189232-42-6

• 常用中文名：Bohemine
• 常用英文名：Bohemine
• CAS号：189232-42-6
• 分子式：C₁₈H₂₄N₆O
• 分子量：340.423
• 相关类别： 信号通路 细胞周期/DNA损伤 CDK
• 发布时间：2016-08-21 21:24:50
• 更新时间：2024-01-04 19:42:11
• Bohemine 是一种嘌呤类似物,也是一种合成的选择性的 CDK 抑制剂,对 Cdk2/cyclin E,Cdk2/cyclin A 和 Cdk9/cyclin T1 的 IC50 分别为 4.6 μM,83 μM 和 2.7 μM。Bohemine 还抑制 ERK2,IC50 为 52 μM,对 CDK1,CDK4 和 CDK6 的抑制作用较小。Bohemine 具有广泛的抗癌活性。

名称

• 英文名: 3-[[6-(benzylamino)-9-propan-2-ylpurin-2-yl]amino]propan-1-ol
• 英文别名: purine deriv. 1; 3-{[6-(Benzylamino)-9-isopropyl-9H-purin-2-yl]amino}-1-propanol; 2-[(3-hydroxypropyl)amino]-6-benzylamino-9-isopropylpurine; HMS3229C10; 3-{[6-(benzylamino)-9-(propan-2-yl)-9H-purin-2-yl]amino}propan-1-ol; [6-Benzylamino-2-(3-hydroxypropylamino)-9-isopropylpurine; 1-Propanol, 3-[[9-(1-methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-; bohemine; 2-(3-Hydroxypropylamino)-6-benzylamino-9-isopropylpurine

物化性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 589.4±60.0 °C at 760 mmHg
• 分子式: C₁₈H₂₄N₆O
• 分子量: 340.423
• 闪点: 310.3±32.9 °C
• 精确质量: 340.201172
• PSA: 91.12000
• LogP: 1.02
• 外观性状: 白色固体
• 蒸汽压: 0.0±1.7 mmHg at 25°C
• 折射率: 1.653
• 储存条件: -20℃

生物活性

• 描述: Bohemine 是一种嘌呤类似物,也是一种合成的选择性的 CDK 抑制剂,对 Cdk2/cyclin E,Cdk2/cyclin A 和 Cdk9/cyclin T1 的 IC50 分别为 4.6 μM,83 μM 和 2.7 μM。Bohemine 还抑制 ERK2,IC50 为 52 μM,对 CDK1,CDK4 和 CDK6 的抑制作用较小。Bohemine 具有广泛的抗癌活性。
• 相关类别:
  研究领域 >> 癌症
  信号通路 >> 细胞周期/DNA损伤 >> CDK
  信号通路 >> MAPK/ERK信号通路 >> ERK
  信号通路 >> 干细胞及 Wnt 通路 >> ERK
• 靶点:

  CDK2/cyclinE:4.6 μM (IC50)

  cdk2/cyclin A:83 μM (IC50)

  CDK9/cyclinT1:2.7 μM (IC50)

  ERK2:52 μM (IC50)

• 体外研究: 波希米亚(0-30μM；72小时；ME-750细胞)处理抑制细胞生长。添加浓度在1-10μM范围内的波希米亚可导致生长和单克隆抗体生产的短期停滞。短期内细胞功能受到抑制,随后比生长率和比生产率出现显著的暂时性增长[1]。杂交瘤细胞在G1/S边界和G2/M边界都被延迟,这取决于波希米亚(0-30μM)浓度[1]。波希米治疗T淋巴细胞CEM,发现5种蛋白表达下调,分别为α烯醇化酶、磷酸三钠异构酶、起始因子5A和Rho-GDP解离抑制剂1的α和β亚基。这些蛋白质在糖酵解、蛋白质合成和细胞骨架重排中发挥着重要作用[1]。波希米亚抑制人肿瘤细胞系的生长,其IC50为27μM[2]。细胞活力测定[1]细胞系：小鼠杂交瘤ME-750细胞浓度：0μM、1μM、3μM、10μM和30μM培养时间：72小时结果：在10μM和30μM浓度下,活细胞计数与对照组相比明显降低,分别为77%和48%。
• 体内研究: 波希米亚(50mg/kg；静脉注射；BALB/c小鼠)治疗显示Cmax为72308nm,观察清除率为0.23l/h,T1/2为1.39h[2]。动物模型：荷结肠癌BALB/c小鼠26只[2]剂量：50mg/kg给药：静脉注射(药代动力学分析)结果：Cmax为72308nm,观察清除率为0.23l/h,T1/2为1.39h。
• 参考文献:

  [1]. Franek F, et al. Diverse effects of the cyclin-dependent kinase inhibitor bohemine: Concentration- and time-dependent suppression or stimulation of hybridoma culture. Cytotechnology. 2001 Jul;36(1-3):117-23.

  [2]. Raynaud FI, et al. In vitro and in vivo pharmacokinetic-pharmacodynamic relationships for the trisubstituted aminopurine cyclin-dependent kinase inhibitors olomoucine, bohemine and CYC202. Clin Cancer Res. 2005 Jul 1;11(13):4875-87.

