Psoromic Acid | CAS#7299-11-8 | Rab-prenylation inhibitor

MedKoo Cat#: 329677 | Name: Psoromic Acid

Featured

Description:

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

Psoromic acid is a selective and covalent Rab-prenylation inhibitor targeting autoinhibited RabGGTase. Psoromic Acid is a bioactive lichen-derived compound which has been tested against both HSV-1 and HSV-2 viruses.

Chemical Structure

Psoromic Acid

CAS#7299-11-8

Theoretical Analysis

MedKoo Cat#: 329677

Name: Psoromic Acid

CAS#: 7299-11-8

Chemical Formula: C18H14O8

Exact Mass: 358.0689

Molecular Weight: 358.30

Elemental Analysis: C, 60.34; H, 3.94; O, 35.72

Price and Availability

Size	Price	Availability	Quantity
0.5mg	USD 450.00	2 Weeks
2.5mg	USD 950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Psoromic Acid; NSC 92186; Parellic Acid;

IUPAC/Chemical Name

4-formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-6-carboxylic acid

InChi Key

FUCWJKJZOHOLEO-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H14O8/c1-7-4-11(20)10(6-19)15-13(7)18(23)26-14-8(2)12(24-3)5-9(17(21)22)16(14)25-15/h4-6,20H,1-3H3,(H,21,22)

SMILES Code

O=C(C1=C(OC2=C(C=O)C(O)=CC(C)=C23)C(OC3=O)=C(C)C(OC)=C1)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

To be determined

Shelf Life

>2 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Psoromic acid shows cytotoxic effects on primary rat cerebral cortex and human cancer U87MG cell lines (IC50s = 79.40 and 56.22 mg/L, respectively). Psoromic acid is cytotoxic against human KB cancer cells (IC50 = 31.6 µM). Psoromic acid shows moderate activity against liver stage P. beghei (IC50 = 31.6 µM) and drug-resistant blood stage P. falciparum (IC50 = 29.2 µM).

In vitro activity:

Psoralidin is a potent radical scavenger in physiological polar media.However, psoralidin is a moderate radical scavenger in lipid media. Psoralidin moderately reduces the basal ROS level in human keratinocytes at non-toxic concentrations, Reference: J Org Chem. 2023 May 5;88(9):5745-5751. https://pubmed.ncbi.nlm.nih.gov/37074959/

In vivo activity:

To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 358.30 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

Formulation protocol:

1. Hassan STS, Šudomová M, Berchová-Bímová K, Šmejkal K, Echeverría J. Psoromic Acid, a Lichen-Derived Molecule, Inhibits the Replication of HSV-1 and HSV-2, and Inactivates HSV-1 DNA Polymerase: Shedding Light on Antiherpetic Properties. Molecules. 2019 Aug 11;24(16):2912. doi: 10.3390/molecules24162912. PMID: 31405197; PMCID: PMC6720901. 2. Emsen B, Aslan A, Togar B, Turkez H. In vitro antitumor activities of the lichen compounds olivetoric, physodic and psoromic acid in rat neuron and glioblastoma cells. Pharm Biol. 2016 Sep;54(9):1748-62. doi: 10.3109/13880209.2015.1126620. Epub 2015 Dec 24. PMID: 26704132.

In vitro protocol:

In vivo protocol:

