1,1,2-三甲基-3-(4-硫代丁基)苯并[e]吲哚鎓内盐 | 63149-24-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,1,2-三甲基-3-(4-硫代丁基)苯并[e]吲哚鎓内盐
• 中文别名: 1,1,2-三甲基-3-(4-磺酸丁基)-1H-苯并[e]吲哚鎓氢氧化物；1,1,2-三甲基-3-(4-硫代丁基)苯并[e]吲哚,内盐；1,1,2-三甲基-3-(4-磺酸丁基)-1H-苯并[E]吲哚内盐
• 英文名称: 4-(1,1,2-trimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonate
• 英文别名: 4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate；2,3,3-trimethyl-1-(sulfobutyl)-4,5-benzoindolium inner salt；2,3,3-trimethyl-1-(4-sulfobutyl)-4,5-benzoindolium；4-(1,1,2-trimethyl-1H-3λ⁴-benzo[e]indol-3-yl)butane-1-sulfonate；1,1,2-Trimethyl-3-(4-sulphonatobutyl)-1H-benz(e)indolium；4-(1,1,2-trimethylbenzo[e]indol-3-ium-3-yl)butane-1-sulfonate
• CAS: 63149-24-6
• 化学式: C₁₉H₂₃NO₃S
• 分子量: 345.463
• InChiKey: GJCURKVOCXJAIV-UHFFFAOYSA-N

物化性质

• 熔点：
  274-278 °C
• 密度：
  1.344-1.358g/cm3 at 20℃
• 溶解度：
  可溶于氯仿（轻微，超声处理）、DMSO（轻微）、甲醇（轻微）
• LogP：
  -0.9 at 20℃ and pH7
• 稳定性/保质期：

  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 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：
  请将贮藏器密封，并将其放入一个紧密封装的容器中。储存时应选择阴凉、干燥的地方。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1,1,2-Trimethyl-3-(4-sulfobutyl)benz[e]indolium,
inner salt
CAS-No. : 63149-24-6

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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
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 1-(4-Sulfobutyl)-2,3,3-trimethyl-4,5-benzindolium,inner salt
1,1,2-Trimethyl-3-(4-sulfobutyl)-1H-benz[e]indolium hydroxide,inner salt
Formula : C19H23NO3S
Molecular Weight : 345,46 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), Sulphur oxides
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.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.
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
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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 245 - 258 °C
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
and is applicable to the product with regard to appropriate safety precautions. It does not represent any

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,1,2-三甲基-3-(4-硫代丁基)苯并[e]吲哚鎓内盐 在 发烟硫酸 作用下， 以 硝基苯 为溶剂， 反应 48.0h， 以46%的产率得到3-(4-sulfobutyl)-1,1,2-trimethyl-1H-sulfobenzo[e]indole
  参考文献：
  名称：

  Cyanine Dyes as Optical Contrast Agents for Ophthalmological Surgery

  摘要：

  Cyanine dyes were prepared as optical contrast media for supporting the surgery of the lamina limitans interna (LLI) of the retina and other structures of the human eye. Their absorption spectra were adapted both to the spectral sensitivity of the human eye and to standard illumination. The contrast could be further amplified by the application of the strong fluorescence of the dyes used. The binding of the dyes to various surfaces was studied. No toxic effects could be detected for the applied dyes.

  DOI：

  10.1021/jm2001986
• 作为产物：
  描述：

  Pentamethylene sulfone 、 1,1,2-三甲基苯-1H-苯并[e]吲哚 生成 1,1,2-三甲基-3-(4-硫代丁基)苯并[e]吲哚鎓内盐
  参考文献：
  名称：

  Visible Diode Laser-Induced Fluorescence Detection in Liquid Chromatography after Precolumn Derivatization of Amines

  摘要：

  To fully exploit the attractive visible diode laser-induced fluorescence (LIF) detection technique in column liquid chromatography (LC), covalent labeling procedures need to be developed which are compatible with near-infrared fluorescence. For this purpose, several red-absorbing labels containing a single succinimidyl ester functionality were synthesized and used for the derivatization of primary and secondary amines. Oxazines/thiazines, squaraines, and dicarbocyanines were examined as red-absorbing fluorophores. The quality of the LC-diode LIF system for the analytes concerned is illustrated by the concentration detection limit of the labeled n-octylamine (a test compound), which was as low as 2 x 10(-12) M. As expected in view of the limited reactivity of the succinimidyl ester group, the analyte concentrations required to obtain quantitative reaction with the label were equal to or higher than 2 x 10(-8) M. To show the applicability of the method to biological samples, urine was spiked with 5 x 10(-7) M. 1-adamantanamine, extracted, derivatized with a dicarbocyanine-based label, and analyzed by LC-diode LIF.

  DOI：

  10.1021/ac00106a015

文献信息

• [EN] INTERMEDIATE COMPOUNDS FOR THE PREPARATION OF MESO-SUBSTITUTED CYANINE, MEROCYANINE AND OXONOLE DYES<br/>[FR] COMPOSÉS INTERMÉDIAIRES POUR LA PRÉPARATION DE COLORANTS DE TYPE CYANINES, MÉROCYANINES ET OXONOLES MÉSO-SUBSTITUÉES
  申请人：AGFA GRAPHICS NV

  公开号：WO2009080689A1

  公开（公告）日：2009-07-02

  The present invention provides new intermediate compounds enabling the preparation of N-meso substituted cyanine, merocyanine or oxonole dyes wherein the N-meso substituent comprises electron withdrawing groups and wherein such N-meso substituents are introduced at the intermediate level. These intermediates enable the formation of dyes having in the meso-position N-substituents comprising electron withdrawing groups without the need for further derivatization of the meso-substituent at the dye level.

  本发明提供了新的中间化合物，使得能够制备N-间位取代的青菁、美洛青或氧酮染料，其中N-间位取代基包括电子吸引基团，并且这种N-间位取代基在中间级别引入。这些中间体使得能够形成在间位具有N-取代基的染料，这些取代基包括电子吸引基团，而无需在染料级别进一步对间位取代基进行衍生化。
• 异烟肼－吲哚七甲川菁偶联化合物及其制备 方法和应用
  申请人：沈阳药科大学

  公开号：CN111072635B

  公开（公告）日：2021-06-11

  本发明属于医药技术领域，涉及一类异烟肼－吲哚七甲川菁偶联化合物及其制备和应用，本发明采用拼合原理，将异烟肼与具有优良的体内荧光成像特性及肿瘤靶向功能的吲哚七甲川菁染料经腙键连接，设计得到新型的靶向肿瘤的异烟肼‑吲哚七甲川菁异烟肼偶联化合物，其结构式如式(I)‑(III)所示，其中，R1，R2，R3，R4，m，n如权利要求书和说明书所述。体外肿瘤细胞生长抑制试验证明该类化合物对前列腺肿瘤细胞具有良好的抑制效果。单胺氧化酶抑制活性测试试验表明该类化合物对单胺氧化酶A具有适中的抑制作用，均明显强于异烟肼。
• Synthetic probes for in vitro purification and in vivo tracking of hepatocytes derived from human pluripotent stem cells
  作者：Ji Young Park、Jiyou Han、Hyo Sung Jung、Gyunggyu Lee、Hyo Jin Kim、Gun-Sik Cho、Han-Jin Park、Choongseong Han、Jong Seung Kim、Jong-Hoon Kim

  DOI：10.1016/j.biomaterials.2019.119431

  日期：2019.11

  Hepatocytes derived from human pluripotent stem cells (hPSCs) are promising candidates for cell therapy and drug discovery. However, it remains challenging to efficiently purify hepatocytes from undesired cell types after differentiation and to accurately monitor grafted cells after transplantation. Indocyanine Green (ICG), an FDA-approved, near-infrared (NIR) dye, has been used for various clinical

