Cytochalasins are fungal metabolites that have the ability to bind to actin filaments and block polymerization and the elongation of actin. As a result of the inhibition of actin polymerization, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and even cause cells to undergo apoptosis. Cytochalasins have the ability to permeate cell membranes, prevent cellular translocation and cause cells to enucleate. Cytochalasins can also have an effect on other aspects of biological processes unrelated to actin polymerization.

For example: Cytochalasin A and Cytochalasin B can also inhibit the transport of monosaccharides across the cell membrane. Cytochalasin H has been found to regulate plant growth, Cytochalasin D inhibits protein synthesis. Cytochalasin E prevents angiogenesis.

Dihydrocytochalasin B

Dihydrocytochalasin B
Molecular Formula
C29H39NO5
M.W.
481.60
CAS number
39156-67-7
MSDS
Source
Semisynthetic
Fermentek product Code
DHB-001
Brand/grade
For research
Appearance
White powder
Purity by HPLC
≥95% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
195°C-205°C
Solubility test
Clear colorless solution at 10mg/ml Methanol
Names and identifiers

Synonyms:  

  • 21,22-Dihydrochalasin B
  • 21,22-Dihydrocytochalasin B
  • 21,22-Dihydrophomin

 

Systematic Name: 7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E)-diene-1,23-dione

EU number
254-324-4
Description

Dihydrocytochalasin B is chemically derived from Cytochalasin B  obtained natural from Drechslera dematoidea fungus.

InChl Key
WIULKAASLBZREV-RXPQEOCGSA-N
Canonical SMILES
CC1CCCC(CCC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O
Isomeric SMILES
C[C@@H]1CCC[C@H](CCC(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)CC4=CC=CC=C4)C)O)O
Solubility ( literature )

Acetone, DMSO, 100% Ethanol, Methanol

Compound Classification
  • Macrolide indol mycotoxin
  • Cytochalasin
  • Actin inhibitor
Storage, handling
Deep frozen (-15 oC to - 20 oC)
Retest time
3 Years
Applications

Cytochalasins are used as tools in cytological research, and in in the field of actin polymerisation.

Cytokinesis inhibitor. Inducer of changes in cell morphology and motility. It disrupts actin structure and inhibits ability of serum growth factors to stimulate DNA synthesis in vitro. Does not inhibit sugar uptake. Active calcium transport inhibitor. Active in vivo.

 

Ingredient type
Fermentek product
Available since
Title
sig
Value
250225
Title
TSE
Value
S
Title
Transport information
Value
Pg III
Title
EU
Value
254-324-4; On REACH List of Pre-Registered Substances, March 2009 Registration Date: 31-MAY-2013
Title
CAS deleted numbers
Value
74409-92-0 ;
Title
Other sites info
Value
Most sites give wrong RTECS number RO0205000 belonging to Phomin
Fermentek Product Category
Food Safety
Mycotoxins
Food Safety Related
Cytochalasins
Signal to sort
D

Quote for

Price
$1.00
Dihydrocytochalasin_B.gif
Dihydrocytochalasin_B.gif

Cytochalasin E

Cytochalasin E
Molecular Formula
C28H33NO7
M.W.
495.56
CAS number
36011-19-5
MSDS
Source
Aspergillus clavatus
Fermentek product Code
CYE-001
Brand/grade
For research
Appearance
White powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
205°C-220°C
Solubility test
Clear colorless solution at 50mg/ml DMSO
Names and identifiers

 

HSDB 3548

RTECS HA5360000

 

EU number
252-835-7
Description

Inhibitor of actin polymerization in blood platelets. It does not inhibit glucose transport.

