P8833

Sigma-Aldrich

Puromycin dihydrochloride from Streptomyces alboniger

greener alternative

powder, BioReagent, suitable for cell culture

Sinônimo(s):
3′-[α-Amino-p-methoxyhydrocinnamamido]-3′-deoxy-N,N-dimethyladenosine dihydrochloride
Empirical Formula (Hill Notation):
C22H29N7O5 · 2HCl
Número CAS:
Peso molecular:
544.43
Beilstein/REAXYS Number:
3853613
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.76

Nível de qualidade

300

fonte biológica

Streptomyces alboniger

linha de produto

BioReagent

teor

≥98% (HPLC)

forma

powder

peso molecular

544.43 g/mol

embalagem

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

pontuação do produto alternativo mais ecológico

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

características do produto alternativo mais ecológico

Atom Economy
Design for Energy Efficiency
Use of Renewable Feedstocks
Design for Degradation
Learn more about the Principles of Green Chemistry.

aplicação(ões)

cell culture | mammalian: suitable

cor

yellow-white

solubilidade

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

Setor em destaque

Agriculture

Modo de ação

protein synthesis | interferes

nº de adesão UniProt

espectro de atividade do antibiótico

Gram-positive bacteria
neoplastics
parasites

categoria alternativa mais ecológica

temperatura de armazenamento

−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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Descrição geral

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

Aplicação

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.

Embalagem

10, 25, 100 mg in glass bottle

Ações bioquímicas/fisiológicas

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.

Atenção

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

Nota de preparo

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.

Outras notas

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

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Declarações de precaução

hazcat

Acute Tox. 4 Oral

storage_class_code

11 - Combustible Solids

WGK Alemanha

WGK 3

Ponto de fulgor (ºF)

Not applicable

Ponto de fulgor (ºC)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificado de análise

Certificado de origem

  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.

  8. 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)
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...
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...
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...
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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