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Chemical Compound Review

cryptophycin     (3S,6R,10R,13E,16S)-10-[(3- chloro-4...

Synonyms: CRYPTOPHYCIN A, Cryptophycin 1, CHEMBL441018, CHEBI:112588, AC1O5PMQ, ...
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Disease relevance of cryptophycin


High impact information on cryptophycin


Biological context of cryptophycin


Anatomical context of cryptophycin


Associations of cryptophycin with other chemical compounds


Gene context of cryptophycin

  • Cryptophycin 52 was tested for its sensitivity to multidrug-resistance in several paired cell lines in which a sensitive parental line was matched with a multidrug-resistant derivative line [8].
  • These peptides inhibit tubulin polymerization into microtubules and, instead, induce the formation of single-walled tubulin rings of 23.8 nm mean diameter for cryptophycin and 44.6 nm mean diameter for hemiasterlin and dolastatin, as revealed by electron microscopy on micromolar drug-tubulin samples [9].
  • Rapid entry into the cryptophycin core via an acyl-beta-lactam macrolactonization: total synthesis of cryptophycin-24 [10].
  • An enantioselective synthesis of tert-butyl (5S,6R)-(E)-5-tert-butyldimethylsilyloxy-6-methyl-2,7-octadieno ate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented [11].

Analytical, diagnostic and therapeutic context of cryptophycin


  1. Cryptophycin: a new antimicrotubule agent active against drug-resistant cells. Smith, C.D., Zhang, X., Mooberry, S.L., Patterson, G.M., Moore, R.E. Cancer Res. (1994) [Pubmed]
  2. The novel antimicrotubule agent cryptophycin 52 (LY355703) induces apoptosis via multiple pathways in human prostate cancer cells. Drew, L., Fine, R.L., Do, T.N., Douglas, G.P., Petrylak, D.P. Clin. Cancer Res. (2002) [Pubmed]
  3. Cellular uptake of a novel cytotoxic agent, cryptophycin-52, by human THP-1 leukemia cells and H-125 lung tumor cells. Chen, B.D., Nakeff, A., Valeriote, F. Int. J. Cancer (1998) [Pubmed]
  4. Mechanism of action cryptophycin. Interaction with the Vinca alkaloid domain of tubulin. Smith, C.D., Zhang, X. J. Biol. Chem. (1996) [Pubmed]
  5. First generation design, synthesis, and evaluation of azepine-based cryptophycin analogues. Smith, A.B., Cho, Y.S., Zawacki, L.E., Hirschmann, R., Pettit, G.R. Org. Lett. (2001) [Pubmed]
  6. Localization of the antimitotic peptide and depsipeptide binding site on beta-tubulin. Mitra, A., Sept, D. Biochemistry (2004) [Pubmed]
  7. Cryptophycins: a novel class of potent antimitotic antitumor depsipeptides. Shih, C., Teicher, B.A. Curr. Pharm. Des. (2001) [Pubmed]
  8. In vitro pharmacology of cryptophycin 52 (LY355703) in human tumor cell lines. Wagner, M.M., Paul, D.C., Shih, C., Jordan, M.A., Wilson, L., Williams, D.C. Cancer Chemother. Pharmacol. (1999) [Pubmed]
  9. Stability of drug-induced tubulin rings by fluorescence correlation spectroscopy. Boukari, H., Nossal, R., Sackett, D.L. Biochemistry (2003) [Pubmed]
  10. Rapid entry into the cryptophycin core via an acyl-beta-lactam macrolactonization: total synthesis of cryptophycin-24. Eggen, M., Nair, S.K., Georg, G.I. Org. Lett. (2001) [Pubmed]
  11. Enantioselective synthesis of a 3'-dephenylcryptophycin synthon. Eggen, M.J., Georg, G.I. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  12. Phase I trial of the cryptophycin analogue LY355703 administered as an intravenous infusion on a day 1 and 8 schedule every 21 days. Stevenson, J.P., Sun, W., Gallagher, M., Johnson, R., Vaughn, D., Schuchter, L., Algazy, K., Hahn, S., Enas, N., Ellis, D., Thornton, D., O'Dwyer, P.J. Clin. Cancer Res. (2002) [Pubmed]
  13. Mechanism of action of the unusually potent microtubule inhibitor cryptophycin 1. Panda, D., Himes, R.H., Moore, R.E., Wilson, L., Jordan, M.A. Biochemistry (1997) [Pubmed]
  14. Enantioselective synthesis of (+)-cryptophycin 52 (LY355703), a potent antimitotic antitumor agent. Ghosh, A.K., Swanson, L. J. Org. Chem. (2003) [Pubmed]
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