5-羧基二乙酰化荧光素琥珀酰亚胺酯 | 150206-05-6

• 物质功能分类: 催化剂及助剂 - 荧光增白剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 5-羧基二乙酰化荧光素琥珀酰亚胺酯
• 英文名称: 5-carboxyfluoresceindiacetate N-succinimidyl ester
• 英文别名: 5-carboxyfluorescein diacetate N-hydroxysuccinimide ester；carboxyfluorescein succinimidyl amino ester；CFSE；5-CFDA N-succinimidyl ester；(2,5-dioxopyrrolidin-1-yl) 3',6'-diacetyloxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylate
• CAS: 150206-05-6
• 化学式: C₂₉H₁₉NO₁₁
• 分子量: 557.47
• InChiKey: SRSXVRUMXPCNAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C(lit.)
• 沸点：
  757.9±70.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

安全信息

• 危险品标志：
  T
• 安全说明：
  S22,S26,S36/37/39,S45,S53
• 危险类别码：
  R23/24/25,R45,R36/37/38,R46
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20℃，惰性气体

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 5-Carboxy-fluorescein diacetate N-succinimidyl
ester
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 150206-05-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: 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
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 5-Carboxy-di-O-acetylfluorescein N-succinimidyl ester
Formula : C29H19NO11
Molecular Weight : 557,46 g/mol
CAS-No. : 150206-05-6
No components need to be disclosed according to the applicable regulations.

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SECTION 4: 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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: 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

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
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.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
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
Store under inert gas. Moisture sensitive.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: 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.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone], test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
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).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: light yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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SECTION 11: 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 sensitisation
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
Additional Information
RTECS: Not available

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SECTION 12: 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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

---

SECTION 14: 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: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用广泛的是5-羧基二乙酰化荧光素琥珀酰亚胺酯，它不仅可用作有机合成中的重要中间体，还能在医药领域中发挥关键作用，支持实验室研发及医药化工产品的合成。

反应信息

• 作为反应物：
  描述：

  5-羧基二乙酰化荧光素琥珀酰亚胺酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  通过过氧化氢反应标记对细胞和组织中氧化条件下的蛋白质进行成像和分析

  摘要：

  过氧化氢 (H2O2) 等活性氧 (ROS) 可在氧化应激下对生物分子造成损害，并在生理水平上充当信号分子。在这里，我们开发了一种独特的化学工具，使用荧光成像和条件蛋白质组学来阐明 ROS 的生物学作用。H2O2 反应性蛋白质标记试剂 (Hyp-L) 旨在在活细胞和组织中的氧化条件下选择性标记蛋白质。即使在样品固定后，Hyp-L 信号仍然存在，这与常规免疫染色兼容。此外，Hyp-L 允许使用条件蛋白质组学工作流程对标记蛋白质进行蛋白质组学分析。综合分析能够以亚细胞分辨率识别 ROS 生成和/或积累位点。首次，我们的特征是自噬体在活化的巨噬细胞中富含 H2O2。Hyp-L 进一步应用于小鼠脑组织，并通过条件蛋白质组学清楚地揭示了线粒体内的氧化应激。

  DOI：

  10.1021/jacs.0c02547
• 作为产物：
  描述：

  5-羧基荧光素 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-羧基二乙酰化荧光素琥珀酰亚胺酯
  参考文献：
  名称：

  分离异构体——高效合成 5 和 6-羧基荧光素二乙酸酯和 5 和 6-羧罗丹明 B 的 N-羟基琥珀酰亚胺酯

  摘要：

  5 和 6-羧基荧光素的二乙酸酯保护，然后合成N-羟基琥珀酰亚胺酯，可以在多克规模上轻松分离两种异构体。5-和6-羧基罗丹明B N-羟基琥珀酰亚胺酯也很容易合成和分离。

  DOI：

  10.1016/j.bmcl.2014.04.090

文献信息

• Bioorthogonal Imaging of Aurora Kinase A in Live Cells
  作者：Katherine S. Yang、Ghyslain Budin、Thomas Reiner、Claudio Vinegoni、Ralph Weissleder

  DOI：10.1002/anie.201200994

  日期：2012.7.2

  In living color: Aurora kinase A (AKA) was imaged in live cells using a bioorthogonal two‐step reaction with a small molecule AKA inhibitor (see scheme) and a fluorescent reporter. The fluorescent molecule was localized to spindle poles and microtubules during metaphase, consistent with the localization of both endogenous and green fluorescent protein tagged AKA. By using this approach, changes in

