68520-00-3

Usage

InChI:InChI=1/C14H15NO/c1-10(16)11-4-5-13-9-14(15(2)3)7-6-12(13)8-11/h4-9H,1-3H3

Upstream product

• 3900-45-6 6-methoxy-2-acetylnaphthalene 
• 124-40-3 dimethyl amine 
• 3585-33-9 lithium dimethylamide 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 764-48-7 ethyleneglycol vinyl ether 
• 5043-03-8 6?bromo?N,N?dimethylnaphthalen?2?amine 
• 506-59-2 N,N-dimethylammonium chloride 
• 10441-41-5 1-(6-hydroxy-2-naphthyl)ethan-1-one 
• 7470-88-4 1-(6-aminonaphthalen-2-yl)ethanone 
• 108781-66-4 (R)-(+)-1-[2-(6-methoxynaphthyl)]ethyl acetate 
• 77301-42-9 (R)-1-(6-methoxynaphthalen-2-yl)ethanol 
• 108781-65-3 1-(6-methoxy-2-naphthyl)ethanol 
• 74-88-4 methyl iodide 
• 1189179-02-9 6-acetylnaphthalen-2-yl trifluoromethanesulfonate 

Downstream Products

• 1552301-13-9 C₂₀H₁₉N₃O₄ 
• 1552301-15-1 2-(α-(3,4-diaminophenoxy)acetyl)-6-(dimethylamino)naphthalene 
• 210832-86-3 6-bromoacetyl-2-dimethylaminonaphthalene 
• 1017610-59-1 (αS,1S)-α-[N-(1-methyl)benzyl]-β-[6'-(dimethylamino)-2'-naphthoyl]alanine 
• 5043-05-0 6-(N,N-dimethylamino)-2-naphthoic acid 

Relevant academic research and scientific papers

Structure modulation on fluorescent probes for biothiols and the reversible imaging of glutathione in living cells

The detection of small molecular biothiols (cysteine, homocysteine and glutathione) is of great importance, as they involve in a series of physiological and pathological processes and are associated with many diseases. To realize the real-time monitoring of a specific biothiol, a rapid and reversible probe is required. Therefore, three probes, namely,o-MNPy,m-MNPyandp-MNPy, with pyridine substituted α, β-unsaturated ketone as the recognition site, were reported here, and the reactivity of the recognition site was finely tuned by the connection mode of the pyridine unit. To single out the optimal one, the response performances of three probes toward each biothiol were systemically studied, taking the differences of the intracellular contents of three biothiols into account during the evaluation. Biothiols reacted with the probes through Michael addition, and results showed that the slight structural variations could affect the performances of the probes obviously.p-MNPywith the pyridine unit connected to the recognition site through thepara-position of the nitrogen atom, revealed the best sensing ability among the three probes. It demonstrated rapid response, good selectivity and sensitivity, excellent pH adaptability to Cys and GSH, and displayed reversible detection toward GSH. Finally,p-MNPywas successfully applied to track the GSH fluctuations under the oxidative stress stimulated by H2O2in living cells.

1,1-Dicyano-2-[6-(dimethylamino)naphthalen-2-yl]propene (DDNP): A solvent polarity and viscosity sensitive fluorophore for fluorescence microscopy

1,1-Dicyano-2-[6-(dimethylamino)naphthalen-2-yl]propene (II, DDNP) has been synthesized as a fluorescent dye whose intramolecular rotational relaxation is solvent polarity and viscosity dependent. Its fluorescence emission (λ max: 470-610 nm in hydrophobic and viscous environments) is in a very favorable region for its use with visible fluorescence microscopy, without interference from cell or tissue autofluorescence. Its fluorescence emission quantum yield in an aqueous environment is very low, allowing for facile differentiation between lipid or protein bound state and aqueous media. II crystallizes into two solid isoforms containing one (red crystals) and two conformers (yellow crystals), exhibiting differing spectral properties. X-ray crystal structures reveal a planar arrangement between dimethylamino and naphthalenyl moieties, with out-of-plane arrangements between the malononitrile and naphthalene ring found in each of the three conformers.

