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V4877

Sigma-Aldrich

Verrucarin A from Myrothecium sp.

≥85.0% (HPLC)

Synonym(e):

Muconomycin A

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About This Item

Empirische Formel (Hill-System):
C27H34O9
CAS-Nummer:
3148-09-2
Molekulargewicht:
502.55
MDL-Nummer:
MFCD00056759
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24900750
NACRES:
NA.77

Qualitätsniveau

200

Assay

≥85.0% (HPLC)

Lagertemp.

−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+

InChIKey

NLUGUZJQJYVUHS-YDFGWWAZSA-N

Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Sonstige Hinweise

Macrocyclic trichothecene mycotoxin.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 3

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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Cycloheximid

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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
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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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