Merck
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

biological source

Streptomyces alboniger

Quality Level

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
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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.

antibiotic activity spectrum

Gram-positive bacteria
neoplastics
parasites

application(s)

agriculture

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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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.

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.

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

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

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Certificate of Origin

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