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Cytochalasin B information


Cytochalasin B
Names
IUPAC name
(1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
Other names
Phomin
Identifiers
CAS Number
  • 14930-96-2 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • L01252
ChEBI
  • CHEBI:23527
ChEMBL
  • ChEMBL411729
ChemSpider
  • 4470791 ☒N
ECHA InfoCard 100.035.440 Edit this at Wikidata
EC Number
  • 239-000-2
KEGG
  • C19954
PubChem CID
  • 5311281
RTECS number
  • RO0205000
UNII
  • 3CHI920QS7 checkY
CompTox Dashboard (EPA)
  • DTXSID30893482 Edit this at Wikidata
InChI
  • 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 ☒N
    Key: GBOGMAARMMDZGR-TYHYBEHESA-N ☒N
  • InChI=1/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
    Key: GBOGMAARMMDZGR-TYHYBEHEBX
SMILES
  • C[C@@H]1CCC[C@H](/C=C/C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)Cc4ccccc4)C)O)O
Properties
Chemical formula
C29H37NO5
Molar mass 479.6 g/mol
Appearance white to off-white powder
Density 1.21 g/cm3 (predicted)
Melting point 215 to 223 °C (419 to 433 °F; 488 to 496 K)
Boiling point 740.56 °C (1,365.01 °F; 1,013.71 K) at 760 mmHg (predicted)
Solubility in water
insoluble
Solubility in DMSO and MeOH soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
acute toxicity, health hazards
GHS labelling:
Pictograms
GHS06: ToxicGHS08: Health hazard
Signal word
Danger
Hazard statements
H300, H310, H330, H361
Precautionary statements
P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P302+P350, P304+P340, P308+P313, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501
Safety data sheet (SDS) Cytochalasin B MSDS from Fermentek
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Cytochalasin B, the name of which comes from the Greek cytos (cell) and chalasis (relaxation),[1] is a cell-permeable mycotoxin. It was found that substoichiometric concentrations of cytochalasin B (CB) strongly inhibit network formation by actin filaments. Due to this, it is often used in cytological research. It inhibits cytoplasmic division by blocking the formation of contractile microfilaments. It inhibits cell movement and induces nuclear extrusion. Cytochalasin B shortens actin filaments by blocking monomer addition at the fast-growing end of polymers.[2] Cytochalasin B inhibits glucose transport[3] and platelet aggregation. It blocks adenosine-induced apoptotic body formation without affecting activation of endogenous ADP-ribosylation in leukemia HL-60 cells.[4] It is also used in cloning through nuclear transfer. Here enucleated recipient cells are treated with cytochalasin B. Cytochalasin B makes the cytoplasm of the oocytes more fluid and makes it possible to aspirate the nuclear genome of the oocyte within a small vesicle of plasma membrane into a micro-needle. Thereby, the oocyte genome is removed from the oocyte, while preventing rupture of the plasma membrane.

This alkaloid is isolated from a fungus, Helminthosporium dematioideum.

  1. ^ Scherlach, K; et al. (2010). "The chemistry and biology of cytochalasans". Natural Product Reports. 27 (6): 869–86. doi:10.1039/b903913a. PMID 20411198.
  2. ^ Theodoropoulos, PA; Gravanis, A; Tsapara, A; Margioris, AN; Papadogiorgaki, E; Galanopoulos, V; Stournaras, C (1994). "Cytochalasin B may shorten actin filaments by a mechanism independent of barbed end capping". Biochemical Pharmacology. 47 (10): 1875–81. doi:10.1016/0006-2952(94)90318-2. PMID 8204105.
  3. ^ Jung, C. Y.; Rampal, A. L. (1977). "Cytochalasin B binding sites and glucose transport carrier in human erythrocyte ghosts". The Journal of Biological Chemistry. 252 (15): 5456–5463. doi:10.1016/S0021-9258(19)63372-7. PMID 885863.
  4. ^ Tanaka, Y.; Yoshihara, K.; Tsuyuki, M.; Kamiya, T. (1994). "Apoptosis Induced by Adenosine in Human Leukemia HL-60 Cells". Experimental Cell Research. 213 (1): 242–559. doi:10.1006/excr.1994.1196. PMID 8020596.

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Cytochalasin B

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Cytochalasin B, the name of which comes from the Greek cytos (cell) and chalasis (relaxation), is a cell-permeable mycotoxin. It was found that substoichiometric...

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angiogenesis and tumor growth. Unlike cytochalasin A and cytochalasin B, it does not inhibit glucose transport. Cytochalasin E, however, was noted to decrease...

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Parthenogenesis

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continual inhibition of MPF/cyclin B. As meiosis proceeds, extrusion of the second polar is blocked by exposure to cytochalasin B. This treatment results in a...

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Amoeboid movement

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(Jul–Aug 1990). "Amoeboid locomotion of Naegleria gruberi: the effects of cytochalasin B on cell-substratum interactions and motile behavior". The Journal of...

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Epiboly

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"purse-string mechanism". Treating embryos with the actin destabilizer cytochalasin b results in delayed or arrested epiboly. There is still debate on the...

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Characeae

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by the microfilaments found inside the cell, as proven by the use of cytochalasin B to stop streaming.[citation needed] There are about 400 extant species...

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Latrunculin

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made to the cellular processes. This property is similar to that of cytochalasin, but has a narrow effective concentration range. Latrunculin has been...

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Angiomotin

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cell-cell junctions. This binding remains after destabilizing actin with cytochalasin B. Like other surface-associated proteins that can bind plasminogen and...

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Micronucleus

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in cells undergoing nuclear division and can be clearly seen using cytochalasin B to block cytokinesis to produce a binucleated cells. Acentric chromosome...

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Cap formation

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energy dependent process and in lymphocytes is partially inhibited by cytochalasin B (which disrupts microfilaments) but unaffected by colchicine (which...

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Pyrenophora seminiperda

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Various secondary metabolites of the fungus, including Cytochalasin B, Pyrenophoric Acid-B, and Spirostaphylotrichin W, appears to be responsible for...

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Tunneling nanotube

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did not form when cultured with cytochalasin D, an F-actin depolymerizing compound. A separate study using cytochalasin B found that it impacted TNT formation...

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Andrzej Tarkowski

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Tarkowski, A.K., Witkowska, A. and Opas, J. (1977) Development of cytochalasin B-induced tetraploid and diploid/tetraploid mosaic mouse embryos. J. Embryol...

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List of biomolecules

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Cyclooxygenase Cyclopamine Cyclopiazonic acid Cysteine Cystine Cytidine Cytochalasin Cytochalasin E Cytochrome Cytochrome C Cytochrome c oxidase Cytochrome c peroxidase...

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Equivalence group

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morphogenesis with cytochalasin B is another method used to determine when the pigment precursor equivalence group is specified. Cytochalasin treatment of early...

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Enterotoxin type B

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In the field of molecular biology, enterotoxin type B, also known as Staphylococcal enterotoxin B (SEB), is an enterotoxin produced by the gram-positive...

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AB toxin

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membrane-bound transport "B" subunit. These proteins consist of two independent polypeptides, which correspond to the A/B subunit moieties. The enzyme...

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Cytoskeletal drugs

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microtubules, or Phalloidin, which stabilizes actin filaments. Others, such as Cytochalasin D, bind to actin monomers and prevent them from polymerizing into filaments...

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Botulinum toxin

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botulinum toxin are named types A to G (A, B, C1, C2, D, E, F and G). New types are occasionally found. Types A and B are capable of causing disease in humans...

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