Irofulven

Irofulven
IUPAC name

(6'R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one
Identifiers
CAS number 158440-71-2
PubChem 148189
ChemSpider 130640 Y
KEGG D04614 Y
ChEMBL CHEMBL118218 Y
Jmol-3D images Image 1
Properties
Molecular formula C15H18O3
Molar mass 246.302 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF of MGI-114) is an antitumor agent.[1][2] It belongs to the family of drugs called alkylating agents.

It inhibits the replication of DNA.[3]

Irofulven is an analogue of illudin S, a sesquiterpene toxin found in mushrooms of the genus Omphalotus. The compound was oringally synthesized by Dr. Trevor McMorris (UCSD) and found to have anticancer properties by Dr. Michael J Kelner (UCSD).[4]

Synthesis

McMorris, Trevor C.; Staake, Michael D.; Kelner, Michael J. (2004). "Synthesis and Biological Activity of Enantiomers of Antitumor Irofulven". The Journal of Organic Chemistry 69 (3): 619. doi:10.1021/jo035084j. PMID 14750783. 

References

  1. ^ Escargueil AE, Poindessous V, Soares DG, Sarasin A, Cook PR, Larsen AK (April 2008). "Influence of irofulven, a transcription-coupled repair-specific antitumor agent, on RNA polymerase activity, stability and dynamics in living mammalian cells". J. Cell. Sci. 121 (Pt 8): 1275–83. doi:10.1242/jcs.023259. PMID 18388315. 
  2. ^ Kelner MJ, McMorris TC, Estes L, Wang W, Samson KM, Taetle R (1996). "Efficacy of HMAF (MGI-114) in the MV522 metastatic lung carcinoma xenograft model nonresponsive to traditional anticancer agents". Invest New Drugs 14 (2): 161–7. doi:10.1007/BF00210787. PMID 8913837. 
  3. ^ Wang Y, Wiltshire T, Senft J, Reed E, Wang W (February 2007). "Irofulven induces replication-dependent CHK2 activation related to p53 status". Biochem. Pharmacol. 73 (4): 469–80. doi:10.1016/j.bcp.2006.10.023. PMC 1800887. PMID 17118344. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1800887. 
  4. ^ MacDonald JR, Muscoplat CC, Dexter DL, Mangold GL, Chen SF, Kelner MJ, McMorris TC, Von Hoff DD (1997). "Preclinical antitumor activity of 6-hydroxymethylacylfulvene, a semisynthetic derivative of the mushroom toxin illudin S". Cancer Res. 57 (2): 279–83. PMID 9000568.  Free full text