63149-33-7

Usage

Uses

Used in Chemical Synthesis:
8-HYDROXYJULOLIDINE-9-ALDEHYDE is used as a reactant for the development of iminocoumarin-based zinc sensors. These sensors are particularly suitable for ratiometric fluorescence imaging of neuronal zinc, which is crucial for understanding the role of zinc in neurological processes and various brain functions.
Used in Neuroscience Research:
In the field of neuroscience, 8-HYDROXYJULOLIDINE-9-ALDEHYDE is used as a key component in the creation of sensors that can detect and monitor zinc levels in the brain. This application is significant because it aids researchers in studying the intricate relationship between zinc and neuronal activity, which can have implications for the diagnosis and treatment of neurological disorders.
Used in Analytical Chemistry:
8-HYDROXYJULOLIDINE-9-ALDEHYDE is also utilized in analytical chemistry as a component of sensors designed for the detection and quantification of zinc ions. These sensors can be employed in various applications, such as environmental monitoring, pharmaceutical research, and quality control in the chemical industry, where accurate measurement of zinc concentrations is essential.

InChI:InChI=1/C13H15NO2/c15-8-10-7-9-3-1-5-14-6-2-4-11(12(9)14)13(10)16/h7-8,16H,1-6H2

Upstream product

• 41175-50-2 8-hydroxyjulolidine 
• 68-12-2 N,N-dimethyl-formamide 
• 536-90-3 m-Anisidine 
• 109-70-6 1.3-chlorobromopropane 
• 591-27-5 m-Hydroxyaniline 
• 63468-83-7 8-methoxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline 

Downstream Products

• 87349-92-6 coumarin 510 
• 55804-66-5 ethyl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f ]-pyrido[3,2,1-ij]quinoline-10-carboxylate 
• 58336-35-9 coumarin-6H 
• 949585-66-4 (E)-3-(8-hydroxy-2,3,6,7-tetrahydro-1H,5H-pyrido(3,2,1-ij)quinolin-9-yl)-acrylic acid ethyl ester 
• 142730-52-7 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde 
• 1597465-95-6 (E)-N’-((8-hydroxy-1,2,3,5,6,7-hexahydropyrido-[3,2,1-ij]quinolin-9-yl)methylene)benzohydrazide 
• 55804-67-6 10-acetyl-2,3,6,7-tetrahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-11(5H)-one 

Relevant academic research and scientific papers

A novel colorimetric chemosensor for Cu2+ with high selectivity and sensitivity based on rhodamine B

9-formyl-8-hydroxy-2,3,6,7-tetrahydro-1H, 5H-benzo[ij]-quinolizine rhodamine B hydrazone (FHQRH), a novel colorimetric chemosensor for Cu2+, was synthesized by a three-step synthetic route. It was found that FHQRH showed a high selectivity for Cu2+ ions and excellent anti-interference capability toward other metal ions. The FHQRH solution exhibited a visual color change after the addition of Cu2+, owing to the open spirocyclic structure via coordination with Cu2+. The complexation coefficient of FHQRH toward Cu2+ was measured to be 1:1. Furthermore, this Cu2+ chemosensor has a remarkable low detection limit of 0.45 μM, which is 2 % of the toxic level (20 μM) in drinking water as defined by the US Environment Protection Agency (EPA).

Synthesis of a NIR fluorescent dye and its application for rapid detection of HSO3? in living cells

SO2 and its derivatives (HSO3?, SO32?) play a significant important role in many industries and organisms. Based on coumarin and benzopyranose, a promising NIR ratiometric fluorescent probe BAOA (11-oxo-2,2′,3,3′,6,7,7′,8′-octahydro -1H,1′H,5H,6′H,11H- [10,12′-bipyrano [2,3-f] pyrido [3,2,1-ij] quinolin]-13′-ium perchlorate) was designed and developed to detect HSO3? rapidly and sensitively. The sensing mechanism was Michael addition reaction, in which, strongly nucleophilic HSO3? attacked carbon-carbon double bonds and BAOA-HSO3 was formed. A superior linear calibration curve between the fluorescence ratio I490/I722 and concentrations of HSO3? was obtained in the range of 1.25–8.75 μmol/L and the LOD was figured out as 63.0 nmol/L. Cell experiments showed that BAOA could not only locate mitochondria, lysosomes, ER and Golgi but also detect exogenous HSO3? in living cells.

Three lysocolorimetric/lysofluorescent probes with mitochondria/lysosome dual targeting positioning

The invention discloses a preparation method of three lysocolorimetric/lysofluorescent probes with mitochondria/lysosome dual targeting positioning and application thereof in biological imaging, which belong to the technical field of chemical analysis and detection. The structure and the detection mechanism of the lysocolorimetric/lysofluorescent probes are as follows: the probes prepared have stronger solvent-induced discoloration characteristics, and the fluorescent quantum yield is relatively high. Cell experiments show that the prepared probe has a good mitochondria/lysosome positioning effect.

