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Merck
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C2149

Cytochalasin E from Aspergillus clavatus

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About This Item

Empirical Formula (Hill Notation):
C28H33NO7
CAS Number:
36011-19-5
Molecular Weight:
495.56
UNSPSC Code:
12352200
NACRES:
NA.77
PubChem Substance ID:
24892467
EC Number:
252-835-7
Beilstein/REAXYS Number:
1096975
MDL number:
MFCD00005178

Key Documents

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InChI key

LAJXCUNOQSHRJO-ZYGJITOWSA-N

InChI

1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+/t16-,17-,19-,20-,21-,23-,26+,27+,28+/m0/s1

SMILES string

C[C@H]1C\C=C\[C@H]2[C@@H]3O[C@]3(C)[C@@H](C)[C@H]4[C@H](Cc5ccccc5)NC(=O)[C@@]24OC(=O)O\C=C\[C@@](C)(O)C1=O

form

powder

storage temp.

−20°C

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Application

Cytochalasin E has been used as:
  • a toxin to study its effects on avocado plants
  • a component of the incubating medium in feline junctional adhesion molecule 1 (fJAM-1) expression assay
  • an inhibitor of actin polymerization to study its effects on mitochondria uptake by mice endothelial cells

Biochem/physiol Actions

Cytochalasin E is a cell-permeable fungal toxin that inhibits actin polymerization stimulated by F-actin. Cytochalasin E does not inhibit glucose transport.
Cytochalasin E is an epoxide that exhibits anti-proliferative activity in endothelial cells in vitro. It also participates in inhibiting tumor growth and angiogenesis in vivo. Cytochalasin E also possesses antimicrobial and antiviral properties.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
067M4106V
0000083811
027M4089V
14160901
0000077997

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Sylvie Delebassée et al.
Fitoterapia, 121, 146-151 (2017-07-15)
A biological screening of sixteen lichen extracts on human HT-29 colorectal cancer cells, led to the selection of Pleurosticta acetabulum, a lichen widely present in tree barks in Europe. Bioguided purification of the acetonic extract resulted in the isolation of
Liwen Lin et al.
American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons, 19(7), 1917-1929 (2019-02-15)
The innate immune system is a critical regulator of the adaptive immune responses that lead to allograft rejection. It is increasingly recognized that endogenous molecules released from tissue injury and cell death are potent activators of innate immunity. Mitochondria, ancestrally
Contribution of Rosellinia necatrix toxins to avocado white root rot
Arjona-Girona I, et al.
European Journal of Plant Pathology, 148(1), 109-117 (2017)
Siwen Yuan et al.
European journal of medicinal chemistry, 202, 112502-112502 (2020-07-12)
Many fungal metabolites show promising anticancer properties both in vitro and in animal models, and some synthetic analogs of those metabolites have progressed into clinical trials. However, currently, there are still no fungi-derived agents approved as anticancer drugs. Two potential reasons
Cíntia Silva dos Santos et al.
Microbiology and immunology, 54(1), 1-10 (2010-01-09)
As interactions between bacteria and macrophages dictate the outcome of most infectious diseases, analyses of molecular mechanisms of non-opsonic phagocytosis should lead to new approaches for the prevention of diphtheria and systemic Corynebacterium diphtheriae infections. The present study aimed to
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