5-羧基四甲基罗丹明琥珀酰亚胺酯 | 150810-68-7

• 物质功能分类: 生物化工 - 生化试剂 - 荧光成像
• 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-羧基四甲基罗丹明琥珀酰亚胺酯
• 中文别名: 5-羧基四甲基罗丹明琥珀酰亚胺脂
• 英文名称: 5-carboxytetramethylrhodamine succinimidyl ester
• 英文别名: 5-carboxy-tetramethylrhodamine N-succinimidyl ester；5-TAMRA SE；TAMRA-NHS ester；5-TAMRA-NHS；2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]-5-(2,5-dioxopyrrolidin-1-yl)oxycarbonylbenzoate
• CAS: 150810-68-7
• 化学式: C₂₉H₂₅N₃O₇
• 分子量: 527.533
• InChiKey: VWFRSNKRTNUMET-UHFFFAOYSA-N

物化性质

• 溶解度：
  在DMF中可溶

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• WGK Germany：
  3
• 海关编码：
  32049010
• 储存条件：
  20°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 5-Carboxy-tetramethylrhodamine N-succinimidyl
ester
CAS-No. : 150810-68-7
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
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 4-Carboxytetramethylrhodamine N-succinimidyl ester
5-TAMRA
Formula : C29H25N3O7
Molecular Weight : 527,52 g/mol

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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
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 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.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
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
Product is sensitive to light and moisture. Light sensitive. Store under inert gas. Moisture sensitive.
Specific end uses
no data available

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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
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
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.
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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: dark violet
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) Evaporation 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) Autoignition 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
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

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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 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
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
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
no data available
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.

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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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

生物活性方面，5-TAMRA-SE是一种胺反应型的荧光标记物，其偶联产物能够发出明亮、pH不敏感的橙红色荧光，并且具有良好的光稳定性。

用途：该试剂可用作指示剂/显色剂/染色剂（黄色）。

反应信息

• 作为反应物：
  描述：

  5-羧基四甲基罗丹明琥珀酰亚胺酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 5-[(2-aminoethyl)carbamoyl]-2-[6-(dimethylamino)-3-(dimethyliminiumyl)-3H-xanthen-9-yl]benzoate trifluoroacetic acid
  参考文献：
  名称：

  TCO CONJUGATES AND METHODS FOR DELIVERY OF THERAPEUTIC AGENTS

  摘要：

  本发明提供了一种方法，通过将生物相容性固体支撑物植入患者并与第一结合剂连接，以及将与治疗或诊断剂连接的第二结合剂注入患者，从而实现对靶器官或组织的选择性输送治疗或诊断剂，使治疗或诊断剂在靶器官或组织中积累。

  公开号：

  US20170087258A1
• 作为产物：
  描述：

  偏苯三酸酐 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 5-羧基四甲基罗丹明琥珀酰亚胺酯
  参考文献：
  名称：

  Native Semisynthesis of Isopeptide-Linked Substrates for Specificity Analysis of Deubiquitinases and Ubl Proteases

  摘要：

  DOI：

  10.1021/jacs.3c04062

文献信息

• Development of Photoswitchable Fluorescent Molecules Using Arylazopyrazole
  作者：Kenji Torii、Yuichiro Hori、Keiichiro Watabe、Kazuya Kikuchi

  DOI：10.1246/bcsj.20200077

  日期：2020.7.15

  Photoswitchable fluorescent molecules (PSFMs) are important tools for fluorescence imaging of biomolecules. To date, PSFMs have been applied for pulse-chase experiments and super-resolution imaging. However, most have limitations in that their fluorophores have low photostability or require cytotoxic additives. Here, we have developed PSFMs using a photochromic compound, arylazopyrazole, to overcome these limitations. These molecules showed reversible changes in fluorescence intensity upon photoirradiation and high photostability in aqueous solutions.

