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Chemical Compound Review

chlamydocin     (3S,9S,12R)-3-benzyl-6,6- dimethyl-9-[6...

Synonyms: AmbotzLS-1109, HDInhib_000038, KST-1A5678, AC1L3XWY, AR-1A4679, ...
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Disease relevance of chlamydocin

  • We show here that these compounds have reciprocal biological activity; HC-toxin is cytostatic against cultured mastocytoma cells, and chlamydocin has host-specific toxin activity against maize [1].

High impact information on chlamydocin

  • Chlamydocin, a related cyclic tetrapeptide, also inhibited HD activity [2].
  • The maleoyl cyclic tetrapeptide 5 did not inhibit [3H]thymidine incorporation into calf thymus lymphocytes at concentrations 1000-fold higher than the IC50 for chlamydocin (6 nM) [3].
  • The synthesis of analogues of the cytostatic cyclic tetrapeptide chlamydocin is described. cyclo(Gly-L-Phe-D-Pro-N beta-Boc-L-Dap) (4) was prepared from N beta-(tert-butyloxycarbonyl)-L-diaminopropionic acid methyl ester (Dap) and Cbz-Gly-L-Phe-D-Pro using DCC/HOBt as the coupling reagent [3].
  • Here we show that chlamydocin is a highly potent histone deacetylase (HDAC) inhibitor, inhibiting HDAC activity in vitro with an IC(50) of 1.3 nM [4].
  • Although our data indicate a potential link between degradation of survivin and activation of the apoptotic pathway induced by HDAC inhibitors, stable overexpression of survivin does not suppress the activation of caspase-3 or cleavage of p21(cip1/waf1) induced by chlamydocin treatment [4].

Biological context of chlamydocin


Associations of chlamydocin with other chemical compounds


Gene context of chlamydocin

  • We replaced the epoxyketone moiety of chlamydocin with hydroxamic acid to design potent and reversible inhibitors of HDAC [6].

Analytical, diagnostic and therapeutic context of chlamydocin

  • We have carried out circular dichroism and molecular modeling studies on chlamydocin-hydroxamic acid analogue and compared it with the solution structure of chlamydocin [6].


  1. Reciprocal biological activities of the cyclic tetrapeptides chlamydocin and HC-toxin. Walton, J.D., Earle, E.D., Stähelin, H., Grieder, A., Hirota, A., Suzuki, A. Experientia (1985) [Pubmed]
  2. Inhibition of maize histone deacetylases by HC toxin, the host-selective toxin of Cochliobolus carbonum. Brosch, G., Ransom, R., Lechner, T., Walton, J.D., Loidl, P. Plant Cell (1995) [Pubmed]
  3. Analogues of the cytostatic cyclic tetrapeptide chlamydocin. Synthesis of N beta-(N-maleoylglycyl) and N beta-(tert-butyloxycarbonyl) derivatives of cyclo(Gly-L-Phe-D-Pro-L-Dap). Rich, D.H., Jasensky, R.D., Mueller, G.C., Anderson, K.E. J. Med. Chem. (1981) [Pubmed]
  4. Inhibition of histone deacetylases by chlamydocin induces apoptosis and proteasome-mediated degradation of survivin. De Schepper, S., Bruwiere, H., Verhulst, T., Steller, U., Andries, L., Wouters, W., Janicot, M., Arts, J., Van Heusden, J. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  5. Inhibitors of histone deacetylases promote hematopoietic stem cell self-renewal. Young, J.C., Wu, S., Hansteen, G., Du, C., Sambucetti, L., Remiszewski, S., O'Farrell, A.M., Hill, B., Lavau, C., Murray, L.J. Cytotherapy. (2004) [Pubmed]
  6. Chlamydocin-hydroxamic acid analogues as histone deacetylase inhibitors. Nishino, N., Jose, B., Shinta, R., Kato, T., Komatsu, Y., Yoshida, M. Bioorg. Med. Chem. (2004) [Pubmed]
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