Avarol | CAS# 55303-98-5 | AChE Inhibitor

MedKoo Cat#: 573331 | Name: Avarol

Description:

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

Avarol induces apoptosis in pancreatic ductal adenocarcinoma cells by activating PERK-eIF2α-CHOP signaling. Avarl also acts as a competitive AChE inhibitor which are non-hepatotoxic and neuroprotective agents for Alzheimer's disease.

Chemical Structure

Avarol

CAS#55303-98-5

Theoretical Analysis

MedKoo Cat#: 573331

Name: Avarol

CAS#: 55303-98-5

Chemical Formula: C21H30O2

Exact Mass: 314.2246

Molecular Weight: 314.47

Elemental Analysis: C, 80.21; H, 9.62; O, 10.18

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Related CAS #

122143-92-4 (monoacetate) 55303-98-5

Synonym

Avarol; Avrol; KZX416VN2B; CHEMBL459814

IUPAC/Chemical Name

(1R-(1alpha,2beta,4abeta,8abeta))-2-((1,2,3,4,4a,7,8,8a-Octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl)methyl)-1,4-benzenediol

InChi Key

JSPUCPNQXKTYRO-LWILDLIXSA-N

InChi Code

1S/C21H30O2/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/h6,8-9,12,15,19,22-23H,5,7,10-11,13H2,1-4H3/t15-,19+,20+,21+/m0/s1

SMILES Code

C[C@H]1CC[C@]2([C@H]([C@]1(C)Cc3cc(ccc3O)O)CCC=C2C)C

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 314.47 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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Nat Prod Res. 2016 Sep;30(17):1956-60. doi: 10.1080/14786419.2015.1091454. Epub 2015 Sep 25. PMID: 26405848. 5: Amigó M, Payá M, Braza-Boïls A, De Rosa S, Terencio MC. Avarol inhibits TNF- alpha generation and NF-kappaB activation in human cells and in animal models. Life Sci. 2008 Jan 30;82(5-6):256-64. doi: 10.1016/j.lfs.2007.11.017. Epub 2007 Dec 5. PMID: 18177902. 6: Stanojkovic TP, Filimonova M, Grozdanic N, Petovic S, Shitova A, Soldatova O, Filimonov A, Vladic J, Shegay P, Kaprin A, Ivanov S, Nikitovic M. Evaluation of In Vitro Cytotoxic Potential of Avarol towards Human Cancer Cell Lines and In Vivo Antitumor Activity in Solid Tumor Models. Molecules. 2022 Dec 19;27(24):9048. doi: 10.3390/molecules27249048. PMID: 36558184; PMCID: PMC9788264. 7: Pejin B, Iodice C, Kojic V, Jakimov D, Lazovic M, Tommonaro G. In vitro evaluation of cytotoxic and mutagenic activity of avarol. Nat Prod Res. 2016 Jun;30(11):1293-6. doi: 10.1080/14786419.2015.1052067. Epub 2015 Jul 16. PMID: 26181496. 8: 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. 9: Sladić D, Gasić MJ. Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida. Molecules. 2006 Jan 31;11(1):1-33. doi: 10.3390/11010001. PMID: 17962742; PMCID: PMC6148525. 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: Amigó M, Schalkwijk J, Olthuis D, De Rosa S, Payá M, Terencio MC, Lamme E. Identification of avarol derivatives as potential antipsoriatic drugs using an in vitro model for keratinocyte growth and differentiation. Life Sci. 2006 Nov 17;79(25):2395-404. doi: 10.1016/j.lfs.2006.08.003. Epub 2006 Aug 16. PMID: 16973179. 12: Müller WE, Sladić D, Zahn RK, Bässler KH, Dogović N, Gerner H, Gasić MJ, Schröder HC. Avarol-induced DNA strand breakage in vitro and in Friend erythroleukemia cells. Cancer Res. 1987 Dec 15;47(24 Pt 1):6565-71. PMID: 2824036. 13: 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. 14: Tommonaro G, Pejin B, Iodice C, Tafuto A, De Rosa S. Further in vitro biological activity evaluation of amino-, thio- and ester-derivatives of avarol. J Enzyme Inhib Med Chem. 2016 Aug;31(4):684-6. doi: 10.3109/14756366.2015.1057724. Epub 2015 Jun 26. Retraction in: J Enzyme Inhib Med Chem. 2017 Dec;32(1):731. PMID: 26114310. 15: Pejin B, Iodice C, Tommonaro G, Stanimirovic B, Ciric A, Glamoclija J, Nikolic M, De Rosa S, Sokovic M. Further in vitro evaluation of antimicrobial activity of the marine sesquiterpene hydroquinone avarol. Curr Pharm Biotechnol. 2014;15(6):583-8. doi: 10.2174/138920101506140910152253. PMID: 25213366. 16: Schröder HC, Bégin ME, Klöcking R, Matthes E, Sarma AS, Gasić M, Müller WE. Avarol restores the altered prostaglandin and leukotriene metabolism in monocytes infected with human immunodeficiency virus type 1. Virus Res. 1991 Nov;21(3):213-23. doi: 10.1016/0168-1702(91)90034-s. PMID: 1662847. 17: Tommonaro G, Pejin B, Iodice C, Tafuto A, De Rosa S. Further in vitro biological activity evaluation of amino-, thio- and ester-derivatives of avarol. J Enzyme Inhib Med Chem. 2015 Apr;30(2):333-5. doi: 10.3109/14756366.2014.913037. Epub 2014 Jun 18. PMID: 24939096. 18: 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. 19: Müller WE, Diehl-Seifert B, Sobel C, Bechtold A, Kljajić Z, Dorn A. Sponge secondary metabolites: biochemical and ultrastructural localization of the antimitotic agent avarol in Dysidea avara. J Histochem Cytochem. 1986 Dec;34(12):1687-90. doi: 10.1177/34.12.3782777. PMID: 3782777. 20: Müller WE, Sobel C, Diehl-Seifert B, Maidhof A, Schröder HC. Influence of the antileukemic and anti-human immunodeficiency virus agent avarol on selected immune responses in vitro and in vivo. Biochem Pharmacol. 1987 May 1;36(9):1489-94. doi: 10.1016/0006-2952(87)90115-8. PMID: 3555507.