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Merck

P7255

Puromycin dihydrochloride from Streptomyces alboniger

greener alternative

≥98% (HPLC), powder

Synonym(s):

3′-[α-Amino-p-methoxyhydrocinnamamido]-3′-deoxy-N,N-dimethyladenosine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H29N7O5 · 2HCl
CAS Number:
58-58-2
Molecular Weight:
544.43
UNSPSC Code:
51281912
NACRES:
NA.77
PubChem Substance ID:
57654556
EC Number:
200-387-8
Beilstein/REAXYS Number:
3853613
MDL number:
MFCD00012691
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
300

Key Documents

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InChI key

MKSVFGKWZLUTTO-FZFAUISWSA-N

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

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

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.

sustainability

Greener Alternative Product

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

Gram-positive bacteria, neoplastics, parasites

greener alternative category

, Re-engineered

mode of action

protein synthesis | interferes

storage temp.

−20°C

Quality Level

300

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General description

Chemical structure: peptidyl nucleoside
Sterilize stock solution by filtration using 0.22 μm filter then store in aliquots at −20 °C.
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

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.
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.

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.

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

Disclaimer

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000477771
0000477770
0000477771
0000477770
0000436145

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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
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
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
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
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