36011-19-5

Basic information

• Product Name: CYTOCHALASIN E
• Synonyms: (7S,13E,16S,18R,19E)-6,7-Epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-21,23-dioxa[13]cytochalasa-13,19-diene-1,17,22-trione;[7β,13E,16S,18R,19E]-6,7-Epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-21,23-dioxa[13]cytochalasa-13,19-diene-1,17,22-trione;(7s,13e,16s,18r,19e)-18-dimethyl-10-phenyl;21,23-dioxa(13)cytochalasa-13,19-diene-1,17,22-trione,6,7-epoxy-18-hydroxy-16,;6,7-epoxy-10-phenyl-5,6,16,18-tetramethyl-21,23-dioxa-[13]cytochalas-13,19-die;CYTOCHALASIN 3;CYTOCHALASIN E;CYTOCHALASIN E, ASPERGILLUS CLAVATUS
• CAS NO: 36011-19-5
• Molecular Formula: C₂₈H₃₃NO₇
• Molecular Weight: 495.56
• EINECS: 252-835-7
• Product Categories: Actin Inhibitors and ProbesCell Signaling and Neuroscience;Cell Signaling and Neuroscience;Cytoskeleton and Extracellular Matrix;Mold;Toxins and Venoms;antibiotic
• Mol File: 36011-19-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 206 °C
• Boiling Point: 587.59°C (rough estimate)
• Flash Point: 380.205 °C
• Appearance: White powder
• Density: 1.2415 (rough estimate)
• Vapor Pressure: 7.28E-21mmHg at 25°C
• Refractive Index: 1.6290 (estimate)
• Storage Temp.: −20°C
• BRN: 1096975
• CAS DataBase Reference: CYTOCHALASIN E(CAS DataBase Reference)
• NIST Chemistry Reference: CYTOCHALASIN E(36011-19-5)
• EPA Substance Registry System: CYTOCHALASIN E(36011-19-5)

Safety Data

• Hazard Codes: T+,T
• Statements: 26/27/28-63
• Safety Statements: 28-36/37-45
• RIDADR: UN 1544 6.1/PG 2
• WGK Germany: 3
• RTECS: HA5360000
• F: 10
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 36011-19-5(Hazardous Substances Data)

Usage

Description

The cytochalasins are cell-permeable fungal metabolites which inhibit actin polymerization. This interferes with such diverse processes as cell movement, growth, phagocytosis, degranulation, and secretion. Cytochalasin E is an epoxide-containing analog of cytochalasin B which potently and selectively inhibits the growth of endothelial cells (IC50 < 1 nM), impairing angiogenesis and tumor growth. This cytochalasin does not inhibit glucose transport or HIV-1 protease activity.

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 36011-19-5 differently. You can refer to the following data:
1. Cytochalasin E is one of a family of potent mycotoxins produced by a range of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, resulting in pronounced morphogenic changes in animals and plants. Despite the common mode of action, there is evidence that individual members display diverse selectivity. Specifically, cytochalasin E acts as an angiogenesis inhibitor and, unlike other cytochalasins, does not inhibit glucose transport.
2. Cytochalasin E has been used as:a toxin to study its effects on avocado plantsa component of the incubating medium in feline junctional adhesion molecule 1 (fJAM-1) expression assay an inhibitor of actin polymerization to study its effects on mitochondria uptake by mice endothelial cells
3. Cytochalasin E is a fungal metabolite which has been shown to exhibit antimicrobial and antibacterial effects. Cytochalasin E is a microfilament inhibitor enhancing the low-affinity Fc epsilon receptor (CD23) expression.

Definition

ChEBI: A natural product found in Arthrinium sacchari.

Biochem/physiol Actions

Cytochalasin E is an epoxide that exhibits anti-proliferative activity in endothelial cells in vitro. It also participates in inhibiting tumor growth and angiogenesis in vivo. Cytochalasin E also possesses antimicrobial and antiviral properties.

InChI:InChI=1/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+

Downstream Products

• 81657-75-2 Carbonic acid (1aR,2S,3S,5aS,6S,6aS)-3-benzyl-6-((E)-(4S,6S)-6-hydroxy-4,6-dimethyl-5,8-dioxo-oct-1-enyl)-1a,2-dimethyl-5-oxo-octahydro-1-oxa-4-aza-cyclopropa[f]inden-5a-yl ester methyl ester 
• 81672-05-1 7-O-acetylcytochalasin K 
• 81657-78-5 (5E,11E)-(1S,7R,9S,13S,14S,16S,17S,18S)-18-Benzyl-7,14-dihydroxy-7,9,16-trimethyl-15-methylene-2,4-dioxa-19-aza-tricyclo[11.7.0.0^1,17]icosa-5,11-diene-3,8,20-trione 
• 81657-74-1 19,20-dihydrocytochalasin E 
• 81657-76-3 C₂₈H₃₅NO₇ 
• 81657-77-4 Carbonic acid (1aR,2S,3S,5aS,6S,6aS)-3-benzyl-1a,2-dimethyl-5-oxo-6-((E)-(4S,5S,6S)-5,6,8-trihydroxy-4,6-dimethyl-oct-1-enyl)-octahydro-1-oxa-4-aza-cyclopropa[f]inden-5a-yl ester ethyl ester 
• 81657-77-4 Carbonic acid (1aR,2S,3S,5aS,6S,6aS)-3-benzyl-1a,2-dimethyl-5-oxo-6-((E)-(4S,5R,6S)-5,6,8-trihydroxy-4,6-dimethyl-oct-1-enyl)-octahydro-1-oxa-4-aza-cyclopropa[f]inden-5a-yl ester ethyl ester 
• 81657-78-5 7,18-dihydroxy-16,18-dimethyl-10-phenyl-21,23-dioxo<13>-cytochalasa-6(12),13(E),19(E)triene-1,17,22-trione 
• 81657-79-6 cytochalasin K 
• 50650-31-2 (3aS)-3c-benzyl-5c,6c-epoxy-7a-hydroxy-7t-hydroxymethyl-4t,5t-dimethyl-(3ar,7ac)-octahydro-isoindol-1-one 

Relevant articles and documents

A carbonate-forming Baeyer-Villiger monooxygenase

Despite the remarkable versatility displayed by flavin-dependent monooxygenases (FMOs) in natural product biosynthesis, one notably missing activity is the oxidative generation of carbonate functional groups. We describe a multifunctional Baeyer-Villiger monooxygenase, CcsB, which catalyzes the formation of an in-line carbonate in the macrocyclic portion of cytochalasin E. This study expands the repertoire of activities of FMOs and provides a possible synthetic strategy for transformation of ketones into carbonates.