50328-50-2

Usage

Uses

Used in Biomedical Research:
MALONALDEHYDE DIANILIDE HYDROCHLORIDE is used as a precursor for creating biological probes for [application reason] high fluorescence intensity cyanine dyes. These probes are valuable in the field of biomedical research, as they can be utilized for various diagnostic and imaging purposes, enhancing the detection and analysis of biological processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, MALONALDEHYDE DIANILIDE HYDROCHLORIDE is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
MALONALDEHYDE DIANILIDE HYDROCHLORIDE is used as a synthetic building block for [application reason] the creation of a wide range of chemical compounds. Its reactivity and structural features make it a valuable component in the synthesis of various organic molecules, including dyes, pigments, and other specialty chemicals.
Used in Material Science:
In the field of material science, MALONALDEHYDE DIANILIDE HYDROCHLORIDE is used as a component in the development of advanced materials with specific properties. Its ability to form cyanine dyes with high fluorescence intensity can be exploited to create materials with enhanced optical, electronic, or sensing capabilities.

InChI:InChI=1/C15H14N2.ClH/c1-3-8-14(9-4-1)16-12-7-13-17-15-10-5-2-6-11-15;/h1-6,8-13H,7H2;1H/b16-12+,17-13+;

Upstream product

• 2581-87-5 N,N’-diphenyl-1,5-diazapenta-1,3-dienium perchlorate 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 62-53-3 aniline 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 142-04-1 aniline hydrochloride 

Downstream Products

• 41505-12-8 5-(3-anilino-allylidene)-3-ethyl-2-thioxo-thiazolidin-4-one 
• 34446-37-2 4-(acetanilido-allylidene)-1-phenyl-3-methyl pyrazolone 
• 114720-67-1 2-[4-(N-acetyl-anilino)-buta-1,3-dienyl]-4-(4-methoxy-phenyl)-3-methyl-thiazolium; iodide 
• 102594-67-2 3-benzoyl-1-methyl-5-[4-(3-methyl-3H-benzothiazol-2-ylidene)-but-2-enylidene]-2-thioxo-imidazolidin-4-one 
• 71467-45-3 2-((1E,3E)-4-(acetyl)-4-(phenyl)aminobuta-1,3-dienyl)-3-methyl-benzothiazolium iodide 
• 63468-67-7 2-[4-(N-acetyl-anilino)-buta-1,3-dienyl]-1-ethyl-quinolinium; iodide 
• 116081-83-5 2-[4-(N-acetyl-anilino)-buta-1,3-dienyl]-1,3-dimethyl-benzimidazolium; iodide 
• 67492-39-1 4-(4-anilino-buta-1,3-dienyl)-1-methyl-quinolinium; iodide 
• 18371-33-0 1,5-bis-[3-(2-hydroxy-ethyl)-benzothiazol-2-yl]-pentamethinium ; bromide 
• 17579-03-2 2-(4-dimethylamino-buta-1,3-dienyl)-3-ethyl-6-methyl-benzothiazolium; chloride 
• 84606-99-5 1-(δ-aminobutadienyl)-3phenylbenzoquinolinium methiodide 
• 84607-00-1 bis<3-phenyl-4-methylbenzoquinolin-1-yl>pentamethylidynecyanine iodide 

Relevant academic research and scientific papers

Unsymmetrical pentamethine cyanines for visualizing physiological acidities from the whole-animal to the cellular scale with pH-responsive deep-red fluorescence

Acidity plays an important role in numerous physiological and pathological events. Non-invasively monitoring pH dynamics would be valuable for understanding pathological processes and optimizing therapeutic strategies. Although numerous near-infrared (NIR) fluorophores have been developed to monitor acidification in vivo, the experimental results are difficult to verify at the molecular or cellular level using a fluorescence microscope or flow cytometer due to the lack of lasers with excitation wavelengths in the NIR wavelength range. This work presents a sequential condensation strategy for obtaining unsymmetrical pentamethine cyanines with fine-tuned pKa values and improved yields. These deep-red fluorophores with pH responsiveness can not only be used to monitor acidification in live cells using confocal microscopic imaging and flow cytometry, but they can also be used to non-invasively identify infected tissue with a low pH value in live mouse models. In addition, the acidity in infected tissue slices was verified under a conventional confocal microscope. Overall, this work demonstrates a new synthetic method with improved yields for unsymmetrical pentamethine cyanines that can report acidity. These pH-responsive deep-red fluorophores not only provide new tools for accessing pH-associated physiological and pathological events, but they can also help in understanding in vivo imaging results at the molecular or cellular level due to their detectability by multiple imaging instruments.

Ratiometric fluorescent probes for selective and sensitive visualization of bacterial microenvironment protease activity

The extracellular SspA protease of the human pathogen S. aureus is essential for evading the host immune defence system. Two novel FRET probes for selective real-time ratiometric imaging of SspA activity in live S. aureus cells are reported.

Polymethine Thiopyrylium Fluorophores with Absorption beyond 1000 nm for Biological Imaging in the Second Near-Infrared Subwindow

Small-molecule fluorescence imaging in the second near-infrared (NIR-II, 1000-1700 nm) window has gained increasing interest in clinical application. Till now, very few studies have been exploited in the small-molecule fluorophores with both excitation and emission in the NIR-II window. Inspired by the indocyanine green structure, a series of polymethine dyes with both absorption and emission in the NIR-II window have been developed for NIR-II imaging, providing the feasibility to directly compare optical imaging in the NIR-IIa (1300-1400 nm) subwindow under 1064 nm excitation with that in the NIR-II window under 808 nm excitation. The signal-background ratio and the tumor-normal tissue ratio achieved great improvement under 1064 nm excitation in the imaging of mouse blood pool and U87 glioma tumors. Our study not only introduces a broadband emission fluorophore for both NIR-II and NIR-IIa imaging, but also reveals the advantages of NIR-II excitation over NIR-I in in vivo imaging.

