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Safety Information

250233

Sigma-Aldrich

Cytochalasin B

from Helminthosporium dematioideum, ≥98% (HPLC), solid, cell-permeable fungal toxin, Calbiochem®

Synonym(s):

Cytochalasin B, Helminthosporium dematioideum

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About This Item

Empirical Formula (Hill Notation):
C29H37NO5
CAS Number:
14930-96-2
Molecular Weight:
479.61
MDL number:
MFCD00077704
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and Inventory is not available. Please check the Merck website for more information.

Product Name

Cytochalasin B, Helminthosporium dematioideum, Cell-permeable fungal toxin.

Quality Level

100

Assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

methanol: 20 mg/mL
DMSO: 50 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

N1[C@H]([C@H]3[C@@]4(OC(=O)\C=C\[C@@H](CCC[C@H](C\C=C\[C@H]4[C@@H](C(=C)[C@H]3C)O)C)O)C1=O)Cc2ccccc2

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

General description

Cell-permeable fungal toxin. Inhibits cytoplasmic division by blocking the formation of contractile microfilaments. Inhibits cell movement and induces nuclear extrusion. Shortens actin filaments by blocking monomer addition at the fast growing end of polymers. Inhibits glucose transport and platelet aggregation. Blocks adenosine-induced apoptotic body formation without affecting activation of endogenous ADP-ribosylation in leukemia HL-60 cells.
Cell-permeable fungal toxin. Inhibits cytoplasmic division by blocking the formation of contractile microfilaments. Inhibits cell movement and induces nuclear extrusion. Shortens actin filaments by blocking monomer addition at the fast-growing end of polymers. Inhibits glucose transport and platelet aggregation. Blocks adenosine-induced apoptotic body formation without affecting activation of endogenous ADP-ribosylation in leukemia HL-60 cells.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Blocking the formation of contractile microfilaments
Product does not compete with ATP.
Reversible: no

Caution

Poor quality DMSO will cause degradation of the product, so high quality DMSO is recommended.

Warning

Toxicity: Highly Toxic & Carcinogenic / Teratogenic (I)

Reconstitution

Following reconstitution store in the refrigerator (4°C). Stock solutions are stable for up to 3 months at 4°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Tanaka, Y., et al. 1994. Exp. Cell Res. 213, 242.
Theodoropoulos, P.A., et al. 1994. Biochem. Pharmacol. 47, 1875.
Benya, P.D., and Padilla, S.R. 1993. Exp. Cell Res. 204, 268.
Cairns, M.T., et al. 1991. J. Biol. Chem.266, 8176.
Nowak, D. 1990. Biomed. Biochim. Acta49, 353.
Wang, F., et al. 1990. Biochem. Biophys. Res. Commun.171, 543.
Edwards, S.W., and Lloyd, D. 1988. FEBS Lett.227, 39.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

250233-0MG:
250233-MG:
250233-50MG:
250233-5MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mitochondrial DNA (mtDNA) mutations are often associated with incurable diseases and lead to detectable pathogenic variants in 1 out of 200 babies. Uncoupling of the inheritance of mtDNA and the nuclear genome by spindle transfer (ST) can potentially prevent the
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Scientific reports, 13(1), 11175-11175 (2023-07-11)
Wild-derived mouse strains have been extensively used in biomedical research because of the high level of inter-strain polymorphisms and phenotypic variations. However, they often show poor reproductive performance and are difficult to maintain by conventional in vitro fertilization and embryo
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The current Organisation for Economic Co-Operation and Development test guideline number 487 (OECD TG No. 487) provides instruction on how to conduct the in vitro micronucleus assay. This assay is one of the gold standard approaches for measuring the mutagenicity
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Tunneling nanotube (TNT), a dynamic cell-cell contact, is dependent on actin polymerization. TNTs are efficient in transporting ions, proteins and organelles intercellularly, which are important mechanisms in physiological and pathological processes. Reported studies on the existence and function of TNTs
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Questions

  1. Cytochalasin B, Helminthosporium dematioideum & other option is Dihydrocytochalasin B. What is the difference?

    1 answer

    1. There is a slight difference in the chemical structure of each compound. Cytochalasin B is a cell-permeable fungal toxin. It Inhibits cytoplasmic division by blocking the formation of contractile microfilaments, inhibits cell movement, and induces nuclear extrusion. Cytochalasin B shortens actin filaments by blocking monomer addition at the fast growing end of polymers. It also Inhibits glucose transport and platelet aggregation, blocks adenosine-induced apoptotic body formation without affecting activation of endogenous ADP-ribosylation in leukemia HL-60 cells. Dihydrocytochalasin B (DCB) is a member of the cytochalasin mycotoxin family that inhibits actin assembly. It has an effect on cell motility and morphology similar to that of cytochalasin B. However, it does not inhibit glucose transport. The following publication may be of interest:
      https://pubmed.ncbi.nlm.nih.gov/272649/

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