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Cytochalasin D

Name: Cytochalasin D
Brand: SIGMA

Ready Made Solution, from Zygosporium mansonii, 5 mg/mL in DMSO

Synonym(s):

Lygosporin A, Zygosporin A

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About This Item

Empirical Formula (Hill Notation):

C₃₀H₃₇NO₆

CAS Number:

22144-77-0

Molecular Weight:

507.62

UNSPSC Code:

51102829

NACRES:

NA.85

PubChem Substance ID:

329775013

MDL number:

MFCD00077706

Beilstein/REAXYS Number:

1632828

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Properties

biological source

Zygosporium mansonii

Quality Level

300

form

ready-to-use solution

concentration

5 mg/mL in DMSO

antibiotic activity spectrum

fungi

application(s)

advanced drug delivery

mode of action

enzyme | interferes

shipped in

wet ice

storage temp.

−20°C

SMILES string

[H][C@@]12[C@H](C)C(=C)[C@@H](O)[C@@H]3\C=C\C[C@H](C)C(=O)[C@](C)(O)\C=C\[C@@H](OC(C)=O)[C@@]13C(=O)N[C@H]2Cc4ccccc4

InChI

1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17-18,22-26,33,36H,3,10,16H2,1-2,4-5H3,(H,31,35)/b13-9+,15-14+/t17-,18+,22-,23-,24+,25-,26+,29+,30+/m0/s1

InChI key

SDZRWUKZFQQKKV-JHADDHBZSA-N

Description

Application

Cytochalasin D are isomeric metabolites of Metarrhizium anisopliae. Cytochalasin D possesses antibiotic and antitumor activity. It also impairs maintenance of long term potentiation (LTP) of actin filaments. It is implicated in promoting conditions favorable for depolymerizing actin.

Biochem/physiol Actions

Cell permeable fungal toxin; potent inhibitor of actin polymerization. Disrupts actin microfilaments and activates the p53-dependent pathways causing arrest of the cell cycle at the G1-S transition. Inhibits smooth muscle contraction. Inhibits insulin-stimulated, but not basal, transport of glucose.

Potent inhibitor of actin polymerization; disrupts actin microfilaments; activates the p53-dependent pathways; inhibits smooth muscle contraction; inhibits insulin-stimulated glucose transport.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

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1 of 1

This Item	5.04776	C8273	250255-M
Sigma-Aldrich C2618 Cytochalasin D	Sigma-Aldrich 5.04776 Cytochalasin D, Zygosporium mansonii	Sigma-Aldrich C8273 Cytochalasin D	Millipore 250255-M Cytochalasin D, Zygosporium mansonii
mode of action enzyme \| interferes	mode of action -	mode of action DNA synthesis \| interferes	mode of action -
antibiotic activity spectrum fungi	antibiotic activity spectrum -	antibiotic activity spectrum fungi	antibiotic activity spectrum -
Quality Level 300	Quality Level 100	Quality Level 300	Quality Level 100
form ready-to-use solution	form liquid	form powder	form solid
storage temp. −20°C	storage temp. −70°C	storage temp. −20°C	storage temp. −20°C
biological source Zygosporium mansonii	biological source -	biological source Zygosporium mansonii	biological source -

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Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

188.6 °F - closed cup - Solvent

flash_point_c

87 °C - closed cup - Solvent

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

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The inhibition of sugar transport in chick embryo fibroblasts by cytochalasin B. Evidence for a membrane-specific effect.

R F Kletzien et al.

The Journal of biological chemistry, 248(2), 711-719 (1973-01-25)

Stimulation by chemotactic factor of actin association with the cytoskeleton in rabbit neutrophils. Effects of calcium and cytochalasin B.

J R White et al.

The Journal of biological chemistry, 258(22), 14041-14047 (1983-11-25)

The amounts of actin and myosin in rabbit neutrophils expressed as micrograms/10(6) cells are 5.6 +/- 0.75 and 0.56 +/- 0.08, respectively. The average value of the total actin in rabbit neutrophils under unstimulated conditions is distributed between Triton X-100

Stimulation of B cells by sequential addition of anti-immunoglobulin antibody and cytochalasin.

T L Rothstein

Journal of immunology (Baltimore, Md. : 1950), 136(3), 813-816 (1986-02-01)

B cells are stimulated to initiate DNA synthesis by modest doses of anti-immunoglobulin antibody in combination with cytochalasin. The ability of these agents to stimulate B cells in a sequential fashion was evaluated. Anti-immunoglobulin prepared cells to respond to subsequently

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Global Trade Item Number

SKU	GTIN
C2618-200UL	04061833484302

Questions

1–2 of 2 Questions

Anonymous

10 months ago

How can I determine the shelf life / expiration / retest date of this product?

1 answer
1. Technical Support
  
  10 months ago
  
  If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
  For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
  For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
  For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf
  
  Helpful?
Anonymous

a year ago

How is shipping temperature determined? And how is it related to the product storage temperature?

1 answer
1. Technical Support
  
  a year ago
  
  Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
  
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