  源自人类多能干细胞（hPSC）的肝细胞有望用于细胞治疗和药物开发。然而，在分化后从不期望的细胞类型中有效纯化肝细胞以及在移植后准确地监测移植的细胞仍然具有挑战性。吲哚菁绿（ICG）是FDA批准的近红外（NIR）染料，已用于各种临床目的，并且仅被肝细胞吸收。但是，ICG的发射波长长（λEM  > 800 nm），超出了荧光激活细胞分选（FACS）系统的检测范围。此外，它很容易从肝细胞中清除，从而阻碍了其在近红外成像中的应用。在这里，我们根据ICG的特性设计和合成了两种不同的探针。1）肝细胞净化剂（HPA， λ EM  = 562纳米），用于体外排序和2）肝细胞成像剂（HIA， λ EM  = 817 nm）的为高效的体内NIR成像。我们使用基于HPA探针的FACS纯化从各种hPSC系中获得了高度富集的hPSC衍生肝细胞（hPSC-HePS）群体。此外，通过HIA标记和NIR成像，可以直接观察
• Protein triggered fluorescence switching of near-infrared emitting nanoparticles for contrast-enhanced imaging
  作者：Ragini Jetty、Yuriy P. Bandera、Michael A. Daniele、David Hanor、Hsin-I. Hung、Venkat Ramshesh、Megan F. Duperreault、Anna-Liisa Nieminen、John J. Lemasters、Stephen H. Foulger

  DOI：10.1039/c3tb20681e

  日期：——

  Sub-100 nm colloidal particles which are surface-functionalized with multiple environmentally-sensitive moieties have the potential to combine imaging, early detection, and the treatment of cancer with a single type of long-circulating “nanodevice”. Deep tissue imaging is achievable through the development of particles which are surface-modified with fluorophores that operate in the near-infrared (NIR) spectrum and where the fluorophore's signal can be maximized by “turning-on” the fluorescence only in the targeted tissue. We present a general approach for the synthesis of NIR emitting nanoparticles that exhibit a protein triggered activation/deactivation of the emission. Dispersing the particles into an aqueous solution, such as phosphate buffered saline (PBS), resulted in an aggregation of the hydrophobic fluorophores and a cessation of emission. The emission can be reinstated, or activated, by the conversion of the surface-attached fluorophores from an aggregate to a monomeric species with the addition of an albumin. This activated probe can be deactivated and returned to a quenched state by a simple tryptic digestion of the albumin. The methodology for emission switching offers a path to maximize the signal from the typically weak quantum yield inherent in NIR fluorophores.

  表面功能化具有多种环境敏感基团的亚100纳米胶体粒子，具有将成像、早期检测与治疗癌症结合在一种长循环"纳米装置"中的潜力。通过开发表面修饰有近红外（NIR）光谱范围内工作的荧光团的粒子，并仅在目标组织中"开启"荧光，可以实现深层组织的成像。我们提出了一种合成NIR发射纳米粒子的通用方法，这些纳米粒子表现出由蛋白质触发的激发/失活。将这些粒子分散在磷酸盐缓冲盐水（PBS）等水溶液中，会导致疏水性荧光团的聚集和发射停止。通过添加白蛋白，将表面附着的荧光团从聚集态转变为单体，可以恢复或激活发射。通过简单的胰蛋白酶消化白蛋白，可以使这种激活的探针失活并返回到淬灭状态。发射开关的方法提供了一条途径，以最大化来自NIR荧光团固有的通常较弱的量子产量的信号。
• Near-infrared bis(indolium heptamethine cyanine) dyes with a spacer derived from oligo(ethylene glycol)
  作者：Ewa Wolinska、Maged Henary、Ekaterina Paliakov、Lucjan Strekowski

  DOI：10.1002/jhet.171

  日期：2009.9

  Synthesis of a series of near-infrared dimeric dyes is presented. The intramolecular dimers contain two chromophores linked with a conformationally flexible ether or oligoether bridge. Optical properties of the dyes are discussed. J. Heterocyclic Chem., (2009).

  介绍了一系列近红外二聚体染料的合成。分子内二聚体包含两个与构象柔性的醚或寡醚桥连接的生色团。讨论了染料的光学性质。J.杂环化​​学，（2009）。