An inhibitor of actin polymerization
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Isomer(s)
44761Cytochalasin Z2
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Cytochalasin B

Item No. 11328

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione
CAS Number
14930-96-2
Synonyms
  • NSC 107658
  • Phomin
Molecular Formula
C29H37NO5
Formula Weight
479.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:20): 0.05 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/ml
SMILES
O=C1/C=C/[C@H](O)CCC[C@@H](C)C/C=C/[C@]([C@H](O)C([C@@H](C)[C@@]2([H])[C@H](CC3=CC=CC=C3)NC4=O)=C)([H])[C@@]24O1
InChi Code
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
InChi Key
GBOGMAARMMDZGR-TYHYBEHESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Cytochalasin B is a cell-permeable mycotoxin which binds to the barbed end of actin, reversibly inhibiting the elongation and shortening of actin filaments.1 By disrupting actin polymerization, cytochalasin B blocks diverse cellular functions, including cell division, migration, phagocytosis, exocytosis, chemotaxis, and glucose transport.2,3,4 Cytochalasin B is broadly used in cytological studies involving any of these many processes that depend on actin polymerization.5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Theodoropoulos, P.A., Gravanis, A., Tsapara, A., et al. Cytochalasin B may shorten actin filaments by a mechanism independent of barbed end capping. Biochem. Pharmacol. 47(10), 1875-1881 (1994).

    2. Steinberg, M.S., and Wiseman, L.L. Do morphogenetic tissue rearrangements require active cell movements? The reversible inhibition of cell sorting and tissue spreading by cytochalasin B. J. Cell Biol. 55, 606-615 (1972).

    3. Spudich, J.A., and Lin, S. Cytochalasin B, its interaction with actin and actomyosin from muscle (cell movement/microfilaments/rabbit striated muscle). Proc. Natl. Acad. Sci. USA 69(2), 442-446 (1972).

    4. Estensen, R.D., and Plagemann, P.G.W. Cytochalasin B: Inhibition of glucose and glucosamine transport. Proc. Natl. Acad. Sci. USA 69(6), 1430-1434 (1972).

    5. Snezhko, A., Barlan, K., Aranson, I.S., et al. Statistics of active transport in Xenopus melanophores cells. Biophys. J. 99, 3216-3223 (2010).

    6. Yu, Y., Dumollard, R., Rossbach, A., et al. Redistribution of mitochondria leads to bursts of ATP production during spontaneous mouse oocyte maturation. J. Cell. Physiol. 224(3), 672-680 (2010).

    7. Yu, Y., Maguire, T.G., and Alwine, J.C. Human cytomegalovirus activates glucose transporter 4 expression to increase glucose uptake during infection. J. Virol. 85(4), 1573-1580 (2011).