3',5'-双乙酰基-5-碘-脱氧尿苷 | 1956-30-5

• 物质功能分类: 生物化工 - 核苷类药物 - 脱氧核苷酸及其类似物
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 3',5'-双乙酰基-5-碘-脱氧尿苷
• 中文别名: 3,5-二乙酰基-5-碘-2-脱氧尿苷；3',5'-二-O-乙酰基-5-碘-2'-脱氧尿苷；3,5-双乙酰基-5-碘代-2-脱氧尿苷
• 英文名称: 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine
• 英文别名: 3',5'-di-O-acetyl-5-iodo-2'-deoxyuridine；3',5'-di-O-acetyl-2'-deoxy-5-iodouridine；5-iodo-3',5'-di-O-acetyl-2'-deoxyuridine；3′,5′-di-O-acetyl-5-iodo-2′-deoxyuridine；2'-Deoxy-5-iodouridine 3',5'-diacetate；[(2R,3S,5R)-3-acetyloxy-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 1956-30-5
• 化学式: C₁₃H₁₅IN₂O₇
• 分子量: 438.176
• InChiKey: LVDYIZDWXVFTQG-HBNTYKKESA-N

物化性质

• 熔点：
  161-163 °C
• 密度：
  1.81
• 稳定性/保质期：
  常温常压下保持稳定，应避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 安全说明：
  S24/25
• 海关编码：
  29389090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封储存，存放在阴凉干燥的库房中。冷藏时温度应保持在-20°C。

SDS

Name:	3 5 -Diacetyl-5-Iodo-2 -Deoxyuridine 99+% Material Safety Data Sheet
Synonym:	None known
CAS:	1956-30-5

Section 1 - Chemical Product MSDS Name:3 5 -Diacetyl-5-Iodo-2 -Deoxyuridine 99+% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1956-30-5	3',5'-Diacetyl-5-Iodo-2'-Deoxyuridine	99+	217-799-9

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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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. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:

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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.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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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. Deep freeze (below -20C).

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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# 1956-30-5: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 161.00 - 163.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C13H15IN2O7
Molecular Weight: 438.16

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen iodide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1956-30-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3',5'-Diacetyl-5-Iodo-2'-Deoxyuridine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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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.

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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# 1956-30-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1956-30-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1956-30-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3',5'-双乙酰基-5-碘-脱氧尿苷 在 potassium fluoride 、 copper(l) iodide 、 氨 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.5h， 生成 三氟胸苷
  参考文献：
  名称：

  Radiosynthesis of the anticancer nucleoside analogue Trifluridine using an automated ¹⁸F-trifluoromethylation procedure

  摘要：

  自动化的¹⁸F-三氟甲基化提供了首个[¹⁸F]三氟胸苷的放射合成，该化合物显示出作用机制的PET探针潜力。

  DOI：

  10.1039/c8ob00432c
• 作为产物：
  描述：

  2-脱氧尿苷 在 吡啶 、 ammonium cerium (IV) nitrate 、 碘 作用下， 以 乙腈 为溶剂， 反应 25.0h， 生成 3',5'-双乙酰基-5-碘-脱氧尿苷
  参考文献：
  名称：

  5-Iodo-4-thio-2′-Deoxyuridine as a Sensitizer of X-ray Induced Cancer Cell Killing

  摘要：

  核苷，尤其是在C5位置改性的嘧啶，可以通过其酶促三磷酸化、纳入DNA和随后的解离性电子附着（DEA）过程作为放射增敏剂。在本文中，我们报告5-碘-4-硫-2'-脱氧尿嘧啶（ISdU）是一种可以有效引起电离辐射（IR）诱导的细胞死亡的化合物，这已通过克隆形成实验证明。测试显示，预处理10或100微米ISdU溶液并暴露于0.5格雷（Gy）IR的细胞的存活率从未经处理的培养基的78.4％降至67.7％和59.8％。对于稍高的1 Gy剂量，存活率从68.2％降至分别为54.9％和40.8％的10或100微米ISdU孵育。组蛋白H2A.X磷酸化的细胞学分析表明，ISdU的放射增敏效应至少部分与双链断裂的形成有关。此外，对MCF-7乳腺癌细胞系和人类皮肤成纤维细胞（HDFa系）的细胞毒性测试证实了ISdU的低细胞毒性活性。根据ISdU的稳态辐解和量子化学计算的结果，解释了MS检测到的放射性产物的起源，提出了ISdU的增敏分子机制。总之，我们发现ISdU是一种潜在的放射增敏剂，可以改善抗癌放射治疗。

