EF-24

Last updated
EF-24
EF-24 Structure.svg
Identifiers
  • (3E,5E)-3,5-bis[(2-fluorophenyl)methylidene]piperidin-4-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C19H15F2NO
Molar mass 311.332 g·mol−1
3D model (JSmol)
  • C\1NC/C(=C\C2=CC=CC=C2F)/C(=O)/C1=C/C3=CC=CC=C3F
  • InChI=1S/C19H15F2NO/c20-17-7-3-1-5-13(17)9-15-11-22-12-16(19(15)23)10-14-6-2-4-8-18(14)21/h1-10,22H,11-12H2/b15-9+,16-10+
  • Key:NIVYQYSNRUIFIF-KAVGSWPWSA-N

EF-24 is a compound that is a synthetic analogue of curcumin, a bioactive phytochemical from turmeric. Curcumin has antioxidant, antibiotic, anti-inflammatory and anti-cancer properties in vitro but has low potency and very poor bioavailability when taken orally, resulting in limited efficacy. EF-24 was developed to try to improve upon these properties, and has been found to be around 10 times more potent than curcumin and with much higher systemic bioavailability. It has never been developed for medical use, though research continues to investigate whether it may be useful as an adjuvant treatment for some cancers alongside conventional chemotherapy drugs. [1] [2] [3] [4] [5]

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References

  1. Adams BK, Cai J, Armstrong J, Herold M, Lu YJ, Sun A, et al. (March 2005). "EF24, a novel synthetic curcumin analog, induces apoptosis in cancer cells via a redox-dependent mechanism". Anti-Cancer Drugs. 16 (3): 263–75. doi:10.1097/00001813-200503000-00005. PMID   15711178. S2CID   33132231.
  2. Mosley CA, Liotta DC, Snyder JP (2007). "Highly Active Anticancer Curcumin Analogues". The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. Advances in Experimental Medicine and Biology. Vol. 595. pp. 77–103. doi:10.1007/978-0-387-46401-5_2. ISBN   978-0-387-46400-8. PMID   17569206.
  3. He Y, Li W, Hu G, Sun H, Kong Q (2018). "Bioactivities of EF24, a Novel Curcumin Analog: A Review". Frontiers in Oncology. 8: 614. doi: 10.3389/fonc.2018.00614 . PMC   6297553 . PMID   30619754.
  4. Li W, He Y, Zhang R, Zheng G, Zhou D (January 2019). "The curcumin analog EF24 is a novel senolytic agent". Aging. 11 (2): 771–782. doi:10.18632/aging.101787. PMC   6366974 . PMID   30694217.
  5. Bazzaro M, Linder S (November 2020). "Dienone Compounds: Targets and Pharmacological Responses". Journal of Medicinal Chemistry. 63 (24): 15075–15093. doi:10.1021/acs.jmedchem.0c00812. PMC   7770821 . PMID   33146523.