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cytochalasin A
7(S)-hydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-triene-1,20,23-trione

Supplier Sponsors

CAS Number: 14110-64-6Picture of molecule3D/inchi
Other(deleted CASRN):11032-94-3
ECHA EINECS - REACH Pre-Reg:237-964-9
FDA UNII: BV8WQ9500E
Beilstein Number:949521
MDL:MFCD00005935
XlogP3:3.30 (est)
Molecular Weight:477.60095000
Formula:C29 H35 N O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 725.09 °C. @ 760.00 mm Hg (est)
Flash Point: 738.00 °F. TCC ( 392.30 °C. ) (est)
logP (o/w): 1.849 (est)
Soluble in:
 water, 0.7633 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Cytochalasin A >98% by HPLC
Odor: characteristic
Use: One of a family of potent mycotoxins produced by several species of fung; exhibits potent inhibition of actin filament function leading to cell death by apoptosis,
Santa Cruz Biotechnology
For experimental / research use only.
Cytochalasin A ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Cytochalasin A from Drechslera dematioidea
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for cytochalasin A usage levels up to:
 not for fragrance use.
 
Recommendation for cytochalasin A flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5458383
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0014110646
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5458383
Pubchem (sid):135039638
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C19953
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.79.1000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
2H-oxacyclotetradecino(2,3-d)isoindole-2,5,18-trione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-
24-oxa(14)cytochalasa-6(12),13,21-triene-1,20,23-trione, 7-hydroxy-16-methyl-10-phenyl-, (7S,13E,16R,21E)-
5-dehydrophomin
5,5-didehydrophomin
7(S)-hydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-triene-1,20,23-trione
 

Articles:

PubMed:Microwounding is a pivotal factor for the induction of actin-dependent penetration resistance against fungal attack.
PubMed:Perturbations of the actin cytoskeleton activate a Dictyostelium STAT signalling pathway.
PubMed:Effects of medium calcium, and agents affecting cytoskeletal function, on cellular volume and morphology in liver tissue in vitro.
PubMed:Effects of transport inhibitors on the cellular uptake of carboxylated polystyrene nanoparticles in different cell lines.
PubMed:Roles of the actin cytoskeleton and an actin-binding protein in wheat resistance against Puccinia striiformis f. sp. tritici.
PubMed:Spitzenkorper, exocyst, and polarisome components in Candida albicans hyphae show different patterns of localization and have distinct dynamic properties.
PubMed:Farnesol misplaces tip-localized Rho proteins and inhibits cell wall integrity signalling in Aspergillus fumigatus.
PubMed:Electrical stimulation induces calcium-dependent release of NGF from cultured Schwann cells.
PubMed:Candida albicans Cyr1, Cap1 and G-actin form a sensor/effector apparatus for activating cAMP synthesis in hyphal growth.
PubMed:[Genomic damage, adaptive response induction in blood lymphocytes at the prostate cancer patients. Connection with the tumour radiotherapy efficiency].
PubMed:Cytoplasmic bulk flow propels nuclei in mature hyphae of Neurospora crassa.
PubMed:Extracellular matrix-specific focal adhesions in vascular smooth muscle produce mechanically active adhesion sites.
PubMed:The tip growth apparatus of Aspergillus nidulans.
PubMed:Movement of stress fibers away from focal adhesions identifies focal adhesions as sites of stress fiber assembly in stationary cells.
PubMed:Role of actin cytoskeletal dynamics in activation of the cyclic AMP pathway and HWP1 gene expression in Candida albicans.
PubMed:Localization of RHO-4 indicates differential regulation of conidial versus vegetative septation in the filamentous fungus Neurospora crassa.
PubMed:Preferential phosphorylation of focal adhesion kinase tyrosine 861 is critical for mediating an anti-apoptotic response to hyperosmotic stress.
PubMed:Priming by tumor necrosis factor-alpha of human neutrophil NADPH-oxidase activity induced by anti-proteinase-3 or anti-myeloperoxidase antibodies.
PubMed:Transcript profiles of Candida albicans cortical actin patch mutants reflect their cellular defects: contribution of the Hog1p and Mkc1p signaling pathways.
PubMed:PKC-dependent stimulation of EAAT3 glutamate transporter does not require the integrity of actin cytoskeleton.
PubMed:Visualization of the endocytic pathway in the filamentous fungus Aspergillus oryzae using an EGFP-fused plasma membrane protein.
