Avarone

• CAT Number: I022704
• CAS Number: 55303-99-6
• Molecular Formula: C21H28O2
• Molecular Weight: 312.45
• Purity: 98%
• Synonyms: Avarone
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2,5-Cyclohexadiene-1,4-dione, 2-((1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl)-, (1R-(1-alpha,2-beta,4a-beta,8a-alpha))-
• InChI: 1S/C21H28O2/c1-14-6-5-7-19-20(14,3)11-10-15(2)21(19,4)13-16-12-17(22)8-9-18(16)23/h6,8-9,12,15,19H,5,7,10-11,13H2,1-4H3/t15-,19+,20+,21+/m0/s1
• InChIKey: VPRHEJGLNUDEEH-LWILDLIXSA-N
• SMILES: C1(C[C@]2([C@H]3[C@](C(C)=CCC3)(C)CC[C@@H]2C)C)=CC(C=CC1=O)=O

Avarone is a cytostatic agent which has potent antileukemic activity in vitro. Avarone also displays antibacterial and antifungal activities against a limited range of microorganisms.

Reference

1: Kolarević S, Milovanović D, Kračun-Kolarević M, Kostić J, Sunjog K, Martinović R, Đorđević J, Novaković I, Sladić D, Vuković-Gačić B. Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models. Drug Chem Toxicol. 2018 Jan 4:1-10. doi: 10.1080/01480545.2017.1413108. [Epub ahead of print] PubMed PMID: 29299944.
2: Pejin B, Tommonaro G, Glumac M, Jakimov D, Kojic V. The redox couple avarol/avarone in the fight with malignant gliomas: the case study of U-251 MG cells. Nat Prod Res. 2018 Mar;32(5):616-620. doi: 10.1080/14786419.2017.1327959. Epub 2017 May 15. PubMed PMID: 28504009.
3: Jeremić M, Pešić M, Dinić J, Banković J, Novaković I, Šegan D, Sladić D. Simple avarone mimetics as selective agents against multidrug resistant cancer cells. Eur J Med Chem. 2016 Aug 8;118:107-20. doi: 10.1016/j.ejmech.2016.04.011. Epub 2016 Apr 11. PubMed PMID: 27128177.
4: Seibert G, Raether W, Dogović N, Gasić MJ, Zahn RK, Müller WE. Antibacterial and antifungal activity of Avarone and Avarol. Zentralbl Bakteriol Mikrobiol Hyg A. 1985 Nov;260(3):379-86. PubMed PMID: 3841441.
5: Müller WE, Maidhof A, Zahn RK, Schröder HC, Gasić MJ, Heidemann D, Bernd A, Kurelec B, Eich E, Seibert G. Potent antileukemic activity of the novel cytostatic agent avarone and its analogues in vitro and in vivo. Cancer Res. 1985 Oct;45(10):4822-6. PubMed PMID: 3839712.