56289-67-9

Usage

Uses

Used in Organic Synthesis:
2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-1,3,3-TRIMETHYL-2 H-INDOL-2-YLIDENE) ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-1,3,3-TRIMETHYLINDOLIUM IODIDE is used as a key intermediate in organic synthesis for the development of new compounds with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-1,3,3-TRIMETHYL-2 H-INDOL-2-YLIDENE) ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-1,3,3-TRIMETHYLINDOLIUM IODIDE is utilized as a starting material or a building block for the synthesis of novel drug candidates. Its unique structure and potential biological activity make it a valuable component in the discovery and development of new therapeutic agents.
It is important to handle and use 2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-1,3,3-TRIMETHYL-2 H-INDOL-2-YLIDENE) ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-1,3,3-TRIMETHYLINDOLIUM IODIDE with caution due to its potentially hazardous nature. Proper safety measures should be taken during its synthesis, storage, and application to minimize any risks associated with its use.

InChI:InChI=1/C32H36ClN2.HI/c1-31(2)24-14-7-9-16-26(24)34(5)28(31)20-18-22-12-11-13-23(30(22)33)19-21-29-32(3,4)25-15-8-10-17-27(25)35(29)6;/h7-10,14-21H,11-13H2,1-6H3;1H/q+1;/p-1

Upstream product

• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 63857-00-1 N-<5-anilino-3-chloro-2,4-(propane-1',3'-diyl)-2,4-pentadien-1-ylidene>anilinium chloride 
• 61010-04-6 2-chloro-1-formyl-3-hydroxymethylenecyclohexene 
• 108-94-1 cyclohexanone 
• 63857-00-1 N-[(3-(anilinomethylene)-2-chloro-1-cyclohexen-1-yl)methylene]aniline hydrochloride 
• 1640-39-7 2,3,3-trimethylindoleniune 
• 100-63-0 phenylhydrazine 
• 563-80-4 3-methyl-butan-2-one 
• 110-82-7 cyclohexane 
• 1100982-61-3 2-chloro-1-formyl-3-hydroxymethylenecyclohexane 
• 118-12-7 1,3,3-Trimethyl-2-methyleneindoline 

Downstream Products

• 1421748-63-1 C₄₂H₄₉N₄⁽¹⁺⁾*I^(1-) 

Relevant academic research and scientific papers

ALP-activated probe for diagnosis of liver injury by multispectral optoacoustic tomography

In this chapter, we highlight the advantages of multispectral optoacoustic tomography (MSOT) technique and the activatable photoacoustic probes in the biomedical field, and give a brief introduction to enzyme-activated probes for disease diagnosis and therapeutic outcome evaluation. We also present a detailed description of the procedures for the synthesis of an activatable small molecule probe C1X-OR1 and confirmation of its specific response to alkaline phosphatase in solution and cells. With MSOT, the liposomal C1X-OR1 can be utilized for detection of hepatic ALP as well as for in vivo diagnosis of drug-induced liver injury in a three-dimensional manner.

The synthesis of a novel Crizotinib heptamethine cyanine dye conjugate that potentiates the cytostatic and cytotoxic effects of Crizotinib in patient-derived glioblastoma cell lines

We describe the synthesis of drug-dye conjugate 1 between anaplastic lymphoma kinase inhibitor Crizotinib and heptamethine cyanine dye IR-786. The drug-dye conjugate 1 was evaluated in three different patient-derived glioblastoma cell lines and showed pot

Optimized Fluorescent Probe for Specific Imaging of Glutathione S-Transferases in Living Cells and Mice

GSTP1 has been considered to be a marker for malignancy in many tissues. However, the existing GST fluorescent probes are unfavorable for in vivo imaging because of the limited emission wavelength or insufficient fluorescence enhancement (six-fold). The limited fluorescence enhancement of GST fluorescent probes is mainly ascribed to the high background signals resulting from the spontaneous reaction between GSH and the probes. In this work, a highly specific GST probe with NIR emission has been successfully developed through optimization of the essential unit of the probe to repress the spontaneous reaction. The novel GST probe exhibits over 100-fold fluorescence enhancement upon incubation with GSTP1/GSH and high selectivity over other potential interference. In addition, the probe has been proved to be capable of tracking endogenous GST in A549 cells. Finally, the in vivo imaging results demonstrate that the probe can be used for effective imaging of endogenous GST activity in subcutaneous tumor mouse with high contrast.

