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Structure Database (LMSD)

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Common Name

Cytochalasin B

Systematic Name

Synonyms

LM ID

LMPK11000002

Formula

C₂₉H₃₇NO₅

Exact Mass

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479.267174

Status

Curated

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Classification

Biological Context

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

This information has been provided by Cayman Chemical

References

1. 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).

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

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. 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).

5. 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).

6. 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).

7. 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).

References

Reference

The Journal of Cell Biology, Vol 92, 69-78, 1982

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Pyrenophora dematioidea (#139229)

Dothideomycetes (#147541)

The cytochalasins, a new class of biologically active mould metabolites,
Chem Commun, 1967

DOI: 10.1039/C19670000026

String Representations

InChiKey (Click to copy)

GBOGMAARMMDZGR-TYHYBEHESA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@@H]1(C)C(=C)[C@@H](O)[C@@H]2C=CC[C@H](C)CCC[C@@H](O)C=CC(=O)O[C@@]32C(=O)N[C@@H](CC2C=CC=CC=2)[C@]13[H]