  光控荧光分子（Photoswitchable fluorescent molecules，简称PSFMs）是生物分子荧光成像的重要工具。迄今为止，PSFMs已被应用于脉冲追踪实验和超分辨率成像。然而，大多数此类分子存在局限性，其荧光团的光稳定性较低，或需要细胞毒性添加剂。在此，我们利用光致变色化合物——芳基偶氮吡唑开发了新型PSFMs，以克服这些局限。这些分子在光照下表现出可逆的荧光强度变化，在水中展现出高度的光稳定性。
• Structure and Biosynthesis of Crocagins: Polycyclic Posttranslationally Modified Ribosomal Peptides from<i>Chondromyces crocatus</i>
  作者：Konrad Viehrig、Frank Surup、Carsten Volz、Jennifer Herrmann、Antoine Abou Fayad、Sebastian Adam、Jesko Köhnke、Dirk Trauner、Rolf Müller

  DOI：10.1002/anie.201612640

  日期：2017.6.19

  Chondromyces crocatus Cm c5, resulted in the isolation and structure elucidation of crocagins, which are novel polycyclic peptides containing a tetrahydropyrrolo[2,3‐b]indole core. The gene cluster was identified through an approach combining genome analysis, targeted gene inactivation in the producer, and in vitro experiments. Based on our findings, we developed a biosynthetic scheme for crocagin biosynthesis

  天然产物的粘菌多生产者中的次生代谢组挖掘工作，就是Chondromyces crocatus Cm c5，导致了crocagins的分离和结构解析，crocagins是含有四氢吡咯并[2,3-b]吲哚核的新型多环肽。通过将基因组分析，生产者中的靶向基因灭活和体外实验相结合的方法，鉴定了基因簇。根据我们的发现，我们开发了一种用于crocagin生物合成的生物合成方案。这些天然产物是由前体肽的三个C末端氨基酸形成的，因此属于核糖体合成和翻译后修饰的肽（RiPPs）的新型类别。我们证明了crocagin A与碳储存调节蛋白CsrA结合，
• Design and synthesis of novel fluorescently labeled analogs of vemurafenib targeting MKK4
  作者：Theresa Kircher、Tatu Pantsar、Andreas Oder、Jens Peter von Kries、Michael Juchum、Bent Pfaffenrot、Philip Kloevekorn、Wolfgang Albrecht、Roland Selig、Stefan Laufer

  DOI：10.1016/j.ejmech.2020.112901

  日期：2021.1

  diseases. Fluorescently labeled compounds are useful tools for high-throughput screenings of large compound libraries. Here we utilized the azaindole-based scaffold of FDA-approved BRAF inhibitor vemurafenib 1, which displays off-target activity on MKK4, as a starting point in our fluorescent compound design. Chemical variation of the scaffold and optimization led to a selection of fluorescent 5-TAMRA

  有丝分裂原活化的蛋白激酶激酶4（MKK4）在肝脏再生中起关键作用，并且正在作为刺激肝细胞增加增殖的靶标进行研究。因此，新的抑制MKK4的小分子可能代表治疗急性和慢性肝病的有前途的方法。荧光标记的化合物是用于大型化合物库的高通量筛选的有用工具。在这里，我们利用了FDA批准的BRAF抑制剂vemurafenib 1的基于氮杂吲哚的支架，该支架对MKK4表现出脱靶活性，以此作为我们荧光化合物设计的起点。支架的化学变化和优化导致选择了在MKK4上具有高结合亲和力的荧光5-TAMRA衍生物。化合物45 代表一种合适的工具化合物，用于荧光偏振测定法以鉴定新的MKK4小分子抑制剂。
• 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] BIOORTHOGONAL COMPOSITIONS<br/>[FR] COMPOSITIONS BIO-ORTHOGONALES
  申请人：SHASQI INC

  公开号：WO2017044983A1

  公开（公告）日：2017-03-16

  The present disclosure provides bioorthogonal compositions for delivering agents in a subject. The disclosure also provides methods of producing the compositions, as well as methods of using the same.

  本公开提供了用于在受试者中传递药剂的生物正交组合物。该公开还提供了生产这些组合物的方法，以及使用相同的方法。