Easily-modified near-infrared region II organic small molecule dye and synthetic method and application thereof

The invention provides an easily-modified near-infrared region II organic small molecule dye and a synthetic method and application of the easily-modified near-infrared region II organic small molecule dye. The near-infrared region II fluorescent dye belongs to polymethenyl pyran or polymethenyl thiapyran salt organic small molecules, and is prepared by a condensation reaction of polymethenyl aniline salt with pyran or thiopyran salt. The synthetic raw materials are easy to obtain, the cost is low, the preparation process is simple, the yield is high, and large-amount synthesis can be achieved. The purpose of adjusting the fluorescence emission spectrum is achieved by changing an intramolecular polymethenyl chain and hetero atom species. The small molecule dye has the maximum emission wavelength range of 1000-1200 nm, and is high in fluorescence quantum yield, good in light stability and quite applicable to living imaging. The small molecule dye can be linked to groups with specific functions by click chemistry for a variety of bioimaging application. Near-infrared region II fluorescent living imaging achieves low background noise, strong fluorescence signal and high signal-to-noise ratio.

Aminoglycoside-based novel probes for bacterial diagnostic and therapeutic applications

Specific detection of pathogens has long been recognized as a vital strategy in the control of infectious diseases. Two novel theranostic neomycin analogs exhibit efficient targeting, labelling and killing of broad spectrum bacteria while not damaging macrophage-like cells. Furthermore, lipidated probe 2 clearly showed antibacterial activity against methicillin-resistant S. aureus.

Real time detection of ESKAPE pathogens by a nitroreductase-triggered fluorescence turn-on probe

The identification of bacterial pathogens is the critical first step in conquering infection diseases. A novel turn-on fluorescent probe for the selective sensing of nitroreductase (NTR) activity and its initial applications in rapid, real-time detection and identification of ESKAPE pathogens have been reported.

Targeting tumor hypoxia: A third generation 2-nitroimidazole-indocyanine dye-conjugate with improved fluorescent yield

Tumor hypoxia is associated with the rapid proliferation and growth of malignant tumors, and the ability to detect tumor hypoxia is important for predicting tumor response to anti-cancer treatments. We have developed a class of dye-conjugates that are related to indocyanine green (ICG, 1) to target tumor hypoxia, based on in vivo infrared fluorescence imaging using nitroimidazole moieties linked to indocyanine fluorescent dyes. We previously reported that linking 2-nitroimidazole to an indocyanine dicarboxylic acid dye derivative (2) using an ethanolamine linker (ethanolamine-2-nitroimidazole-ICG, 3), led to a dye-conjugate that gave promising results for targeting cancer hypoxia in vivo. Structural modification of the dye conjugate replaced the ethanolamine unit with a piperazineacetyl unit and led a second generation dye conjugate, piperzine-2-nitroimidazole-ICG (4). This second generation dye-conjugate showed improved targeting of tumor hypoxia when compared with 3. Based on the hypothesis that molecules with more planar and rigid structures have a higher fluorescence yield, as they could release less absorbed energy through molecular vibration or collision, we have developed a new 2-nitroimidazole ICG conjugate, 12, with two carbon atoms less in the polyene linker. Dye-conjugate 12 was prepared from our new dye (8), and coupled to 2-nitroimidazole using a piperazine linker to produce this third-generation dye-conjugate. Spectral measurements showed that the absorption/emission wavelengths of 657/670 were shifted ～100 nm from the second-generation hypoxia dye of 755/780 nm. Its fluorescence quantum yield was measured to be 0.467, which is about 5 times higher than that of 4 (0.083). In vivo experiments were conducted with balb/c mice and 12 showed more than twice the average in vivo fluorescence intensity in the tumor beyond two hours post retro-orbital injection as compared with 4. These initial results suggest that 12 may significantly improve in vivo tumor hypoxia targeting.

FLUORESCENT CYANINE-POLYAMINE DERIVATIVES AS A DIAGNOSTIC PROBE

The invention relates to fluorescent derivatives of cyanines conjugated with a polyamine group, having formula (I), or a pharmaceutically acceptable salt thereof. The invention also relates to the method for preparing said derivatives, diagnostic compositions containing same and the use thereof as a diagnostic probe for the detection of cancer tumours, in particular in vivo.

INDICYANINE DYES AND THE DERIVATIVES THEREOF FOR ANALYSING BIOLOGICAL MICROMOLECULES

The invention relates to two series of synthesised indolenine pentamethine dyes (37 compounds) comprising a reactive group in the third and fifth positions of the indolenine cycle, respectively. A method for producing, extracting and purifying the dyes and the precursors thereof, consisting in determining the absorption and fluorescence maxima, molecular extinction factors, fluorescence quantum yields, relative fluorescence effectiveness at excitation on a wavelength of 635 nm (detection of 670 nm) and 655 nm (detection of 690 nm), relative light stability and comparative sensitivity of detection of marked oligonucleotides on biochips of the claimed dyes, is disclosed. The use of the claimed dyes in the form of fluorescent marks for oligonucleotide and protein chips is also disclosed.

Vinamidinium salts as nucleophiles

2,3-Dihydro-1,4-diazepinium salts could not be aminomethylated with conventional methods, but the hydrochlorides produced with methyleniminium salts the C-Mannich-compounds. The reactivity of the substrate was mainly controlled by electronic effects of the substituents. Aminomethylation of 1,5-diazapentadienium salts occurred only if the conformations caused no steric hindrance of the β-C-atom. Methyl substituted 2,3-dihydro-1,4-diazepinium salts reacted with 1,3,5 triazine to pyrimidine anellated derivatives.