C2743

Cytochalasin B from Drechslera dematioidea

Ready Made Solution, 10 mg/mL in DMSO

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

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H302,H330
• pcodes: P260 - P264 - P270 - P271 - P301 + P312 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 2 Inhalation - Acute Tox. 4 Oral
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 2
• flash_point_f: 185.0 °F - closed cup - Solvent
• flash_point_c: 85 °C - closed cup - Solvent
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter