23051-44-7

Usage

Uses

Used in Cancer Treatment:
(3 5 5-TRIMETHYLCYCLOHEX-2-ENYLIDENE)MALONITRILE is used as a cytotoxic agent for its potential anti-cancer properties. It interferes with the microtubule network and disrupts cell division, making it a promising candidate for cancer treatment.
Used in Anti-inflammatory Applications:
(3 5 5-TRIMETHYLCYCLOHEX-2-ENYLIDENE)MALONITRILE is used as an anti-inflammatory agent due to its ability to exhibit anti-inflammatory activities, which can be beneficial in treating various inflammatory conditions.
Used in Antioxidant Applications:
(3 5 5-TRIMETHYLCYCLOHEX-2-ENYLIDENE)MALONITRILE is used as an antioxidant agent because of its anti-oxidant activities, which can help protect cells from oxidative damage and contribute to overall health and well-being.

InChI:InChI=1/C12H14N2/c1-9-4-10(11(7-13)8-14)6-12(2,3)5-9/h4H,5-6H2,1-3H3

Upstream product

• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 109-77-3 malononitrile 

Downstream Products

• 61681-27-4 [5,5-dimethyl-3-(3-methyl-thiazolidin-2-ylidenemethyl)-cyclohex-2-enylidene]-malononitrile 
• 122071-05-0 [3-(1-ethyl-1H-[4]chinolyLiDenemethyl)-5,5-dimethyl-cyclohex-2-enylidene]-malononitrile 
• 114986-62-8 [3-(1,3-diethyl-1,3-dihydro-benzoimidazol-2-ylidenemethyl)-5,5-dimethyl-cyclohex-2-enylidene]-malononitrile 
• 1219686-65-3 2,2'-(3,3'-(1E,1'E)-2,2'-(4,4'-(hexylazanediyl)bis(4,1-phenylene))bis(ethene-2,1-diyl)bis(5,5-dimethylcyclohex-2-en-3-yl-1-ylidene))dimalononitrile 
• 27334-35-6 2-{3-[(E)-2-(1H-Indol-3-yl)-vinyl]-5,5-dimethyl-cyclohex-2-enylidene}-malononitrile 
• 1367361-17-8 C₃₁H₂₉N₅ 
• 27334-24-3 (2-(3-(4-hydroxystyryl)-5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile) 
• 27334-19-6 2-[5,5-Dimethyl-3-((E)-styryl)-cyclohex-2-enylidene]-malononitrile 
• 27334-25-4 C₂₀H₂₀N₂O 
• 27374-64-7 2-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-5,5-dimethyl-cyclohex-2-enylidene}-malononitrile 
• 296778-76-2 C₂₁H₂₂N₂O₂ 
• 27334-26-5 3-(dicyanomethylene)-5,5-dimethyl-1-(4-dimethylamino-styryl) cyclohexene 
• 1428149-23-8 (E)-2-(3-(4-(1H-imidazole-1-yl)styryl)-5,5-dimethylcyclohexo-2-enylidene) malononitrile 
• 1521270-54-1 [Ag((E)-2-(3-(4-(1H-imidazol-1-yl)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile)2]NO₃ 

Relevant academic research and scientific papers

Synthesis of a water soluble red fluorescent dye and its application to living cells imaging

Abstract A water soluble red fluorescent dye (TD-mPEG750) has been prepared by treatment of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile with 4-(diethylamino)-2-mPEG benzaldehyde (mPEG-OH, average MW = 750). TD-mPEG750 exhibits red emission at λem = 664 nm in water, a small fluorescence quantum yield (Pdblf = 0.01) and a large Stoke's shift (Δλ = 145 nm) are obtained. Using HeLa cells as prototype, the application of TD-mPEG750 to living cells imaging has been investigated. It is found that TD-mPEG750 can be clearly expressed in mitochondria with high contrast in HeLa cells imaging.

