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1797332-84-3

26833-85-2

26833-85-2 structure
26833-85-2 structure
  • Name: Harringtonine
  • Chemical Name: Harringtonin
  • CAS Number: 26833-85-2
  • Molecular Formula: C28H37NO9
  • Molecular Weight: 531.595
  • Catalog: Natural product Alkaloid
  • Create Date: 2018-07-15 20:47:54
  • Modify Date: 2024-01-02 15:08:21
  • Harringtonine is a natural Cephalotaxus alkaloid that inhibits protein synthesis.
Name Harringtonin
Synonyms harringtonine
O-[(2R)-2,5-Dihydroxy-2-(2-methoxy-2-oxoethyl)-5-methylhexanoyl]cephalotaxine
Cephalotaxine, O-[(2R)-2,5-dihydroxy-2-(2-methoxy-2-oxoethyl)-5-methyl-1-oxohexyl]-
Harringtonine (8CI)
Description Harringtonine is a natural Cephalotaxus alkaloid that inhibits protein synthesis.
Related Catalog
In Vitro Harringtonine inhibits the elongation phase of translation by preventing substrate binding to the acceptor site on the 60-S ribosome subunit and therefore block aminoacyl-tRNA binding and peptide bond formation[1]. Harringtonine displays potent inhibition of Chikungunya virus infection with an EC50 of 0.24 μM. Harringtonine could inhibit other alphaviruses[2]. Harringtonine inhibits the growth of human myeloid leukemia cells in vitro at low concentrations. The mechanism of the antitumor action of harringtonine is considered to be an effect on protein synthesis and is characterized by breakdown of polysomes to monosomes[3].
Cell Assay For harringtonine treatment studies with Sindbis virus, BHK21 cells are seeded into 96-well plates and infected with Sindbis virus at an MOI of 1 for 1 h prior to being washed twice with PBS and incubated with various concentrations of harringtonine (0.1 μM, 1 μM, 5 μM, and 10 μM) at 37°C with 5% CO2. Cell supernatants are harvested for plaque assays at 24 h postinfection[2].
References

[1]. Fresno M, et al. Inhibition of translation in eukaryotic systems by harringtonine. Eur J Biochem. 1977 Jan;72(2):323-30.

[2]. Kaur P, et al. Inhibition of chikungunya virus replication by harringtonine, a novel antiviral that suppresses viral protein expression. Antimicrob Agents Chemother. 2013 Jan;57(1):155-67.

[3]. Piao YF, et al. Growth inhibition of human myeloid leukemia cells in vitro by harringtonine. Gan To Kagaku Ryoho. 1990 Feb;17(2):281-5.
Density 1.4±0.1 g/cm3
Boiling Point 679.4±55.0 °C at 760 mmHg
Melting Point 73-75ºC
Molecular Formula C28H37NO9
Molecular Weight 531.595
Flash Point 364.7±31.5 °C
Exact Mass 531.246826
PSA 123.99000
LogP 2.58
Vapour Pressure 0.0±2.2 mmHg at 25°C
Index of Refraction 1.610
Storage condition -20℃

CHEMICAL IDENTIFICATION

RTECS NUMBER :
FK0250000
CHEMICAL NAME :
Cephalotaxine, 4-methyl-, 2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate (ester), (3(R))-
CAS REGISTRY NUMBER :
26833-85-2
LAST UPDATED :
199703
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C28-H37-N-O9
MOLECULAR WEIGHT :
531.66
WISWESSER LINE NOTATION :
T5 H5 F675 1A T AX IO KO QN BU JHT&&TTJ CO1 DOVXQ1VQ2XQ1&1 T1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4170 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
4200 ug/kg/5D-I
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Blood - leukopenia Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
5200 ug/kg/5D-I
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Blood - leukopenia Related to Chronic Data - death
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
200 ug/L
REFERENCE :
CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 7,173,1986
Hazard Codes Xi
RIDADR UN 1544
Packaging Group II
Hazard Class 6.1(a)
Precursor  3

DownStream  0


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