Merck
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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
Numéro EC:
Numéro MDL:
ID de substance PubChem:
NACRES:
NA.76

Source biologique

Streptomyces alboniger

Niveau de qualité

300

Gamme de produits

BioReagent

Essai/Dosage

≥98% (HPLC)

Forme

powder

Poids mol.

544.43 g/mol

Conditionnement

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

Score du produit alternatif plus écologique

old score: 88
new score: 79
Find out more about DOZN™ Scoring

Caractéristiques du produit alternatif plus écologique

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

Couleur

yellow-white

Solubilité

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

N° d'accession UniProt

Spectre d'activité de l'antibiotique

Gram-positive bacteria
neoplastics
parasites

application(s)

agriculture

Autre catégorie plus écologique

Mode d’action

protein synthesis | interferes

Temp. de stockage

−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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Description générale

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.

Conditionnement

10, 25, 100 mg in glass bottle

Actions biochimiques/physiologiques

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.

Attention

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

Notes préparatoires

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.

Autres remarques

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place

Pictograms

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Conseils de prudence

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Point d'éclair C

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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