  活体颜色：使用小分子 AKA 抑制剂（见方案）和荧光报告基因的生物正交两步反应，在活细胞中对极光激酶 A (AKA) 进行成像。荧光分子在中期定位于纺锤体极和微管，与标记 AKA 的内源性和绿色荧光蛋白的定位一致。通过使用这种方法，还观察到了有丝分裂过程中 AKA 分布的变化。
• [EN] NEW TECHNOLOGY TO CONJUGATE THE TACCALONOLIDE MICROTUBULE STABILIZERS WITH LINKERS/PAYLOADS<br/>[FR] NOUVELLE TECHNOLOGIE POUR CONJUGUER LES STABILISATEURS TACCALONOLIDES DE MICROTUBULES AVEC DES LIEURS/CHARGES UTILES
  申请人：DU LIN

  公开号：WO2020185610A1

  公开（公告）日：2020-09-17

  The present disclosure is concerned with taccalonolide analogs and conjugated taccalonolide analogs useful as cellular probes and in the treatment of, for example, hyperproliferative disorders such as cardiovascular diseases and cancer. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本公开涉及可用作细胞探针和用于治疗高增殖性疾病，如心血管疾病和癌症的塔卡龙内酯类似物和共轭塔卡龙内酯类似物。本摘要旨在作为在特定领域搜索的扫描工具，并不意味着对本发明的限制。
• [EN] CARBOHYDRATE-MEDIATED TUMOR TARGETING<br/>[FR] CIBLAGE DE TUMEURS MÉDIÉ PAR UN HYDRATE DE CARBONE
  申请人：UNIV ARIZONA

  公开号：WO2011019419A1

  公开（公告）日：2011-02-17

  Tumors can be selectively targeted via compounds provided herein according to the formula, or a pharmaceutically acceptable salt thereof, wherein RA and RB are as defined herein. Tumors can be imaged or targeted for therapeutic treatment using compounds described herein where at least one RA or at least one RB group comprises a imaging agent, a therapeutic agent, or a member of a specific binding pair which can be associated with a secondary imaging agent, such as a microbubble for ultrasonic imaging.

  本文提供的化合物可选择性地针对肿瘤，其中根据以下公式或其药用可接受的盐，其中RA和RB如本文所定义。肿瘤可通过本文描述的化合物进行成像或靶向治疗，其中至少一个RA或至少一个RB基团包含成像剂、治疗剂或特定结合对的成员，可与次级成像剂（如用于超声成像的微泡）结合。
• Live‐Cell Protein Sulfonylation Based on Proximity‐driven <i>N</i> ‐Sulfonyl Pyridone Chemistry
  作者：Kazuya Matsuo、Yuki Nishikawa、Marie Masuda、Itaru Hamachi

  DOI：10.1002/anie.201707972

  日期：2018.1.15

  multimolecular crowding conditions of live cells is highly desirable for the analysis and engineering of proteins without using genetic manipulation. N‐Sulfonyl pyridone (SP) is reported as a new reactive group for protein sulfonylation. The ligand‐directed SP chemistry was able to modify not only purified proteins in vitro, but also endogenous ones on the surface of and inside live cells selectively and rapidly

  在不使用基因操作的情况下，非常需要开发用于在活细胞多分子拥挤条件下标记内源蛋白的生物正交方法。据报道，N-磺酰基吡啶酮（SP）是蛋白质磺酰化的一个新的反应基团。配体导向的SP化学不仅能够在体外修饰纯化的蛋白质，而且能够选择性且快速地修饰活细胞表面和内部的内源性蛋白质，从而可以将内源性蛋白质原位转化为基于FRET的生物传感器。
• A proteomic strategy for the identification of caspase-associating proteins
  作者：Eunice L. P. Tan、Resmi C. Panicker、Grace Y. J. Chen、Shao Q. Yao

  DOI：10.1039/b415506h

  日期：——

  We report the efficient in vivo labelling of caspases expressed inside apoptotic HeLa cells using fluoromethyl ketone (fmk)-containing probes; preliminary results indicated that these probes may be used to identify caspase-associating proteins.

  我们报告了使用含氟甲基酮（fmk）探针对凋亡的 HeLa 细胞内表达的 Caspase 进行体内高效标记的情况；初步结果表明，这些探针可用于鉴定 Caspase 相关蛋白。