An ICT-based ratiometric fluorescent probe for cysteine and its application in biological issues

As a biothiol in human body, cysteine (Cys) is related to many diseases. To specifically monitor the level of Cys, a ratiometric fluorescent probe (DDEA) with a large Stokes shift (186 nm) was developed. Due to the excellent spectral performance and stabl

A novel dicyanoisophorone-based ratiometric fluorescent probe for selective detection of cysteine and its bioimaging application in living cells

A selective and ratiometric turn-on fluorescent probe was designed and synthesized by using a novel dicyanoisophorone-based derivative and acrylate moiety. The probe displayed high stability and good selectivity to cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH). It also exhibited rapid response to Cys within 180 s. Most importantly, the fluorescence intensity ratio at 590 and 525 nm (I590/I525) was linearly dependent on the Cys concentration in the range from 0 to 40 μM and the detection limit calculated to be 0.48 μM. This probe was also applied for bioimaging of intracellular Cys in living HeLa cells with low cytotoxicity.

Development of a new ratiometric probe with near-infrared fluorescence and a large Stokes shift for detection of gasotransmitter CO in living cells

A near-infrared (NIR) ratiometric fluorescent probe, NIR-Ratio-CO, was developed for rapid detection of carbon monoxide (CO) in both solution and living cells through the strategy of Pd0-mediated Tsuji-Trost reaction. This probe shows a rapid,

Monitoring of Au(III) species in plants using a selective fluorescent probe

A colorimetric and ratiometric probe with a push-pull chromophore dicyanoisophorone system, AuP, has been developed for the detection of Au(iii) species with highly sensitive and selective response to real-water samples and living tissues of Arabidopsis thaliana.

A novel isophorone-based red-emitting/NIR probe for thiophenol and its application in real water sample and vivo

Fast, highly selective and sensitive thiophenol probes are highly desirable in the field of bioimaging and environmental monitoring. For that, based on the mechanism that thiophenol can effectively cleave the sulfonamide bond selectively, we herein report a dicyanoisophorone-based Red-emitting/NIR probe for thiophenol detection. This probe had some desirable properties such as rapid response, high selectivity and sensitivity, remarkable large Stokes shift (181 nm), Red-emitting/NIR fluorescence region and low LOD value (80 nM, according to 3σ/s). Moreover, this novel Red-emitting/NIR probe can potentially be applied to the detection of thiophenols in real water samples quantitatively and fluorescent imaging in living cells and zebrafishes.

Aminopeptidase N Activatable Fluorescent Probe for Tracking Metastatic Cancer and Image-Guided Surgery via in Situ Spraying

The recurrence of malignant tumors is mostly caused by incompleted surgical resection. Especially, it is difficult for surgeons to detect and accurately remove metastatic tumors by predominantly using visual examination and palpation owing to the lack of effective means to specifically distinguish the boundary range between normal and tumor tissues. Thus, the development of activated fluorescent probe with superior tumor-to-normal (T/N) tissue ratios is particularly urgent in clinics. In view of CD13/aminopeptidase N (APN) regarded as a cancer-specific biomarker, mediating with progression, invasion, and migration of malignant tumor, herein, we reported an APN-responsive fluorescent probe YH-APN and demonstrated its application to distinguish cancer cells. Through in situ spraying manner, fluorescent superior tumor-to-normal (T/N) tissue ratios (subcutaneous transplantation tumor, 13.86; hepatic metastasis, 4.42 and 6.25; splenic metastasis, 4.99) were achieved. More importantly, we have demonstrated the ability to image metastasis tumor tissue less than 1 mm in diameter, highlighting the potential for this probe to be used as a tool in surgical resection. This research may spur the use of enzyme-activatable fluorescent probes for the progress of tumor diagnosis and image-guided surgery (IGS).

Isophorone-based aldehyde for “ratiometric” detection of cyanide by hampering ESIPT

A new red-emitting fluorescent materials (EP1) has been designed by taking consideration of the typical asymmetrical π-conjugation structure of the isophorone skeleton, which showed a special nucleophilicity for cyanide ion. The novel probe EP1 using an i

A NIR fluorescent sensor for biothiols based on a dicyanoisophorone derivative with a large Stokes shift and high quantum yield

Herein, a NIR fluorescent probe N-Bio was developed for the effective detection of biothiols by exploiting a dicyanoisophorone derivative (N-OH) as the fluorophore and a thiol-responsive 2,4-dinitro-benzenesulfonyl (DNBS) group as the recognition group. T

High contrast off-on fluorescence photo-switching: Via copper ion recognition, trans - Cis isomerization and ring closure of a thiosemicarbazide Schiff base

An easily available triphenylamine-isophorone-based Schiff base was synthesized and its specifically triple-addressable molecular photo-switching behaviour via copper ion recognition, trans-cis isomerization and ring closure were investigated in detail. F