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Chemical Compound Review

S-adenosylhomocysteine     (2S)-2-amino-4- [[(2R,3S,4R,5R)-5-(6...

Synonyms: AdoHcy, SureCN8836, CHEMBL418052, AG-J-54393, A9384_SIGMA, ...
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Disease relevance of S-adenosylhomocysteine

  • Here we report four crystal structures of TrmD from Haemophilus influenzae, as binary complexes with either AdoMet or S-adenosyl-L-homocysteine (AdoHcy), as a ternary complex with AdoHcy and phosphate, and as an apo form [1].
  • We report here the crystal structures of the bacteriophage T4Dam DNA adenine methyltransferase (MTase) in a binary complex with the methyl-donor product S-adenosyl-L-homocysteine (AdoHcy) and in a ternary complex with a synthetic 12-bp DNA duplex and AdoHcy [2].
  • We have tried to determine whether inactivation of AdoHcyase might also contribute to dAdo toxicity to adenosine deaminase-inhibited cells. dAdo rapidly inactivates intracellular AdoHcyase and causes the accumulation of AdoHcy in WI-L2 human B lymphoblastoid cells [3].
  • Reactivation of AdoHcy hydrolase with a concomitant decrease in cellular level of AdoHcy could also be demonstrated with mouse plasmacytoma (MPC-11) cells and mouse fibroblasts (L-929) exposed to ara-A, but the reactivation process was far less pronounced than with hepatocytes [4].
  • Thus, in the presence of Hcy, lower concentrations of DHCA are needed to increase the intracellular concentration of AdoHcy and the AdoHcy/AdoMet ratio to levels that suppress replication of vaccinia virus [5].

High impact information on S-adenosylhomocysteine


Biological context of S-adenosylhomocysteine


Anatomical context of S-adenosylhomocysteine

  • However, the rate of elimination of the complex in the hepatocytes exceeded the rate of reactivation of AdoHcy hydrolase [4].
  • Whereas the inactivation in cell-free systems is an irreversible process, the AdoHcy hydrolase activity in rat hepatocytes exposed to ara-A gradually recovered upon prolonged incubation of the cells in a medium devoid of ara-A [4].
  • This selective suppression was also observed when enriched murine T and B cells were stimulated with mitogens, although S-adenosyl-L-homocysteine (AdoHcy), the substrate of AdoHcyase, was similarly elevated in both populations [11].
  • AdoHcy hydrolase activity in spleens of DZ2002-treated mice was substantially blocked, and not surprisingly, AdoHcy levels were significantly elevated compared with controls [12].
  • Progesterone production by cells from 4 CL was unaffected by the presence of SAH when treated with Medium 199 (M199) (75 +/- 32), 10 micrograms cholera toxin, which directly stimulates adenylate cyclase on the cytoplasmic side of plasma membranes (168 +/- 19), or 3 mM dibutyryl cAMP (210 +/- 40).(ABSTRACT TRUNCATED AT 250 WORDS)[13]

