Avarone | CAS# 55303-99-6 | Antileukemic Agent

MedKoo Cat#: 573332 | Name: Avarone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Avarone

CAS#55303-99-6

Theoretical Analysis

MedKoo Cat#: 573332

Name: Avarone

CAS#: 55303-99-6

Chemical Formula: C21H28O2

Exact Mass: 312.2089

Molecular Weight: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

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Synonym

Avarone

IUPAC/Chemical 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 Key

VPRHEJGLNUDEEH-LWILDLIXSA-N

InChi Code

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

SMILES Code

C1(C[C@]2([C@H]3[C@](C(C)=CCC3)(C)CC[C@@H]2C)C)=CC(C=CC1=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 312.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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New avarone and avarol derivatives from the marine sponge Dysidea cinerea. J Nat Prod. 1991 Jan-Feb;54(1):92-7. doi: 10.1021/np50073a005. PMID: 1710654. 5: Imperatore C, Gimmelli R, Persico M, Casertano M, Guidi A, Saccoccia F, Ruberti G, Luciano P, Aiello A, Parapini S, Avunduk S, Basilico N, Fattorusso C, Menna M. Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone. Mar Drugs. 2020 Feb 14;18(2):112. doi: 10.3390/md18020112. PMID: 32075136; PMCID: PMC7074381. 6: Belisario MA, Maturo M, Pecce R, De Rosa S, Villani GR. Effect of avarol and avarone on in vitro-induced microsomal lipid peroxidation. Toxicology. 1992;72(2):221-33. doi: 10.1016/0300-483x(92)90114-t. PMID: 1566281. 7: 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. PMID: 28504009. 8: Bozić T, Novaković I, Gasić MJ, Juranić Z, Stanojković T, Tufegdzić S, Kljajić Z, Sladić D. Synthesis and biological activity of derivatives of the marine quinone avarone. Eur J Med Chem. 2010 Mar;45(3):923-9. doi: 10.1016/j.ejmech.2009.11.033. Epub 2009 Nov 26. PMID: 19995673. 9: Pejin B, Iodice C, Tommonaro G, Bogdanovic G, Kojic V, De Rosa S. Further in vitro evaluation of cytotoxicity of the marine natural product derivative 4'-leucine-avarone. Nat Prod Res. 2014;28(5):347-50. doi: 10.1080/14786419.2013.863201. Epub 2014 Jan 14. PMID: 24422776. 10: Ferrándiz ML, Sanz MJ, Bustos G, Payá M, Alcaraz MJ, De Rosa S. Avarol and avarone, two new anti-inflammatory agents of marine origin. Eur J Pharmacol. 1994 Feb 21;253(1-2):75-82. doi: 10.1016/0014-2999(94)90759-5. PMID: 8013550. 11: Novaković I, Anđelković U, Zlatović M, Gašić MJ, Sladić D. Bioconjugate of lysozyme and the antibacterial marine sesquiterpene quinone avarone and its derivatives. Bioconjug Chem. 2012 Jan 18;23(1):57-65. doi: 10.1021/bc200330m. Epub 2012 Jan 4. PMID: 22148500; PMCID: PMC3263428. 12: Casertano M, Genovese M, Santi A, Pranzini E, Balestri F, Piazza L, Del Corso A, Avunduk S, Imperatore C, Menna M, Paoli P. Evidence of Insulin- Sensitizing and Mimetic Activity of the Sesquiterpene Quinone Avarone, a Protein Tyrosine Phosphatase 1B and Aldose Reductase Dual Targeting Agent from the Marine Sponge Dysidea avara. Pharmaceutics. 2023 Feb 4;15(2):528. doi: 10.3390/pharmaceutics15020528. PMID: 36839851; PMCID: PMC9964544. 13: Tsoukatou M, Maréchal JP, Hellio C, Novaković I, Tufegdzic S, Sladić D, Gasić MJ, Clare AS, Vagias C, Roussis V. Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms. Molecules. 2007 May 15;12(5):1022-34. doi: 10.3390/12051022. PMID: 17873837; PMCID: PMC6149471. 14: Belisario MA, Pecce R, Arena AR, De Giulio A, Strazzullo G, De Rosa S. Effect of avarol, avarone and nine of their natural and synthetic derivatives on microsomal drug-metabolizing enzymes. Toxicol Lett. 1991 Jul;57(2):183-93. doi: 10.1016/0378-4274(91)90145-v. PMID: 1853363. 15: Vilipić J, Novaković I, Stanojković T, Matić I, Šegan D, Kljajić Z, Sladić D. Synthesis and biological activity of amino acid derivatives of avarone and its model compound. Bioorg Med Chem. 2015 Nov 1;23(21):6930-42. doi: 10.1016/j.bmc.2015.09.044. Epub 2015 Sep 30. PMID: 26476666. 16: An J, Wiemer DF. Stereoselective Synthesis of (+)-Avarol, (+)-Avarone, and Some Nonracemic Analogues. J Org Chem. 1996 Dec 13;61(25):8775-8779. doi: 10.1021/jo961048r. PMID: 11667853. 17: Belisario MA, Maturo M, Avagnale G, De Rosa S, Scopacasa F, De Caterina M. In vitro effect of avarone and avarol, a quinone/hydroquinone couple of marine origin, on platelet aggregation. Pharmacol Toxicol. 1996 Dec;79(6):300-4. doi: 10.1111/j.1600-0773.1996.tb00013.x. PMID: 9000256. 18: 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. doi: 10.1016/s0176-6724(85)80026-2. PMID: 3841441. 19: Loya S, Hizi A. The inhibition of human immunodeficiency virus type 1 reverse transcriptase by avarol and avarone derivatives. FEBS Lett. 1990 Aug 20;269(1):131-4. doi: 10.1016/0014-5793(90)81137-d. PMID: 1696911. 20: Kurelec B, Zahn RK, Gasić MJ, Britvić S, Lucić D, Müller WE. Antimutagenic activity of the novel antileukemic agents, avarone and avarol. Mutat Res. 1985 Oct;144(2):63-6. doi: 10.1016/0165-7992(85)90002-8. PMID: 3900707.