Puromycin dihydrochloride from Streptomyces alboniger
SIGMA/P8833 - powder, BioReagent, suitable for cell culture
Synonym: 3′-[α-Amino-p-methoxyhydrocinnamamido]-3′-deoxy-N,N-dimethyladenosine dihydrochloride
CAS Number: 58-58-2
Empirical Formula (Hill Notation): C22H29N7O5 · 2HCl
Molecular Weight: 544.43
EC Number: 200-387-8
MDL Number: MFCD00012691
Linear Formula: C22H29N7O5 · 2HCl
Product Type: Chemical
Puromycin mimics aminoacyl-tRNA, binds to the ribosome′s A-site, and forms a peptide bond with the peptidyl-tRNA in the P-site causing the release of a premature chain during translation; thus, it stops the protein synthesis from its intercalation into the peptide.
12 Principles of Green Chemistry: Principle 2—Atom Economy. This product was designed to maximize the incorporation of all raw materials used in the manufacturing process.
12 Principles of Green Chemistry: Principle 7—A raw material or feedstock should be renewable rather than depleting whenever technically and economically practicable.
12 Principles of Green Chemistry: Principle 10—Chemical products should be designed so that at the end of their function they break down into innocuous degradation products and do not persist in the environment.
| antibiotic activity spectrum | Gram-positive bacteria |
| neoplastics | |
| parasites | |
| application(s) | agriculture |
| assay | ≥98% (HPLC) |
| biological source | Streptomyces alboniger |
| color | yellow-white |
| form | powder |
| greener alternative category | Re-engineered  , |
| 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 . |
| greener alternative product score | old score: 88 new score: 79 Find out more about DOZN™ Scoring |
| InChI | 1S/C22H29N7O5.2ClH/c1-28( |
| InChI key | MKSVFGKWZLUTTO-FZFAUISWSA |
| mode of action | protein synthesis | interferes |
| mol wt | 544.43 g/mol |
| packaging | pkg of 10 mg |
| pkg of 100 mg | |
| pkg of 25 mg | |
| product line | BioReagent |
| Quality Level | 300 |
| SMILES string | Cl.Cl.COc1ccc(C[C@H](N)C( |
| storage temp. | −20°C |
| sustainability | Greener Alternative Product |
| technique(s) | cell culture | mammalian: suitable |
| UniProt accession no. | P13249  |
| Application: | 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. |
| 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. |
| Application: | 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. |
| 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. |
| 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. |
| Disclaimer: | As supplied, this product remains active for four years when stored at -20°C. |
| General description: | Chemical structure: peptidyl nucleoside |
| 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. |
| General description: | 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. |
| Other Notes: | Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place |
| Packaging: | 10, 25, 100 mg in glass bottle |
| 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. |
| Symbol |  GHS07 |
| Signal word | Warning |
| Hazard statements | H302 |
| Precautionary statements | P301 + P312 + P330 |
| Hazard Codes | Xn |
| Risk Statements | 22 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (HPLC) |
| Storage Temp. | −20°C |
| UNSPSC | 12352207 |