(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编号: 154171
• 分子式: C22H31Cl2N7O5
• 平均质量: 544.43144
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: puromycin dihydrochloride
• 别名: 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; Puromycin dihydrochloride; 3′-[α-Amino-p-methoxyhydrocinnamamido]-3′-deoxy-N,N-dimethyladenosine dihydrochloride; Puromycin dihydrochloride from Streptomyces alboniger

登记号

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

理论计算性质

• Acid pKa: 12.349177
• 质子受体: 10
• 质子供体: 4
• LogD (pH = 5.5): -2.7910688
• LogD (pH = 7.4): -1.0220252
• Log P: -0.29873976
• 摩尔折射率: 122.9609 cm^3
• 极化性: 47.873817 Å^3
• 极化表面积: 160.88 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: 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.)
• 外观: powder

安全信息

• RTECS编号: AU7355000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2; 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• 保存温度: -20°C

产品相关信息

• 纯度: >98% (HPLC); ≥98% (HPLC); ≥98.0% (HPLC)
• 浓度: 10 mg/mL in H2O
• 适用性: cell culture tested; suitable for cell culture
• 生物来源: from Streptomyces alboniger
• 无菌消毒: 0.2 μm filtered
• 产品质量级别: PREMIUM
• 运输包装: wet ice
• 产品线: BioReagent
• Empirical Formula (Hill Notation): C22H29N7O5 · 2HCl

详细说明

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.
包装
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.