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

CAS: 14110-64-6 C29 H35 N O5 MW: 477.60095000

Identification

Namecytochalasin A
CAS Number14110-64-6
EINECS237-964-9
FDA UNIIBV8WQ9500E
Molecular FormulaC29 H35 N O5
Molecular Weight477.60095000
MDL NumberMFCD00005935
Beilstein949521
XlogP33.30 (est)

Regulatory

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)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for cytochalasin A usage levels up tonot for fragrance use.
Recommendation for cytochalasin A flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

2H-oxa cyclotetradecino(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 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.