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V4877

Verrucarin A

Name: Verrucarin A
Brand: SIGMA

from Myrothecium sp., ≥85.0% (HPLC), CCRCC inhibitor

Synonym(s):

Muconomycin A

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₃₄O₉

CAS Number:

3148-09-2

Molecular Weight:

502.55

UNSPSC Code:

12352200

PubChem Substance ID:

24900750

NACRES:

NA.77

MDL number:

MFCD00056759

Assay:

≥85.0% (HPLC)

Quality level:

200

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Product Name

Verrucarin A from Myrothecium sp., ≥85.0% (HPLC)

Quality Level

200

assay

≥85.0% (HPLC)

storage temp.

−20°C

SMILES string

CC1CCOC(=O)\C=C\C=C\C(=O)OC2CC3OC4C=C(C)CCC4(COC(=O)C1O)C2(C)C35CO5

InChI

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+

InChI key

NLUGUZJQJYVUHS-YDFGWWAZSA-N

Related Categories

Bioactive Small Molecules

General description

Verrucarin derived from the Myrothecium verrucari, a fungal plant pathogen is a macrocyclic trichothecene compound.

Application

Verrucarin A from Myrothecium sp has been used:

as a translation initiation inhibitor in P. falciparum W2 strain
as a peptidyl transfer inhibitor to test sensitivity in methyltransferase knock-out S. cerevisiae cells
to test its cytotoxicity in renal cell carcinoma cells

Biochem/physiol Actions

Verrucarin A binds to the P and A sites in ribosomes and blocks peptide-bond and translation initiation. It inhibits the clear cell renal cell carcinoma (CCRCC) proliferation. Verrucarin A blocks the peptidyl transferase activity and favors apoptosis induction in cancer cells

Verrucarin A is phytotoxic to plantlet cultures and cytotoxic to cultured mammalian cell lines.

Other Notes

Macrocyclic trichothecene mycotoxin.

pictograms

GHS06

signalword

Danger

hcodes

H300 + H310 + H330

pcodes

P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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A coactivator trap identifies NONO (p54nrb) as a component of the cAMP-signaling pathway.

Antonio L Amelio et al.

Proceedings of the National Academy of Sciences of the United States of America, 104(51), 20314-20319 (2007-12-14)

Signal transduction pathways often use a transcriptional component to mediate adaptive cellular responses. Coactivator proteins function prominently in these pathways as the conduit to the basic transcriptional machinery. Here we present a high-throughput cell-based screening strategy, termed the "coactivator trap,"

Paraspeckles: nuclear bodies built on long noncoding RNA.

Charles S Bond et al.

The Journal of cell biology, 186(5), 637-644 (2009-09-02)

Paraspeckles are ribonucleoprotein bodies found in the interchromatin space of mammalian cell nuclei. These structures play a role in regulating the expression of certain genes in differentiated cells by nuclear retention of RNA. The core paraspeckle proteins (PSF/SFPQ, P54NRB/NONO, and

New therapeutic aspects of steroidal cardiac glycosides: the anticancer properties of Huachansu and its main active constituent Bufalin.

Chien-Shan Cheng et al.

Cancer cell international, 19, 92-92 (2019-04-24)

In the past decade, increasing research attention investigated the novel therapeutic potential of steroidal cardiac glycosides in cancer treatment. Huachansu and its main active constituent Bufalin have been studied in vitro, in vivo and clinical studies. This review aims to

Lack of a functional VHL gene product sensitizes renal cell carcinoma cells to the apoptotic effects of the protein synthesis inhibitor verrucarin A.

Girma M Woldemichael et al.

Neoplasia (New York, N.Y.), 14(8), 771-777 (2012-09-07)

Verrucarin A (VA) is a small molecule derived from the fungal plant pathogen Myrothecium verrucaria and was identified as a selective inhibitor of clear cell renal cell carcinoma (CCRCC) cell proliferation in a high-throughput screen of a library of naturally

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.

Dorrah Deeb et al.

International journal of oncology, 49(3), 1139-1147 (2016-08-31)

Pancreatic ductal adenocarcinoma (PDA) remains one of the most difficult to treat of all malignancies. Multimodality regimens provide only short-term symptomatic improvement with minor impact on survival, underscoring the urgent need for novel therapeutics and treatment strategies for PDA. Trichothecenes

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Global Trade Item Number

SKU	GTIN
V4877-5MG	04061832943503
V4877-1MG	04061837481062

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