4-Cyanoindole
(Synonyms: 4-氰基吲哚) 目录号 : GC42368
Synthetic intermediate
Cas No.:16136-52-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
4-Cyanoindole is a synthetic intermediate useful for pharmaceutical synthesis.
| Cas No. | 16136-52-0 | SDF | |
| 别名 | 4-氰基吲哚 | ||
| Canonical SMILES | N#CC1=CC=CC2=C1C=CN2 | ||
| 分子式 | C9H6N2 | 分子量 | 142.2 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 7.0323 mL | 35.1617 mL | 70.3235 mL |
| 5 mM | 1.4065 mL | 7.0323 mL | 14.0647 mL |
| 10 mM | 0.7032 mL | 3.5162 mL | 7.0323 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Synthesis of 4-Cyanoindole Nucleosides, 4-Cyanoindole-2'-Deoxyribonucleoside-5'-Triphosphate (4CIN-TP), and Enzymatic Incorporation of 4CIN-TP into DNA
Curr Protoc Nucleic Acid Chem 2020 Mar;80(1):e101.PMID:31909864DOI:10.1002/cpnc.101.
4-Cyanoindole-2'-deoxyribonucleoside (4CIN) is a fluorescent isomorphic nucleoside analogue with superior spectroscopic properties in terms of Stokes shift and quantum yield in comparison to the widely utilized isomorphic nucleoside analogue, 2-aminopurine-2'-deoxyribonucleoside (2APN). Notably, when inserted into single- or double-stranded DNA, 4CIN experiences substantially less in-strand fluorescence quenching compared to 2APN. Given the utility of these properties for a spectrum of research applications involving oligonucleotides and oligonucleotide-protein interactions (e.g., enzymatic processes, DNA hybridization, DNA damage), we envision that additional reagents based on 4-Cyanoindole nucleosides may be widely utilized. This protocol expands on the previously published synthesis of 4CIN to include synthetic routes to both 4-cyanoindole-ribonucleoside (4CINr) and 4-cyanoindole-2'-deoxyribonucleoside-5'-triphosphate (4CIN-TP), as well as a method for the enzymatic incorporation of 4CIN-TP into DNA by a polymerase. These methods are anticipated to further enable the utilization of 4CIN in diverse applications involving DNA and RNA oligonucleotides. © 2020 by John Wiley & Sons, Inc. Basic Protocol 1: Synthesis of 4-cyanoindole-2'-deoxyribonucleoside (4CIN) and 4CIN phosphoramidite 4 Basic Protocol 2: Synthesis of 4-cyanoindole-ribonucleoside (4CINr) Basic Protocol 3: Synthesis of 4-cyanoindole-2'-deoxyribonucleoside-5'-triphosphate (4CIN-TP) Basic Protocol 4: Steady state incorporation kinetics of 2AP-TP and 4CIN-TP by a DNA polymerase.
4-Cyanoindole-2'-deoxyribonucleoside as a Dual Fluorescence and Infrared Probe of DNA Structure and Dynamics
Molecules 2019 Feb 8;24(3):602.PMID:30744004DOI:10.3390/molecules24030602.
Unnatural nucleosides possessing unique spectroscopic properties that mimic natural nucleobases in both size and chemical structure are ideally suited for spectroscopic measurements of DNA/RNA structure and dynamics in a site-specific manner. However, such unnatural nucleosides are scarce, which prompts us to explore the utility of a recently found unnatural nucleoside, 4-cyanoindole-2'-deoxyribonucleoside (4CNI-NS), as a site-specific spectroscopic probe of DNA. A recent study revealed that 4CNI-NS is a universal nucleobase that maintains the high fluorescence quantum yield of 4-Cyanoindole and that among the four natural nucleobases, only guanine can significantly quench its fluorescence. Herein, we further show that the C≡N stretching frequency of 4CNI-NS is sensitive to the local environment, making it a useful site-specific infrared probe of oligonucleotides. In addition, we demonstrate that the fluorescence-quencher pair formed by 4CNI-NS and guanine can be used to quantitatively assess the binding affinity of a single-stranded DNA to the protein system of interest via fluorescence spectroscopy, among other applications. We believe that this fluorescence binding assay is especially useful as its potentiality allows high-throughput screening of DNA⁻protein interactions.
Solvent Dependence of Cyanoindole Fluorescence Lifetime
Chem Phys Lett 2017 Oct 1;685:133-138.PMID:29225366DOI:10.1016/j.cplett.2017.07.038.
Several cyanotryptophans have been shown to be useful biological fluorophores. However, how their fluorescence lifetimes vary with solvent has not been examined. In this regard, herein we measure the fluorescence decay kinetics as well as the absorption and emission spectra of six cyanoindoles in different solvents. In particular, we find, among other results, that only 4-Cyanoindole affords a long fluorescence lifetime and hence high quantum yield in H2O. Therefore, our measurements provide not only a guide for choosing which cyanotryptophan to use in practice but also data for computational modeling of the substitution effect on the electronic transitions of indole.
Structures, dipole moments and excited state lifetime of isolated 4-Cyanoindole in its ground and lowest electronically excited singlet states
Phys Chem Chem Phys 2019 Jul 10;21(27):14766-14774.PMID:31222195DOI:10.1039/c9cp01618j.
The rotationally resolved electronic spectrum of 4-Cyanoindole and some N-D and C-D deuterated isotopologues has been measured and analyzed. Dipole moments in the ground and electronically excited state have been determined, using electronic Stark spectroscopy. From the geometry changes upon excitation, orientation of the transition dipole moment, and the values for the permanent dipole moments, the lowest excited singlet state could be shown to be of La symmetry. The excited state lifetime of isolated 4-Cyanoindole has been determined to be 11 ns, while for the ringdeuterated isotopologues lifetimes between 5 and 6 ns have been found. The different behavior of 3-, 4-, and 5-cyanoindole is discussed on the basis of the different electronic nature of the electronically excited singlet states.
Theoretical Investigation of Positional Substitution and Solvent Effects on n-Cyanoindole Fluorescent Probes
J Phys Chem B 2019 Aug 29;123(34):7424-7435.PMID:31373821DOI:10.1021/acs.jpcb.9b05961.
The absorption and fluorescence of indole and n-cyanoindole derivatives are modeled in the gas phase and aqueous solution using high-level quantum mechanical methods and implicit solvation. These molecules have been experimentally examined as fluorescent probes for studying the structure, function, and hydration status of proteins and it is found that substitution of the cyano group on different positions of indole has diverse effects on the absorption and fluorescence spectra in water solvent. Our calculations predict that in absorption the Lb excited state is lower in energy than the La state for all positional isomers in the gas phase and in solution. In fluorescence, however, water solvent causes level inversion leading to emission from the La excited state for indole and n-cyanoindole derivatives with the cyano on the six-membered ring. However, when cyano substitution is on the five-membered ring, La is not stabilized enough and emission occurs from the Lb excited state. In addition, we predict that the relatively high fluorescence intensity of 4-Cyanoindole in aqueous solution results from minimization of radiationless decay pathways since both absorption and fluorescence occur from the lowest excited state (unlike the other derivatives).