(2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide dihydrochloride

• ChemBase ID: 154171
• Molecular Formular: C22H31Cl2N7O5
• Molecular Mass: 544.43144
• Monoisotopic Mass: 543.17637249
• SMILES: CN(C)c1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)NC(=O)[C@H](Cc1ccc(cc1)OC)N)O.Cl.Cl
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1NC(=O)[C@H](Cc1ccc(cc1)OC)N)O)n1cnc2c1ncnc2N(C)C.Cl.Cl
• InChI: 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
• InChIKey: MKSVFGKWZLUTTO-FZFAUISWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide dihydrochloride
• IUPAC Traditional name: puromycin dihydrochloride
• Synonyms: Puromycin dihydrochloride; 3′-[α-Amino-p-methoxyhydrocinnamamido]-3′-deoxy-N,N-dimethyladenosine dihydrochloride; Puromycin dihydrochloride from Streptomyces alboniger; Puromycin; 3′-[α-Amino-p-methoxyhydrocinnamamido]-3′-deoxy-N,N-dimethyladenosine 二盐酸盐; Puromycin dihydrochloride 二盐酸盐 来源于白色链球菌

Database IDs

• CAS Number: 58-58-2
• EC Number: 200-387-8
• MDL Number: MFCD00012691
• Beilstein Number: 3853613
• PubChem SID: 162248310; 24898984; 24898832
• PubChem CID: 443311

CALCULATED PROPERTIES

• Acid pKa: 12.349177
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -2.7910688
• LogD (pH = 7.4): -1.0220252
• Log P: -0.29873976
• Molar Refractivity: 122.9609 cm^3
• Polarizability: 47.873817 Å^3
• Polar Surface Area: 160.88 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL; H2O: soluble50 mg/mL (Sterilize stock solution by filtration using 0.22 μm filter then store in aliquots at -20 °C.)
• Apperance: powder

Safety Information

• RTECS: AU7355000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2; 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: >98% (HPLC); ≥98% (HPLC); ≥98.0% (HPLC)
• Concentration: 10 mg/mL in H2O
• Suitability: cell culture tested; suitable for cell culture
• Biological Source: from Streptomyces alboniger
• Sterility: 0.2 μm filtered
• Quality Level: PREMIUM
• Shipped in: wet ice
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C22H29N7O5 · 2HCl

DETAILS

Sigma Aldrich - P9620

Application
Puromycin is an aminonucleoside antibiotic that is derived from Streptomyces alboniger. It allows selection for cells that contain the resistance gene puromycin N-acetyl-transferase (PAC). It has been used to study vascular smooth muscle cell viability after treatment in the rabbit model 1. Puromycin is used to produce enhanced green fluorescent protein (EGFP) transgenic piglets after somatic cell cloning and embryo transfer2.
Biochem/physiol Actions
Puromycin inhibits bacterial and mammalian protein synthesis by causing premature chain termination during translation taking place in the ribosome. Puromycin is a reversible inhibitor of dipeptidyl-peptidase II (serine peptidase) and cytosol alanyl aminopeptidase.
Suitability
Tested on HeLa cells for cell growth arrest and selection of cells after transfection of the pac resistance gene.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - P7255

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Recommended for use as a selection agent at a range of 1-10 μg/mL.
Packaging
1 g in glass bottle
25, 100, 250, 500 mg in glass bottle
Biochem/physiol Actions
Nucleoside antibiotic. Protein synthesis inhibitor that causes premature chain termination by acting as an analog of the 3′-terminal end of aminoacyl-tRNA. Prevents growth of bacteria, protozoa, algae, and mammalian cells. Acts very quickly and can kill 99% of cells within 2 days, the resistance gene (puromycin acetyltransferase) gives very effective protection.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - P8833

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
May be used in vitro as a selection agent for cells transfected with puromycin N-acetyl transferase gene (pac).
Biochem/physiol Actions
Nucleoside antibiotic. Protein synthesis inhibitor that causes premature chain termination by acting as an analog of the 3′-terminal end of aminoacyl-tRNA. Prevents growth of bacteria, protozoa, algae, and mammalian cells. Acts very quickly and can kill 99% of cells within 2 days, the resistance gene (puromycin acetyltransferase) gives very effective protection.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 82595

Other Notes
Causes premature chain termination in protein synthesis by acting as an analog of aminoacyl-tRNA.; Inhibitor of aminopeptidase and enkephalinase. Photoincorporation of puromycin into rat liver ribosomes1; Immunosuppressive effect2
Biochem/physiol Actions
Nucleoside antibiotic. Protein synthesis inhibitor that causes premature chain termination by acting as an analog of the 3′-terminal end of aminoacyl-tRNA. Prevents growth of bacteria, protozoa, algae, and mammalian cells. Acts very quickly and can kill 99% of cells within 2 days, the resistance gene (puromycin acetyltransferase) gives very effective protection.