PubMed:Giardia lamblia behavior under cytochalasins treatment.
PubMed:Actin is required for endocytosis at the apical surface of Madin-Darby canine kidney cells where ARF6 and clathrin regulate the actin cytoskeleton.
PubMed:Cyclase-associated protein is essential for the functioning of the endo-lysosomal system and provides a link to the actin cytoskeleton.
PubMed:Direct block of cloned hKv1.5 channel by cytochalasins, actin-disrupting agents.
PubMed:CsmA, a class V chitin synthase with a myosin motor-like domain, is localized through direct interaction with the actin cytoskeleton in Aspergillus nidulans.
PubMed:Effects of protein transport inhibitors on the distribution and secretion of the fusion protein RntA-EGFP in Aspergillus oryzae.
PubMed:A mutation in the Neurospora crassa actin gene results in multiple defects in tip growth and branching.
PubMed:Apical growth and mitosis are independent processes in Aspergillus nidulans.
PubMed:RGD-containing peptides and cyclic AMP have antagonistic roles in the morphology of Mucor rouxii.
PubMed:Phagocytosis of Dictyostelium discoideum studied by the particle-tracking method.
PubMed:RacB regulates cytoskeletal function in Dictyostelium spp.
PubMed:Defects in cytokinesis, actin reorganization and the contractile vacuole in cells deficient in RhoGDI.
PubMed:The WASp-like protein scar regulates macropinocytosis, phagocytosis and endosomal membrane flow in Dictyostelium.
PubMed:Myosin II-dependent cylindrical protrusions induced by quinine in Dictyostelium: antagonizing effects of actin polymerization at the leading edge.
PubMed:Signaling pathways initiated in macrophages after engagement of type A scavenger receptors.
PubMed:A study of the protein secretory pathway of Aspergillus niger using a glucoamylase-GFP fusion protein.
PubMed:Blue light-induced branching in Vaucheria. Requirement of nuclear accumulation in the irradiated region.
PubMed:Cytochalasin A inhibits the binding of phenylalanine ammonia-lyase mRNA to ribosomes during induction of phytoalexin in pea seedlings.
PubMed:Cytoskeletal disruption induces T cell apoptosis by a caspase-3 mediated mechanism.
PubMed:Mitochondrial movement and morphology depend on an intact actin cytoskeleton in Aspergillus nidulans.
PubMed:Cytoplasmic elongation and rupture in megakaryoblastic leukemia cells via activation of adhesion and motility by staurosporine on fibronectin-bound substratum.
PubMed:Multiplication of Legionella pneumophila in HeLa cells in the presence of cytoskeleton and metabolic inhibitors.
PubMed:Effect of cytochalasin A on apical growth, actin cytoskeleton organization and enzyme secretion in Aspergillus nidulans.
PubMed:Coronin involved in phagocytosis: dynamics of particle-induced relocalization visualized by a green fluorescent protein Tag.
PubMed:Chemoattractant-controlled accumulation of coronin at the leading edge of Dictyostelium cells monitored using a green fluorescent protein-coronin fusion protein.
PubMed:Correlation of melanoma cell motility and invasion in vitro.
PubMed:Activation of alpha-2-adrenoceptors results in an increase in F-actin formation in HIT-T15 pancreatic B-cells.
PubMed:Class II cytoplasmic and transmembrane domains are not required for class II-mediated B cell spreading.
PubMed:Induction of apoptosis by T-2 toxin and other natural toxins in HL-60 human promyelotic leukemia cells.
PubMed:Cytochalasin inhibition of slow tension increase in rat aortic rings.
PubMed:Quantitative assessment of melanoma single-cell motility in vitro.
PubMed:New sources of cytochalasins A and B from dematiaceous hyphomycetes.
PubMed:The role of the cytoskeleton in the polarized growth of the germ tube in Candida albicans.
PubMed:Identification and characterization of Aspergillus nidulans mutants defective in cytokinesis.
PubMed:Cytoskeletal remodeling during growth cone-target interactions.
PubMed:N-formyl peptide receptors in human neutrophils display distinct membrane distribution and lateral mobility when labeled with agonist and antagonist.
PubMed:Differential effects of anticytoskeletal compounds on the localization and chemical patterns of actin in germinating conidia of Neurospora crassa.
PubMed:L-696,474, a novel cytochalasin as an inhibitor of HIV-1 protease. III. Biological activity.
