66-81-9 Usage
Description
Different sources of media describe the Description of 66-81-9 differently. You can refer to the following data:
1. Cycloheximide is a glutarimide-type antibiotic produced by Streptomyces
griseus. Colorless crystals, C15H23NO4 (281.4), melting
point: 115.5–117 ?C, weak acidic substance (pKa 11.2),
Soluble in chloroform, isopropanol and methanol; water >
21 g/L (2 ?C). Stable in pH 3–5, but rapidly destroyed in
alkaline solutions.
2. Cycloheximide is a glutarimide antibiotic produced by S. griseus that inhibits protein synthesis in eukaryotes (IC50 = 5-50 μM) by interfering with translational elongation. Its effects on protein synthesis can either induce or inhibit apoptosis depending on cell type. Cycloheximide is widely used as a tool in molecular biology research for ribosome profiling and translational profiling as well as to determine the half-life of a protein.
Uses
Different sources of media describe the Uses of 66-81-9 differently. You can refer to the following data:
1. immunomodulator
2. Cycloheximide is an antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus. Cycloheximide is used as fungicide.
3. Cycloheximide is the most recognised member of the glutarimide microbial metabolites. Cycloheximide was isolated from Streptomyces griseus in the late 1940s as a potent and broad spectrum antifungal. Cycloheximide inhibits protein synthesis by interfering with translocation. Cycloheximide is an established bioprobe and widely-used antifungal reagent in research with over 25,000 literature citations.
4. potent and selective 5-HT uptake inhibitor
General Description
Colorless crystals. Used as a fungicide and as a anticancer drug.
Air & Water Reactions
Water soluble.
Reactivity Profile
Actidione is an imide. Actidione is incompatible with strong oxidizing agents, acid chlorides and acid anhydrides. Actidione decomposes rapidly in alkali at room temperature.
Health Hazard
Actidione is extremely toxic; the probable oral lethal dose in humans is 5-50 mg/kg, or 7 drops to 1 teaspoonful for a 150-lb. person.
Fire Hazard
When exposed to heat, Actidione emits toxic fumes, including nitrogen oxides.
Agricultural Uses
Fungicide; plant growth regulator: A U.S. EPA restricted Use Pesticide (RUP). Used
as an antibiotic, plant growth regulator, and protein synthesis inhibitor. Inhibits growth of many plant pathogenic
fungi. Effective for control of powdery mildew on roses
and many other ornamentals, rusts and leaf spots on lawn
grasses, and azalea petal blight. Also used as a repellent for
rodents and other animal pests and in cancer therapy. Not
listed for use in EU countries
Trade name
ACTI-AID?[C]; ACTIDIONE?[C];
ACTIDIONE? TGF[C]; ACTIDONE?; ACTIDONE?
PM; ACTIDONE? TGF; ACTISPRAY; HIZAROCIN?;
KAKEN?; NARAMYCIN?; NARAMYCIN A?;
NEOCYCLOHEXIMIDE?; U-4527
Biological Activity
Selective inhibitor of eukaryotic (over prokaryotic) protein synthesis, blocking tRNA binding and release from ribosomes. Induces apoptosis in a variety of transformed and normal cell lines, including T-cells. Competitively inhibits the PPIase hFKBP12 (K i = 3.4 μ M). Antifungal antibiotic.
Pharmacology
Strongly inhibits the growth of pathogenic fungi but no
effects on bacterial growth, even at 100 mg/ml. Inhibits
protein synthesis by interfering with the translocation
step in eukaryotes, but not in prokaryotes. When
ingested by animals, the agent causes excitement, tremors,
salivation, diarrhea, and melena.
in vitro
cycloheximide blocks the movement of peptidyl-trna from acceptor site to the donor site on reticulocyte ribosomes. this translocation reaction is dependent on the transfer enzyme, tf-ii, and gtp hydrolysis. cycloheximide has no effect on the ribosome dependent gtpase activity of tf-ii or peptidyl transferase reaction by which peptides on trna in the donor ribosomal site are transferred to an amino acid on trna in the acceptor site [1].
in vivo
cycloheximide treatment was effective in attenuating rat brain injury within a 6 hr therapeutic window after hypoxia-ischemia in a newborn rat pup model. these data support the possibility that protein synthesis inhibitors, as well as other anti-apoptotic strategies, may have therapeutic utility in hypoxic-ischemic (hi) events of the developing newborn brain even when treatment is delayed for up to 6 hr after the primary asphyxial insult [2].
