C6762

Cytochalasin B from Drechslera dematioidea

≥98% (HPLC), powder

• Synonym(s): Phomin
• Empirical Formula (Hill Notation): C₂₉H₃₇NO₅
• CAS Number: 14930-96-2
• Molecular Weight: 479.61
• Beilstein/REAXYS Number: 1096207
• EC Number: 239-000-2
• MDL number: MFCD00077704
• UNSPSC Code: 12352202
• PubChem Substance ID: 24892890
• NACRES: NA.32

Properties

• Quality Level: 300
• assay: ≥98% (HPLC)
• form: powder
• color: white
• solubility: DMSO: 10 mg/mL
• antibiotic activity spectrum: fungi
• mode of action: DNA synthesis | 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

Description

General description

Cytochalasin B is a cell-permeable fungal toxin / mycotoxin that binds to the ′barbed′ end of actin / actin filaments. This binding leads to:

• Disruption of actin filaments and of interaction of actin filaments in solution
• Inhibition of actin polymerization
• Inhibition of subunit association and dissociation

Cytochalasin B is widely used in studies of glucose transporters (GLUT). Cytochalasin B is also used as an integral part of various in vitro micronucleus assay protocols.

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.

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.

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300 + H310 + H330,H361
• pcodes: P201 - P202 - P260 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Repr. 2
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges