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About This Item

Empirical Formula (Hill Notation):
C29H37NO5
CAS Number:
14930-96-2
Molecular Weight:
479.61
Beilstein:
1096207
MDL number:
MFCD00077704
UNSPSC Code:
51102829
PubChem Substance ID:
329774749
NACRES:
NA.85
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Quality Level

200

form

solution

concentration

10 mg/mL in DMSO

antibiotic activity spectrum

fungi

Mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

C[C@@H]1CCC[C@@H](O)\C=C\C(=O)O[C@]23[C@@H](\C=C\C1)[C@H](O)C(=C)[C@@H](C)[C@H]2[C@H](Cc4ccccc4)NC3=O

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

InChI key

GBOGMAARMMDZGR-TYHYBEHESA-N

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Application

Cytochalasin B from Drechslera dematioidea has been used:
  • to block cytokinesis, to obtain binucleated cells
  • as a specific glucose transporter inhibitor
  • to inhibit glucose transport by class I and III GLUTs to determine the 50% inhibitory concentration (IC50) in HCMV-infected and mock-infected cells

Cytochalasin B is used to inhibit sugar transport in fibroblasts , decrease cytoskeletal actin and myosin in rabbit neutrophils , and to stimulate B lymphocytes .

Biochem/physiol Actions

Cell permeable fungal toxin that disrupts contractile microfilaments by inhibiting actin polymerization. This, in turn, induces DNA fragmentation, inhibits cell division, and disrupts many cell processes. Inhibits glucose transport.
Cytochalasin B can prevent cytoplasmic division without affecting nuclear division.
One of a group of fungal metabolites that interfere with a wide variety of cellular movements. Useful tool for characterizing some of the polymerization properties of actin, and in studies on cytokinesis. Probe for the two hexose-transport systems in rat L6 myoblasts.

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H302,H330

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

185.0 °F - closed cup - Solvent

Flash Point(C)

85 °C - closed cup - Solvent

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
049M4147V
11181027
028M4156V
11171204
037M4083V

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