Aplidine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Aplidine
Aplidine.svg
Identifiers
CAS number 137219-37-5 YesY
ChemSpider 26001665 YesY
Jmol-3D images Image 1
Properties
Molecular formula C57H87N7O15
Molar mass 1,110.34 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Aplidine, also known as dihydrodidemnin B, is a chemical compound extracted from the ascidian Aplidium albicans.[1] It is currently undergoing clinical trial testing. It is a member of the class of compounds known as didemnins.

Chemical structure[edit]

Aplidine is a cyclic depsipeptide, meaning it is a cyclic peptide in which there is one or more ester bond in place of one or more of a peptide bond. Its chemical structure is very close to that of didemnin B, the only difference being that the lactate residue in didemnin B is present in the oxidized pyruvate version.

Pharmacological activity[edit]

Like all didemnin compounds, it exhibits antitumor, antiviral and immunosuppressive activities. It shows promise in shrinking tumors in pancreatic, stomach, bladder, and prostate cancers.[2][3] As of 2007, it was undergoing multicenter phase II clinical trials.[3] In July 2003, aplidine was granted orphan drug status by the European Medicines Agency for treating acute lymphoblastic leukemia.[4]

References[edit]

  1. ^ Cragg, G.M. and Newman, D.J. (2004). Journal of Natural Products 67 (8): 1216–1238. doi:10.1021/np040031y. PMID 15332835. 
  2. ^ Garrison, Tom. Oceanography: An Invitation to Marine Science 4th ed. United States: Brooks/Cole. 2002. 98.
  3. ^ a b Adrio, J. et al (2007). "Total Synthesis and Biological Evaluation of Tamandarin B Analogues". Journal of Organic Chemistry 72 (14): 5129–5138. doi:10.1021/jo070412r. 
  4. ^ Public Summary of Positive Opinion for Orphan Designation of Aplidine for the Treatment of Acute Lymphoblastic Leukaemia