Aplidine

Aplidine

IUPAC name (S)-N-((R)-1-(((3S,6R,7S,10R,11S,15S,17S,20S,25aS)-10-((S)-sec-butyl)-11-hydroxy-20-isobutyl-15-isopropyl-3-(4-methoxybenzyl)-2,6,17-trimethyl-1,4,8,13,16,18,21-heptaoxodocosahydro-1H-pyrrolo[2,1-f][1,15,4,7,10,20]dioxatetraazacyclotricosin-7-yl)amino)-4-methyl-1-oxopentan-2-yl)-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide
Other names Aplidin; Dihydrodidemnin B; Plitidepsin
Identifiers
CAS number	137219-37-5^Y
ChemSpider	26001665^Y
Jmol-3D images	Image 1
SMILES CC[C@H](C)[C@@H]1[C@H](CC(=O)O[C@H](C(=O)[C@@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)CN([C@H](C(=O)C[C@@H]([C@@H](C(=O)N1)NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]3CCCN3C(=O)C(=O)C)C)Cc4ccc(cc4)OC)C)CC(C)C)C)C(C)C)O
InChI InChI=1S/C59H91N7O14/c1-15-35(8)50-47(69)30-49(71)80-53(34(6)7)52(72)37(10)54(73)60-41(26-32(2)3)58(77)65-24-16-18-42(65)48(70)31-63(12)44(29-39-20-22-40(79-14)23-21-39)46(68)28-36(9)51(56(75)61-50)62-55(74)45(27-33(4)5)64(13)59(78)43-19-17-25-66(43)57(76)38(11)67/h20-23,32-37,41-45,47,50-51,53,69H,15-19,24-31H2,1-14H3,(H,60,73)(H,61,75)(H,62,74)/t35-,36-,37-,41-,42-,43-,44-,45+,47-,50+,51-,53-/m0/s1^Y Key: RZFJKZZAZSUBCF-VETSTYKFSA-N^Y
Properties
Molecular formula	C₅₇H₈₇N₇O₁₅
Molar mass	1110.34 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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

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

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