22144-77-0C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23[C@H](OC(C)=O)/C=C/[C@@](C)(O)C(=O)[C@@H](C)C/C=C/[C@H]3[C@@H]1OSDZRWUKZFQQKKV-JHADDHBZSA-NCytochalasin d appears as needles or fluffy white powder. (NTP, 1992)
491 to 500 °F (decomposes) (NTP, 1992)
267-271 °C
Cytochalasin d appears as needles or fluffy white powder. (NTP, 1992)
Solid; [HSDB] White solid; [CAMEO] White powder; [MSDSonline]
THE CYTOCHALASINS GENERALLY CAN BE DESCRIBED AS A PHENYLALANINE OR TRYPTOPHAN MOIETY LINKED TO PERHYDROISOINDOLE MOIETY WHICH IS IN TURN LINKED TO A C16-C18 POLYKETIDE RING SYSTEM CONTAINING A CARBOCYCLIC (CYTOCHALASIN C), A LACTONE (CYTOCHALASIN A), OR A CYCLIC CARBONATE (CYTOCHALASIN E) MOIETY /CYTOCHALASINS/
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 69 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
1H-Cycloundecdisoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)-: Does not have an individual approval but may be used under an appropriate group standard
Causes spastic paralysis in mice at lethal doses; Intraperitoneal LD50 (mouse) = 2 mg/kg; [RTECS] Causes inhibitory effects on cell processes; 10 times more potent that cytochalasin B in inhibiting movement and cytoplasmic cleavage; No reports of chronic effects or carcinogenicity in humans; [HSDB] See Cytochalasin B.
MAJOR BIOLOGICAL EFFECTS ARE THE BLOCKAGE OF CYTOPLASMIC CLEAVAGE RESULTING IN MULTINUCLEATE CELL FORMATION, THE INHIBITION OF CELL MOVEMENT, & THE INDUCTION OF NUCLEAR EXTRUSION... OTHER REPORTED EFFECTS INCLUDE THE INHIBITION OF GLUCOSE TRANSPORT, OF THYROID SECRETION, OF GROWTH HORMONE RELEASE, OF PHAGOCYTOSIS, & OF PLATELET AGGREGATION & CLOT CONTRACTION. /CYTOCHALASINS/
IN THE EARLY STAGE OF CYTOLOGICAL RESEARCH USING CYTOCHALASINS THE MODE OF ACTION OF THE COMPOUNDS WAS EXPLAINED AS DIRECT DISRUPTION OF MICROFILAMENTS INTERFERRING WITH CONTRACTILE MOVEMENTS OF THE MAMMALIAN CELLS. FURTHER STUDY, ESPECIALLY THE OBSERVATION OF THEIR EFFECTS ON THE TRANSPORT OF A NUMBER OF SUBSTANCES INTO THE CELLS, REVEALED A MORE COMPLEX MODE OF ACTION. IT IS CLEAR THAT THE NATURE OF THE BINDING BETWEEN THE CYTOCHALASINS & ACTIVE SITES IS NOT COVALENT BECAUSE OF THE RAPID REVERSIBILITY OF THE ACTION. /CYTOCHALASINS/
THROUGH THE USE OF (3)H-LABELLED CYTOCHALASINS B & D THE PRECISE BINDING SITES & SUB-CELLULAR LOCALIZATION ARE NOW UNDER INVESTIGATION... EXPERIMENTAL RESULTS OBTAINED THUS FAR SUPPORT THE IDEA THAT THE PRIMARY EFFECT IS MEMBRANOTROPIC, PERHAPS INVOLVING THE ASSOCIATION OF MICROFILAMENTS WITH THE PLASMA MEMBRANE.
CYTOCHALASIN D DID NOT PREVENT ATTACHMENT BUT DID PREVENT ENTRY OF TOXOPLASMA GONDII INTO PERITONEAL MACROPHAGES AND BLADDER TUMOR 4934 CELLS.
For more Mechanism of Action (Complete) data for CYTOCHALASIN D (9 total), please visit the HSDB record page.
IN...WORK USING STEREOSPECIFICALLY LABELLED PRECURSORS, L-PHENYLALANINE WAS SHOWN TO BE THE PRIMARY PRECURSOR OF CYTOCHALASIN D, & THE RAPID EQUILIBRIUM OF D- & L-ISOMERS THROUGH PHENYLPYRUVIC ACID WAS SHOWN TO ACCOUNT FOR THE EQUALLY EFFICIENT INCORPORATION OF BOTH ENANTIOMERS.
IN...THE BIOSYNTHESIS OF CYTOCHALASIN D BY ZYGOSPORIUM MASONII, [1,2-(13)C]-ACETATE WAS FED TO A GROWING CULTURE OF THIS FUNGUS. THE ARRANGEMENT OF INTACT ACETATE UNITS WAS ESTABLISHED... CYTOCHALASIN D ORIGINATED FROM PHENYLALANINE, METHIONINE & 9 INTACT ACETATE UNITS. EIGHT OF THE ACETATE UNITS COUPLE IN A HEAD-TO-TAIL FASHION TO FORM THE C16-POLYKETIDE MOIETY. THE FEEDING OF HIGHER EVEN-NUMBERED SATURATED ACIDS SUCH AS C1-LABELLED BUTYRATE, MYRISTATE & PALMITATE SHOWED NO DIRECT INCORPORATION. THEY DO, HOWEVER, UNDERGO BETA-OXIDATION TO YIELD C1-LABELLED ACETATE WHICH IS INCORPORATED INTO CYTOCHALASIN D.
