58-58-2

• 常用中文名：嘌呤霉素二盐酸盐
• 常用英文名：Puromycin 2HCl
• CAS号：58-58-2
• 分子式：C₂₂H₃₁Cl₂N₇O₅
• 分子量：544.43
• 相关类别： 原料药 抗生素类药物 其它抗生素类药
• 发布时间：2018-06-18 13:03:23
• 更新时间：2024-01-02 16:07:59
• Puromycin dihydrochloride是嘌呤霉素的二盐酸盐。 Puromycin是一种抑制 protein synthesis 的氨基糖苷类抗生素。

名称

• 中文名: 嘌呤霉素盐酸盐
• 英文名: Puromycin dihydrochloride hydrate
• 中文别名: 嘌呤霉素二盐酸盐; 二氢氯化嘌呤毒素
• 英文别名: PUROMYCIN; EINECS 200-387-8; MFCD00067313; L-3'-(a-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine Dihydrochloride; PUROMYCIN HYDROCHLORIDE; Puromycin dihydrochloride; Purine, 6-dimethylamino-9-[3-(p-methoxy-L-phenylalanylamino)-3-deoxy-.β.-D-ribofuranosyl]-, dihydrochloride; L-3'-(a-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine; (S)-3'-[[2-Amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyladenosine; puromycinum [INN_la]; 6-Dimethylamino-9-[3-deoxy-3-(p-methoxy-L-phenylalanylamino)-b-D-ribofuranosyl]-b-purine; Adenosine, 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyl-, hydrochloride (1:2); P 638 dihydrochloride; 3'-{(E)-[(2S)-2-Amino-1-hydroxy-3-(4-methoxyphenyl)propylidene]amino}-3'-deoxy-N,N-dimethyladenosine; 3123-L; 3'-Deoxy-N,N-dimethyl-3'-[(O-methyl-L-tyrosyl)amino]adenosine dihydrochloride; 3'-(a-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine; 3'-(a-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine Dihydrochloride; Stylomycin dihydrochloride; 6-Dimethylamino-9-[3-deoxy-3-(p-methoxy-L-phenylalanylamino)-b-D-ribofuranosyl]-b-purine Dihydrochloride; Stillomycin; Adenosine, 3'-[[(1E,2S)-2-amino-1-hydroxy-3-(4-methoxyphenyl)propylidene]amino]-3'-deoxy-N,N-dimethyl-; Adenosine, 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyl-; 3'-Deoxy-N,N-dimethyl-3'-[(O-methyl-L-tyrosyl)amino]adenosine

物化性质

• 密度: 1.5±0.1 g/cm3
• 熔点: 168-170℃
• 分子式: C₂₂H₃₁Cl₂N₇O₅
• 分子量: 544.43
• PSA: 160.88000
• LogP: 0.93
• 外观性状: 白色粉末
• 折射率: 1.701
• 储存条件:

  本品应充氩气密封于0℃以下干燥避光保存。

• 稳定性: Stable. Heat sensitive. Incompatible with strong oxidizing agents.
• 水溶解性: H2O: soluble50mg/mL (Sterilize stock solution by filtration using 0.22 μm filter then store in aliquots at 20 °C.) | Soluble in water
• 分子结构:

  五、分子性质数据：

  1、 摩尔折射率：120.56

• 更多:

  1. 性状：结晶。有吸湿性。对光敏感。

  2. 密度（g/mL,25/4℃）： 未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：175.5～177.0

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC）：140-150℃（1.33×10-5kPa）

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：-11

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：易溶于水。

生物活性

• 描述: Puromycin dihydrochloride是嘌呤霉素的二盐酸盐。 Puromycin是一种抑制 protein synthesis 的氨基糖苷类抗生素。
• 相关类别:
  信号通路 >> 抗感染 >> 细菌
  天然产物 >> 其他
  研究领域 >> 感染
• 体外研究: 嘌呤霉素在氨酰基-sRNA形成后阻断蛋白质合成,同时它导致小肽的积累。这两种效应似乎都是由于核糖体结合的肽基-sRNA的分裂,导致不完整肽链的释放[1]。嘌呤霉素是氨酰基-tRNA的3'末端的类似物,通过与生长的多肽链非特异性连接而导致翻译过早终止。嘌呤霉素具有两种抑制作用模式。第一种是通过作为受体底物,其攻击P位点中的肽基-tRNA以形成新生肽。第二种是通过与氨酰基-tRNA竞争结合A'位点[2]。当以最小量使用时,嘌呤霉素掺入新合成的蛋白质直接反映体外mRNA翻译的速率。嘌呤霉素免疫检测是放射性氨基酸标记的有利替代方案。它允许通过免疫荧光显微镜直接评估单细胞中的翻译活性,并通过荧光激活细胞分选直接评估异质细胞群[3]。
• 参考文献:

  [1]. Nathans D, et al. Puromycin inhibition of protein synthesis: incorporation of puromycin intopeptide chains. Proc Natl Acad Sci U S A. 1964 Apr;51:585-92.