Controlling the structures and photonic properties of organic nanomaterials by molecular design

Exploring the stacks: Two different but related naphthalene compounds were shown to form different nanostructures (see picture) depending on the π-π stacking and hydrogen bonding of the molecules. These nanostructures had unique photonic confinement and l

Two-Photon Excited FRET Dyads for Lysosome-Targeted Imaging and Photodynamic Therapy

Two-photon excitable fluorescent dyes with integrated functions of targeted imaging and photodynamic therapy (PDT) are highly desired for the development of cancer theranostic agents. Herein, fluorescence resonance energy transfer (FRET) dyads, AceDAN-Hs

Synthesis method of Acrylodan and analogues thereof

The invention belongs to the technical field of synthesis of fluorescent probes in biochemistry, and particularly relates to an environment-sensitive fluorescent probe and a synthesis process route of Acrylodan and analogues thereof. A method comprises the following steps: taking 6-methoxy-2-acetyl naphthalene as a raw material, carrying out substitution reaction on the 6-methoxy-2-acetyl naphthalene and a lithium amide salt, carrying out addition elimination reaction on an obtained amino-substituted acetyl naphthalene product and trifluoroacetic acid, and then carrying out addition elimination reaction on the obtained amino-substituted acetyl naphthalene product and aldehydes to finally obtain the high-purity Acrylodan compound and analogues. The method has the advantages of simple synthesis steps, short reaction time, high yield, low production cost and the like, and solves the problems of complex synthesis steps, harsh synthesis conditions and expensive synthesis raw materials in original synthesis methods. The optimization and improvement of the synthetic process route of Acrylodan and analogues can greatly promote the application of the environment-sensitive probe in the field of biochemistry.

Quantitative Design of Bright Fluorophores and AIEgens by the Accurate Prediction of Twisted Intramolecular Charge Transfer (TICT)

Inhibition of TICT can significantly increase the brightness of fluorescent materials. Accurate prediction of TICT is thus critical for the quantitative design of high-performance fluorophores and AIEgens. TICT of 14 types of popular organic fluorophores

Azetidine-Containing Heterospirocycles Enhance the Performance of Fluorophores

Fluorescent dyes are extensively utilized in various fluorescence imaging techniques. However, many existing modification strategies could not balance the performance (such as brightness, photostability, water solubility, and permeability) of fluorophores. Herein we report a general strategy to enhance the performance of donor-acceptor-type fluorophores by introducing azetidine-containing heterospirocycles to the commonly used fluorophore scaffolds. Such a strategy turned out to be a general way to develop high-quality fluorophores.

A FRET-based two-photon probe for: In vivo tracking of pH during a traumatic brain injury process

The traumatic brain injury (TBI) process, a significant cause of neurodegenerative diseases, is generally thought to be accompanied by a decrease in pH of the intracellular environment. In this work, a fluorescence resonance energy transfer (FRET)-based ratiometric two-photon fluorescent pH probe, FRET-pH, has been designed and fully characterized to monitor the pH change so as to understand the extent of the TBI process. FRET-pH, which has nearly 100% energy transfer efficiency and ～100-fold ratio signal changes, is constructed from a naphthalene derivative ADN as a two-photon fluorophore and SRhB as a recognition domain for pH. FRET-pH displays both one- A nd two-photon ratiometric responses towards pH in aqueous solution. The appropriate pKa value (5.89) supports its use in subsequent biological applications. Finally, two-photon microscopic imaging of pH in living HeLa cells, BV-2 cells and rat brain tissue has been achieved.

Fluorogenic kinetic assay for high-throughput discovery of stereoselective ketoreductases relevant to pharmaceutical synthesis

Enantiomerically pure 1-(6-methoxynaphth-2-yl) and 1-(6-(dimethylamino)naphth-2-yl) carbinols are fluorogenic substrates for aldo/keto reductase (KRED) enzymes, which allow the highly sensitive and reliable determination of activity and kinetic constants of known and unknown enzymes, as well as an immediate enantioselectivity typing. Because of its simplicity in microtiter plate format, the assay qualifies for the discovery of novel KREDs of yet unknown specificity among this vast enzyme superfamily. The suitability of this approach for enzyme typing is illustrated by an exemplary screening of a large collection of short-chain dehydrogenase/reductase (SDR) enzymes arrayed from a metagenomic approach. We believe that this assay format should match well the pharmaceutical industry's demand for acetophenone-type substrates and the continuing interest in new enzymes with broad substrate promiscuity for the synthesis of chiral, non-racemic carbinols.

Assessing the guest-accessible volume in MOFs using two-photon fluorescence microscopy

The assessment of guest-accessible volume in MOFs can be reliably done by using two-photon confocal fluorescence microscopy (TPM) with a tool-box of dyes with a wide range of sizes. It would be applicable to any porous materials, whose single-crystal structures are not available, or non-crystalline materials.