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Cytochalasin D (CAS 22144-77-0)

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Alternate Names:
Cytochalasin D also known as Zygosporin A; (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)-15-(Acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-1H-cycloundec[d]isoindole-1,11(2H)-dione; (7S,13E,16S,18R,19E,21R)-[11]21-(Acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10-phenylcytochalasa-6(12),13,19-triene-1,17-dione; (−)-Cytochalasin D; 1H-Cycloundec[d]isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, [3S-(3R*,3aS*,4R*,6R*,6aS*,7E,10R*,12S*,13E,15S*,15aS*)]-; Cytochalasin D; NSC 209835
Application:
Cytochalasin D is a cell cycle arresting compound used in actin polymerization studies and cytological research
CAS Number:
22144-77-0
Purity:
≥97%
Molecular Weight:
507.62
Molecular Formula:
C30H37NO6
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Cytochalasin D is used in actin polymerization studies and cytological research. Cytochalasins are fungal toxins characterized by a highly substituted hydrogenated isoindole ring to which is fused a macrocyclic ring. They are believed to bind to the barbed end of actin filaments resulting in inhibition of both the association and dissociation of subunits. Cytochalasin D is about 10-fold more effective than cytochalasin B (sc-3519) and does not inhibit monosaccharide transport across cell membranes. Treatment of cells with cytochalasin D results in rapid tyrosine phosphorylation of fish (SH3PXD2A), along with activation of Src. It may act to increase intracellular Ca2+ levels and to activate p53-dependent pathways, causing arrest of the cell cycle. It may also act as an inhibitor of DNA synthesis, thyroid secretion, and growth hormone release. Other Cytochalasins available: Cytochalasin A (sc-204705) Cytochalasin C (sc-202118) Cytochalasin E, Aspergillus clavatus (sc-202561) Cytochalasin H (sc-202119) Cytochalasin J (sc-202120)


Cytochalasin D (CAS 22144-77-0) References

  1. Cytochalasin D reduces Ca2+ sensitivity and maximum tension via interactions with myofilaments in skinned rat cardiac myocytes.  |  Calaghan, SC., et al. 2000. J Physiol. 529 Pt 2: 405-11. PMID: 11101650
  2. Crystal structures of monomeric actin bound to cytochalasin D.  |  Nair, UB., et al. 2008. J Mol Biol. 384: 848-64. PMID: 18938176
  3. Arterial biomechanics after destruction of cytoskeleton by Cytochalasin D.  |  Roy, S., et al. 2009. J Biomech. 42: 2562-8. PMID: 19647827
  4. Cytochalasin D, LY294002 and olomoucine synergize in promoting death of melanoma cells through activation of caspase-3 and apoptosis.  |  Małecki, JM., et al. 2010. Melanoma Res. 20: 52-8. PMID: 20010439
  5. Cytochalasin D, a tropical fungal metabolite, inhibits CT26 tumor growth and angiogenesis.  |  Huang, FY., et al. 2012. Asian Pac J Trop Med. 5: 169-74. PMID: 22305779
  6. Cytochalasin D acts as an inhibitor of the actin-cofilin interaction.  |  Shoji, K., et al. 2012. Biochem Biophys Res Commun. 424: 52-7. PMID: 22728040
  7. Cytochalasin D inhibits penetration of hamster eggs by guinea pig and human spermatozoa.  |  Rogers, BJ., et al. 1989. J Androl. 10: 275-82. PMID: 2777719
  8. Cytochalasin D Promotes Osteogenic Differentiation of MC3T3-E1 Cells via p38-MAPK Signaling Pathway.  |  Liu, Q., et al. 2019. Curr Mol Med. 20: 79-88. PMID: 31589123
  9. Evaluation of zoledronate, cytochalasin-D, and desferrioxamine on osseointegration in an intra-medullary femoral implant model.  |  Leatherwood, WH., et al. 2020. J Musculoskelet Neuronal Interact. 20: 121-127. PMID: 32131376
  10. Effects of cytochalasin and phalloidin on actin.  |  Cooper, JA. 1987. J Cell Biol. 105: 1473-8. PMID: 3312229
  11. A proposed mechanism of action of cytochalasin D on muscle actin.  |  Selden, LA., et al. 1980. Biochem Biophys Res Commun. 95: 1854-60. PMID: 6448056
  12. Cytochalasin D inhibits smooth muscle contraction by directly inhibiting contractile apparatus.  |  Saito, SY., et al. 1996. J Smooth Muscle Res. 32: 51-60. PMID: 8845566
  13. A new method for isolating tyrosine kinase substrates used to identify fish, an SH3 and PX domain-containing protein, and Src substrate.  |  Lock, P., et al. 1998. EMBO J. 17: 4346-57. PMID: 9687503

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Cytochalasin D, 1 mg

sc-201442
1 mg
$145.00

Cytochalasin D, 5 mg

sc-201442A
5 mg
$442.00

Should this chemical be protected from light?

Asked by: chemicalsmg
Thank you for your question. Cytochalasin D: sc-201442 should be protected from light during handling and storage.
Answered by: Chemical Support 3
Date published: 2017-03-07

What is the appearance of this product?

Asked by: chemicalsmg
Thank you for your question. Cytochalasin D: sc-201442 is expected to be a white to off-white solid.
Answered by: Chemical Support 3
Date published: 2017-03-07
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Rated 2 out of 5 by from Cytochalasin D workdsI ordered this chemical one monthe ago and it works well
Date published: 2018-07-01
Rated 5 out of 5 by from Great productGreat product. We have purchased this multiple times.
Date published: 2015-10-07
Rated 5 out of 5 by from We are happy with the products we buy oftenWe are happy with the products we buy often.
Date published: 2015-09-17
Rated 5 out of 5 by from An increase in cytochrome c protein expressionAn increase in cytochrome c protein expression was observed by WB in HeLa cells post treatment with Cytochalasin D. -SCBT QC
Date published: 2015-02-22
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Cytochalasin D is rated 4.3 out of 5 by 4.
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