Jasplakinolide

Last updated
Jasplakinolide
Jasplakinolide.svg
Names
IUPAC name
Cyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C36H45BrN4O6/c1-20-15-21(2)17-23(4)47-32(43)19-30(25-11-13-26(42)14-12-25)40-35(45)31(18-28-27-9-7-8-10-29(27)39-33(28)37)41(6)36(46)24(5)38-34(44)22(3)16-20/h7-15,21-24,30-31,39,42H,16-19H2,1-6H3,(H,38,44)(H,40,45)/b20-15+/t21-,22-,23-,24-,30+,31+/m0/s1
    Key: GQWYWHOHRVVHAP-DHKPLNAMSA-N
  • C[C@@H]\1C[C@@H](OC(=O)C[C@@H](NC(=O)[C@H](N(C(=O)[C@@H](NC(=O)[C@H](C/C(=C1)/C)C)C)C)CC2=C(NC3=CC=CC=C32)Br)C4=CC=C(C=C4)O)C
Properties
C36H45BrN4O6
Molar mass 709.682 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Jasplakinolide is a naturally occurring cyclo-depsipeptide. It was first isolated from a species of marine sponge named Jaspis johnstoni . It is permeable to the cell membrane meaning that it is able to cross the membrane. [1] Once it crosses the cell membrane, it is a potent inducer and stabilizer of actin filaments meaning that it rapidly stabilizes pre-existing filaments and polymerize the protein actin. [2] It also inhibits the disassembly of theses filaments. When doing this, it competes with phalloidin making it unable to bind with F-actin. [3]

Applications

Jasplakinolide is potentially important in medical applications showing anti-cancer, fungicidal and antiproliferative properties. It also has important scientific applications for the study of organelles, and actin filaments. [1] [2] [4]

References

  1. 1 2 Holzinger, Andreas (2009). "Jasplakinolide: an actin-specific reagent that promotes actin polymerization". Cytoskeleton Methods and Protocols. Methods in Molecular Biology (Clifton, N.J.). Vol. 586. pp. 71–87. doi:10.1007/978-1-60761-376-3_4. ISBN   978-1-60761-375-6. ISSN   1940-6029. PMID   19768425.
  2. 1 2 Bubb, Michael R.; Spector, Ilan; Beyer, Bret B.; Fosen, Katina M. (2000-02-18). "Effects of Jasplakinolide on the Kinetics of Actin Polymerization: AN EXPLANATION FOR CERTAIN IN VIVO OBSERVATIONS*". Journal of Biological Chemistry. 275 (7): 5163–5170. doi: 10.1074/jbc.275.7.5163 . ISSN   0021-9258. PMID   10671562.
  3. ↑ "Jasplakinolide | Actin Polymerization Inducer | MedChemExpress". MedchemExpress.com. Retrieved 2025-08-02.
  4. ↑ Bubb, M. R.; Senderowicz, A. M.; Sausville, E. A.; Duncan, K. L.; Korn, E. D. (1994-05-27). "Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin". Journal of Biological Chemistry. 269 (21): 14869–14871. doi: 10.1016/S0021-9258(17)36545-6 . ISSN   0021-9258. PMID   8195116.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.