Near-infrared fluorescent probe for simultaneously detecting DNA and RNA under double channels as well as preparation method and application of the near-infrared fluorescent probe

The invention discloses a fluorescent probe for simultaneously detecting DNA and RNA in cells under double channels as well as a preparation method and application of the fluorescent probe. The structure of the fluorescent probe is shown as a formula (I) or (II), wherein the Ar is an aromatic ring or an aromatic heterocyclic ring; the R1 and R2 are respectively and independently hydrogen, N-piperazine, N-methyl piperazine, -NH(CH2)nR3 and -NR3R4; the n is any integer from 1 to 5, and R3 and R4 are respectively and independently hydrogen, C1-C5 alkyl or C1-C5 haloalkyl; the A- is halide ions orp-toluenesulfonic acid ions. The fluorescent probe disclosed by the invention can be used for simultaneously detecting DNA and RNA in vitro and in cells under double channels; meanwhile, the fluorescent probe has the characteristics of rapid synthesis, near-infrared emission wavelength, good light stability, high detection sensitivity and the like, and is convenient to popularize and apply.

A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation

Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.

A novel fluorescent probe with dual-sites for simultaneously monitoring metabolisms of cysteine in living cells and zebrafishes

Understanding cellular metabolism holds immense potential for developing new drugs that regulate metabolic pathways. Two gas signal molecules, SO2 and H2S, are the main metabolites from cysteine (Cys) via oxidation and desulfurization pathways, respectively. However, a few fluorescent probes for real-time monitor of the metabolic pathways of cysteine have been reported. To understand metabolic alterations of cysteine, we have rationally designed and prepared a dual-signal fluorescent probe HN, which could differentiate SO2 and H2S through two different fluorescence channels simultaneously, along with similar reaction kinetics and both “off-on” fluorescence responses. Probe HN exhibits the potential to monitor the metabolism pathways of cysteine, and the distinguishment of cancer cells from normal cells could be realized. This methodology will promote further understanding of the physiological and pathological roles of cysteine.

Endoplasmic reticulum targeted fluorescent probe for the detection of hydrogen sulfide based on a twist-blockage strategy

Hydrogen sulfide (H2S) is very important for humans and is involved in many physiological processes. Here, we designed and reported a new naked-eye colorimetric fluorescent probe Z1 for detecting H2S in absolute HEPES solution. The fluorescence intensity, after the reaction of the probe and H2S, is about 32 times that of the probe alone. When the concentration of H2S is 0-100 μM, the detection limit (DL) is rather low at about 0.15 μM (3σ/slope). The response mechanism is based on the leaving of the 2,4-dinitrobenzene moiety, followed by intramolecular cyclization to give a fluorescent iminocoumarin-benzothiazole group. Moreover, Z1 was applied to endogenous and exogenous H2S imaging in living cells. The high overlap coefficient proved that probe Z1 has good ER-tracker localization in living cells.

A novel colorimetric and ratiometric fluorescent probe for selective detection of bisulfite in real samples and living cells

An abnormal level of bisulfite can induce toxicological effects associated with lung cancer, cardiovascular and neurological disorders. Therefore, it is of significance to develop an effective fluorescent probe to detect bisulfite in living cells. Herein, a novel fluorescent probe QPCT, based on a 1,4-addition mechanism, was constructed for the colorimetric and ratiometric detection of bisulfite. QPCT displayed high selectivity and anti-interference ability to bisulfite over other anions and biothiols. The probe renders a sensitive ratiometric response to bisulfite with a remarkable fluorescence blue shift from 590 to 537 nm and the fluorescence ratio was linear with bisulfite concentration over the range of 0–120 μM. More importantly, QPCT has been successfully applied to detect bisulfite in sugars and living A549 cells, which indicated that QPCT had a great capability for monitoring bisulfite in complex systems.

(7-Dialkylamino-3-coumarinyl)pyrazolines – new effective push-pull photogenerators of acidity

(7-Dialkylamino-3-coumarinyl)pyrazolines and their julolidine analog have been synthesized and proved as new effective photogenerators of acidity. Having D-π-linker ?A conjugated system of push-pull type these compounds possess intensive absorption in visible region of electronic spectra, high photosensitivity and undergo photodehydrogenation with proton elimination in the presence of CCl4 or C2Cl6 with a high speed.

Reaction-based fluorescent turn-on probe for selective detection of thiophenols in aqueous solution and living cells

A novel turn-on florescent probe based on a nucleophilic substitution reaction was developed for the detection of thiophenols in aqueous solution and in living cells. In this probe, 10-hydroxyl derivative of coumarin 6H was selected as fluorophore, 2, 4-dinitrophenlate moiety acted simultaneously as recognition unit and fluorophore quencher. This probe features a remarkable large Stokes shift (128?nm) and shows a highly selective detection process for thiophenols with significant fluorescence turn-on response. Notably, biothiols, aliphatic thiols, amino acids and reducing anions do not interfere with the sensing of thiophenols. The probe shows good linearity ranges with low detection limit of 36?nM for thiophenols. More importantly, it was successfully applied for practical detection of thiophenols in real water samples with a good recovery and imaging of thiophenols in living cells, demonstrating its practical application in environmental samples and biological systems.