Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

AC1LAQM7 4-amino-1-[(1R,4S,5R)-4,5- dihydroxy-3...

Synonyms:

Kang, G.J. et al., Ostrander, D.B. et al., Li, M.L. et al., Gharehbaghi, K. et al., De Clercq, E. et al., et al.

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Disease relevance of Cyclopentenylcytosine

Resistance to cyclopentenylcytosine in murine leukemia L1210 cells [1].
We now describe a mutant of Sindbis virus, SVCPC, that is resistant to cyclopentenylcytosine (CPC), a compound that interferes only with the synthesis of CTP [2].

High impact information on Cyclopentenylcytosine

Cells expressing the E161K mutant enzymes on a multicopy plasmid exhibited an increase in resistance to the pyrimidine poison and cancer therapeutic drug cyclopentenylcytosine and accumulated elevated (6-15-fold) levels of CTP when compared with cells expressing the wild-type enzymes [3].
Cyclopentenylcytosine triphosphate. Formation and inhibition of CTP synthetase [4].
Partially purified uridine-cytidine kinase catalyzes the initial phosphorylation of cyclopentenylcytosine with an apparent Km of 196 +/- 9 microM, and cyclopentenylcytosine is a competitive inhibitor of cytidine phosphorylation by this enzyme with a Ki value of 144 +/- 14 microM [4].
Only one amino acid change in nsP4, Leu 585 to Phe, was required for the CPC resistance phenotype [2].
Broad-spectrum antiviral and cytocidal activity of cyclopentenylcytosine, a carbocyclic nucleoside targeted at CTP synthetase [5].

Anatomical context of Cyclopentenylcytosine

Cyclopentenylcytosine (CPEC) is cytotoxic to HT-29 cells in vitro and in vivo [6].

Associations of Cyclopentenylcytosine with other chemical compounds

Sensitizing human colon carcinoma HT-29 cells to cisplatin by cyclopentenylcytosine, in vitro and in vivo [6].

References

Resistance to cyclopentenylcytosine in murine leukemia L1210 cells. Zhang, H., Cooney, D.A., Zhang, M.H., Ahluwalia, G., Ford, H., Johns, D.G. Cancer Res. (1993) [Pubmed]
A mutant of Sindbis virus which is able to replicate in cells with reduced CTP makes a replicase/transcriptase with a decreased Km for CTP. Li, M.L., Lin, Y.H., Simmonds, H.A., Stollar, V. J. Virol. (2004) [Pubmed]
Effect of CTP synthetase regulation by CTP on phospholipid synthesis in Saccharomyces cerevisiae. Ostrander, D.B., O'Brien, D.J., Gorman, J.A., Carman, G.M. J. Biol. Chem. (1998) [Pubmed]
Cyclopentenylcytosine triphosphate. Formation and inhibition of CTP synthetase. Kang, G.J., Cooney, D.A., Moyer, J.D., Kelley, J.A., Kim, H.Y., Marquez, V.E., Johns, D.G. J. Biol. Chem. (1989) [Pubmed]
Broad-spectrum antiviral and cytocidal activity of cyclopentenylcytosine, a carbocyclic nucleoside targeted at CTP synthetase. De Clercq, E., Murase, J., Marquez, V.E. Biochem. Pharmacol. (1991) [Pubmed]
Sensitizing human colon carcinoma HT-29 cells to cisplatin by cyclopentenylcytosine, in vitro and in vivo. Gharehbaghi, K., Szekeres, T., Yalowitz, J.A., Fritzer-Szekeres, M., Pommier, Y.G., Jayaram, H.N. Life Sci. (2000) [Pubmed]

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