  DOI：

  10.3390/ijms20061308
• 作为试剂：
  描述：

  2-(4-bromo-benzylidenamino)-phenol 在 氢氧化钾 、 copper(l) iodide 、 四(三苯基膦)钯 、 二苯并-18-冠醚-6 、 碘苯二乙酸 、 3',5'-双乙酰基-5-碘-脱氧尿苷 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 36.0h， 生成 1,4-bis<4-(2-benzoxazolyl)phenyl>butadiyne-1,3
  参考文献：
  名称：

  Malakhova; Malakhov; Kuznitsova, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 9, p. 611 - 617

  摘要：

  DOI：

文献信息

• SYNTHESIS OF 5-(2,2′-BIPYRIDINYL AND 2,2′-BIPYRIDINEDIIUMYL)-2′-DEOXYURIDINE NUCLEOSIDES: PRECURSORS TO METALLO-DNA CONJUGATES
  作者：Samir T. Gaballah、Charles E. Kerr、Bruce E. Eaton、Thomas L. Netzel

  DOI：10.1081/ncn-120015068

  日期：2002.11

  The synthesis of 2,2'-bipyridinyl-2'-deoxyuridine metal-chelator nucleosides (Bipy-dU) with either ethynyl or ethylenyl linkers was now been accomplished. These new nucleosides will permit the construction of a number of corresponding metallo-DNA conjugates where many types of metals can be complexed to the 2,2'-bipyridinyl chelator group and the resulting metallo-dU conjugates incorporated into DNA

  现在已经完成了具有乙炔基或乙烯基连接基的2,2'-联吡啶基-2'-脱氧尿苷金属螯合剂核苷（Bipy-dU）的合成。这些新的核苷将允许构建许多相应的金属-DNA缀合物，其中许多类型的金属可与2,2'-联吡啶基螯合剂基团络合，并将所得的金属-dU缀合物掺入DNA寡核苷酸。此外，本文还报道了带有乙烯基连接基的二-N-烷基化联吡啶二鎓-2'-脱氧尿苷核苷（Bipy（2 +）-dU）的合成。发现Bipy（2 +）-dU核苷在基本条件下会分解，从而阻止了其在通过亚磷酰胺方法进行的标准自动DNA合成中的使用。对于此处报道用作金属螯合剂的两个Bipy-dU核苷没有此类限制。
• Systematic assignment of NMR spectra of 5-substituted-4-thiopyrimidine nucleosides
  作者：Xiaohui Zhang、Jian Wang、Yao-Zhong Xu

  DOI：10.1002/mrc.3980

  日期：2013.9

  characterization of 5‐substituted‐4‐thiopyrimidine nucleosides (ribonucleosides and 2'‐deoxynucleosides) was performed using NMR spectroscopy. Assignments of all proton and carbon signals of 5‐bromo‐4‐thiouridine and related nucleosides were systematically carried out and firmly established by COSY and HMQC techniques. The NMR data of various 4‐thiopyrimidine nucleosides are compared, and the key contributing

  使用 NMR 光谱对 5-取代-4-硫代嘧啶核苷（核糖核苷和 2'-脱氧核苷）进行明确表征。5-溴-4-硫尿苷和相关核苷的所有质子和碳信号的分配是通过 COZY 和 HMQC 技术系统地进行并牢固建立的。比较了各种 4-硫代嘧啶核苷的 NMR 数据，并讨论了关键影响因素。这里介绍的方法适用于其他修饰的核苷和核苷酸，以及核碱基。版权所有 © 2013 John Wiley & Sons, Ltd.
• Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction
  作者：Renata Kaczmarek、Dariusz Korczyński、James R Green、Roman Dembinski

