Cytochalasin E

495.56

495.56

252-835-7

CRYSTALS FROM ACETONE-HEXANE

29349990

114.46000

1.92

1.3±0.1 g/cm3

206-208 °C (decomp)

587.59°C (rough estimate)

380.2±32.9 °C

1.608

SOL IN DICHLOROMETHANE, CHLOROFORM, ACETONE, & METHANOL; SPARINGLY SOL IN WATER

−20°C

SPECIFIC OPTICAL ROTATION: -25.6 DEG @ 25 °C/D (IN METHANOL); WEAK ABSORPTIONS BETWEEN 240 & 300 NM DUE IN PART TO THE PI BOND TO PI BOND* TRANSITION OF THE MONOSUBSTITUTED AROMATIC RING

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/

I

6.1(a)

UN 1544 6.1/PG 2

3

26/27/28-63

28-36/37-45

HA5360000

T+,T

UNSTABLE IN CHLOROFORM SOLN & UNDER ACIDIC CONDITIONS.

P260-P264-P280-P284-P301 + P310-P302 + P350

H300-H310-H330-H361

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P302+P350, P304+P340, P308+P313, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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/|FUNGAL SOURCE: ROSELLINIA NECUTRIX & ASPERGILLUS CLAVATUS.

Angiogenesis Inhibitors

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)

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/|THE INFLUENCE OF CYTOCHALASIN B & E ON INTESTINAL DIGESTION OF MALTOSE & SUCROSE, & THEIR DIGESTION PRODUCTS AS GLUCOSE & FRUCTOSE WAS INVESTIGATED IN THE MOUSE IN VITRO. NEITHER DIGESTION OF MALTOSE OR SUCROSE NOR ACTIVITIES OF MALTASE OR SUCRASE IN EVERTED SACS OF MOUSE JEJUNUM WAS AFFECTED BY CYTOCHALASIN B OR E AT 5.0 & 10.0 MUG/ML AFTER 60 MIN INCUBATION. HOWEVER, ABSORPTION OF GLUCOSE DERIVED FROM MALTOSE OR SUCROSE DIGESTION WAS INHIBITED BY 68.5 & 65.9% DUE TO CYTOCHALASIN E (5.0 MUG/ML) & BY 29.5 & 13.1% DUE TO CYTOCHALASIN B AT THE SAME CONCN. CYTOCHALASINS B & E SEEMED TO STIMULATE ABSORPTION OF FRUCTOSE DERIVED FROM SUCROSE DIGESTION IN MOUSE JEJUNUM.|THE INHIBITORY EFFECT OF CYTOCHALASIN E ON GALACTOSE ABSORPTION IN EVERTED SACS OF MOUSE JEJUNUM WAS STUDIED. CYTOCHALASIN B HAD THE HIGHEST POTENCY ON THE INHIBITION OF GALACTOSE ABSORPTION WHEN IT WAS ADDED IN THE MUCOSAL SOLN FOLLOWED BY CYTOCHALASIN E, A, C, & D, RESPECTIVELY.|IN MICE Y-1 ADRENAL TUMOR CELLS, CYTOCHALASINS E, D, B, & H2B, INHIBITED STEROIDOGENESIS & PRODUCED ROUNDING OF CELLS BY INTERFERING WITH POLYMERIZATION OF ACTIN & NOT AS THE RESULT OF EFFECTS UNRELATED TO BINDING TO ACTIN.|For more Mechanism of Action (Complete) data for CYTOCHALASIN E (10 total), please visit the HSDB record page.

IN PURIFIED HUMAN PERIPHERAL BLOOD LYMPHOCYTES, LOW (0.01-10 MUMOL) CONCN OF CYTOCHALASINS A, B, E, & D PRODUCED MARKED AUGMENTATION OF TRANSPORT & METABOLIC RESPONSES TO PHYTOHEMAGGLUTININ (PHA) & CONCANAVALIN A (CON A), INCLUDING EFFECTS ON DNA SYNTHESIS, CYCLIC AMP ACCUMULATION, PHOSPHATIDYLINOSITOL TURNOVER, & SODIUM-DEPENDENT AMINO ACID TRANSPORT.|TREATMENT OF HUMAN POLYMORPHONUCLEAR LEUKOCYTES (PMNS) WITH CYTOCHALASIN E (CE), CYTOCHALASIN D (CD), CYTOCHALASIN B (CB), AND DIHYDROCYTOCHALASIN D (H2CB) RESULTS IN ALTERATION OF CELL MORPHOLOGY & INHIBITION OF CELL MOTILITY. MORPHOLOGICAL CHANGES ARE SIMILAR TO THOSE REPORTED FOR NONAMEBOID FIBROBLASTS: ROUNDING, ZEIOSIS, & ARBORIZATION. MEAN CELL VELOCITY OF PMNS, AS MEASURED BY QUANTITATIVE ANALYSIS OF TIME-LAPSE VIDEOTAPE RECORDINGS, WAS REDUCED TO 0.1 MUM/MIN (CONTROL, 7.3 MUM/MIN). PHAGOCYTOSIS BY PMNS, AS MEASURED BY PHAGOCYTOSIS OF LATEX BEADS, WAS INHIBITED BY 75%.|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 E

TLC DATA; DETECTION: H2SO4 SPRAYING & HEAT. GLINSUKON T ET AL; TOXICOL APPL PHARMACOL 32: 135 (1975). TLC DATA; DETECTION: A DARK PURPLE FLUORESCENT SPOT UNDER UV LIGHT AFTER SPRAYING WITH 50% ETHANOLIC H2SO4 & HEATING. WELLS JM ET AL; CAN J MICROBIOL 22: 1137 (1976).