No reaction records under the current filter.
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22144-77-0CHEMBL260287EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
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. (A704)
PRETREATMENT OF RABBIT KIDNEY CELLS WITH CYTOCHALASIN D ENHANCED HERPES SIMPLEX VIRUS TYPE 2 INFECTIVITY 3- TO 6-FOLD OVER VALUES OBTAINED USING THE STANDARD CALCIUM CHLORIDE TECHNIQUE.
CYTOCHALASIN D TREATMENT OF PERMISSIVE OR SEMIRESTRICTIVE CELL LINES ENHANCED THEIR SUSCEPTIBILITY TO INFECTION WITH POLIOVIRUS.
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. (L1916)
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. Cytochalasin D also inhibits protein synthesis. (A2910, A2911, L1913)
...IN THE BIOSYNTHESES OF CYTOCHALASIN B (PHOMIN) BY PHOMA SPECIES & CYTOCHALASIN D BY ZYGOSPORIUM MASONII...A NUMBER OF (14)C & (3)H PRECURSORS WERE FED TO PHOMA SPECIES & PRECISE DEGRADATION REACTIONS WERE PERFORMED TO REVEAL THE FORMATION OF CYTOCHALASIN B FROM ONE UNIT OF PHENYLALANINE, NINE UNITS OF ACETATE-MALONATE, & TWO UNITS OF METHIONINE. THE LABELLING PATTERN WAS ALSO CONFIRMED IN THE CASE OF CYTOCHALASIN D.
A CLASS OF MOLD METABOLITES EXHIBITING INHIBITORY EFFECTS ON CELL PROCESSES. SIX CYTOCHALASINS HAVE BEEN ISOLATED: CYTOCHALASINS A, B & F FROM HELMINTHOSPORIUM DEMATIOIDEUM; C & D FROM METARRHIZIUM ANISOPLIAE; E FROM ROSELLINIA NECATRIX. /CYTOCHALASINS/
CYTOTOXICITY OF CYTOCHALASIN D ON HELA CELLS: SAMPLES WERE DISSOLVED IN DMSO AT 10 MG/ML & DILUTED IN THE MEDIUM. CELLS ON COVER-GLASSES WERE TREATED FOR 3-DAYS. DEGREE OF CYTOTOXICITY WAS ESTIMATED ON A SCALE RANGING '0' (LITTLE CELLULAR DAMAGE) THROUGH '4' (COMPLETE CYTOLYSIS) IN OBSERVING THE STAINED COVER-GLASSES. '2' DENOTES APPROXIMATE 50% GROWTH-INHIBITORY DOSE. SPECIFIC DOSAGE WITH RESPECTIVE CYTOTOXICITY RATING WAS NOTED: 32 UG/ML= 3.5 RATING; 10 UG/ML= 3 RATING; 3.2 UG/ML= 3 RATING; 1.0 UG/ML= 2.5 RATING; 0.32 UG/ML= 1 RATING. /FROM TABLE/
...ONE REPORT HAS DESCRIBED THE STRUCTURE-ACTIVITY RELATIONSHIP AMONG /CYTOCHALASINS/...ZYGOSPORIN A (CYTOCHALASIN D), E, F, G, & MORE THAN 30 DERIVATIVES...FOR CYTOTOXICITY TO HELA CELLS ALONG WITH SKIN IRRITATION TESTS. THE RESULTS INDICATED THAT THE HYDROXYL GROUP AT C(7) & THE PHENYL GROUP AT C(10) IN THE SKELETON ARE ESSENTIAL FOR CYTOTOXICITY.
CYTOCHALASIN D INDUCED A GENERALIZED CELL CONTRACTION AND ZEIOSIS IN HELA AND HEP2 CELLS, TOGETHER WITH A CENTRIPETAL TRANSLOCATION OF ACTIN, MYOSIN, AND TROPOMYOSIN.
ONE DAY AFTER THE ADDITION OF CYTOCHALASIN D (0.2-0.5 UG/ML) TO A CULTURE OF HUMAN ESOPHAGEAL EPITHELIAL CELLS (CELL LINE, ECA-109), THE CELLS BECAME WRINKLY AND TRANSFORMED INTO VARIOUS SHAPES AND SIZES WITH AN ARBORIZED CYTOPLASMIC PROTRUBERANCE, BOUQUET-LIKE AND BUD-LIKE PROTRUSIONS ON THE CELL SURFACE, WHILE THE MICROVILLI DISAPPEARED.
