed]
  9. Metabolism and action of neplanocin A in Chinese hamster ovary cells. Saunders, P.P., Tan, M.T., Robins, R.K. Biochem. Pharmacol. (1985) [Pubmed]
  10. Neplanocin A inhibition of S-adenosylhomocysteine hydrolase in Alcaligenes faecalis has no effect on growth of the microorganism. Fisher, E.W., Decedue, C.J., Keller, B.T., Borchardt, R.T. J. Antibiot. (1987) [Pubmed]
  11. The synergism of nucleoside antibiotics combined with guanine 7-N-oxide against a rhabdovirus, infectious hematopoietic necrosis virus (IHNV). Hasobe, M., Saneyoshi, M., Isono, K. J. Antibiot. (1986) [Pubmed]
  12. The methyltransferase inhibitor Neplanocin A interferes with influenza virus replication by a mechanism different from that of 3-deazaadenosine. Woyciniuk, P., Linder, M., Scholtissek, C. Virus Res. (1995) [Pubmed]
  13. Purification and characterization of some metabolic effects of S-neplanocylmethionine. Keller, B.T., Clark, R.S., Pegg, A.E., Borchardt, R.T. Mol. Pharmacol. (1985) [Pubmed]
  14. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase. Borcherding, D.R., Narayanan, S., Hasobe, M., McKee, J.G., Keller, B.T., Borchardt, R.T. J. Med. Chem. (1988) [Pubmed]
  15. Substrate binding stabilizes S-adenosylhomocysteine hydrolase in a closed conformation. Yin, D., Yang, X., Hu, Y., Kuczera, K., Schowen, R.L., Borchardt, R.T., Squier, T.C. Biochemistry (2000) [Pubmed]
  16. 9-(trans-2',trans-3'-Dihydroxycyclopent-4'-enyl)-adenine and -3-deazaadenine: analogs of neplanocin A which retain potent antiviral activity but exhibit reduced cytotoxicity. Hasobe, M., McKee, J.G., Borcherding, D.R., Borchardt, R.T. Antimicrob. Agents Chemother. (1987) [Pubmed]
  17. Protein carboxyl methylation in synaptic membrane of rat brain: the possible presence of adenosine-bound S-adenosyl-L-homocysteine hydrolase in the membrane. Miyake, M., Innami, T. J. Neurochem. (1987) [Pubmed]
  18. Neplanocin A, a potent inhibitor of S-adenosylhomocysteine hydrolase, potentiates granulocytic differentiation of acute promyelocytic leukemia cells induced by all-trans retinoic acid. Niitsu, N., Yamamoto-Yamaguchi, Y., Kanatani, Y., Shuto, S., Matsuda, A., Umeda, M., Honma, Y. Exp. Hematol. (1997) [Pubmed]
  19. Antimalarial activity of neplanocin A with perturbations in the metabolism of purines, polyamines and S-adenosylmethionine. Whaun, J.M., Miura, G.A., Brown, N.D., Gordon, R.K., Chiang, P.K. J. Pharmacol. Exp. Ther. (1986) [Pubmed]
  20. Effects of 9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl)-adenine and -3-deazaadenine on the metabolism of S-adenosylhomocysteine in mouse L929 cells. Hasobe, M., Mckee, J.G., Borcherding, D.R., Keller, B.T., Borchardt, R.T. Mol. Pharmacol. (1988) [Pubmed]
  21. Association of the Sindbis virus RNA methyltransferase activity with the nonstructural protein nsP1. Mi, S., Durbin, R., Huang, H.V., Rice, C.M., Stollar, V. Virology (1989) [Pubmed]
  22. Effects of adenosine analogues on ATP concentrations in human erythrocytes. Further evidence for a route independent of adenosine kinase. Smolenski, R.T., Montero, C., Duley, J.A., Simmonds, H.A. Biochem. Pharmacol. (1991) [Pubmed]
  23. GH4 pituitary cell variants selected as nonresponsive to thyrotropin-releasing hormone-enhanced substratum adhesion are nonresponsive to epidermal growth factor: evidence for a common signaling defect. Ramsdell, J.S., Tashjian, A.H. J. Cell. Physiol. (1989) [Pubmed]
  24. Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase. Jeong, L.S., Yoo, S.J., Lee, K.M., Koo, M.J., Choi, W.J., Kim, H.O., Moon, H.R., Lee, M.Y., Park, J.G., Lee, S.K., Chun, M.W. J. Med. Chem. (2003) [Pubmed]
  25. Quantitation of S-adenosylhomocysteine hydrolase in mouse L929 cells using the inhibitor neplanocin A. Bartel, R.L., Borchardt, R.T. Anal. Biochem. (1985) [Pubmed]
  26. Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization. Yaginuma, S., Muto, N., Tsujino, M., Sudate, Y., Hayashi, M., Otani, M. J. Antibiot. (1981) [Pubmed]
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