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C6762

Cytochalasin B from Drechslera dematioidea

Name: Cytochalasin B from <I>Drechslera dematioidea</I>
Brand: SIGMA

from drechslera dematioidea, ≥98% (HPLC), actin polymerization inhibitor, powder

Synonym(s):

Phomin

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₇NO₅

CAS Number:

14930-96-2

Molecular Weight:

479.61

NACRES:

NA.32

PubChem Substance ID:

24892890

UNSPSC Code:

12352202

EC Number:

239-000-2

MDL number:

MFCD00077704

Beilstein/REAXYS Number:

1096207

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Properties

Product Name

Cytochalasin B from Drechslera dematioidea, ≥98% (HPLC), powder

Quality Level

300

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: 10 mg/mL

antibiotic activity spectrum

fungi

mode of action

DNA synthesis | interferes

storage temp.

−20°C

SMILES string

C[C@@H]1CCC[C@@H](O)\C=C\C(=O)O[C@]23[C@@H](\C=C\C1)[C@H](O)C(=C)[C@@H](C)[C@H]2[C@H](Cc4ccccc4)NC3=O

InChI

1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1

InChI key

GBOGMAARMMDZGR-TYHYBEHESA-N

Description

General description

Cytochalasin B is a cell-permeable fungal toxin / mycotoxin that binds to the ′barbed′ end of actin / actin filaments. This binding leads to:

Disruption of actin filaments and of interaction of actin filaments in solution
Inhibition of actin polymerization
Inhibition of subunit association and dissociation

Cytochalasin B is widely used in studies of glucose transporters (GLUT). Cytochalasin B is also used as an integral part of various in vitro micronucleus assay protocols.

Biochem/physiol Actions

Cell permeable fungal toxin that disrupts contractile microfilaments by inhibiting actin polymerization. This, in turn, induces DNA fragmentation, inhibits cell division, and disrupts many cell processes. Inhibits glucose transport.

One of a group of fungal metabolites that interfere with a wide variety of cellular movements. Useful tool for characterizing some of the polymerization properties of actin, and in studies on cytokinesis. Probe for the two hexose-transport systems in rat L6 myoblasts.