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CYTOCHALASIN B

Product Name
CYTOCHALASIN B
CAS No.
14930-96-2
Chemical Name
CYTOCHALASIN B
Synonyms
cytochalasin;PHOMIN;-23-one;CYTOCHALACINB;CYTOCHALICINB;CYTOCHALASIN B;CYTOCHALASIN B(RG);Cytochalasin B (Phomin);CYTOCHALASIN B USP/EP/BP;(7s,13e,16r,20r,21e)-0-phenyl
CBNumber
CB6323824
Molecular Formula
C29H37NO5
Formula Weight
479.61
MOL File
14930-96-2.mol
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CYTOCHALASIN B Property

Melting point:
218-223 °C
Boiling point:
577.96°C (rough estimate)
Density 
1.1490 (rough estimate)
refractive index 
1.6290 (estimate)
Flash point:
85℃
storage temp. 
-20°C
solubility 
ethanol: 20 mg/mL
form 
powder
pka
13.60±0.70(Predicted)
color 
white
Merck 
13,2819
BRN 
1096207
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.
InChIKey
UXVDBQLLXVKPRS-UZBFCAAUSA-N
LogP
3.370
EPA Substance Registry System
Cytochalasin B (14930-96-2)
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Safety

Hazard Codes 
T+,T
Risk 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
HS Code 
29349990
Hazardous Substances Data
14930-96-2(Hazardous Substances Data)
Toxicity
LD50 intraperitoneal in mouse: 30mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C2743
Product name
Cytochalasin B from Drechslera dematioidea
Purity
Ready Made Solution, 10?mg/mL in DMSO, 0.2 μm filtered
Packaging
200μL
Price
$154
Updated
2024/03/01
Sigma-Aldrich
Product number
250233
Product name
Cytochalasin B,
Packaging
5mg
Price
$208
Updated
2024/03/01
Alfa Aesar
Product number
J65342
Product name
Cytochalasin B
Packaging
5mg
Price
$273
Updated
2024/03/01
Alfa Aesar
Product number
J65342
Product name
Cytochalasin B
Packaging
10mg
Price
$431
Updated
2024/03/01
Cayman Chemical
Product number
11328
Product name
Cytochalasin B
Purity
≥98%
Packaging
1mg
Price
$44
Updated
2024/03/01
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CYTOCHALASIN B Chemical Properties,Usage,Production

Description

Cytochalasin B (14930-96-2) is a cell permeable fungal toxin which binds to the barbed end of actin, inhibiting its polymerization.1 Inhibits cell division, migration and glucose transport.2 Causes cell cycle arrest at G2/M and induces apoptosis in HCT-116 colorectal carcinoma cells.3? Cytochalasin B-induced membrane vesicles (CIMVs) retain cell surface receptors of the parent cells and retain fusion specificity with target cells.4 CIMVs are a promising new vector system for drug and biomolecule delivery due to their natural origin and participation in intercellular communication.5

Chemical Properties

white to off-white powder

Uses

Cytochalasin B is one of the most extensively studied members of a family of potent mycotoxins produced by several species of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, giving rise to pronounced morphogenic activity in animals and plants. Like most cytochalsins, cytochalasin B exhibits potent inhibition of actin filament function leading to cell death by apoptosis, and displays a broad range of resultant cellular actions. Despite the common mode of action, there is evidence that individual members of this class display diverse selectivity. However, lack of comparative co-metabolite analysis has restricted a more complete understanding of their individual selectivity.

Uses

A cell-permeable fungal toxin used in actin polymerization studies and cytological

Uses

As tools in cytological research and in characterization of polymerization properties of actin, q.v.

Definition

ChEBI: An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.

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.

storage

Store at -20°C

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

CYTOCHALASIN B Preparation Products And Raw materials

Raw materials

Preparation Products

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CYTOCHALASIN B Suppliers

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View Lastest Price from CYTOCHALASIN B manufacturers

Career Henan Chemical Co
Product
CYTOCHALASIN B 14930-96-2
Price
US $1.00/ASSAYS
Min. Order
1ASSAYS
Purity
98%
Supply Ability
1kg,2kg,100kg
Release date
2019-07-09

14930-96-2, CYTOCHALASIN BRelated Search:

CYTOCHALASIN E CYTOCHALASIN A CYTOCHALASIN C CYTOCHALASIN D CYTOCHALASIN B, DIHYDRO,CYTOCHALASIN B, DIHYDRO ETHYL TRANS-2-DECENOATE ISO-AMYL-CROTONATE cis-Octahydro-isoindole (S)-(+)-1-Cyclohexylethylamine 2-METHOXY-2-METHYL-PROPYLAMINE 1-AMINOMETHYL-1-CYCLOHEXANOL HYDROCHLORIDE OCTYL-CROTONATE 2-Ethylhexyl acrylate 2,2-DI-N-PROPYLACETAMIDE TRANS-2-AMINOMETHYL-1-CYCLOHEXANOL Cyclohexyl acrylate 2-Methyl-2-hydroxypropionamide CYTOCHALASIN B

  • 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
  • CYTOCHALASIN B
  • ,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-,(e,e)
  • ,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-2h-oxacyclotetrad
  • -23-one
  • 24-oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione,7,20-dihydroxy-16-methyl-1
  • 2h-oxacyclotetradec(2,3-d)isoindole-2,18(5h)-dione,16-benzyl-6,7,8,9,10,12a,13
  • 3-d)isoindole-2,18(5h)-dione,16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-2h-oxacyclotetradec(
  • 7,20-dihydroxy-10-phenyl-5,16-dimethyl-24-oxa-[14]cytochalas-6(12),13,21-trien
  • Cytochalasin B, Helminthosporium dematioideum - CAS 14930-96-2 - Calbiochem
  • (3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-6,7,8,9,10,12a,13,14,15,15a,16,17-Dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione
  • Cytochalasin B (Phomin)
  • Cytochalasin B (Synonyms: Phomin)
  • 7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
  • Cytochalasin beta,helminthosporium dematioideum
  • cytochalasin b from drechslera dematioidea
  • CYTOCHALASIN B(RG)
  • CYTOCHALACINB
  • CYTOCHALICINB
  • CYTOCHALASIN B FROM HELMINTHOSPORIUM DEMATIODEUM
  • (7S,13E,16R,20R,21E)-7,20-Dihydroxy-16-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13,21-triene-1,23-dione
  • (7S),(20R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
  • PHOMIN
  • (7s,13e,16r,20r,21e)-0-phenyl
  • (e,e)-(5s,9r,12as,13s,15s,15as,16s,18as)-16-benzyl-6,7,8,9,10,12a,13,14,15,15a
  • ,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-,(e)-(
  • 9r,12as,13s,15s,15as,16as,18as)-5
  • 9r,12as,13s,15s,15as,16s,18as)--(5
  • Cytochalasin B, 98%, from Drechslera dematoidea
  • CYTOCHALASIN B FROM DRESCHSLERA DEMATIOIDEA
  • CYTOCHALASIN B SYNTHETIC >97%
  • CYTOCHALASIN B FROM DRESCHSLERA DEMATIOIDEA, BIOCHEMIKA, >= 95.0% (HPLC)
  • 2H-Oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione,6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-,(3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-
  • CYTOCHALASIN B USP/EP/BP
  • 16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,12aH,13H,14H,15H,15aH,16H,17H,18H-oxacyclotetradeca[3,2-e]isoindole-2,18-dione
  • Cytochalasin B, actin polymerization inhibitor
  • 14930-96-2
  • C29H37NO5
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