A novel fibroblast activation protein-targeted near-infrared fluorescent off-on probe for cancer cell detection, in vitro and in vivo imaging

A new hemicyanine-based fibroblast activation protein-targeted near-infrared fluorescent probe is designed and it shows high selectivity and sensitivity to cancer cell detection, and in vitro and in vivo imaging. This probe is successfully applied in fluorescence detection of living cells (with a detection limit of 1500 cells per mL). It is believed that many new functions or distributions of FAP could be discovered by this new probe later.

Substitution nitrogen for chlorine of heptamethine cyanines for large Stokes shift fluorescent probes

On the basis of syntheses of three heptamethine indocyanines with methyl, ethyl, or p-carboxybenzyl groups on N atoms in the indole rings, nine novel aminoderivatives were designed and synthesized by butylamine, taurine, or benzylamine reacting with the indocyanines for substitution nitrogen for chlorine. The obtained products were purified by SiO2 column chromatography, and confirmed by ESI-MS and 1H NMR. Compared to the parents, the aminoderivatives showed blue shifts, larger Stokes shifts, and stronger fluorescence intensity, which were mainly related to the electron-donating ability of the amino substituents in the aminoderivatives. The stronger electron-donating ability of the amino substituents made the maximum absorption wavelengths show greater blue shifts.

A near-infrared and colorimetric fluorescent probe for palladium detection and bioimaging

A near-infrared (NIR) and colorimetric fluorescent probe was developed for palladium species via a palladium catalyzed deallylation reaction. In this probe, 6-hydroxy-2,3-dihydro-xanthene-indolium (CyH) was acted as the signal unit and an allyl carbonate group was acted as the recognition unit. This non-fluorescent probe molecule can release the relevant fluorophore after interaction with palladium. The sensing mechanism was investigated by optical spectrum and NMR spectra. The probe can be used for “naked-eye” detection of palladium, and exhibited high selectivity to palladium over various other metal ions. Furthermore, the probe can be applied to imaging intracellular palladium ions in living HeLa cells, indicating its great potential for in vivo bioanalytical applications.

A NIR fluorescent probe for the detection of fluoride ions and its application in in vivo bioimaging

A novel near-infrared (NIR) fluorescent probe for the detection of fluoride ions has been developed, which is based on the F-triggered cleavage reaction of the Si-O bond. This probe exhibits excellent selectivity and sensitivity towards fluoride ions. The results of bioimaging experiments with HepG2 cells and mice show that the fluoride probe is available for visualizing exogenous fluoride ions in vitro and in vivo.

Synthesis, molecular docking calculation, fluorescence and bioimaging of mitochondria-targeted ratiometric fluorescent probes for sensing hypochloritein vivo

Mitochondria are the main sites for the production of hypochlorite (OCl?). The protein adenine nucleotide translocase (ANT) is located in the inner mitochondria membrane, which is mainly participated in the transportation of ions and metabolites. At the cellular organelle level, overexpression of ANT is associated with enhanced production of OCl?, however, abnormal levels of OCl?cause redox imbalance and loss of function of mitochondria. Herein, a novel mitochondria-targeted ratiometric fluorescent probeMi-OCl-RPhas been developed. Molecular docking calculation suggested a potential molecular target for the probe in the ANT, and the high binding energy (?8.58 kcal mol?1) may explain the high mitochondria selectivity ofMi-OCl-RP. The unique probe exhibits excellent spectral properties including ratiometric fluorescence response signals to OCl?(within 7 s), high selectivity and sensitivity, and a large Stokes shift (278 nm). In addition, the colocalization coefficient confirms thatMi-OCl-RPcan effectively target mitochondria. Furthermore,Mi-OCl-RPhas low toxicity and good permeability, and was successfully employed in ratiometric imaging of OCl?in vivo, affording a robust molecular tool for investigating the biological functions of OCl?in living systems.

A “turn-on” near-infrared fluorescent probe with high sensitivity for detecting reduced glutathione based on red shift in vitro and in vivo

Fluorescence imaging has become a powerful tool for detecting reduced glutathione (GSH) to comprehend the physiological and pathological roles of GSH and the potential clinical diagnosis of GSH-related diseases, such as AIDS, liver damage, cancer, and leu

Near infrared ratio fluorescent probe for detecting nitroreductase as well as preparation method and application thereof (by machine translation)

The invention discloses a novel near-infrared ratio fluorescent probe for detecting nitroreductase and a preparation method thereof as well as a, preparation method of :2, 3, 3 - the novel near-infrared ratio fluorescence 1, 2, 3, 3 - probe; Vilsmeier 2 - 1, 2, 3, 3 - 2 - 2 - [2 - [2 -)] - 1 -]] - 1, 3, 3 - 2 - [2 - [2 -)] - 1 -]] - 1, 3, 3 . (by machine translation)