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C2743

Sigma-Aldrich

Cytochalasin B from Drechslera dematioidea

Ready Made Solution, 10 mg/mL in DMSO

Synonym(s):
Phomin
Empirical Formula (Hill Notation):
C29H37NO5
CAS Number:
Molecular Weight:
479.61
Beilstein:
1096207
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

form

solution

concentration

10 mg/mL in DMSO

Mode of action

cell membrane | interferes

antibiotic activity spectrum

fungi

shipped in

wet ice

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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Related Categories

Application

Cytochalasin B is used to inhibit sugar transport in fibroblasts , decrease cytoskeletal actin and myosin in rabbit neutrophils , and to stimulate B lymphocytes .
Cytochalasin B from Drechslera dematioidea has been used:
  • to block cytokinesis, to obtain binucleated cells
  • as a specific glucose transporter inhibitor
  • to inhibit glucose transport by class I and III GLUTs to determine the 50% inhibitory concentration (IC50) in HCMV-infected and mock-infected cells

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.
Cytochalasin B can prevent cytoplasmic division without affecting nuclear division.
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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral

Storage Class Code

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

WGK Germany

WGK 2

Flash Point(F)

185.0 °F - closed cup - Solvent

Flash Point(C)

85 °C - closed cup - Solvent

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  6. Is Product C2743, Cytochalasin B, cell culture grade?

    The product has been sterile filtered, but it has not been cell culture tested by Sigma.

  7. I have a solution of Product C2743, Cytochalasin B, in DMSO. Is the DMSO toxic to cultured cells?

    At a low enough concentration, the DMSO should not hurt the cells. The final concentration of DMSO in the aqueous working medium typically should not exceed 0.1% because higher DMSO concentrations can adversely affect many cultured cells. Dilute the product in the appropriate aqueous medium to provide a physiologically acceptable final concentration.  

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

J R White et al.
The Journal of biological chemistry, 258(22), 14041-14047 (1983-11-25)
The amounts of actin and myosin in rabbit neutrophils expressed as micrograms/10(6) cells are 5.6 +/- 0.75 and 0.56 +/- 0.08, respectively. The average value of the total actin in rabbit neutrophils under unstimulated conditions is distributed between Triton X-100...
T L Rothstein
Journal of immunology (Baltimore, Md. : 1950), 136(3), 813-816 (1986-02-01)
B cells are stimulated to initiate DNA synthesis by modest doses of anti-immunoglobulin antibody in combination with cytochalasin. The ability of these agents to stimulate B cells in a sequential fashion was evaluated. Anti-immunoglobulin prepared cells to respond to subsequently...
Human Cytomegalovirus Activates Glucose Transporter 4 Expression To Increase Glucose Uptake during Infection
Yu Y, et al.
Journal of virology, 85(4), 1573-1580 (2011)
Alternative In Vitro Models for Safety and Toxicity Evaluation of Nutraceuticals
Nutraceuticals, 355-385 (2016)
[18 F] FDG PET signal is driven by astroglial glutamate transport
Zimmer ER, et al.
Nature Neuroscience, 20(3), 393-393 (2017)

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