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 |
| KEGG | D04614 |
| ChEMBL | CHEMBL118218 |
| Jmol-3D images | {{#if:O=C1C/3=C/C(=C(C\3=C(/C2([C@]1(O)C)CC2)C)CO)C|Image 1 |
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| Properties | |
| Molecular formula | C15H18O3 |
| Molar mass | 246.302 g/mol |
| Density | 1.285 g/mL |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 originally synthesized by Dr. Trevor McMorris (UCSD) and found to have anticancer properties by Dr. Michael J Kelner (UCSD).[4]
Synthesis
McMorris, T. C.; Staake, M. D.; Kelner, M. 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
- ↑ Escargueil, A. E.; Poindessous, V.; Soares, D. G.; Sarasin, A.; Cook, P. R.; Larsen, A. K. (April 2008). "Influence of Irofulven, a Transcription-Coupled Repair-Specific Antitumor Agent, on RNA Polymerase Activity, Stability and Dynamics in Living Mammalian Cells" (pdf). Journal of Cell Science 121 (Pt 8): 1275–1283. doi:10.1242/jcs.023259. PMID 18388315.
- ↑ Kelner, M. J.; McMorris, T. C.; Estes, L.; Wang, W.; Samson, K. M.; Taetle, R. (1996). "Efficacy of HMAF (MGI-114) in the MV522 Metastatic Lung Carcinoma Xenograft Model Nonresponsive to Traditional Anticancer Agents". Investigational New Drugs 14 (2): 161–167. doi:10.1007/BF00210787. PMID 8913837.
- ↑ Wang, Y.; Wiltshire, T.; Senft, J.; Reed, E.; Wang, W. (February 2007). "Irofulven Induces Replication-Dependent CHK2 Activation Related to p53 Status" (pdf). Biochemical Pharmacology 73 (4): 469–480. doi:10.1016/j.bcp.2006.10.023. PMC 1800887. PMID 17118344.
- ↑ MacDonald, J. R.; Muscoplat, C. C.; Dexter, D. L.; Mangold, G. L.; Chen, S. F.; Kelner, M. J.; McMorris, T. C.; Von Hoff, D. D. (1997). "Preclinical Antitumor Activity of 6-hydroxymethylacylfulvene, a Semisynthetic Derivative of the Mushroom Toxin Illudin S" (pdf). Cancer Research 57 (2): 279–283. PMID 9000568.