Merck

P8833

Sigma-Aldrich

Puromycin dihydrochloride from Streptomyces alboniger

greener alternative

powder, BioReagent, suitable for cell culture

Synonim(y):
3′-[α-Amino-p-methoxyhydrocinnamamido]-3′-deoxy-N,N-dimethyladenosine dihydrochloride
Empirical Formula (Hill Notation):
C22H29N7O5 · 2HCl
Numer CAS:
Masa cząsteczkowa:
544.43
Beilstein:
3853613
Numer EC:
Numer MDL:
Identyfikator substancji w PubChem:
NACRES:
NA.76

pochodzenie biologiczne

Streptomyces alboniger

Poziom jakości

linia produktu

BioReagent

Próba

≥98% (HPLC)

forma

powder

masa cząsteczkowa

544.43 g/mol

opakowanie

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

wynik ekologicznej alternatywy

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

charakterystyka ekologicznej alternatywy

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

kolor

yellow-white

rozpuszczalność

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

numer dostępu UniProt

spektrum działania antybiotyku

Gram-positive bacteria
neoplastics
parasites

application(s)

agriculture

kategoria ekologicznej alternatywy

Tryb działania

protein synthesis | interferes

temp. przechowywania

−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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Ta pozycja
P7255P9620P7130
product line

BioReagent

product line

-

product line

-

product line

-

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

>98% (HPLC)

assay

-

form

powder

form

powder

form

solution

form

powder

technique(s)

cell culture | mammalian: suitable

technique(s)

-

technique(s)

cell culture | mammalian: suitable

technique(s)

-

color

yellow-white

color

-

color

-

color

-

Opis ogólny

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.

Zastosowanie

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.

Działania biochem./fizjol.

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.

Przestroga

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

Uwaga dotycząca przygotowania

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.

Inne uwagi

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

piktogramy

Exclamation mark

Hasło ostrzegawcze

Warning

Zwroty wskazujące rodzaj zagrożenia

Zwroty wskazujące środki ostrożności

Klasyfikacja zagrożeń

Acute Tox. 4 Oral

Kod klasy składowania

11 - Combustible Solids

WGK

WGK 3

Temperatura zapłonu °F

Not applicable

Temperatura zapłonu °C

Not applicable

Środki ochrony indywidualnej

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Przykład

T1503
Numer produktu
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25G
Wielkość opakowania/ilość

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705578-5MG-PW

PL860-CGA/SHF-1EA

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1000309185

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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)
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
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
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Produkty

Inhibition of Protein Synthesis by Antibiotics

Protein synthesis is a complex, multi-step process involving many enzymes as well as conformational alignment. However, the majority of antibiotics that block bacterial protein synthesis interfere with the processes at the 30S subunit or 50S subunit of the 70S bacterial ribosome.

Antibiotic Kill Curve

Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic

Protokoły

Induced Pluripotent Stem Cell Reprogramming Protocols

Stem cell reprogramming protocols to generate human induced pluripotent stem cells (iPSCs) including viral and non-viral RNA based methods.

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