61010-04-6

Usage

Uses

Used in Pharmaceutical Industry:
2-chloro-3-(hydroxyMethylene)cyclohex-1-enecarbaldehyde is used as a synthetic intermediate for the development of new drugs. Its ability to react with multiple functional groups allows for the creation of a wide range of bioactive molecules, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Agrochemical Industry:
In the agrochemical sector, 2-chloro-3-(hydroxyMethylene)cyclohex-1-enecarbaldehyde serves as a building block for the synthesis of complex organic compounds with potential applications in agriculture. Its versatility in organic synthesis aids in the development of innovative agricultural products, such as pesticides and other crop protection agents.
Used as a Reagent in Organic Synthesis:
2-chloro-3-(hydroxyMethylene)cyclohex-1-enecarbaldehyde is utilized as a reagent in organic synthesis due to its reactivity with various functional groups. This property makes it valuable for the preparation of complex organic compounds, which can be further used in different industries, including pharmaceuticals and agrochemicals, for the development of new products.

Upstream product

• 4394-85-8 4-morpholinecarboxaldehyde 
• 108-94-1 cyclohexanone 
• 127685-40-9 Chlormethylendiethylammoniumion 
• 90732-56-2 4-Chloromethylene-morpholin-4-ium 
• 75-09-2 dichloromethane 
• 4224-70-8 6-bromohexanoic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 110-83-8 cyclohexene 

Downstream Products

• 1196490-92-2 C₂₇H₃₁ClNO⁽¹⁺⁾*I^(1-) 
• 1196491-02-7 C₂₇H₃₀ClNO₄S 
• 1196490-98-8 C₂₃H₂₈ClNO₄S 
• 1196490-88-6 C₂₃H₂₉ClNO⁽¹⁺⁾*I^(1-) 
• 207399-07-3 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide 
• 1255954-17-6 C₄₅H₅₅N₄O⁽¹⁺⁾*I^(1-) 
• 1313374-54-7 C₅₁H₇₁N₄O₃⁽¹⁺⁾*Cl^(1-) 
• 1313374-55-8 C₅₀H₆₉N₄O₃⁽¹⁺⁾*Cl^(1-) 
• 1313513-58-4 CyNE₇₉₀ 
• 1316211-08-1 Br^(1-)*C₄₁H₅₃ClN₃O₂⁽¹⁺⁾ 
• 1316211-06-9 BrH*Br^(1-)*C₃₆H₄₅ClN₃⁽¹⁺⁾ 
• 1391582-09-4 C₄₀H₄₇ClN₂O₄ 
• 1391582-11-8 C₄₂H₅₁ClN₂O₄ 
• 213621-37-5 C₄₀H₄₅Cl₃N₂O₄ 

Relevant academic research and scientific papers

Monitoring pancreatic carcinogenesis by the molecular imaging of Cathepsin E in vivo using confocal laser endomicroscopy

The monitoring of pancreatic ductal adenocarcinoma (PDAC) in high-risk populations is essential. Cathepsin E (CTSE) is specifically and highly expressed in PDAC and pancreatic intraepithelial neoplasias (PanINs), and its expression gradually increases alo

Integration of Indocyanine Green Analogs as Near-Infrared Fluorescent Carrier for Precise Imaging-Guided Gene Delivery

Codelivery of diagnostic probes and therapeutic molecules often suffers from intrinsic complexity and premature leakage from or degradation of the nanocarrier. Inspired by the “Y” shape of indocyanine green (ICG), the dye is integrated in an amphiphilic lipopeptide (RNF). The hydrophilic segment is composed of arginine-rich dendritic peptides, while cyanine dyes are modified with two long carbon chains and employed as the hydrophobic moiety. They are linked through a disulfide linkage to improve the responsivity in the tumor microenvironment. After formulation with other lipopeptides at an optimized ratio, the theranostic system (RNS-2) forms lipid-based nanoparticles with slight positive zeta potential enabling efficient condensation of DNA. The RNS-2 displays glutathione responded gene release, activatable fluorescence recovery, and up to sevenfold higher in vitro transfection than Lipofectamine 2000. Compared with a Cy3 and Cy5 labeled fluorescence resonance energy transfer indicator for gene release, the “turn-on” indocyanine green analogs exhibit longer emission wavelength and better positive correlation with the dynamic processes of gene delivery. More importantly, the RNS-2 system enables efficient near infrared imaging guided gene transfer in tumor-bearing mice and thus provides more precise and accurate information on location of the cargo gene and synthesized carriers.

