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P7255

Sigma-Aldrich

Puromycin dihydrochloride from Streptomyces alboniger

greener alternative

≥98% (HPLC), powder

Synonym(s):
3′-[α-Amino-p-methoxyhydrocinnamamido]-3′-deoxy-N,N-dimethyladenosine dihydrochloride
Empirical Formula (Hill Notation):
C22H29N7O5 · 2HCl
CAS Number:
Molecular Weight:
544.43
Beilstein:
3853613
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

greener alternative product score

old score: 88
new score: 79
Find out more about DOZN™ Scoring

greener alternative product characteristics

Atom Economy
Design for Energy Efficiency
Use of Renewable Feedstocks
Design for Degradation
Learn more about the Principles of Green Chemistry.

solubility

H2O: 50 mg/mL (Sterilize stock solution by filtration using 0.22 μm filter then store in aliquots at −20 °C.)

antibiotic activity spectrum

Gram-positive bacteria
neoplastics
parasites

greener alternative category

Mode of action

protein synthesis | interferes

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

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This Item
P8833P9620SBR00017
form

powder

form

powder

form

solution

form

liquid

solubility

H2O: 50 mg/mL (Sterilize stock solution by filtration using 0.22 μm filter then store in aliquots at −20 °C.)

solubility

H2O: soluble 50 mg/mL, clear, colorless to faintly yellow

solubility

H2O: soluble 10 mg/mL

solubility

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

300

Quality Level

300

Quality Level

300

Quality Level

200

greener alternative product score

old score: 88
new score: 79
Find out more about DOZN™ Scoring

greener alternative product score

old score: 88
new score: 79
Find out more about DOZN™ Scoring

greener alternative product score

-

greener alternative product score

-

General description

Chemical structure: peptidyl nucleoside
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Atom Economy”, “Design for Energy Efficiency”, “Use of Renewable Feedstock” and “Design for Degradation”. Click here to view its DOZN scorecard.

Application

Recommended for use as a selection agent at a range of 1-10 μg/mL.

Biochem/physiol Actions

Puromycin dihydrochloride is a part of the amino-nucleoside family of antibiotics and is derived from Streptomyces alboniger. It is a broad spectrum antibiotic with antitumor activity, as an inhibitor of protein synthesis and has been used to study transcription regulatory mechanisms that control the sequential and coordinate expression of genes during cell differentiation. The recommended working concentration in eukaryotic cell culture is 1-10 μg/mL.
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.

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

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Caution

As supplied, this product remains active for four years when stored at -20°C.

Preparation Note

This product is soluble in water at 50 mg/mL. A stock solution should be prepared by filtration using a 0.22 μm filter and then stored in aliquots at -20°C. This product is also soluble in methanol at 10 mg/mL.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place. Keep in a dry place

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

Slide 1 of 6

1 of 6

Robert A J Signer et al.
Nature, 509(7498), 49-54 (2014-03-29)
Many aspects of cellular physiology remain unstudied in somatic stem cells, for example, there are almost no data on protein synthesis in any somatic stem cell. Here we set out to compare protein synthesis in haematopoietic stem cells (HSCs) and
Shingo Ueno et al.
Journal of biotechnology, 162(2-3), 299-302 (2012-09-25)
cDNA display using a puromycin-linker to covalently bridge a protein and its coding cDNA is a stable and efficient in vitro protein selection method. The optimal design of the often-used puromycin-linker is vital for effective selection. In this report, an
Claudia Fritsch et al.
Genome research, 22(11), 2208-2218 (2012-08-11)
So far, the annotation of translation initiation sites (TISs) has been based mostly upon bioinformatics rather than experimental evidence. We adapted ribosomal footprinting to puromycin-treated cells to generate a transcriptome-wide map of TISs in a human monocytic cell line. A
Antonina J Kruppa et al.
Biochimica et biophysica acta, 1832(12), 2115-2126 (2013-08-06)
The accumulation of β-amyloid (Aβ) peptide in the brain is one of the pathological hallmarks of Alzheimer's disease and is thought to be of primary aetiological significance. In an unbiased genetic screen, we identified puromycin-sensitive aminopeptidase (PSA) as a potent
Robert J Huber et al.
Biochimica et biophysica acta, 1833(1), 11-20 (2012-10-16)
Cyclin-dependent kinase 5 (Cdk5) is a serine/threonine kinase that has been implicated in a number of cellular processes. In Dictyostelium, Cdk5 localizes to the nucleus and cytoplasm, interacts with puromycin-sensitive aminopeptidase A (PsaA), and regulates endocytosis, secretion, growth, and multicellular

Articles

Inhibition of Protein Synthesis by Antibiotics

Protein synthesis is a complex, multi-step process involving many enzymes as well as conformational alignment. However, the majority of antibiotics that block bacterial protein synthesis interfere with the processes at the 30S subunit or 50S subunit of the 70S bacterial ribosome.

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Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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