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T3D3682 - Dihydrocytochalasin B

Record Information
Version 1.0
Creation Date 2010-04-17 21:57:45 UTC
Update Date 2013-04-25 08:48:34 UTC
Accession Number T3D3682
Identification
Common Name Dihydrocytochalasin B
Description Cytochalasins are mycotoxins that have the ability to bind to actin filaments and block polymerization and the elongation of actin. As a result, they can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. Cytochalasins also have the ability to permeate cell membranes, prevent cellular translocation, cause cells to enucleate, and affect other aspects of biological processes unrelated to actin polymerization. Dihydrocytochalasin B is a semi-synthetic derivative of cytochalasin B and is a useful probe for studying cytochalasin binding sites. (W713, W714, W715, W718)
Compound Type
  • Organic Compound
  • Mycotoxin
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms Not Available
Chemical Formula C28H37NO5
Average Molecular Weight 467.5971
Monoisotopic Molecular Weight 467.267173299
Chemical IUPAC Name
15-benzyl-4,12-dihydroxy-8,14-dimethyl-13-methylidene-3H,4H,5H,6H,7H,8H,9H,12H,14H,14aH,15H,16H,17bH-oxacyclotrideca[3,2-e]isoindole-2,17-dione
CAS Registry Number 39156-67-7
SMILES
CC1C2C(CC3=CC=CC=C3)NC(=O)C22OC(=O)CC(O)CCCC(C)C\C=C\C2C(O)C1=C
InChI Identifier
InChI=1S/C28H37NO5/c1-17-9-7-13-21(30)16-24(31)34-28-22(14-8-10-17)26(32)19(3)18(2)25(28)23(29-27(28)33)15-20-11-5-4-6-12-20/h4-6,8,11-12,14,17-18,21-23,25-26,30,32H,3,7,9-10,13,15-16H2,1-2H3,(H,29,33)/b14-8+
InChI Key InChIKey=ZFGBJIDXDYHNLX-RIYZIHGNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Heterocyclic Compounds
Class Isoindoles and Derivatives
Sub Class Isoindlines
Direct Parent Isoindolones
Alternative Parents
  • Isoindoles
  • Cyclohexanols
  • Benzene and Substituted Derivatives
  • Pyrrolidones
  • Lactams
  • Secondary Carboxylic Acid Amides
  • Lactones
  • Cyclic Alcohols and Derivatives
  • Carboxylic Acid Esters
  • Polyols
  • Alkanolamines
Molecular Framework Aromatic Heteropolycyclic Compounds
Substituents
  • benzene
  • organonitrogen compound
  • carboxylic acid ester
  • cyclohexanol
  • lactam
  • cyclic alcohol
  • secondary alcohol
  • secondary carboxylic acid amide
  • carboxamide group
  • polyol
  • alkanolamine
  • alcohol
  • lactone
  • pyrrolidine
  • pyrrolidone
External Descriptors Not Available
DrugBank ID Not Available
PubChem Compound ID Not Available
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID Not Available
BioCyc ID Not Available
CTD ID Not Available
Stitch ID Not Available
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link Not Available
Physical Properties
Appearance White powder.
Melting Point 203-205C
Solubility Not Available
Predicted LogP 3.4066313553333334
Toxicity Profile
Route of Exposure Oral, dermal, inhalation, and parenteral (contaminated drugs). (W967)
Mechanism of Action Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (W713, W714, W715)
Metabolism Not Available
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Dihydrocytochalasin B is a semi-synthetic derivative of cytochalasin B and is a useful probe for studying cytochalasin binding sites. (W718)
Minimum Risk Level Not Available
Health Effects Major biological effects of cytochalasins include inhibition of the division of cytoplasm, reversible inhibition of cell movement, induction of nuclear extrusion, inhibition of such processes as phagocytosis, platelet aggregation and clot retraction, glucose transport, thyroid secretion, and release of growth hormone. Some cytochalasins have been shown to have developmental effects. (W718)
Symptoms Not Available
Treatment Consider activated charcoal after gastrointestinal absportion. Nitroprusside is recommended to reverse peripheral ischemia secondary to vasoconstriction and for the treatment of hypertension. Anticoagulant therapy with intravenous heparin is also recommended. (W574)
References
General References
  • W713 — Haidle AM, Myers AG. An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 Link_out]
  • W714 — Cooper JA. Effects of cytochalasin and phalloidin on actin. J Cell Biol. 1987 Oct;105(4):1473-8. [3312229 Link_out]
  • W715 — Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]
  • W718 — Sigma Aldrich 1996. Technical Bulletin AL-126: The Cytochalasins. [Link]
  • W574 — Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010.
  • W967 — Peraica M, Domijan AM. Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 Link_out]

Targets

1. Actin, alpha cardiac muscle 1

Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.

Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (W713, W715)
UniProt ID: P68032 Link_out
Gene: ACTC1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W713 — Haidle AM, Myers AG. An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 Link_out]
  • W715 — Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]

2. Actin, alpha skeletal muscle

Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.

Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (W713, W715)
UniProt ID: P68133 Link_out
Gene: ACTA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W713 — Haidle AM, Myers AG. An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 Link_out]
  • W715 — Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]

3. Actin, aortic smooth muscle

Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.

Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (W713, W715)
UniProt ID: P62736 Link_out
Gene: ACTA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W713 — Haidle AM, Myers AG. An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 Link_out]
  • W715 — Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]

4. Actin, cytoplasmic 1

Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.

Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (W713, W715)
UniProt ID: P60709 Link_out
Gene: ACTB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W713 — Haidle AM, Myers AG. An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 Link_out]
  • W715 — Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]

5. Actin, cytoplasmic 2

Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.

Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (W713, W715)
UniProt ID: P63261 Link_out
Gene: ACTG1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W713 — Haidle AM, Myers AG. An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 Link_out]
  • W715 — Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]

6. Actin, gamma-enteric smooth muscle

Actins are highly conserved proteins that are involved in various types of cell motility and are ubiquitously expressed in all eukaryotic cells.

Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (W713, W715)
UniProt ID: P63267 Link_out
Gene: ACTG2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W713 — Haidle AM, Myers AG. An enantioselective, modular, and general route to the cytochalasins: synthesis of L-696,474 and cytochalasin B. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12048-53. Epub 2004 Jun 18. [15208404 Link_out]
  • W715 — Cytochalasin. Wikipedia. Last Updated 12 April 2010. [Link]