Cytochalasin B
Cytochalasin B, the name of which comes from the Greek cytos (cell) and chalasis (relaxation), is a cell-permeable mycotoxin. It was found that substoichiometric concentrations of cytochalasin B (CB) strongly inhibit network formation by actin filaments. Due to this, it is often used in cytological research. It inhibits cytoplasmic division by blocking the formation of contractile microfilaments. It inhibits cell movement and induces nuclear extrusion. Cytochalasin B shortens actin filaments by blocking monomer addition at the fast-growing end of polymers. Cytochalasin B inhibits glucose transport and platelet aggregation. It blocks adenosine-induced apoptotic body formation without affecting activation of endogenous ADP-ribosylation in leukemia HL-60 cells. It is also used in cloning through nuclear transfer. Here enucleated recipient cells are treated with cytochalasin B. Cytochalasin B makes the cytoplasm of the oocytes more fluid and makes it possible to aspirate the nuclear genome of the oocyte within a small vesicle of plasma membrane into a micro-needle. Thereby, the oocyte genome is removed from the oocyte, while preventing rupture of the plasma membrane.
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IUPAC name
(1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione | |
Other names
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Identifiers | |
3D model (JSmol) |
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3DMet | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.035.440 |
EC Number |
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KEGG | |
PubChem CID |
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RTECS number |
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CompTox Dashboard (EPA) |
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SMILES
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Properties | |
C29H37NO5 | |
Molar mass | 479.6 g/mol |
Appearance | white to off-white powder |
Density | 1.21 g/cm3 (predicted) |
Melting point | 215 to 223 °C (419 to 433 °F; 488 to 496 K) |
Boiling point | 740.56 °C (1,365.01 °F; 1,013.71 K) at 760 mmHg (predicted) |
insoluble | |
Solubility in DMSO and MeOH | soluble |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
acute toxicity, health hazards |
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Danger | |
H300, H310, H330, H361 | |
P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P302+P350, P304+P340, P308+P313, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501 | |
Safety data sheet (SDS) | Cytochalasin B MSDS from Fermentek |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references |
This alkaloid is isolated from a fungus, Helminthosporium dematioideum.