All Photos(5)

P8833

Sigma-Aldrich

Puromycin dihydrochloride from Streptomyces alboniger

greener alternative

powder, BioReagent, suitable for cell culture

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.76

Quality Level

biological source

Streptomyces alboniger

product line

BioReagent

assay

≥98% (HPLC)

form

powder

mol wt

544.43 g/mol

packaging

pkg of 10 mg
pkg of 100 mg
pkg of 25 mg

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.

application(s)

cell culture | mammalian: suitable

color

yellow-white

solubility

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

Featured Industry

Agriculture

Mode of action

protein synthesis | interferes

UniProt accession no.

antibiotic activity spectrum

Gram-positive bacteria
neoplastics
parasites

greener alternative category

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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General description

Puromycin is a broad spectrum antibiotic produced by Streptomyces alboniger. It is an analog of the 3′ end of aminoacyl-tRNA. It is an inhibitor of peptidyl transferase and is active in both prokaryotes and eukaryotes.
Chemical structure: peptidyl nucleoside

Application

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.
Puromycin dihydrochloride from Streptomyces alboniger has been used:
  • in the preparation of puromycin stock solution for puromycin sensitivity assay.
  • to select lentivirus-infected cells containing puromycin resistant selection marker.
Used as a selective agent for cells that contain the resistance gene puromycin N-acetyl-transferase (PAC). Recommended for use at a range of 1-10 μg/ml. Sterilize stock solution by filtration using 0.22 μm filter then store in aliquots at −20 °C.

Packaging

10, 25, 100 mg in glass bottle

Biochem/physiol Actions

Puromycin associates in a non-specific manner with growing polypeptide chains, and thus, leads to premature termination of translation. It inhibits protein synthesis in two ways. It associates with the donor substrate, peptidyl-tRNA, in the P site and thus, functions as an acceptor substrate. Second, it competes with aminoacyl tRNA to bind with the A′ site within the peptidyl transferase center.
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.

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What are the approximate concentrations of Product P8833, Puromycin dihydrochloride, suitable for HeLa human uterus,  B16 mouse melanoma and PC1.0 hamster adenocarcinoma cells?

    HeLa human uterus: 3 μg/mL; B16 mouse melanoma: 1-3 μg/mL; PC1.0 hamster adenocarcinoma: 10 μg/mL.

  6. What are the approximate concentrations of Product P8833, Puromycin dihydrochloride, suitable for HEK293, A431 and Jurkat cells?

    HEK293: 2-3 μg/mL; A431: 1 μg/mL; Jurkat: 4 μg/mL.

  7. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Heterocyclic analogs of nucleosides: synthesis and biological evaluation of novel analogs of puromycin.
Hultin P G and Walter A S
Canadian Journal of Chemistry, 72(9), 1978-1989 (1994)
E Miyamoto-Sato et al.
Nucleic acids research, 28(5), 1176-1182 (2000-02-10)
Puromycin, an analog of the 3' end of aminoacyl-tRNA, causes premature termination of translation by being linked non-specifically to growing polypeptide chains. Here we report the interesting phenomenon that puromycin acting as a non-inhibitor at very low concentration (e.g. 0.04...
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...
Hansjörg Schwertz et al.
Blood, 115(18), 3801-3809 (2010-01-21)
Platelets are classified as terminally differentiated cells that are incapable of cellular division. However, we observe that anucleate human platelets, either maintained in suspension culture or captured in microdrops, give rise to new cell bodies packed with respiring mitochondria and...
Bing-Hsiean Tzeng et al.
Cardiovascular research, 96(3), 533-542 (2012-08-14)
Restenosis is an undesirable consequence following percutaneous vascular interventions. However, the current strategy for preventing restenosis is inadequate. The aim of this study was to investigate the role of low-voltage gated T-type calcium channels in regulating vascular smooth muscle cell...

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