Associations of S-adenosylhomocysteine with other chemical compounds


Gene context of S-adenosylhomocysteine


Analytical, diagnostic and therapeutic context of S-adenosylhomocysteine


  1. Crystal structure of tRNA(m1G37)methyltransferase: insights into tRNA recognition. Ahn, H.J., Kim, H.W., Yoon, H.J., Lee, B.I., Suh, S.W., Yang, J.K. EMBO J. (2003) [Pubmed]
  2. Structure of the bacteriophage T4 DNA adenine methyltransferase. Yang, Z., Horton, J.R., Zhou, L., Zhang, X.J., Dong, A., Zhang, X., Schlagman, S.L., Kossykh, V., Hattman, S., Cheng, X. Nat. Struct. Biol. (2003) [Pubmed]
  3. Resistance of an adenosine kinase-deficient human lymphoblastoid cell line to effects of deoxyadenosine on growth, S-adenosylhomocysteine hydrolase inactivation, and dATP accumulation. Hershfield, M.S., Kredich, N.M. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  4. Reactivation of S-adenosylhomocysteine hydrolase activity in cells exposed to 9-beta-D-arabinofuranosyladenine. Helland, S., Ueland, P.M. Cancer Res. (1982) [Pubmed]
  5. Elucidation of the mechanism by which homocysteine potentiates the anti-vaccinia virus effects of the S-adenosylhomocysteine hydrolase inhibitor 9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl)-adenine. Hasobe, M., McKee, J.G., Ishii, H., Cools, M., Borchardt, R.T., De Clercq, E. Mol. Pharmacol. (1989) [Pubmed]
  6. Involvement of S-adenosylmethionine in G1 cell-cycle regulation in Saccharomyces cerevisiae. Mizunuma, M., Miyamura, K., Hirata, D., Yokoyama, H., Miyakawa, T. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  7. The active site of the SET domain is constructed on a knot. Jacobs, S.A., Harp, J.M., Devarakonda, S., Kim, Y., Rastinejad, F., Khorasanizadeh, S. Nat. Struct. Biol. (2002) [Pubmed]
  8. The X-ray structure of a cobalamin biosynthetic enzyme, cobalt-precorrin-4 methyltransferase. Schubert, H.L., Wilson, K.S., Raux, E., Woodcock, S.C., Warren, M.J. Nat. Struct. Biol. (1998) [Pubmed]
  9. Amino acid sequence of S-adenosyl-L-homocysteine hydrolase from rat liver as derived from the cDNA sequence. Ogawa, H., Gomi, T., Mueckler, M.M., Fujioka, M., Backlund, P.S., Aksamit, R.R., Unson, C.G., Cantoni, G.L. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  10. Binding of adenosine to intracellular S-adenosylhomocysteine hydrolase in isolated rat hepatocytes. Ueland, P.M., Helland, S. J. Biol. Chem. (1983) [Pubmed]
  11. Selective inhibition of T cell activation by an inhibitor of S-adenosyl-L-homocysteine hydrolase. Wolos, J.A., Frondorf, K.A., Davis, G.F., Jarvi, E.T., McCarthy, J.R., Bowlin, T.L. J. Immunol. (1993) [Pubmed]
  12. S-adenosyl-L-homocysteine hydrolase inactivation curtails ovalbumin-induced immune responses. Fu, Y.F., Wang, J.X., Zhao, Y., Yang, Y., Tang, W., Ni, J., Zhu, Y.N., Zhou, R., He, P.L., Li, C., Li, X.Y., Yang, Y.F., Lawson, B.R., Zuo, J.P. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  13. Methylation in bovine luteal cells as a regulator of luteinizing hormone action. Milvae, R.A., Alila, H.W., Hansel, W. Biol. Reprod. (1983) [Pubmed]
  14. Adenosine and homocysteine together enhance TNF-mediated cytotoxicity but do not alter activation of nuclear factor-kappa B in L929 cells. Bergmann, S., Shatrov, V., Ratter, F., Schiemann, S., Schulze-Osthoff, K., Lehmann, V. J. Immunol. (1994) [Pubmed]
  15. Inhibition of CYP2E1 catalytic activity in vitro by S-adenosyl-L-methionine. Caro, A.A., Cederbaum, A.I. Biochem. Pharmacol. (2005) [Pubmed]
  16. Structure of human DNMT2, an enigmatic DNA methyltransferase homolog that displays denaturant-resistant binding to DNA. Dong, A., Yoder, J.A., Zhang, X., Zhou, L., Bestor, T.H., Cheng, X. Nucleic Acids Res. (2001) [Pubmed]
  17. Crystal complexes of a predicted S-adenosylmethionine-dependent methyltransferase reveal a typical AdoMet binding domain and a substrate recognition domain. Miller, D.J., Ouellette, N., Evdokimova, E., Savchenko, A., Edwards, A., Anderson, W.F. Protein Sci. (2003) [Pubmed]
  18. Water-assisted dual mode cofactor recognition by HhaI DNA methyltransferase. Swaminathan, C.P., Sankpal, U.T., Rao, D.N., Surolia, A. J. Biol. Chem. (2002) [Pubmed]
  19. Decreased transmethylation of biogenic amines after in vivo elevation of brain S-adenosyl-l-homocysteine. Schatz, R.A., Wilens, T.E., Sellinger, O.Z. J. Neurochem. (1981) [Pubmed]
  20. Inhibitory effect of Epimedium extract on S-adenosyl-L-homocysteine hydrolase and biomethylation. Zhang, X., Li, Y., Yang, X., Wang, K., Ni, J., Qu, X. Life Sci. (2005) [Pubmed]
  21. Gene expression analysis in human gastric cancer cell line treated with trichostatin A and S-adenosyl-L-homocysteine using cDNA microarray. Lee, H.S., Park, M.H., Yang, S.J., Jung, H.Y., Byun, S.S., Lee, D.S., Yoo, H.S., Yeom, Y.I., Seo, S.B. Biol. Pharm. Bull. (2004) [Pubmed]
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