To be determined

1: Wang A, Guan C, Wang T, Mu G, Tuo Y. Changes in Intracellular and Extracellular Metabolites of Mixed Lactobacillus Strains Enhance Inhibition of Pathogenic Bacterial Growth and Lipopolysaccharide-Induced Alleviation of RAW264.7 Cellular Inflammation. Probiotics Antimicrob Proteins. 2023 Aug 26. doi: 10.1007/s12602-023-10132-z. Epub ahead of print. PMID: 37632677. 2: Hassan STS, Šudomová M, Berchová-Bímová K, Šmejkal K, Echeverría J. Psoromic Acid, a Lichen-Derived Molecule, Inhibits the Replication of HSV-1 and HSV-2, and Inactivates HSV-1 DNA Polymerase: Shedding Light on Antiherpetic Properties. Molecules. 2019 Aug 11;24(16):2912. doi: 10.3390/molecules24162912. PMID: 31405197; PMCID: PMC6720901. 3: Hassan STS, Šudomová M, Berchová-Bímová K, Gowrishankar S, Rengasamy KRR. Antimycobacterial, Enzyme Inhibition, and Molecular Interaction Studies of Psoromic Acid in Mycobacterium tuberculosis: Efficacy and Safety Investigations. J Clin Med. 2018 Aug 20;7(8):226. doi: 10.3390/jcm7080226. PMID: 30127304; PMCID: PMC6111308. 4: Sweidan A, Chollet-Krugler M, Sauvager A, van de Weghe P, Chokr A, Bonnaure- Mallet M, Tomasi S, Bousarghin L. Antibacterial activities of natural lichen compounds against Streptococcus gordonii and Porphyromonas gingivalis. Fitoterapia. 2017 Sep;121:164-169. doi: 10.1016/j.fitote.2017.07.011. Epub 2017 Jul 21. PMID: 28736072. 5: Emsen B, Aslan A, Togar B, Turkez H. In vitro antitumor activities of the lichen compounds olivetoric, physodic and psoromic acid in rat neuron and glioblastoma cells. Pharm Biol. 2016 Sep;54(9):1748-62. doi: 10.3109/13880209.2015.1126620. Epub 2015 Dec 24. PMID: 26704132. 6: Lauinger IL, Vivas L, Perozzo R, Stairiker C, Tarun A, Zloh M, Zhang X, Xu H, Tonge PJ, Franzblau SG, Pham DH, Esguerra CV, Crawford AD, Maes L, Tasdemir D. Potential of lichen secondary metabolites against Plasmodium liver stage parasites with FAS-II as the potential target. J Nat Prod. 2013 Jun 28;76(6):1064-70. doi: 10.1021/np400083k. Epub 2013 Jun 19. PMID: 23806111; PMCID: PMC4119598. 7: Behera BC, Mahadik N, Morey M. Antioxidative and cardiovascular-protective activities of metabolite usnic acid and psoromic acid produced by lichen species Usnea complanata under submerged fermentation. Pharm Biol. 2012 Aug;50(8):968-79. doi: 10.3109/13880209.2012.654396. PMID: 22775414. 8: Deraeve C, Guo Z, Bon RS, Blankenfeldt W, DiLucrezia R, Wolf A, Menninger S, Stigter EA, Wetzel S, Choidas A, Alexandrov K, Waldmann H, Goody RS, Wu YW. Psoromic acid is a selective and covalent Rab-prenylation inhibitor targeting autoinhibited RabGGTase. J Am Chem Soc. 2012 May 2;134(17):7384-91. doi: 10.1021/ja211305j. Epub 2012 Apr 22. PMID: 22480322. 9: Samatov TR, Wolf A, Odenwälder P, Bessonov S, Deraeve C, Bon RS, Waldmann H, Lührmann R. Psoromic acid derivatives: a new family of small-molecule pre-mRNA splicing inhibitors discovered by a stage-specific high-throughput in vitro splicing assay. Chembiochem. 2012 Mar 19;13(5):640-4. doi: 10.1002/cbic.201100790. Epub 2012 Feb 14. PMID: 22334518. 10: Correché ER, Enriz RD, Piovano M, Garbarino J, Gómez-Lechón MJ. Cytotoxic and apoptotic effects on hepatocytes of secondary metabolites obtained from lichens. Altern Lab Anim. 2004 Dec;32(6):605-15. doi: 10.1177/026119290403200611. PMID: 15757498. 11: ARATANI H, NAKAGAWA A, TANIGUCHI T, TANAKA M. [Pharmacological studies on psoromic acid, a constituent of lichens]. J Antibiot B. 1963 Feb;16:4-7. Japanese. PMID: 14040789.