Verrucarin A | CAS# 3148-09-2 | Antibiotic

MedKoo Cat#: 573182 | Name: Verrucarin A

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Description:

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

Verrucarin A is an antibiotic which has been shown to inhibit proliferation of prostate cancer cells by inhibiting prosurvival Akt/NF-kB/mTOR signaling.

Chemical Structure

Verrucarin A

CAS#3148-09-2

Theoretical Analysis

MedKoo Cat#: 573182

Name: Verrucarin A

CAS#: 3148-09-2

Chemical Formula: C27H34O9

Exact Mass: 502.2203

Molecular Weight: 502.56

Elemental Analysis: C, 64.53; H, 6.82; O, 28.65

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 400.00	2 Weeks

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Related CAS #

No Data

Synonym

Antibiotic 379Y, Muconomycin A, Verrucarin A

IUPAC/Chemical Name

Spiro(16,18-methano-1H,3H,23H-(1,6,12)trioxacyclooctadecino(3,4-d)(1)benzopyran-17(18H),2'-oxirane)-3,9,14-trione, 4,5,6,7,16,16a,19a,22-octahydro-4-hydroxy-5,16a,21-trimethyl-, stereoisomer

InChi Key

NLUGUZJQJYVUHS-IDXDZYHTSA-N

InChi Code

1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3/b6-4+,7-5-/t17-,18-,19-,20-,23+,25-,26-,27+/m1/s1

SMILES Code

C[C@@H]1CCOC(=O)\C=C\C=C/C(=O)O[C@@H]2C[C@H]3O[C@@H]4C=C(C)CC[C@]4(COC(=O)[C@H]1O)[C@]2(C)[C@]35CO5

Appearance

Solid powder

Purity

>70% (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 502.56 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

1: Park J, Lee Y, Kim E, Choe JK. In Silico Analysis of Binding Sites for a Novel ssDNA Aptamer Specific to Verrucarin A and Detection in Dust Extracts. Anal Chem. 2024 Oct 29;96(43):17262-17270. doi: 10.1021/acs.analchem.4c03307. Epub 2024 Oct 15. PMID: 39404132. 2: Guo L, Huang E, Wang T, Ling Y, Li Z. Exploring the molecular mechanisms of asthma across multiple datasets. Ann Med. 2024 Dec;56(1):2258926. doi: 10.1080/07853890.2023.2258926. Epub 2024 Mar 15. PMID: 38489401; PMCID: PMC10946276. 3: Parvatkar PT, Maher SP, Zhao Y, Cooper CA, de Castro ST, Péneau J, Vantaux A, Witkowski B, Kyle DE, Manetsch R. In Vitro Antimalarial Activity of Trichothecenes against Liver and Blood Stages of Plasmodium Species. J Nat Prod. 2024 Feb 23;87(2):315-321. doi: 10.1021/acs.jnatprod.3c01019. Epub 2024 Jan 23. PMID: 38262446; PMCID: PMC10897926. 4: Chen K, Si Y, Guan JS, Zhou Z, Kim S, Kim T, Shan L, Willey CD, Zhou L, Liu X. Correction: Chen et al. Targeted Extracellular Vesicles Delivered Verrucarin A to Treat Glioblastoma. Biomedicines 2022, 10, 130. Biomedicines. 2023 Dec 29;12(1):86. doi: 10.3390/biomedicines12010086. Erratum for: Biomedicines. 2022 Jan 07;10(1):130. doi: 10.3390/biomedicines10010130. PMID: 38255327; PMCID: PMC10813734. 5: Fang ST, Song YP, Miao FP, Yin XL, Ji NY. Myrochromanol analogues and trichothecene derivatives from the shellfish-derived fungus Albifimbriaverrucaria. Phytochemistry. 2023 May;209:113645. doi: 10.1016/j.phytochem.2023.113645. Epub 2023 Mar 15. PMID: 36924814. 6: Wang M, Gong L, Luo Y, He S, Zhang X, Xie X, Li X, Feng X. Transcriptomic analysis of asthma and allergic rhinitis reveals CST1 as a biomarker of unified airways. Front Immunol. 2023 Jan 17;14:1048195. doi: 10.3389/fimmu.2023.1048195. PMID: 36733482; PMCID: PMC9888248. 7: Kondo T, Yamamoto T, Okayama K, Narumi H, Inoue H. Metabolites of soil microorganisms modulate amyloid β production in Alzheimer's neurons. Sci Rep. 2022 Mar 2;12(1):2690. doi: 10.1038/s41598-022-06513-z. PMID: 35236875; PMCID: PMC8891331. 8: Mahato DK, Pandhi S, Kamle M, Gupta A, Sharma B, Panda BK, Srivastava S, Kumar M, Selvakumar R, Pandey AK, Suthar P, Arora S, Kumar A, Gamlath S, Bharti A, Kumar P. Trichothecenes in food and feed: Occurrence, impact on human health and their detection and management strategies. Toxicon. 2022 Mar;208:62-77. doi: 10.1016/j.toxicon.2022.01.011. Epub 2022 Jan 31. PMID: 35104534. 9: Si Y, Chen K, Ngo HG, Guan JS, Totoro A, Zhou Z, Kim S, Kim T, Zhou L, Liu X. Targeted EV to Deliver Chemotherapy to Treat Triple-Negative Breast Cancers. Pharmaceutics. 2022 Jan 7;14(1):146. doi: 10.3390/pharmaceutics14010146. PMID: 35057042; PMCID: PMC8781632. 10: Chen K, Si Y, Guan JS, Zhou Z, Kim S, Kim T, Shan L, Willey CD, Zhou L, Liu X. Targeted Extracellular Vesicles Delivered Verrucarin A to Treat Glioblastoma. Biomedicines. 2022 Jan 7;10(1):130. doi: 10.3390/biomedicines10010130. Erratum in: Biomedicines. 2023 Dec 29;12(1):86. doi: 10.3390/biomedicines12010086. PMID: 35052809; PMCID: PMC8773723. 11: Venkatesh C, Doorneweerd DD, Xia W, Putt KS, Low PS. Folate-targeted verrucarin A reduces the number of activated macrophages in a mouse model of acute peritonitis. Bioorg Med Chem Lett. 2021 Jun 15;42:128091. doi: 10.1016/j.bmcl.2021.128091. Epub 2021 May 6. PMID: 33964441. 12: Si Y, Guan J, Xu Y, Chen K, Kim S, Zhou L, Jaskula-Sztul R, Liu XM. Dual- Targeted Extracellular Vesicles to Facilitate Combined Therapies for Neuroendocrine Cancer Treatment. Pharmaceutics. 2020 Nov 11;12(11):1079. doi: 10.3390/pharmaceutics12111079. PMID: 33187322; PMCID: PMC7696983. 13: Nguyen LTT, Jang JY, Kim TY, Yu NH, Park AR, Lee S, Bae CH, Yeo JH, Hur JS, Park HW, Kim JC. Nematicidal activity of verrucarin A and roridin A isolated from Myrothecium verrucaria against Meloidogyne incognita. Pestic Biochem Physiol. 2018 Jun;148:133-143. doi: 10.1016/j.pestbp.2018.04.012. Epub 2018 Apr 26. PMID: 29891364. 14: Wu Q, Wang X, Nepovimova E, Miron A, Liu Q, Wang Y, Su D, Yang H, Li L, Kuca K. Trichothecenes: immunomodulatory effects, mechanisms, and anti-cancer potential. Arch Toxicol. 2017 Dec;91(12):3737-3785. doi: 10.1007/s00204-017-2118-3. Epub 2017 Nov 20. PMID: 29152681. 15: Siciliano I, Bosio P, Gilardi G, Gullino ML, Garibaldi A. Verrucarin A and roridin E produced on spinach by Myrothecium verrucaria under different temperatures and CO2 levels. Mycotoxin Res. 2017 May;33(2):139-146. doi: 10.1007/s12550-017-0273-2. Epub 2017 Mar 9. PMID: 28281009. 16: Liu Y, Gao X, Deeb D, Zhang Y, Shaw J, Valeriote FA, Gautam SC. Mycotoxin verrucarin A inhibits proliferation and induces apoptosis in prostate cancer cells by inhibiting prosurvival Akt/NF-kB/mTOR signaling. J Exp Ther Oncol. 2016 Nov;11(4):251-260. PMID: 27849335. 17: Deeb D, Gao X, Liu Y, Zhang Y, Shaw J, Valeriote FA, Gautam SC. The inhibition of cell proliferation and induction of apoptosis in pancreatic ductal adenocarcinoma cells by verrucarin A, a macrocyclic trichothecene, is associated with the inhibition of Akt/NF-кB/mTOR prosurvival signaling. Int J Oncol. 2016 Sep;49(3):1139-47. doi: 10.3892/ijo.2016.3587. Epub 2016 Jun 29. PMID: 27573873. 18: Uchida R, Namiguchi S, Ishijima H, Tomoda H. Therapeutic effects of three trichothecenes in the silkworm infection assay with Candida albicans. Drug Discov Ther. 2016 Feb;10(1):44-8. doi: 10.5582/ddt.2016.01013. PMID: 26971555. 19: Mondol MA, Surovy MZ, Islam MT, Schüffler A, Laatsch H. Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae. J Agric Food Chem. 2015 Oct 14;63(40):8777-86. doi: 10.1021/acs.jafc.5b02366. Epub 2015 Sep 29. PMID: 26320597. 20: Bae EY, Lee SW, Seong S, Cho W, Ahn JS, Cho HS. Inhibitory Effects of Verrucarin A on Tunicamycin-Induced ER Stress in FaO Rat Liver Cells. Molecules. 2015 May 19;20(5):8988-96. doi: 10.3390/molecules20058988. PMID: 25996208; PMCID: PMC6272334.