P8833

Puromycin dihydrochloride from Streptomyces alboniger

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: 58-58-2
• Molecular Weight: 544.43
• Beilstein: 3853613
• EC Number: 200-387-8
• MDL number: MFCD00012691
• PubChem Substance ID: 24898984
• NACRES: NA.76

Properties

• biological source: Streptomyces alboniger
• Quality Level: 300
• 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.
• technique(s): cell culture | mammalian: suitable
• color: yellow-white
• solubility: H₂O: soluble 50 mg/mL, clear, colorless to faintly yellow
• UniProt accession no.: P13249
• antibiotic activity spectrum: Gram-positive bacteria; neoplastics; parasites
• application(s): agriculture
• greener alternative category: Re-engineered
• 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

Description

General description

Chemical structure: peptidyl nucleoside

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.

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

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.

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.

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

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P301 + P312 + P330
• 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