Dual Channel Activatable Cyanine Dye for Mitochondrial Imaging and Mitochondria-Targeted Cancer Theranostics

Because mitochondria are the key regulators for many cellular behaviors and are susceptible to hyperthermia and reactive oxygen species, mitochondria-specific reagents for simultaneous targeting, imaging, and treatment are highly desirable in cancer theranostics. Herein, we developed a mitochondria-targeted cyanine dye IR825-Cl, which possesses two separated excitation wavelength channels for both red fluorescence imaging and near-infrared (NIR) photothermal therapy (PTT). For imaging, IR825-Cl rapidly entered cells and selectively targeted mitochondria. Although IR825-Cl was completely quenched in water, interestingly, this dye had a turn-on response of red fluorescence (610 nm) in mitochondria under 552 nm excitation due to its polarity-responsive fluorescence emission. More interestingly, IR825-Cl realized the selective mitochondrial staining of cancer cells over normal cells and thus served as an ideal fluorescent probe for identifying cancer cells in normal tissues, which is extremely beneficial for cancer theranostics. For PTT, we demonstrated that under 808 nm NIR laser irradiation, this dye efficiently converted optical energy into heat, realizing mitochondria-targeted photothermal cancer therapy. Collectively, this molecule realized both high fluorescence emission (quantum yield > 43%) and effective light-to-heat conversion (17.4%), enabling its applications for wash-free fluorescence imaging for mitochondria and highly efficient fluorescence imaging-guided PTT.

A Vilsmeier Chloroformylation by Continuous Flow Chemistry

Chloroformylation reactions are versatile reactions that allow the introduction of a chlorine atom and an aldehyde group in enolizable ketones, employing the well-known Vilsmeier reagent. However, the use of this unstable reagent is usually associated with hazards, especially when it is used on an industrial scale. The present article describes the preparation and use of the Vilsmeier reagent under continuous flow conditions for the preparation of an important intermediate in the synthesis of cyanine dyes. In addition, the traditionally used dimethylformamide has been substituted with more desirable formamides, together with the removal of the halogenated solvent usually employed in the reaction. Consequently, the optimized conditions allow the continuous production of the target compound in a 79-81% isolated yield in a more environmentally friendly, fast, and secure manner.

A hemicyanine derivative for near-infrared imaging of β-amyloid plaques in Alzheimer's disease

The formation of amyloid-β (Aβ) plaques in the brain is one of the main pathological features of Alzheimer's disease (AD). The imaging probes, capable of detecting Aβ deposition, are important tools for early diagnosis of AD. In this article, we designed, synthesized and evaluated a cyanine-based near-infrared fluorescence (NIRF) probe ZT-1 for the detection of Aβ deposits in the brain. The probe had excellent fluorescent properties with an emission maximum above 720 nm upon binding to Aβ aggregates with affinity of 445.0 nM (Kd). Furthermore, ZT-1 exhibited good biostability, photostability, and binding selectivity toward Aβ1-42 aggregates by in vitro fluorescence staining experiments. In vivo NIRF imaging result also revealed that our probe could efficiently differentiate transgenic and wild-type mice. All these studies indicated that ZT-1 is a promising fluorescent probe for Aβ plaques in the AD brains.

A bimodal MRI and NIR liposome nanoprobe for tumor targeted molecular imaging

The combination of complementary MRI and NIR imaging methods evolved to provide an even more powerful bioimaging tool. Herein, a novel bimodal MRI/NIR nanoprobe GCF-HDA was prepared via a facile self-assembly approach of three types of amphiphilic structures in aqueous solution. The Stokes shift of the NIR moiety increased from 30 to 150 nm and fluorescence quantum yield increased from 1.5 to 8% after conjugation with electron-rich hexadecylamine (HDA) to organic dye Cy7. The photostability of the nanoprobe GCF-HDA was dramatically improved after involving the newly synthesized dye. Molecular dynamics simulation demonstrated that the GCF-HDA is composed of 2.0-3.5 nm clusters and in each cluster the head groups of the amphiphilic molecules assemble together and the tail groups point outwards. The r1 and r2 relaxivities of GCF-HDA were found to be 11.87 and 19.91 mM-1 s-1 per Gd(iii) chelate at 0.5 T, respectively. In vitro cellular imaging with human glioma U-87 MG cells showed that the GCF-HDA was able to enter the cells and accumulate in the cytoplasm. The targeted GCF-HDA resulted in higher MR contrast enhancement and stronger fluorescence intensity than the corresponding non-targeted probe GC-HDA in the tumor tissue 96 hours post injection. Ex vivo fluorescence imaging and histological analysis of the tumor tissue further confirmed the specific binding ability of the GCF-HDA.