InChl Key
LAJXCUNOQSHRJO-ZYGJITOWSA-N
Canonical SMILES
CC1CC=CC2C3C(O3)(C(C4C2(C(=O)NC4CC5=CC=CC=C5)OC(=O)OC=CC(C1=O)(C)O)C)C
Isomeric SMILES
C[C@H]1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4[C@]2(C(=O)N[C@H]4CC5=CC=CC=C5)OC(=O)O/C=C/[C@@](C1=O)(C)O)C)C
Solubility ( literature )

DMSO, ethyl acetate, ethanol, dichloromethane

Compound Classification

Macrolide indol mycotoxin

Cytochalasin

Actin polymerization inhibitor

Antiangiogenic

 

Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Retest time
3 Years
Ingredient type
Fermentek product
Available since
Title
since
Value
1999
Fermentek Product Category
Food Safety
Mycotoxins
Food Safety Related
Cytochalasins
Angiogenesis related
Signal to sort
C
Cytochalasin_E.gif
Cytochalasin_E.gif

Cytochalasin D

Cytochalasin D
Molecular Formula
C30H37NO6
M.W.
507.62
CAS number
22144-77-0
MSDS
Source
Zygosporium mansonii
Fermentek product Code
CYD-001
Brand/grade
For research
Appearance
White powder
Purity by HPLC
≥97% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
230°C-245°C
Solubility test
Clear colorless solution at 25mg/ml DMSO, Clear colorless solution at 5mg/ml Ethanol
Names and identifiers

Synonyms: Zygosporin A

Chemical Name: (7S,13E,16S,18R,19E,21R)-21-(Acetyloxy)- 7,18-dihydroxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,19-triene-1,17-dione

EU number
244-804-1
Description

Cytochalasin D is a cell permeable mycotoxin, which causes both the association and dissociation of actin subunits. Cytochalasin D disrupts actin filaments and inhibits actin polymerization.

InChl Key
SDZRWUKZFQQKKV-JHADDHBZSA-N
Canonical SMILES
CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1=O)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O
Isomeric SMILES
C[C@H]1C/C=C/[C@H]2[C@@H](C(=C)[C@H]([C@@H]3[C@@]2([C@@H](/C=C/[C@@](C1=O)(C)O)OC(=O)C)C(=O)N[C@H]3CC4=CC=CC=C4)C)O
Solubility ( literature )

DMSO, Ethanol, Methanol

Compound Classification
  • Macrolide indol mycotoxin
  • Cytochalasin
  • Actin inhibitor
Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Protect from moisture
Open carefully.
Use the original container to store the product.
Avoid exposing to strong direct light.
Store under argon.
Other vendors may recommend higher temperatures for storage.
Retest time
3 Years
Applications

Cytochalasins are used as tools in cytological research, and in the field of actin polymerization. Cytochalasin D is 10 times more effective than cytochalasin B and does not inhibit glucose transport across cell membranes.

Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Available since
Title
Deleted CAS Numbers
Value
11032-97-6 ; 25852-72-6 ; 28455-04-1 ; 69401-32-7
Title
TSE
Value
V
Title
sig
Value
250255
Fermentek Product Category
Food Safety
Mycotoxins
Food Safety Related
Cytochalasins
Enzyme-inhibitors
Apoptosis related
Anti Viral
Cancer Related Compounds
Anti Tumor agents
Signal to sort
C

Quote for

Price
$1.00
Cytochalasin_D.gif
Cytochalasin_D.gif

Cytochalasin C

Cytochalasin C
Molecular Formula
C30H37NO6
M.W.
507.62
CAS number
22144-76-9
MSDS
Source
Metarhizium anisopliae
Fermentek product Code
CYC-001
Brand/grade
For research
Appearance
White powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
265°C-280°C
Solubility test
Clear colorless solution at 5mg/ml Dichloromethane
Names and identifiers

RTECS: HA5300500

EU number
244-803-6
Description

A fungal metabolite that acts as a potent inhibitor of actin filament and contractile microfilaments.

