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C2618

Sigma-Aldrich

Cytochalasin D

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

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Synonym(s):
Lygosporin A, Zygosporin A
Empirical Formula (Hill Notation):
C30H37NO6
CAS Number:
22144-77-0
Molecular Weight:
507.62
Beilstein:
1632828
MDL number:
MFCD00077706
UNSPSC Code:
51101500
PubChem Substance ID:
329775013
NACRES:
NA.85

biological source

Zygosporium mansonii

Quality Level

300

form

solution

concentration

5 mg/mL in DMSO

antibiotic activity spectrum

fungi

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

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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.

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

高风险级别生物产品--毒素类产品

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)
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
Sangbom Michael Lyi et al.
Virology, 456-457, 342-352 (2014-06-04)
Cell infection by parvoviruses requires that capsids be delivered from outside the cell to the cytoplasm, followed by genome trafficking to the nucleus. Here we microinject capsids into cells that lack receptors and followed their movements within the cell over
Ronald S Flannagan et al.
Molecular biology of the cell, 25(9), 1511-1522 (2014-03-14)
T-cell immunoglobulin mucin protein 4 (TIM4), a phosphatidylserine (PtdSer)-binding receptor, mediates the phagocytosis of apoptotic cells. How TIM4 exerts its function is unclear, and conflicting data have emerged. To define the mode of action of TIM4, we used two distinct
Yi-Chin Toh et al.
Biomaterials, 50, 87-97 (2015-03-05)
Heterogeneity in human pluripotent stem cell (PSC) fates is partially caused by mechanical asymmetry arising from spatial polarization of cell-cell and cell-matrix adhesions. Independent studies have shown that integrin and E-cadherin adhesions promote opposing differentiation and pluripotent fates respectively although
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