Inhibitor of actin polymerization
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Cytochalasin A

Item No. 11327

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E,9R,11E,12aS,13S,15S,15aS,16S,18aS)-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino[2,3-d]isoindole-2,5,18-trione
CAS Number
14110-64-6
Synonyms
  • Dehydrophomin
  • NSC 174119
  • Phomin
Molecular Formula
C29H35NO5
Formula Weight
477.6
Purity
≥98%
Formulation (Request formulation change)
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(C([C@@H](C)[C@@]2([H])[C@H](CC3=CC=CC=C3)NC4=O)=C)=O)([H])[C@@]24O1
InChi Code
InChI=1S/C29H35NO5/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/h4-6,8,11-12,14-16,18-19,23-24,26-27,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,23+,24+,26+,27-,29-/m1/s1
InChi Key
ZMAODHOXRBLOQO-TZVKRXPSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Cytochalasin A is an oxidized analog of cytochalasin B that uniquely inhibits HIV-1 protease (IC50 = 3 μM).1 Cytochalasins A and B differ from other cytochalasins in being able to rapidly and reversibly inhibit glucose transport by competitively binding glucose transporters (Ki = 4.0 and 0.6 μM, respectively).2,3 Cytochalasin A also induces the phosphorylation of the tyrosine phosphatase PTP3 of Dictyostelium, activating STATc.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lingham, R.B., Hsu, A., Silverman, K.C., et al. L-696,474, a novel cytochalasin as an inhibitor of HIV-1 protease. III. Biological activity. J. Antibiot. (Tokyo) 45(5), 686-691 (1992).

    2. Kletzien, R.F., Perdue, J.F., and Springer, A. Cytochalasin A and B. Inhibition of sugar uptake in cultured cells. The Journal of Biological Chemisty 247(9), 2964-2966 (1972).

    3. Griffin, J.F., Rampal, A.L., and Jung, C.Y. Inhibition of glucose transport in human erythrocytes by cytochalasins: A model based on diffraction studies. Proc. Natl. Acad. Sci. USA 79(12), 3759-3763 (1982).

    4. Araki, T., and Williams, J.G. Perturbations of the actin cytoskeleton activate a Dictyostelium STAT signalling pathway. Eur. J. Cell Biol. 91(5), 420-425 (2012).