14930-96-2

Basic information

• Product Name: CYTOCHALASIN B
• Synonyms: CytochalasinB from Drechslera dematioidea,Phomin;Cytochalasin B, froM Drechslera deMatoidea;Cytochalasin B (7S),(20R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione;Cytochalasin B from Helminthosporium dematioideum ;cytochalasin;ec[2,3-d]isoindole-2,18(5h)-dione;(E,E)-16-BENZYL-6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-5,13-DIHYDROXY-9,15-DIMETHYL-14-METHYLENE-2H-OXACYCLOTETRADE[2,3-D]ISOINDOLE-2,18(5H)-DIONE;CYTOCHALASIN B, HELMINTHOSPORIUM DEMATIOIDEUM
• CAS NO: 14930-96-2
• Molecular Formula: C₂₉H₃₇NO₅
• Molecular Weight: 479.61
• EINECS: 239-000-2
• Product Categories: antibiotic
• Mol File: 14930-96-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 218-223 °C
• Boiling Point: 577.96°C (rough estimate)
• Flash Point: 85℃
• Appearance: white/powder
• Density: 1.1490 (rough estimate)
• Vapor Pressure: 4.98E-23mmHg at 25°C
• Refractive Index: 1.6290 (estimate)
• Storage Temp.: −20°C
• Solubility: ethanol: 20 mg/mL
• PKA: 13.60±0.70(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• Merck: 13,2819
• BRN: 1096207
• CAS DataBase Reference: CYTOCHALASIN B(CAS DataBase Reference)
• NIST Chemistry Reference: CYTOCHALASIN B(14930-96-2)
• EPA Substance Registry System: CYTOCHALASIN B(14930-96-2)

Safety Data

• Hazard Codes: T+,T
• Statements: 26/27/28-63-23/24/25
• Safety Statements: 28-36/37-45
• RIDADR: UN 1544 6.1/PG 2
• WGK Germany: 3
• RTECS: RO0205000
• F: 10
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 14930-96-2(Hazardous Substances Data)

Usage

Description

Cytochalasin B is a cell-permeable fungal toxin/mycotoxin that binds to the barbed end of actin, inhibiting its polymerization. It is a potent inhibitor of actin filament function, leading to cell death by apoptosis and exhibiting a broad range of cellular actions. Cytochalasin B is widely used in various research applications, including studies of glucose transporters (GLUT) and in vitro micronucleus assay protocols.

Uses

Used in Cytological Research:
Cytochalasin B is used as a tool in cytological research for studying actin polymerization and the characterization of polymerization properties of actin.
Used in Actin Polymerization Studies:
Cytochalasin B is employed in actin polymerization studies to understand the effects of its inhibition on cell division, migration, and glucose transport.
Used in Glucose Transporter Studies:
Cytochalasin B is used in studies of glucose transporters (GLUT) to investigate its role in inhibiting cell division and migration.
Used in Micronucleus Assay Protocols:
Cytochalasin B is an integral part of various in vitro micronucleus assay protocols, which are used to assess the genotoxic potential of substances.
Used in Drug and Biomolecule Delivery:
Cytochalasin B-induced membrane vesicles (CIMVs) are a promising new vector system for drug and biomolecule delivery due to their natural origin and participation in intercellular communication.
Used in Cell Cycle Arrest and Apoptosis Induction:
Cytochalasin B causes cell cycle arrest at G2/M and induces apoptosis in HCT-116 colorectal carcinoma cells, making it a potential tool in cancer research and treatment.
Chemical Properties:
Cytochalasin B is an organic heterotricyclic compound, appearing as a white to off-white powder. It is a mycotoxin that is cell permeable and inhibits cytoplasmic division by blocking the formation of contractile microfilaments.

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.

Purification Methods

Purify it by MeOH extraction, reverse phase C18 silica gel batch extraction by selective elution with 1:1 v/v hexane/tetrahydrofuran, crystallisation, subjected to TLC and recrystallisation [Lipski et al. Anal Biochem 161 332 1987]. It is soluble in EtOH (3.6%), Me2CO (1%), Me2SO (37%) and Me2NCHO (49%) at 24o, and can be crystallised from the first two solvents. It interferes with cellular movement [Korm Physiol Reviews 62 672 1982].

References

Threadoropoulos et al. (1994), Cytochalasin B may shorten actin filaments by a mechanism independent of barbed end capping; Biochem. Pharmacol., 47 1875 Whitesell et al. (2005), Compartmentalization of transport and phosphorylation of glucose in a hepatoma cell line; Biochem. J., 386 245 Buldak et al. (2014), Changes in subcellular localization of visfatin in human colorectal HCT-116 carcinoma cell line after cytochalasin B treatment; Eur. J. Histochem., 58 2408 Gomzikova et al. (2018), Evaluation of cytochalasin B-Induced Membrane Vesicles Fusion specificity with Target Cells; Biomed. Res. Int., 2018 7053623 Gomzikova et al. (2017), Cytochalasin B-induced membrane vesicles convey angiogenic activity of parental cells; Oncotarget, 8 70496

InChI:InChI=1/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

Upstream product

• 14903-09-4 7,20-O,O'-di-acetyl-cytochalasin B 
• 64760-39-0 (16R,20R)-7β,20-diacetoxy-9-hydroxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t,21t-triene-23-thioic acid S-phenyl ester 
• 86542-46-3 C₃₇H₅₃NO₆Si 
• 86527-61-9 (E)-(1R,6R,10S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione 
• 86527-45-9 (E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione 
• 86527-63-1 (4E,12E)-(1R,6R,10S,14S,17S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-4,12,15-triene-3,21-dione 
• 86527-62-0 (4E,12E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-4,12,15-triene-3,21-dione 

Downstream Products

• 39156-67-7 7β,20β-dihydroxy-16α-methyl-10-phenyl-24-oxa-[14]cytochalasa-6(12),13t-diene-1,23-dione 
• 14110-64-6 7β-hydroxy-16α-methyl-10-phenyl-24-oxa-[14]cytochalasa-6(12),13t,21t-triene-1,20,23-trione 
• 39156-67-7 21,22-dihydrocytochalasin B 
• 59861-37-9 (16R,20R,21Ξ)-7β,9,20-trihydroxy-21-methoxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 20-lactone 
• 14110-64-6 cytochalasin A 
• 14697-25-7 7β,20β-dihydroxy-16α-methyl-10-phenyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione 
• 14110-71-5 (16R,20Ξ)-7β,9,20-trihydroxy-16-methyl-1-oxo-10-phenyl-(4α)-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 20-lactone 
• 14110-63-5 10-cyclohexyl-7β,20β-dihydroxy-16α-methyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione 
• 39156-68-8 21,22-dihydro-cytochalasin B 
• 27031-48-7 7,20-O,O'-di-(p-bromobenzoyl)cytochalasin B 
• 39156-70-2 7β,20β-diacetoxy-1-methoxy-16α-methyl-10-phenyl-24-oxa-[14]cytochalasa-1,6(12),13t,21t-tetraen-23-one 
• 14697-26-8 7β,20β-diacetoxy-16α-methyl-10-phenyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione 
• 14110-72-6 (16R,20Ξ)-7β-acetoxy-9,20-dihydroxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 20-lactone 
• 14119-72-3 7β,20β-diacetoxy-10-cyclohexyl-16α-methyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione 

Relevant articles and documents

A Simplified Total Synthesis of Cytochalasins via an Intramolecular Diels-Alder Reaction

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