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

MedKoo CAT#: 573182

CAS#: 3148-09-2

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


Price and Availability

Size
Price

1mg
USD 275
Size
Price

5mg
USD 775
Size
Price

Verrucarin A, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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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


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


Technical Data

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).

Harmonized System Code:
2934.99.90.01


References

1: 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. PubMed PMID: 27849335.

2: 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. PubMed PMID: 25996208.

3: Liu J, Simmons SO, Pei R. Regulation of IL-8 promoter activity by verrucarin A in human monocytic THP-1 cells. J Toxicol Environ Health A. 2014;77(19):1125-40. doi: 10.1080/15287394.2013.874246. PubMed PMID: 25119735.

4: Palanivel K, Kanimozhi V, Kadalmani B. Verrucarin A alters cell-cycle regulatory proteins and induces apoptosis through reactive oxygen species-dependent p38MAPK activation in the human breast cancer cell line MCF-7. Tumour Biol. 2014 Oct;35(10):10159-67. doi: 10.1007/s13277-014-2286-1. Epub 2014 Jul 16. PubMed PMID: 25027398.

5: Palanivel K, Kanimozhi V, Kadalmani B, Akbarsha MA. Verrucarin A induces apoptosis through ROS-mediated EGFR/MAPK/Akt signaling pathways in MDA-MB-231 breast cancer cells. J Cell Biochem. 2014 Nov;115(11):2022-32. doi: 10.1002/jcb.24874. PubMed PMID: 24963595.

6: Yan F, Yu Y, Chow DC, Palzkill T, Madoux F, Hodder P, Chase P, Griffin PR, O'Malley BW, Lonard DM. Identification of verrucarin a as a potent and selective steroid receptor coactivator-3 small molecule inhibitor. PLoS One. 2014 Apr 17;9(4):e95243. doi: 10.1371/journal.pone.0095243. eCollection 2014. PubMed PMID: 24743578; PubMed Central PMCID: PMC3990629.

7: Jayasooriya RG, Moon DO, Park SR, Choi YH, Asami Y, Kim MO, Jang JH, Kim BY, Ahn JS, Kim GY. Combined treatment with verrucarin A and tumor necrosis factor-α sensitizes apoptosis by overexpression of nuclear factor-kappaB-mediated Fas. Environ Toxicol Pharmacol. 2013 Sep;36(2):303-10. doi: 10.1016/j.etap.2013.04.008. Epub 2013 Apr 25. PubMed PMID: 23708311.

8: Palanivel K, Kanimozhi V, Kadalmani B, Akbarsha MA. Verrucarin A, a protein synthesis inhibitor, induces growth inhibition and apoptosis in breast cancer cell lines MDA-MB-231 and T47D. Biotechnol Lett. 2013 Sep;35(9):1395-403. doi: 10.1007/s10529-013-1238-y. Epub 2013 May 21. PubMed PMID: 23690045.

9: Jayasooriya RG, Moon DO, Yun SG, Choi YH, Asami Y, Kim MO, Jang JH, Kim BY, Ahn JS, Kim GY. Verrucarin A enhances TRAIL-induced apoptosis via NF-κB-mediated Fas overexpression. Food Chem Toxicol. 2013 May;55:1-7. doi: 10.1016/j.fct.2012.12.045. Epub 2013 Jan 7. PubMed PMID: 23306790.

10: Moon DO, Asami Y, Long H, Jang JH, Bae EY, Kim BY, Choi YH, Kang CH, Ahn JS, Kim GY. Verrucarin A sensitizes TRAIL-induced apoptosis via the upregulation of DR5 in an eIF2α/CHOP-dependent manner. Toxicol In Vitro. 2013 Feb;27(1):257-63. doi: 10.1016/j.tiv.2012.09.001. Epub 2012 Sep 12. PubMed PMID: 22982206.

11: Woldemichael GM, Turbyville TJ, Vasselli JR, Linehan WM, McMahon JB. Lack of a functional VHL gene product sensitizes renal cell carcinoma cells to the apoptotic effects of the protein synthesis inhibitor verrucarin A. Neoplasia. 2012 Aug;14(8):771-7. PubMed PMID: 22952429; PubMed Central PMCID: PMC3431183.