Puromycin 2HCl

Names

[ CAS No. ]:
58-58-2

[ Name ]:
Puromycin 2HCl

[Synonym ]:
PUROMYCIN
EINECS 200-387-8
MFCD00067313
L-3'-(a-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine Dihydrochloride
PUROMYCIN HYDROCHLORIDE
Puromycin dihydrochloride
Purine, 6-dimethylamino-9-[3-(p-methoxy-L-phenylalanylamino)-3-deoxy-.β.-D-ribofuranosyl]-, dihydrochloride
L-3'-(a-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine
(S)-3'-[[2-Amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyladenosine
puromycinum [INN_la]
6-Dimethylamino-9-[3-deoxy-3-(p-methoxy-L-phenylalanylamino)-b-D-ribofuranosyl]-b-purine
Adenosine, 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyl-, hydrochloride (1:2)
P 638 dihydrochloride
3'-{(E)-[(2S)-2-Amino-1-hydroxy-3-(4-methoxyphenyl)propylidene]amino}-3'-deoxy-N,N-dimethyladenosine
3123-L
3'-Deoxy-N,N-dimethyl-3'-[(O-methyl-L-tyrosyl)amino]adenosine dihydrochloride
3'-(a-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine
3'-(a-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine Dihydrochloride
Stylomycin dihydrochloride
6-Dimethylamino-9-[3-deoxy-3-(p-methoxy-L-phenylalanylamino)-b-D-ribofuranosyl]-b-purine Dihydrochloride
Stillomycin
Adenosine, 3'-[[(1E,2S)-2-amino-1-hydroxy-3-(4-methoxyphenyl)propylidene]amino]-3'-deoxy-N,N-dimethyl-
Adenosine, 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyl-
3'-Deoxy-N,N-dimethyl-3'-[(O-methyl-L-tyrosyl)amino]adenosine

Biological Activity

[Description]:

Puromycin dihydrochloride is the dihydrochloride salt of puromycin. Puromycin is an aminoglycoside antibiotic that inhibits protein synthesis.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Natural Products >> Others

Research Areas >> Infection

[In Vitro]

Puromycin blocks protein synthesis after aminoacyl-sRNA formation, and at the same time it leads to the accumulation of small peptides. Both of these effects appear to be due to the splitting of ribosome-bound peptidyl-sRNA,4 which results in release of incomplete peptide chains.[1]. Puromycin, an analog of the 3' end of aminoacyl-tRNA, causes premature termination of translation by being linked non-specifically to growing polypeptide chains. Puromycin has two modes of inhibitory action. The first is by acting as an acceptor substrate which attacks peptidyl-tRNA in the P site to form a nascent peptide. The second is by competing with aminoacyl-tRNA for binding to the A' site[2]. When used in minimal amounts, puromycin incorporation in neosynthesized proteins reflects directly the rate of mRNA translation in vitro. Puromycin immunodetection is an advantageous alternative to radioactive amino acid labeling. It allows the direct evaluation of translation activity in single cells by immunofluorescence microscopy and in heterogenous populations of cells by fluorescenceactivated cell sorting[3].

[References]

[1]. Nathans D, et al. Puromycin inhibition of protein synthesis: incorporation of puromycin intopeptide chains. Proc Natl Acad Sci U S A. 1964 Apr;51:585-92.

[2]. Miyamoto-Sato E, et al. Specific bonding of puromycin to full-length protein at the C-terminus. Nucleic Acids Res. 2000 Mar 1;28(5):1176-82.

[3]. Schmidt EK, et al. SUnSET, a nonradioactive method to monitor protein synthesis. Nat Methods. 2009 Apr;6(4):275-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Melting Point ]:
168-170℃

[ Molecular Formula ]:
C₂₂H₃₁Cl₂N₇O₅

[ Molecular Weight ]:
544.43

[ PSA ]:
160.88000

[ LogP ]:
0.93

[ Index of Refraction ]:
1.701

[ Storage condition ]:
−20°C

[ Stability ]:
Stable. Heat sensitive. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
H2O: soluble50mg/mL (Sterilize stock solution by filtration using 0.22 μm filter then store in aliquots at 20 °C.) | Soluble in water

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU7355000

CHEMICAL NAME :: Adenosine, 3'-((2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3 '-deoxy-N,N-dimethyl-, Dihydrochloride, (S)-

CAS REGISTRY NUMBER :: 58-58-2

LAST UPDATED :: 199801

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C22-H29-N7-O5.2Cl-H

MOLECULAR WEIGHT :: 544.50

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ IN1&1 D- BT5OTJ CQ DMVYZ1R DO1& E1Q &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 720 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 580 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 335 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 600 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Behavioral - muscle weakness

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 287 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Behavioral - muscle weakness

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 202 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Behavioral - muscle weakness

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg/10D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 150 mg/kg/3D-I

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Related to Chronic Data - death

TYPE OF TEST :: DNA inhibition

TYPE OF TEST :: Mutation test systems - not otherwise specified

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

REFERENCE :: FOBLAN Folia Biologica (Prague). (Academic Press Inc. Ltd., 24-28 Oval Rd., London NW1 7DX, UK) V.1- 1955- Volume(issue)/page/year: 21,60,1975

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
UN 3249

[ WGK Germany ]:
3

[ RTECS ]:
AU7355000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

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Related Compounds

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