  [2]. Miyamoto-Sato E, et al. Specific bonding of puromycin to full-length protein at the C-terminus. Nucleic Acids Res. 2000 Mar 1;28(5):1176-82.

  [3]. Schmidt EK, et al. SUnSET, a nonradioactive method to monitor protein synthesis. Nat Methods. 2009 Apr;6(4):275-7.

MSDS

Name: Puromycin dihydrochloride hydrate Material Safety Data Sheet Synonym: 3'- CAS: 58-58-2 Section 1 - Chemical Product MSDS Name: Puromycin dihydrochloride hydrate Material Safety Data Sheet Synonym: 3'- SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 58-58-2 Puromycin dihydrochloride hydrate 100 200-387-8 Hazard Symbols: None Listed. Risk Phrases: None Listed. SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW The toxicological properties of this material have not been fully investigated. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. Inhalation: May cause respiratory tract irritation. Chronic: Laboratory experiments have resulted in mutagenic effects. SECTION 4 - FIRST AID MEASURES Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Ingestion: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: SECTION 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing Media: Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam. SECTION 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation. SECTION 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Hormones and antibiotics room. SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 58-58-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use. SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Powder Color: White Powder Odor: None reported. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: Not available. Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: Specific Gravity/Density: Molecular Formula: C22H29N7O5.2HCl.xH2O Molecular Weight: 544.44 SECTION 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, dust generation, strong oxidants. Incompatibilities with Other Materials: Strong oxidizing agents. Hazardous Decomposition Products: Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen. Hazardous Polymerization: Will not occur. SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 58-58-2: AU7355000 LD50/LC50: CAS# 58-58-2: Oral, mouse: LD50 = 720 mg/kg. Carcinogenicity: Puromycin dihydrochloride hydrate - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. SECTION 12 - ECOLOGICAL INFORMATION SECTION 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. SECTION 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material. SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: Not available. Risk Phrases: Safety Phrases: S 24/25 Avoid contact with skin and eyes. S 28A After contact with skin, wash immediately with plenty of water. S 37 Wear suitable gloves. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 58-58-2: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 58-58-2 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 58-58-2 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION MSDS Creation Date: 12/12/1998 Revision #2 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 1 、急性毒性：小鼠经口LD50：720mg/kg；小鼠腹腔LD50：580mg/kg；小鼠静脉LD50：.335mg/kg；豚鼠经口LD50：600mg/kg； 豚鼠腹腔LD50：287mg/kg；豚鼠肌内LD50：202mg/kg 2、其它多剂量毒性：大鼠腹腔TDLo：1mg/kg/10D-I；狗肌内TDLo：150mg/kg/3D-I 3、致突变性：DNA抑制试验：小鼠腹腔：333mg/kg；突变测试系统-而不是另有规定：小鼠腹腔：333mg/kg； 细胞遗传学分析：小鼠腹腔：100mg/kg CHEMICAL IDENTIFICATION RTECS NUMBER : AU7355000 CHEMICAL NAME : Adenosine, 3'-((2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3 '-deoxy-N,N-dimethyl-, Dihydrochloride, (S)- CAS REGISTRY NUMBER : 58-58-2 LAST UPDATED : 199801 DATA ITEMS CITED : 11 MOLECULAR FORMULA : C22-H29-N7-O5.2Cl-H MOLECULAR WEIGHT : 544.50 WISWESSER LINE NOTATION : T56 BN DN FN HNJ IN1&1 D- BT5OTJ CQ DMVYZ1R DO1& E1Q &GH HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 720 mg/kg TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 580 mg/kg TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 335 mg/kg TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 600 mg/kg TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain Behavioral - muscle weakness TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 287 mg/kg TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain Behavioral - muscle weakness TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 202 mg/kg TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain Behavioral - muscle weakness TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 1 gm/kg/10D-I TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 150 mg/kg/3D-I TOXIC EFFECTS : Gastrointestinal - nausea or vomiting Related to Chronic Data - death TYPE OF TEST : DNA inhibition TYPE OF TEST : Mutation test systems - not otherwise specified MUTATION DATA TEST SYSTEM : Rodent - mouse DOSE/DURATION : 100 mg/kg REFERENCE : FOBLAN Folia Biologica (Prague). (Academic Press Inc. Ltd., 24-28 Oval Rd., London NW1 7DX, UK) V.1- 1955- Volume(issue)/page/year: 21,60,1975

安全

• 符号: GHS07
• 信号词: Warning
• 危害声明: H302
• 个人防护装备: Eyeshields;Faceshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)
• 危害码 (欧洲): Xn
• 风险声明 (欧洲): R22
• 安全声明 (欧洲): S36
• 危险品运输编码: UN 3249
• WGK德国: 3
• RTECS号: AU7355000
• 包装等级: III
• 危险类别: 6.1(b)

制备

由白色链球菌（Streptomyces.alboniger）发酵制得。