PUROMYCIN Chemical Properties

Melting point:

175.5-177°

alpha 

D25 -11° (ethanol)

Boiling point:

572.65°C (rough estimate)

Density 

1.3119 (rough estimate)

refractive index 

1.7010 (estimate)

RTECS 

AU7350000

solubility 

DMF: Soluble
DMSO: Soluble
Ethanol: Soluble
Methanol: Soluble

pka

6.8, 7.2(at 25℃)

form 

Liquid

color 

White to off-white

Water Solubility 

Soluble in water (50 mg/ml at 20°C).

EPA Substance Registry System

Adenosine, 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyl- (53-79-2)

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

LD50 in mice (mg/kg): 350 i.v.; 525 i.p.; 675 orally (Porter, 1952)

PUROMYCIN Usage And Synthesis

Description

Puromycin is an aminonucleoside antibiotic produced by Streptomyces alboniger. It is a very common antibiotic routinely used by scientists in biomedical research to select cells modified by genetic engineering. It specifically inhibits peptidyl transfer on both prokaryotic and eukaryotic ribosomes. The antibiotic inhibits the growth of Gram-positive bacteria and various animal and insect cells. Fungi and Gram-negative bacteria are resistant due to the low permeability of the antibiotic. For more than 30 years, puromycin has been widely used as a basic tool for studying protein synthesis. Now, puromycin hydrochloride is particularly useful for the selection of cell types harboring plasmids carrying puromycin resistance genes. Puromycinresistant cells express pac gene, which encodes an N-acetyl puromycin transferase. The pac gene can be mobilized on a plasmid and used to transfect a host cell in an attempt to provide resistance; therefore, puromycin can be used in gene selections for mammalian host cells.
This aminonucleoside antibiotic causes premature chain termination during translation in the ribosomes. Part of the molecule resembles the 30 end of the aminoacylated tRNA. It enters the A site and transfers to the growing chain, causing premature chain release. The exact mechanism of action is unknown, but the 30 position contains an amide linkage instead of the normal ester linkage of tRNA; the amide bond makes the molecule much more resistant to hydrolysis and thus causes the ribosome to become stopped. It is not selective for either prokaryotes or eukaryotes.
Also of note, puromycin is critical in mRNA display as it allows the growing peptide chain to be covalently bonded to its own mRNA template. Additionally, puromycin is a reversible inhibitor of dipeptidyl-peptidase II (serine peptidase) and cytosol alanyl aminopeptidase (metallopeptidase). The mechanism of inhibition is not well understood; however, puromycin can be used to distinguish between aminopeptidase M (active) and cytosol alanyl aminopeptidase (inhibited by puromycin) and therefore extremely useful in biochemistry and nephrology research.

Chemical Properties

Crystals.

Uses

Puromycin is an aminonuclease antibiotic produced by the soil actinomycete?Streptomyces alboniger; which induces apoptosis.

Uses

Puromycin has been widely used as a basic tool in research for studying protein synthesis. It is an antibiotic used by scientists in bioresearch to select cells modified by genetic engineering. It inhibits protein synthesis by binding to RNA. It is also an antineoplastic and antitrypanosomal agent.

Uses

Puromycin is a nucleoside antibiotic isolated from Streptomyces alboniger in the 1950s as an anti-trypansomal agent with antibiotic activity. Puromycin is non-selective, inhibiting RNA by blocking ribosomal translation. Puromycin is used in cell biology to select mammalian cell lines that have been transformed by vectors that express puromycin-N-acetyl-transferase.

Definition

ChEBI: An aminonucleoside antibiotic, derived from the Streptomyces alboniger bacterium, that causes premature chain termination during translation taking place in the ribosome.

Hazard

Toxic to living cells of all kinds.

Toxicity evaluation

Puromycin is a specific metabolic inhibitor of protein synthesis and acts as an aminoacyl-tRNA analog and peptidyl acceptor. The latter causes premature chain termination of the protein and the release of nascent or growing polypeptide chains. In liver, it has been shown to cause fat accumulation without causing death of the hepatocytes. Puromycin causes focal glomerular sclerosis and alters the morphology, localization of anionic sites, and metabolism of renal epithelial cells. This injury is attributable to the production of reactive oxygen species.

References

[1] ABOU-ZEID A. ABOU-ZEID  Ahmed I E D  Ahmed B Shaheen. Fermentative production of puromycin by Streptomyces alboniger[C]//23 11. 1973: 837-845. DOI: 10.1002/jctb.5020231107
[2] C RODRIGUEZ-FONSECA. Puromycin-rRNA interaction sites at the peptidyl transferase center.[J]. RNA, 2000, 6 5: 744-754. DOI: 10.1017/s1355838200000091
[3] M E AZZAM  I D A. Mechanism of puromycin action: fate of ribosomes after release of nascent protein chains from polysomes.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1973, 70 12: 3866-3869. DOI: 10.1073/pnas.70.12.3866
[4] R LÜHRMANN. Localization of the puromycin binding site on the large ribosomal subunit of Escherichia coli by immunoelectron microscopy.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1981, 78 12: 7276-7280. DOI: 10.1073/pnas.78.12.7276
[5] ROHIT SINGH  Robert V  Jessica Williams. Puromycin based inhibitors of aminopeptidases for the potential treatment of hematologic malignancies[J]. European Journal of Medicinal Chemistry, 2017, 139: Pages 325-336. DOI: 10.1016/j.ejmech.2017.07.048
[6] ROSEMARY M. EKONG . Comparison of the in vitro activities of quassinoids with activity against Plasmodium falciparum, anisomycin and some other inhibitors of eukaryotic protein synthesis[J]. Biochemical pharmacology, 1990, 40 2: Pages 297-301. DOI: 10.1016/0006-2952(90)90691-d
[7] AVINER R. The science of puromycin: From studies of ribosome function to applications in biotechnology.[J]. Computational and structural biotechnology journal, 2020: 1074-1083. DOI: 10.1016/j.csbj.2020.04.014

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