Intratumorally Injected Photothermal Agent-Loaded Photodynamic Nanocarriers for Ablation of Orthotopic Melanoma and Breast Cancer

Traditional chemotherapy of cancers may lead to serious adverse reactions due to little drug distribution in tumors. Here, a combination of photothermal therapy (PTT) and photodynamic therapy (PDT) was used for local treatment of orthotopic melanoma and breast cancer via intratumoral (i.t.) injection of photothermal agent-loaded photodynamic nanocarriers. A hydrophobic derivative of indocyanine green, DCC, was synthesized and entrapped into a pH-sensitive photosensitizer-core copolymer, PDCZP, to form DCC@PDCZP. The nanocarriers showed remarkable fluorescence, high singlet oxygen quantum yields, and a strong photothermal effect. Flow cytometry suggested that the nanocarriers were efficiently internalized by cancer cells. Near infrared thermal imaging and fluorescence self-imaging showed that the i.t. injected DCC@PDCZP mainly remained in the tumors, but the intravenous (i.v.) nanocarriers were distributed a little. One i.t. injection of DCC@PDCZP was enough to ablate the orthotopic B16-F10 and 4T1 mouse tumors under 830 and 660 nm irradiation at 4 h postinjection. More importantly, no local recurrences were found, though swabs were formed at 9 days post-treatment. The major anticancer mechanisms included improvement of cancer cell necrosis due to hyperthermia, inhibition of neovascularization, and enhancement of cell apoptosis. The i.t. injection of PTT/PDT nanoformulations is thus a promising local treatment of superficial tumors.

Lysosome-specific sensing and imaging of pH variations in vitro and in vivo utilizing a near-infrared boron complex

As a focus issue, the study of lysosomal pH has attracted much attention as it is closely associated with the state of lysosome, which plays a vital role in endocytosis and autophagy. In order to investigate the lysosomal pH, fluorescence bioimaging is one of the most widely-explored approaches. Unfortunately, the probes are insufficient to absorb or emit in the near-infrared (NIR) region, which could minimize photodamage to organisms and maximize tissue penetration in living systems. As a novel family of NIR dyes, hemicyanine has been selected for NIR bioimaging and biosensing owing to its excellent optical properties, easy preparation and good biocompatibility. Employing a classic rhodamine-hemicyanine hybrid, we first designed and synthesized a NIR boron complex (HCy-BIZ-BF2) with lysosome-targeting and pH-sensing properties. It is worth mentioning that after HCy-BIZ was coordinated with boron fluoride, HCy-BIZ-BF2 exhibited an improved photostability as well as an enlarged Stokes shift, and was subsequently applied to monitor the lysosomal pH in cells stimulated with chloroquine. Further investigation of pH changes in mice illustrated that HCy-BIZ-BF2 performed well in detecting the pH in living organisms. Therefore, this concept of boron complex derived from hemicyanine is not only applicable in pH detection, but also conducive for preparing promising novel NIR bioprobes and obtaining precise measurements of physiological parameters in specific physiological processes.

A lysosome-Targeting dual-functional fluorescent probe for imaging intracellular viscosity and beta-Amyloid

A lysosome-Targeting dual-functional fluorescent probe was rationally designed and developed for imaging intracellular lysosomal viscosity and beta-Amyloid. More importantly, the real-Time tracking of the dynamic movement of lysosomes, as vesicle structures, has been achieved using Lyso-MC.

Controlling Coagulation in Blood with Red Light

Precise control of blood clotting and rapid reversal of anticoagulation are essential in many clinical situations. We were successful in modifying a thrombin-binding aptamer with a red-light photocleavable linker derived from Cy7 by Cu-catalyzed Click chemistry. We were able to show that we can successfully deactivate the modified aptamer with red light (660 nm) even in human blood—restoring the blood's natural coagulation capability.