Carcinogenicity
Cycloheximide is genotoxic in Escherichia
coli with metabolic activation and in the mouse
sperm morphology assay. Carcinogenicity
bioassays in the mouse and rat are inconclusive.
Environmental Fate
CHX is a potent inhibitor of protein synthesis in animals. It
binds to E-site of 70S ribosome-mRNA complex, blocking the
translational step of protein biosynthesis. It causes an increase
in adrenal RNA and increased production of glucocorticoids.
Metabolism
Rapidly inactivated at room temperature by diluted alkali
with the formation of a volatile, fragrant ketone, 2,4-
dimethylcyclohexanone. Hazardous to fish and wildlife.
Purification Methods
It crystallises from H2O /MeOH (4:1), amyl acetate, isopropyl acetate/isopropyl ether or H2O. [Beilstein 21/13 V 434.]
Toxicity evaluation
Skin irritant. LD50 2 mg/kg (rat, orl);
133 mg/kg (mice, Ipr); 65 mg/kg (guinea pig); 60 mg/kg
(monkey). Teratogenic effects.To remove toxicant
from gut, activated charcoal and a catharitic dose of sodium sulfate are effective. Mechanisms of toxicity
are not well defined, but hydrocortisone is antidotal,
particularly in combination with the adrenergic agent
methoxyphenamine.
References
1) Merck 14:2728
Check Digit Verification of cas no
The CAS Registry Mumber 66-81-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 6 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 66-81:
(4*6)+(3*6)+(2*8)+(1*1)=59
59 % 10 = 9
So 66-81-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1
66-81-9Relevant articles and documents
Versatile Synthetic Route to Cycloheximide and Analogues That Potently Inhibit Translation Elongation
Park, Yongho,Koga, Yumi,Su, Cindy,Waterbury, Amanda L.,Johnny, Christopher L.,Liau, Brian B.
, p. 5387 - 5391 (2019/03/26)
Cycloheximide (CHX) is an inhibitor of eukaryotic translation elongation that has played an essential role in the study of protein synthesis. Despite its ubiquity, few studies have been directed towards accessing synthetic CHX derivatives, even though such efforts may lead to protein synthesis inhibitors with improved or alternate properties. Described here is the total synthesis of CHX and analogues, and the establishment of structure–activity relationships (SAR) responsible for translation inhibition. The SAR studies aided the design of more potent compounds, one of which irreversibly blocks ribosomal elongation, preserves polysome profiles, and may be a broadly useful tool for investigating protein synthesis.
KINETICALLY AND THERMODYNAMICALLY CONTROLLED SYNTHESIS OF 2,6-DISUBSTITUTED CYCLOHEXANONE SEMICARBAZONES. A MOLECULAR MECHANICS STUDY OF A1,3-STRAIN
Castello, Assumpta,Jaime, Carlos,Marquet, Jorge,Moreno-Manas, Marcial
, p. 3791 - 3802 (2007/10/02)
Reasonable values for Me-Me, H-Me and Me-H A1,3-strain have been evaluated by molecular mechanics calculations on differently substituted methylenecyclohexanes (5.46-6.75, 1.03 and 0.71 kcal/mol, respectively).The chair-to-chair inversion barri
Cycloheximide transformations. I. Kinetics and mechanisms in aqueous acid.
Garrett,Notari
, p. 425 - 434 (2007/10/08)
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