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C2743

Sigma-Aldrich

Cytochalasin B from Drechslera dematioidea

Ready Made Solution, 10 mg/mL in DMSO

Synonym(s):

Phomin

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200 μL
£134.00

About This Item

Empirical Formula (Hill Notation):
C29H37NO5
CAS Number:
Molecular Weight:
479.61
Beilstein:
1096207
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85

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Quality Level

form

solution

concentration

10 mg/mL in DMSO

antibiotic activity spectrum

fungi

Mode of action

cell membrane | 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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Application

Cytochalasin B from Drechslera dematioidea has been used:
  • to block cytokinesis, to obtain binucleated cells[1]
  • as a specific glucose transporter inhibitor[2]
  • to inhibit glucose transport by class I and III GLUTs to determine the 50% inhibitory concentration (IC50) in HCMV-infected and mock-infected cells[3]

Cytochalasin B is used to inhibit sugar transport in fibroblasts [4], decrease cytoskeletal actin and myosin in rabbit neutrophils [5], and to stimulate B lymphocytes [6].

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.[7]
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

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

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Alternative In Vitro Models for Safety and Toxicity Evaluation of Nutraceuticals
Nutraceuticals, 355-385 (2016)
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)
[18 F] FDG PET signal is driven by astroglial glutamate transport
Zimmer ER, et al.
Nature Neuroscience, 20(3), 393-393 (2017)
Michael V Zuccaro et al.
Cell, 183(6), 1650-1664 (2020-10-31)
Correction of disease-causing mutations in human embryos holds the potential to reduce the burden of inherited genetic disorders and improve fertility treatments for couples with disease-causing mutations in lieu of embryo selection. Here, we evaluate repair outcomes of a Cas9-induced
Adam R Akkad et al.
PloS one, 17(5), e0268508-e0268508 (2022-05-21)
Biological materials can be shipped off-site for diagnostic, therapeutic and research purposes. They usually are kept in certain environments for their final application during transportation. However, active reagent handling during transportation from a collection site to a laboratory or biorepository

Questions

1–4 of 4 Questions  
  1. How does the storage temperature relate to shipping conditions?

    1 answer
    1. 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.

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

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

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

    1 answer
    1. 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.

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

    1 answer
    1. 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.

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