InChl Key
NAIODHJWOHMDJX-BBXOWAOSSA-N
Canonical SMILES
CC1CC=CC2C(C(=C(C3C2(C(C=CC(C1=O)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)C)O
Isomeric SMILES
CC1C/C=C/C2C(C(=C(C3C2(C(/C=C/C(C1=O)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)C)O
Solubility ( literature )

Dichloromethane , Ethyl acetate

Compound Classification

Macrolide indol mycotoxinCytochalasinActin inhibitor

Storage, handling
-20°C. Protect from light.
Retest time
3 Years
Applications

Cytochalasins are used as tools in cytological research, and in the field of actin polymerisation

Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Available since
Fermentek Product Category
Food Safety
Mycotoxins
Food Safety Related
Cytochalasins
Signal to sort
C

Quote for

Price
$1.00
Cytochalasin_C.gif
Cytochalasin_C.gif

Cytochalasin B

Cytochalasin B
Molecular Formula
C29H37NO5
M.W.
479.61
CAS number
14930-96-2
MSDS
Source
Drechslera dematoidea
Fermentek product Code
CYB-001
Brand/grade
For research
Appearance
White to off-white powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
215°C-226°C
Solubility test
Clear colorless solution at 20 mg/ml Methanol or DMSO
Names and identifiers

Synonyms: Phomin

RTECS: RO0205000

EU number
239-000-2
Description

Mycotoxin capable of interfering microfilament formation.

InChl Key
MAARMMDZGR-IYKJBVLXSA-N
Canonical SMILES
CC1CCCC(C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O
Isomeric SMILES
C[C@@H]1CCC[C@@H](/C=C/C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)CC4=CC=CC=C4)C)O)O
Solubility ( literature )

DMSO or Ethanol.

Compound Classification

Macrolide indol mycotoxin

Cytochalasin

Actin inhibitor

Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Protect from moisture
Use the original container to store the product.
Keep the lid tightly closed.
Avoid exposing to strong direct light.
Other vendors may recommend higher temperatures for storage.
Retest time
3 Years
Applications

Inhibits cell division by interfering with the formation of contractile microfilaments. Inhibits cell movement and induces nuclear extrusion. Interferes with actin polymerization. Inhibits glucose transport

Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Available since
Title
TSE
Value
P
Title
Transport information
Value
PgII
Title
Deleted CAS numbers
Value
11032-95-4; 11042-65-2; 16006-03-4; 21476-12-0
Title
REACH status
Value
On REACH List of Pre-Registered Substances, March 2009 Registration Date: 31-MAY-2013. On EINECS Annex to June 1990
Fermentek Product Category
Food Safety
Mycotoxins
Food Safety Related
Cytochalasins
Signal to sort
C

Quote for

Price
$1.00
Cytochalasin_B.gif
Cytochalasin_B.gif

Cytochalasin A

Cytochalasin A
Molecular Formula
C29H35NO5
M.W.
477.59
CAS number
14110-64-6
MSDS
Source
Drechslera dematoidea
Fermentek product Code
CYA-001
Brand/grade
For research
Appearance
White powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
185°C-193°C
Solubility test
Clear colorless solution at 10mg/ml Dichloromethane
EU number
237-964-9
Description

Cytochalasin A is a fungal toxin which inhibits glucose transport, actine polymerization and blocks the formation of microtubuli. Inhibits cell division. Inhibits HIV-1 protease

InChl Key
ZMAODHOXRBLOQO-TZVKRXPSSA-N
Canonical SMILES
CC1CCCC(=O)C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O
Isomeric SMILES
C[C@@H]1CCCC(=O)/C=C/C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)CC4=CC=CC=C4)C)O
Solubility ( literature )

DMSO, Acetone, Ethanol.

Compound Classification

Macrolide indol mycotoxinCytochalasinActin inhibitor

Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Avoid exposing to strong direct light.
Other vendors may recommend higher temperatures for storage.
Retest time
3 Years
Applications

Cytochalasins are used as tools in cytological research, and in the field of actin polymerization

Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Available since
Fermentek Product Category
Food Safety
Mycotoxins
Food Safety Related
Cytochalasins
Signal to sort
C

Quote for

Price
$1.00
Cytochalasin_A.gif
Cytochalasin_A.gif
Subscribe to Cytochalasins