  DOI：10.3762/bjoc.16.1

  日期：——

  Dicobalt hexacarbonyl nucleoside complexes of propargyl ether or esters of 5-substituted uridines react with diverse C-nucleophiles. Synthetic outcomes confirmed that the Nicholas reaction can be carried out in a nucleoside presence, leading to a divergent synthesis of novel metallo-nucleosides enriched with alkene, arene, arylketo, and heterocyclic functions, in the deoxy and ribo series.

  炔丙基醚或5-取代的尿苷的酯的二钴六羰基核苷络合物与各种C-亲核试剂反应。合成结果证实，尼古拉斯反应可在核苷存在下进行，从而导致脱氧和核糖系列中富含烯烃，芳烃，芳基酮和杂环功能的新型金属核苷的发散合成。
• Development of ethynyl-2′-deoxyuridine chemical probes for cell proliferation
  作者：Carrie J. Lovitt、David H. Hilko、Vicky M. Avery、Sally-Ann Poulsen

  DOI：10.1016/j.bmc.2016.07.021

  日期：2016.9

  A common method of evaluating cellular proliferation is to label DNA with chemical probes. 5-Ethynyl-2'-deoxyuridine (EdU) is a widely utilized chemical probe for labeling DNA, and upon incorporation, EdU treatment of cells is followed by a reaction with a small molecule fluorescent azide to allow detection. The limitations when using EdU include cytotoxicity and a reliance on nucleoside active transport

  评估细胞增殖的常用方法是用化学探针标记DNA。5-乙炔基-2'-脱氧尿苷（EdU）是一种广泛使用的用于标记DNA的化学探针，掺入后，对细胞进行EdU处理后，会与小分子叠氮化物进行反应以进行检测。使用EdU的局限性包括细胞毒性和对进入细胞的核苷主动转运机制的依赖。在这里，我们开发了六种新颖的EdU前标签，它们由用可变的亲脂性酰基酯部分修饰的EdU组成。这种前标签：化学探针关系与在药物化学中广泛使用的前药：药物关系相似。评估了EdU和EdU前标记的标记功效和细胞毒性。几种EdU前标记类似物以与EdU相似的水平掺入DNA，这表明前标记可以绕过核苷转运蛋白。与EdU相比，这些EdU前标签的毒性也有所降低。
• Studies on organic fluorine compounds. Part 35. Trifluoromethylation of pyrimidine- and purine-nucleosides with trifluoromethyl–copper complex
  作者：Yoshiro Kobayashi、Kenjiro Yamamoto、Toyohira Asai、Masanori Nakano、Itsumaro Kumadaki

  DOI：10.1039/p19800002755

  日期：——

  Halogenated nucleoside derivatives were trifluoromethylated using a solution of a trifluoromethyl–copper complex, which was prepared by shaking trifluoromethyl iodide and copper powder in hexamethylphosphoric triamide and filtering off the excess of copper powder. The following trifluoromethylated nucleosides were obtained in moderate to good yields: 5-trifluoromethyl-uridine, -deoxyuridine, -cytidine

  使用三氟甲基-铜络合物的溶液将卤代的核苷衍生物进行三氟甲基化，该溶液是通过将三氟甲基碘和铜粉在六甲基磷酸三酰胺中振摇并滤出过量的铜粉而制得的。以中等至良好的产率获得以下三氟甲基化的核苷：5-三氟甲基-尿苷，-脱氧尿苷，-胞苷，-脱氧胞苷和-阿拉伯糖基胞嘧啶；8-三氟甲基-腺苷，-脱氧腺苷和-肌苷；和6-三氟甲基核呋喃呋喃糖基嘌呤。该程序提供了许多三氟甲基化合物的简单合成方法。