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Chemical Compound Review:

AC1L3XWA (2S)-2-amino-4-[[(2R,3S,4R)- 5-(5-amino-4,7...

Synonyms: 53199-57-8, 3-Deazaadenosylhomocysteine, S-(3-Deazaadenosyl)homocysteine, S-(3-Deazaadenosyl)-L-homocysteine

Scarpa, S. et al., Endresen, P.C. et al., Gordon, R.K. et al., Kim, I.K. et al., Aksamit, R.R. et al.

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High impact information on S-(3-Deazaadenosyl)-L-homocysteine monohydrate

Stimulation of myofiber formation by 3-deazaadenosine suggests a requirement for one or more methylation reactions in myoblast differentiation and the potentiation by homocysteine thiolactone indicates that myofiber formation is specifically stimulated by an intracellular accumulation of 3-deazaadenosylhomocysteine [1].
Chemotaxis by a macrophage cell line, RAW264, is specifically inhibited by the intracellular accumulation of 3-deazaadenosylhomocysteine (3-deaza-AdoHcy) [2].
The modifying action of Hcy on c3 Ado initiated apoptosis in HL-60 cells and this suggests that c3 Ado and 3-deazaadenosylhomocysteine (c3 AdoHcy) interact with different targets during initiation and progression of cell death in this cell line [3].
In hamsters, however, the administration of 3-deazaadenosine results only in the accumulation of 3-deazaadenosylhomocysteine (P. K. Chiang and G. L. Cantoni (1979) Biochem. Pharmacol. 28, 1897) [4].
Adenosylmethionine decarboxylase isolated from HeLa cells could also be inhibited by 3-deaza-(+/-)aristeromycin and 3-deazaadenosine, 3-deazaadenosylhomocysteine, and 3-deaza-(+/-)aristeromycinylhomocysteine [5].

References

Differentiation of myoblast cell lines and biological methylation: 3-deazaadenosine stimulates formation of multinucleated myofibers. Scarpa, S., Strom, R., Bozzi, A., Aksamit, R.R., Backlund, P.S., Chen, J., Cantoni, G.L. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
Inhibition of chemotaxis by S-3-deazaadenosylhomocysteine in a mouse macrophage cell line. Aksamit, R.R., Falk, W., Cantoni, G.L. J. Biol. Chem. (1982) [Pubmed]
Cell death initiated by 3-deazaadenosine in HL-60 cells is apoptosis and is partially inhibited by homocysteine. Endresen, P.C., Eide, T.J., Aarbakke, J. Biochem. Pharmacol. (1993) [Pubmed]
S-Adenosylhomocysteine hydrolase from hamster liver: purification and kinetic properties. Kim, I.K., Zhang, C.Y., Chiang, P.K., Cantoni, G.L. Arch. Biochem. Biophys. (1983) [Pubmed]
Inhibition of adenosylmethionine decarboxylase and perturbation of polyamine metabolism by 3-deaza-(+/-)aristeromycin. Gordon, R.K., Brown, N.D., Chiang, P.K. Biochem. Biophys. Res. Commun. (1983) [Pubmed]

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