PubMed:Characterization of the signaling function of MHC class II molecules during antigen presentation by B cells.
PubMed:Cytochalasin-induced nitroblue tetrazolium dye (NBT) reduction in polymorphonuclear leukocytes.
PubMed:Effect of platelet activation on the agglutination of platelets by von Willebrand factor.
PubMed:Chemotropism and branching as alternative responses of Achlya bisexualis to amino acids.
PubMed:The inhibitory effects of N-ethylmaleimide, colchicine and cytochalasins on human T-cell functions.
PubMed:Generation of cytotoxic factor by human large granular lymphocytes during interaction with autologous tumor cells: lysis of fresh human tumor cells.
PubMed:[The effect of cytochalasin A on the composition of subcellular fractions of hyphae in the growth of Mucor mucedo. II. Composition of the cell wall].
PubMed:[The effect of cytochalasin A on the composition of subcellular fractions of hyphae in the growth of Mucor mucedo L. I. Composition of the plasmalemma].
PubMed:Platelet enhancement of tumor cell adhesion to subendothelial matrix: role of platelet cytoskeleton and platelet membrane.
PubMed:Cytochalasin inhibition of hexose transport by platelets.
PubMed:Inhibition of transepithelial osmotic water flow by blockers of the glucose transporter.
PubMed:Cytochalasin B: preparation, analysis in tissue extracts, and pharmacokinetics after intraperitoneal bolus administration in mice.
PubMed:Chemical modification of thiol group(s) in protein: application to the study of anti-microtubular drugs binding.
PubMed:Effects of low temperature and calcium on microfilament structure in flagellates of Physarum polycephalum.
PubMed:Inhibitory effect of cytochalasins on the motility of rat epididymal spermatozoa in vitro.
PubMed:Fodrin is part of a filamentous cortical sheath of the detergent resistant cytoskeleton of cultured cells before and after cytochalasin treatment.
PubMed:NADPH and "cocktails" containing polyarginine reactivate superoxide generation in leukocytes lysed by membrane-damaging agents.
PubMed:Quinones as toxic metabolites of benzene.
PubMed:Superoxide generation by human blood leucocytes under the effect of cytolytic agents.
PubMed:Effects of various cytochalasins on the IgE-mediated serotonin release from rat basophilic leukemia cells.
PubMed:Pharmacologic modulation of the IgE or Ca2+ ionophore A23187 mediated Ca2+ influx, phospholipase activation, and histamine release in rat basophilic leukemia cells.
PubMed:Soluble immune response suppressor (SIRS) inhibits microtubule function in vivo and microtubule assembly in vitro.
PubMed:Effect of cytochalasins on surfactant release from alveolar type II cells.
PubMed:Modulation of rabbit neutrophil chemotaxis by cytochalasin A. A comparison with other neutrophil functions.
PubMed:Structure-activity relationships of cytochalasins in the differentiation of cytolytic T lymphocytes.
PubMed:Natural cytotoxicity of human blood monocytes: production of monocyte cytotoxic factors (MCF) during interaction with tumor cells.
PubMed:Effects of cytochalasins on lymphocytes: some distinctive features of cytochalasin-E.
PubMed:Augmentation of natural killer activity of human peripheral blood lymphocytes by human leukocyte interferon: characterization of the augmented activity.
PubMed:Neutrophil-assisted DNA synthesis by human lymphocytes in response to mevalonic acid; enhancement by cytochalasin B.
PubMed:Cytochalasin B is a potent mitogen for chronic lymphocytic leukemia cells in vitro.
PubMed:Effects of cytochalasins on lymphocytes: mechanism of inhibition of rosette formation.
PubMed:Structural features of cytochalasins responsible for gram-positive bacterial inhibitions.
PubMed:Viscometric analysis of effects of cytochalasins on in vitro polymerization and depolymerization of microtubules.
PubMed:Inhibition of glucose transport in human erythrocytes by cytochalasins: A model based on diffraction studies.
PubMed:The role of the conjugated carbonyl of cytochalasin A in contractility inhibitions.
PubMed:The effects of cytochalasins on lymphocytes: mechanism of action of Cytochalasin A on responses to phytomitogens.
PubMed:The apparent inducibility of tumour marker glycoproteins in a melanoma cell line selected for growth in low levels of glucose.
PubMed:Identification of the stereospecific hexose transporter from starved and fed chicken embryo fibroblasts.