MSDS

Section1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE Product identifiers Product name: Bohemine CAS-No.: 189232-42-6 Relevant identified uses of the substance or mixture and uses advised against Identified uses: Laboratory chemicals, Manufacture of substances Section2. HAZARDS IDENTIFICATION Classification of the substance or mixture Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008 This substance is not classified as dangerous according to Directive 67/548/EEC. Label elements Caution - substance not yet tested completely. Other hazards - none Section3. COMPOSITION/INFORMATION ON INGREDIENTS Substances Synonyms: 2-(3-Hydroxypropylamino)-6-benzylamino-9-isopropylpurine Formula: C18H24N6O Molecular Weight: 340,42 g/mol Section4. FIRST AID MEASURES Description of first aid measures If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. In case of skin contact Wash off with soap and plenty of water. In case of eye contact Flush eyes with water as a precaution. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Most important symptoms and effects, both acute and delayed Indication of any immediate medical attention and special treatment needed no data available Section5. FIREFIGHTING MEASURES Extinguishing media Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special hazards arising from the substance or mixture Carbon oxides, nitrogen oxides (NOx) Advice for firefighters Wear self contained breathing apparatus for fire fighting if necessary. Further information no data available Section6. ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions Do not let product enter drains. Methods and materials for containment and cleaning up Sweep up and shovel. Keep in suitable, closed containers for disposal. Reference to other sections For disposal see section 13. Section7. HANDLING AND STORAGE Precautions for safe handling Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire protection. Conditions for safe storage, including any incompatibilities Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: -20 °C Packaged under inert gas. Air and light sensitive. Specific end uses no data available Section8. EXPOSURE CONTROLS/PERSONAL PROTECTION Control parameters Components with workplace control parameters Exposure controls Appropriate engineering controls General industrial hygiene practice. Personal protective equipment Eye/face protection Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Body Protection Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place., The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Respiratory protection Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Section9. PHYSICAL AND CHEMICAL PROPERTIES Information on basic physical and chemical properties a) AppearanceForm: powder Colour: white b) Odourno data available c) Odour Thresholdno data available d) pHno data available e) Melting point/freezingno data available point f) Initial boiling point and no data available boiling range g) Flash pointno data available h) Evaporation rateno data available i) Flammability (solid, gas) no data available j) Upper/lowerno data available flammability or explosive limits k) Vapour pressureno data available l) Vapour densityno data available m) Relative densityno data available n) Water solubilityno data available o) Partition coefficient: n- no data available octanol/water p) Autoignitionno data available temperature q) Decompositionno data available temperature r) Viscosityno data available s) Explosive propertiesno data available t) Oxidizing propertiesno data available Other safety information no data available Section10. STABILITY AND REACTIVITY Reactivity no data available Chemical stability no data available Possibility of hazardous reactions no data available Conditions to avoid no data available Incompatible materials Strong oxidizing agents Hazardous decomposition products Other decomposition products - no data available Section11. TOXICOLOGICAL INFORMATION Information on toxicological effects Acute toxicity no data available Skin corrosion/irritation no data available Serious eye damage/eye irritation no data available Respiratory or skin sensitization no data available Germ cell mutagenicity no data available Carcinogenicity IARC:No component of this product present at levels greater than or equal to 0.1% is identified as probable, possible or confirmed human carcinogen by IARC. Reproductive toxicity no data available Specific target organ toxicity - single exposure no data available Specific target organ toxicity - repeated exposure no data available Aspiration hazard no data available Potential health effects InhalationMay be harmful if inhaled. May cause respiratory tract irritation. IngestionMay be harmful if swallowed. SkinMay be harmful if absorbed through skin. May cause skin irritation. EyesMay cause eye irritation. Additional Information RTECS: Not available Section12. ECOLOGICAL INFORMATION Toxicity no data available Persistence and degradability no data available Bioaccumulative potential no data available Mobility in soil no data available Results of PBT and vPvB assessment no data available Other adverse effects no data available Section13. DISPOSAL CONSIDERATIONS Waste treatment methods Product Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging Dispose of as unused product. Section14. TRANSPORT INFORMATION UN number ADR/RID: -IMDG: -IATA: - UN proper shipping name ADR/RID: Not dangerous goods IMDG: Not dangerous goods IATA:Not dangerous goods Transport hazard class(es) ADR/RID: -IMDG: -IATA: - Packaging group ADR/RID: -IMDG: -IATA: - Environmental hazards ADR/RID: noIMDG Marine pollutant: noIATA: no Special precautions for user no data available SECTION 15 - REGULATORY INFORMATION N/A SECTION 16 - ADDITIONAL INFORMATION N/A

安全

• 个人防护装备: Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 3
• 海关编码: 2933990090

合成路线

156-87-6 186692-41-1 ~80% 189232-42-6

文献：Institute of Experimental Botany of the Academy of Sciences of the Czech Republic Patent: US6221873 B1, 2001 ; US 6221873 B1

1175562-42-1 ~88% 189232-42-6

文献：Fletcher, Steven; Shahani, Vijay M.; Gunning, Patrick T. Tetrahedron Letters, 2009 , vol. 50, # 29 p. 4258 - 4261

10310-21-1 ~% 189232-42-6

文献：Austin, Richard E.; Okonya, John F.; Bond, Daniel R.S.; Al-Obeidi, Fahad Tetrahedron Letters, 2002 , vol. 43, # 35 p. 6169 - 6171

上下游产品

上游产品  3
156-87-6 186692-41-1 10310-21-1
下游产品  0

海关

海关编码	2933990090
中文概述	2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%