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C6762

Sigma-Aldrich

Cytochalasin B from Drechslera dematioidea

≥98% (HPLC), 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
Beilstein:
1096207
EC Number:
239-000-2
MDL number:
MFCD00077704
UNSPSC Code:
12352202
PubChem Substance ID:
24892890
NACRES:
NA.32

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

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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.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H361

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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C B Chien et al.
Neuron, 11(2), 237-251 (1993-08-01)
We have developed an exposed brain preparation for observing growth cone pathfinding behavior while performing in vivo pharmacological manipulations, and we used it to test whether Xenopus retinal growth cones need filopodia to navigate. Time-lapse video observation showed that cytochalasin
Kinga Brzozowska et al.
International journal of radiation biology, 85(10), 891-899 (2009-07-30)
It has been reported that the level of cytogenetic damage in human peripheral blood lymphocytes (PBL) is higher following irradiation at 37 degrees C than at 0-4 degrees C. The mechanisms of this cytogenetic temperature effect are not fully known.
Christian Johannes et al.
Mutation research, 701(1), 80-85 (2010-05-18)
There are conflicting data regarding the effect of culturing time of human peripheral blood lymphocytes on the yield of chromosomal aberrations induced by sparsely ionising radiation in the G0 phase of the cell cycle. While some authors find that the
Fabiana S Paula et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 47(1), 163-170 (2008-11-22)
The tamarind (Tamarindus indica L.) is indigenous to Asian countries and widely cultivated in the American continents. The tamarind fruit pulp extract (ExT), traditionally used in spices, food components and juices, is rich in polyphenols that have demonstrated anti-atherosclerotic, antioxidant
N V Ballal et al.
International endodontic journal, 52(8), 1228-1234 (2019-03-09)
To test whether the incorporation of a chelation powder, etidronate, marketed for root canal irrigation (Dual Rinse HEDP) into a sodium hypochlorite (NaOCl) solution induced additional cytotoxic and genotoxic effects not observed with NaOCl alone. Fresh and 24-h-old mixtures of
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