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P9620

Sigma-Aldrich

Puromycin dihydrochloride

Ready Made Solution, from Streptomyces alboniger, 10 mg/mL in H2O, suitable for cell culture

Synonym(s):

3′-(L-α-Amino-p-methoxyhydrocinnamamido)-3′-deoxy-N,N-dimethyladenosine dihydrochloride, Stylomycin dihydrochloride

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About This Item

CAS Number:
58-58-2
MDL number:
MFCD00012691
UNSPSC Code:
51281906
PubChem Substance ID:
329820352
NACRES:
NA.85

biological source

Streptomyces alboniger

Quality Level

300

type

for cell culture

assay

>98% (HPLC)

form

solution

storage condition

(Store in cool place. Keep container tightly closed in a dry and well -ventilated place. )

concentration

10 mg/mL in H2O

technique(s)

cell culture | mammalian: suitable

color

colorless to yellow

solubility

H2O: soluble 10 mg/mL

antibiotic activity spectrum

Gram-positive bacteria
neoplastics
parasites

mode of action

protein synthesis | interferes

shipped in

wet ice

storage temp.

−20°C

SMILES string

Cl.Cl.COc1ccc(C[C@H](N)C(=O)N[C@H]2[C@@H](O)[C@@H](O[C@@H]2CO)n3cnc4c(ncnc34)N(C)C)cc1

InChI

1S/C22H29N7O5.2ClH/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12;;/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32);2*1H/t14-,15+,16+,18+,22+;;/m0../s1

InChI key

MKSVFGKWZLUTTO-FZFAUISWSA-N

General description

Puromycin, also known as clomycin or stylomycin hydrochloride, is an aminonuclease antibiotic and protein synthesis inhibitor. It is produced by the soil actinomycete bacterium Streptomyces alboniger through a series of enzymatic reactions. Puromycin is effective against both prokaryotic and eukaryotic cells, working by interfering with RNA function, leading to the inhibition of protein synthesis. It also serves as an inhibitor of aminopeptidase and enkephalinase. The growth of bacteria, protozoa, algae, and mammalian cells is quickly halted by puromycin, but cells with the pac gene exhibit resistance. The gene product of the pac gene is puromycin-N-acetyl-transferase, which inactivates puromycin through acetylation.

Puromycin′s structural similarity to the amino acid-bearing end of tRNA allows it to enter the ribosome during protein synthesis, bind to the nascent polypeptide chain, and halt chain elongation. Widely used in cell culture, puromycin serves as a selective agent for cells that have been transformed with a gene conferring resistance to puromycin.

Application

Puromycin is an aminonucleoside antibiotic that is derived from Streptomyces alboniger. It allows selection for cells that contain the resistance gene puromycin N-acetyl-transferase (PAC). It has been used to study vascular smooth muscle cell viability after treatment in the rabbit model . Puromycin is used to produce enhanced green fluorescent protein (EGFP) transgenic piglets after somatic cell cloning and embryo transfer.

Biochem/physiol Actions

Mode of Action: Puromycin inhibits protein synthesis by causing premature chain termination acting as an analog of the 3′-terminal end of the aminoacyl-tRNA. Puromycin also acts as a reversible inhibitor of dipeptidyl-peptidase II (serine peptidase) and cytosol alanyl aminopeptidase.

Mode of Resistance: Puromycin acetyltransferase is an effective resistance gene.

Antimicrobial Spectrum: This product is active against gram-positive microorganisms, less active against acid-fast bacilli and more weakly active against gram-negative microorganisms. Puromycin can prevent growth of bacteria, protozoa, algae and mammalian cells and acts quickly, killing 99% of cells within 2 days.

Features and Benefits

  • High-quality antibiotic suitable for multiple research applications
  • Antibiotic and protein synthesis inhibitor
  • Effective against prokaryotic and eukaryotic cells
  • Inhibits protein synthesis by interfering with RNA function
  • Commonly used as a selective agent in cell biology research

Preparation Note

This product is concentrated at 10 mg/mL in water. It has been tested on HeLa cells for cell growth arrest and selection of cells after transfection of the pac resistance gene.

Other Notes

For additional information on our range of Biochemicals, please complete this form.
Keep container tightly closed in a dry and well-ventilated place.

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Certificates of Analysis (COA)

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Satoshi Watanabe et al.
Biology of reproduction, 72(2), 309-315 (2004-09-24)
Puromycin N-acetyl transferase gene (pac), of which the gene product catalyzes antibiotic puromycin (an effective inhibitor of protein synthesis), has been widely used as a dominant selection marker in embryonic stem (ES) cell-mediated transgenesis. The present study is the first
Jacinta P W Lee et al.
Autophagy, 12(6), 907-916 (2016-05-11)
MIF (macrophage migration inhibitory factor [glycosylation-inhibiting factor]) is a pro-inflammatory cytokine expressed in multiple cells types, including macrophages. MIF plays a pathogenic role in a number of inflammatory diseases and has been linked to tumor progression in some cancers. Previous
Ming Lee Lin et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(8), 3029-3034 (2008-02-15)
Cross-presentation as a fundamental pathway of activating CD8(+) T cells has been well established. So far the application of this concept in vivo is limited, and the mechanisms that specialize CD8(+) dendritic cells (DCs) for this task are not fully
S Eyckerman et al.
Nature cell biology, 3(12), 1114-1119 (2002-01-10)
Ligand-induced clustering of type I cytokine receptor subunits leads to trans-phosphorylation and activation of associated cytosolic janus kinases (JAKs). In turn, JAKs phosphorylate tyrosine residues in the receptor tails, leading to recruitment and activation of signalling molecules. Among these, signal
Valerie Croons et al.
The Journal of pharmacology and experimental therapeutics, 325(3), 824-832 (2008-03-07)
Recent evidence indicates that the protein synthesis inhibitor cycloheximide triggers selective macrophage death in rabbit atheroma-like lesions without affecting smooth muscle cells (SMCs) or the endothelium, thereby favoring a stable plaque phenotype. In this study, we report that puromycin, a
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