PubMed:Sequential analysis of T-cell mediated cytolysis: a brief reminder of some possibly informative markers at the recognition and lethal hit stages.
PubMed:Activation of superoxide production and differential exocytosis in polymorphonuclear leukocytes by cytochalasins A, B, C, D and E. Effects of various ions.
PubMed:The effects of quercetin, 1-tosylamido-2-phenylethyl chloromethyl ketone, cytochalasin A and nordihydroguaiaretic acid on lysosomal enzyme secretion, arachidonic acid metabolism and Ca2+ fluxes in rabbit neutrophils.
PubMed:The enhancing effect of cytochalasin A on concanavalin A-induced superoxide anion release from polymorphonuclear leukocytes.
PubMed:Cytochalasin A inhibits B-lymphocyte capping and activation by antigens.
PubMed:Curvularia lunata, a New Source of Cytochalasin B.
PubMed:The effect of cytochalasin A on polymorphonuclear leukocytes activated by chemotactic peptide.
PubMed:Inhibition by ADP of prostaglandin induced accumulation of cyclic AMP in intact human platelets.
PubMed:Calcium oxalate crystal-induced cytolysis in polymorphonuclear leukocytes and erythrocytes.
PubMed:Regulation of microtubule assembly in cultured fibroblasts.
PubMed:Effects of sulfhydryl reagents on phagocytosis and exocytosis in rabbit polymorphonuclear leukocytes.
PubMed:Analysis of the lytic step in the herpes simplex virus antibody-dependent cellular cytotoxicity system.
PubMed:Inhibition of tubulin assembly by ethylacetylacrylate, a sulfhydryl reagent and potential analog of cytochalasin A.
PubMed:Evaluation of ten potential organic spermicides.
PubMed:Inhibition of histamine release from rat mast cells by cytochalasin A and other sulfhydryl reagents.
PubMed:Physiological responses of bacteria to cytochalasin A: effects on growth, transport, and enzyme induction.
PubMed:Evidence for selective sulfhydryl reactivity in cytochalasin A--mediated bacterial inhibitions.
PubMed:Basic mechanisms of lymphocyte recirculation in Lewis rats.
PubMed:Recognition by cytolytic T and K cells: identification in both systems of a divalent cation-independent, cytochalasin A-sensitive step.
PubMed:Effects of cytochalasin A on the morphology of plasmodia and sclerotia of Physarum polycephalum.
PubMed:Requirement for hexose, unrelated to energy provision, in T-cell-mediated cytolysis at the lethal hit stage.
PubMed:Effects of microfilament-active drugs, phalloidin and the cytochalasins A and B, on exocytosis in mast cells evoked by 48/80 or A23187.
PubMed:Modulation of macrophage C3b receptor function by cytochalasin-sensitive structures.
PubMed:Rod-like elements from actin-containing microfilament bundles observed in cultured cells after treatment with cytochalasin A (CA).
PubMed:Binding of [3H]ctyochalasin B and [3H]colchicine to isolated liver plasma membranes.
PubMed:The reaction of cytochalasin A with sulfhydryl groups.
PubMed:Cell surface receptors for insulin and human growth hormone. Effect of microtubule and microfilament modifiers.
PubMed:Binding of thrombin to human platelets and its possible significance.
PubMed:A non-penetrating thiol reagent mimics cytochalasin A inhibition of secretory protein synthesis.
PubMed:Cytochalasin A inhibits the in vitro polymerization of brain tubulin and muscle actin.
PubMed:The action of cytochalasin A on the in vitro polymerization of brain tubulin and muscle G-actin.
PubMed:Studies on the mechanism of lymphocyte-mediated cytolysis. V. The use of cytochalasins A and B to dissociate glucose transport from the lytic event.
PubMed:Action of cytochalasin A, a sulfhydryl-reactive agent, on sugar metabolism and membrane-bound adenosine triphosphatase of yeast.
PubMed:Antibody-dependent cytotoxicity: modulation by the cytochalasins and microtubule-disruptive agents.
PubMed:Dissociation of the immunologic release of histamine and slow reacting substance of anaphylaxis from human lung using cytochalasins A and B-1.
PubMed:The action of antibiotics on enzyme secretion in yeasts: studies with cytochalasin A.
PubMed:Effects of cytochalasin B, colchicine and vincristine on the metabolism of isolated fat-cells.
PubMed:Cytochalasin A and B. Inhibition of sugar uptake in cultured cells.
 
Notes:
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