THERE HAS BEEN NO REPORT ON CHRONIC TOXICITY & CARCINOGENICITY OF CYTOCHALASINS... ALTHOUGH MANY CYTOLOGICAL STUDIES HAVE BEEN DONE, THE VARIETY OF EFFECTS THUS FAR OBSERVED INDICATE THE IMPORTANCE OF THE COMPOUNDS FOR ANIMAL & HUMAN HEALTH. ...STRONG ACUTE TOXICITIES EXHIBITED BY SOME CYTOCHALASINS & THE WIDE NATURAL OCCURRENCE OF THE FUNGI THAT PRODUCE CYTOCHALASINS SHOULD BE CONSIDERED IN FUTURE STUDIES ON MYCOTOXINS. /CYTOCHALASINS/
CYTOCHALASIN D SHOWS ESSENTIALLY SIMILAR ACTIVITY TO CYTOCHALASIN B, EXCEPT IT IS ABOUT 10 TIMES MORE POTENT IN MAMMALIAN CELLS (INHIBITS MOVEMENT & CYTOPLASMIC CLEAVAGE); AT HIGHER DOSES CAUSES NUCLEAR EXTRUSION WHICH MAY LEAD TO TOTAL ENUCLEATION.
EFFECTS OF CYTOCHALASINS ON MAMMALIAN CELLS: AMONG THE MORE PROMINENT EFFECTS ARE SEVERAL WHICH ARE CHARACTERIZED AS MORPHOLOGICAL IN NATURE, SUCH AS CYTOSKELETAL VARIATION, MULTINUCLEATION, DIFFUSE ORGANELLE ALTERATION, NUCLEAR EXTRUSION, & SURFACE PHENOMENA SUCH AS DIMINISHED MEMBRANE RUFFLING. OTHER EFFECTS ARE DESCRIBED AS FUNCTIONAL OR PHYSIOLOGICAL, & INCLUDE INHIBITION OF CELL MOTILITY, MITOTIC REPRODUCTION, & PHAGOCYTOSIS & PINOCYTOSIS; ALTERATION OF SURFACE ADHESION PROPERTIES & MICROFILAMENTS; DEPRESSION OF SYNTHESIS; & UPTAKE OF MEMBRANE COMPONENTS. THESE STUDIES WERE PERFORMED MAINLY WITH CYTOCHALASIN B & OCCASIONALLY WITH CYTOCHALASIN A, D (ZYGOSPORIN A), & E.
...INJECTED IP 0.4 TO 0.9 MG PER KG ON DAYS 7 THROUGH 11 & PRODUCED EXENCEPHALY, HYPOGNATHIA & SKELETAL REDUCTION DEFECTS IN C-57 & BALB-C STRAIN MICE BUT NOT IN SWISS WEBSTER MICE.
...PRODUCED EXENCEPHALY IN HAMSTERS TREATED ON THE 8TH DAY WITH 1.5 MG PER KG IP.
For more Non-Human Toxicity Excerpts (Complete) data for CYTOCHALASIN D (12 total), please visit the HSDB record page.
Cytochalasins are a group of mold metabolites having various effects on animal cells; More than twenty cytochalasins have been isolated from different mold species; Used in cytological research and in studying the polymerization properties of actin; Most studied is cytochalasin B; [Merck Index]
MEDICATION
Cytochalasin D is has been isolated from the fungi Metarrhizium anisopliae and Zygosporium masonii. (A2912)
ISOLATION & STRUCTURE OF CYTOCHALASINS A, B, C, D: ALDRIDGE ET AL, J CHEM SOC (C) 1967, 1667; ALDRIDGE ET AL, CHEM COMMUN 1967, 26; OF E & F: ALDRIDGE ET AL, CHEM COMMUN 1972, 148. REVISED STRUCTURES OF CYTOCHALASINS E & F: ALDRIDGE ET AL, CHEM COMMUN 1973, 551; BUCHI ET AL, J AM CHEM SOC 95, 5423 (1973). /CYTOCHALASINS/
DescriptionCytochalasin D (22144-77-0) is a potent inhibitor of actin polymerization which also causes the disruption of actin filaments. More potent that cytochalasin B (10-fold) and does not inhibit monosaccharide transport across cell membranes. Disruption of actin microfilaments leads to activation of p53. Cell permeable
UsesA cell cycle arresting compound used in actin polymerization studies and cytological research
UsesCytochalasin D acts as an anti-hypertensive drug acting on human intestinal epithelial caco-2 cells. Also has activity in HMG-CoA reductase inhibitors used in the lowering of cholesterol. Actin inhib itor, actin polymerization inhibitor affecting cell movement, growth, phagocytosis and even secretion.
UsesCytochalasin D is the most studied of the cytochalasins. Like most of the members of this mycotoxin class, cytochalasin D exhibits potent inhibition of actin filament function leading to cell death by apoptosis. This led to early investigation of the metabolite as an antitumour agent. Cytochalasin D has become one of the standard cellular probes for investigating the role of actin in cell biology.
General DescriptionNeedles or fluffy white powder.
DefinitionChEBI: An organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis.