Quinoline based fluorescent zinc sensors and software

In comparison to previous reports on hydrazonebased zn sensing, which dealt. Dec 21, 2004 read tetrakis2quinolinylmethylethylenediamine tqen as a new fluorescent sensor for zinc, dalton transactions on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Among the most widely used znii fluorescent sensors are those based on. The probe is designed with a photoinduced electron transfer pet mechanism and shows 12fold fluorescence enhancement toward no. Quinolinebased twophoton fluorescent probe for nitric oxide. In particular, recent work has demonstrated the excitotoxic roles of zinc in the brain, 1 2 3 as well as its potential role as a signaling ion in the brain 4 which recent evidence suggests participates in long term potentiation. Molecular and biomolecular spectroscopy 2014, 118, 883887. Aqueous coordination chemistry of quinolinebased fluorescence probes for the biological chemistry of zinc, journal of american chemical society, vol. Adopting a quinoline derivative as the fluorophore, qno has a large twophoton action cross section value of 52 gm and longwavelength emission. Synthesis and characterization of zinc sensors based on a. Third, to allow concentration changes to be monitored, fluorescent sensors should have a k d near the median concentration of the species under investigation. Fluorescent zinciibased metalorganic frameworks for.

Quinoline based receptor in fluorometric discrimination of. Zinc binding not only redshifts the emission band to 500 nm, but also enhances the. Massachusetts institute of technology mit technology licensing office technology licensing office. This chemosensor was synthesized from diisopropylamine and 2chloronquinolin8ylacetamide. Fluorescent sensors for sodium ions analytical methods. The sensor exhibited a large stokes shift 171 nm in the detection process. We present here a general approach for acetylating petbased probes containing a variety of fluorophores and zincbinding units. First, fluorescent sensors should produce a perceptible change in.

Tetrakis2quinolinylmethylethylenediamine tqen as a. Excitation ratiometric fluorescent biosensor for zinc ion at. Jun 23, 2010 zinc is an essential element for humans and plays an important role in a wide range of biological processes, prompting the development of a large number of zniiselective small molecule sensors as tools to better understand the biological trafficking of this metal ion. Chelatable, or mobile, forms of zinc play critical signaling roles in numerous biological processes. So how to improve quinolinebased sensor is still a challenge. A highly selective and sensitive of a carbonic anhydrasebased method for measurement of zinc ion by an excitation ratiometric format based on resonance energy transfer. Quinoline based fluorescent zinc sensors with enhanced fluorescence intensity, zncd selectivity and metal binding affinity by conformational restriction article may 20. Design, synthesis and raft polymerisation of a quinoline. Np was achieved based on the inner filter effect ife mechanism. Quinoline fluorescent probes for zinc from diagnostic to.

A highly selective quinoline based fluorescent sensor for znii. Quinoline and naphthalenebased fluororeceptors 1 and 2 have been designed and synthesized for detection of hydroxy carboxylic. Quinoline based fluorescent chemosensor for in water. Phosphorescent sensor for biological mobile zinc europe pmc. Chattopadhyay1 and purnendu roy chowdhury2 full research paper open access address.

Zinc is an ion of growing importance in many fields of biology and medicine. These zincactivated fluorochromes are usually capable of permeating the cell, with moderately strong zn complexation firststep log k f values ranged from 7 to 8. A highly selective fluorescent sensor for zinc ion based on quinoline. Determination of spatial distributions of zinc and active. Np in water, honey, strawberry, and tomato samples. Noh i, kim y, kim sj, kim c, harrison rg 20 selective zinc sensor based on pyrazoles and quinoline used to image cells. The receptor 1 comprises the quinoline moiety as fluorophore and the n,n. Rapid discovery and structureproperty relationships of metalion. There are many criteria for a fluorescent znii sensor that operates in. In this regard, molecular sensors built on this scaffold may be useful not only as analytical but also as therapeutic agents. Design, synthesis and raft polymerisation of a quinolinebased monomer for use in electrospun composite microfibres.

Fluorescent sensors for zn based on a fluorescein platform. Read tetrakis2quinolinylmethylethylenediamine tqen as a new fluorescent sensor for zinc, dalton transactions on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. These studies validate a transferrable technology for. The invention can be applied to a variety of fluorophore scaffolds including fluorescein, coumarin, resorufin, and benzoresorufin. We describe here the synthesis and characterization of zp1 sensors containing a carboxylic acid or ethyl ester functionality at the 5 or 6 position of the. Quinoline based molecules have been used extensively as fluoroscopic agents for the detection of zinc ion. Low molecular weight fluorescent probes lmfps to detect. A red fluorescent bodipy probe for iridium iii ion and. Second, fluorescent sensors should selectively bind a particular analyte.

Three new asymmetrical fluorescent zn ii sensors, based on parent compound zp4 x h, are presented and their syntheses and photophysical characterization described. A novel quinolinebased twophoton fluorescent probe for. The development of zinc sensors is an active research field. Guo z, kim gh, shin i, yoon j 2012 a cyaninebased fluorescent sensor for detecting endogenous zinc ions in live cells and organisms.

Elucidating the action of mobile znii in complex biological environments requires sensitive tools for visualizing, tracking, and manipulating znii ions. Fluorescent indicators for zinc introduction zinc is an important divalent cation in biological systems, influencing dna synthesis, microtubule polymerization, gene expression, apoptosis, immune system function, and the activity of enzymes such as carbonic anhydrase and. Fluorescent indicators for zinc introduction zinc is an important divalent cation in biological systems, influencing dna synthesis, microtubule polymerization, gene expression, apoptosis, immune system function, and the activity of enzymes such as carbonic anhydrase and matrix metalloproteinases mmp. Us patent for fluoresceinbased metal sensors patent. Esterification of fluorescent biosensors is a common strategy used to trap probes within the cell. Topham a chemical engineering and applied chemistry, aston university, aston triangle, birmingham, b4 7et, uk. Smallmolecule fluorescent sensors for investigating zinc. A new structural metalorganic framework with fluorescence properties, namely zn4btc2oh2ch3oh6 njmu001, was synthesized by using 1,3,5benzenetricarboxylic acid h3btc and zinc nitrate through a solvothermal reaction. Zinc is an essential element for humans and plays an important role in a wide range of biological processes, prompting the development of a large number of zniiselective small molecule sensors as tools to better understand the biological trafficking of this metal ion. So how to improve quinoline based sensor is still a challenge. A quinolinebased ratiometric and reversible fluorescent. Quinolinebased fluorescent zinc sensors with enhanced fluorescence intensity, zncd. Fierke excitation ratiometric fluorescent biosensor for zinc ion at picomolar levels. Imagej software was used to extract all red, green, and blue color intensity from.

Dec 21, 2016 a new ratiometric fluorescent sensor dqo based on n,n. A sensitive schiffbase fluorescent chemosensor for the. Fluorescent metal sensors, and methods of making and using. Lack of celltype selectivity prevents translational use of. This sensor was facilely synthesized via a simple linker nh 2 nh 2 connected quinoline2carboxylic acid and salicylaldehyde. This ratiometric fluorescent probe possesses favorable photophysical properties. A twophoton fluorescent probe qno for nitric oxide is reported.

Quinoline attached triazacyclononane tacn derivatives as fluorescent zinc sensors. A sensitive ratiometric fluorescent sensor for zinc ii with high selectivity. A new ratiometric fluorescent sensor dqo based on n,n. Jan 20, 2009 we consider first the fluorescent properties of zp, zs and qz, dividing them into three categories defined by the nature of the metalbinding unit. Reactionbased fluorescent sensor for investigating mobile zn in. A quinolinebased fluorescent chemosensor for distinguishing cadmium from zinc ions using cysteine as an auxiliary reagent. The proposed approach was successfully applied for the determination of 4. Quinoline group based fluorescent sensor for detecting zinc ions in aqueous media and its logic gate behaviour. Quinolinebased molecules have been used extensively as fluoroscopic agents for the detection of zinc ion.

It shows a large 55 nm redshift from 515 nm to 570 nm in the emission spectrum. Fluorescent sensors for sodium ions analytical methods rsc. Thompson, michele cramer, rebecca bozym, and carol a. Quinolinebased fluorescent zinc sensors with enhanced. A quinolinebased ratiometric and reversible fluorescent probe for cadmium imaging in living cells. Fluorescent zinciibased metalorganic frameworks for nitroaromatics sensing yujie ma, a guanhong xu, a fangdi wei, a yao cen, a yueyue song, a menglan shi, a xiaoman xu, a muhammad sohail a and qin hu a. Fluorescent sensors for zinc ii detection in biological systems. Ziping liu, guangying li, qiang ma, linlin liu and xingguang su, a nearinfrared turnon fluorescent nanosensor for zinc ii based on cuins2 quantum dots modified with 8aminoquinoline, microchimica acta, 181, 1112, 85, 2014.

Quinolinebased fluorescence sensors are usua lly used to measure intensity changes of fluorescence andor shift of fluorescence wavele ngth. In order to obtain good single crystals of njmu001, the factors affecting the re. These particular metal ions play essential roles in biological, industrial, and environmental applications, therefore, there has been a drive to measure, detect, and remediate these metal ions. The new sensors provide substantially improved zinc sensitivity and allow for incubation of live cells and tissue slices with nm probe concentrations, a significant improvement compared to the. In particular, much attention has been recently paid to quinolinebased fluorescent zinc sensors, because the quinoline moiety acts as both metal binding ligand and fluorophore by means of chef. Zincsecreting paneth cells studied by zp fluorescence. A quinolinebased fluorescent probe for selective detection and real.

Isoquinolinebased tqen family as tpenderived fluorescent. Zinpyr1 zp1 is a fluoresceinbased bright fluorescent sensor for divalent zinc that is cell permeable without prior modification. Excitation ratiometric fluorescent biosensor for zinc ion. Various molecules have been used as fluorophores, one of which has been quinoline 3, 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k. Rapid discovery and structureproperty relationships of metal.

The fluorescent sensor exhibited low detection limit 2. Quinoline occurs naturally in small amounts in coal tar and in slightly decomposed sphagnum peats. Moreover, it is a reversible probe which makes it more competitive in practice. When aniline and quinolinebased sensors chelate these particular metal ions. This chemosensor was synthesized from diisopropylamine and 2chloron quinolin8ylacetamide. In addition, the zp dyes fluoresce green when excited with blue light, thus preventing uvinduced cell damage that can occur from the nearultraviolet excitation of the quinolinebased probes. In summary, a bisquinolinebased acyl hydrazone fluorescent probe bqh. Fluorescence based sensing has dramatically changed the way of visualizing and. An efficient quinolinebased fluorescence sensor for zincii. Quinolinebased fluorescent zinc sensors with enhanced fluorescence intensity, zncd selectivity and metal binding affinity by conformational restriction article may 20. Synthesis and characterization of zinc sensors based on a monosubstituted fluorescein platform inorganic chemistry. We consider first the fluorescent properties of zp, zs and qz, dividing them into three categories defined by the nature of the metalbinding unit. While most efforts were made in developing small molecule based fluorescent sensors, recent developments in dna.

Zinpyr1 zp1 is a fluorescein based bright fluorescent sensor for divalent zinc that is cell permeable without prior modification. Reactionbased probes for imaging mobile zinc in live cells. Fluorescent indicators for zinc thermo fisher scientific. Quinolinebased fluorescent zinc sensors with enhanced fluorescence intensity, zncd selectivity and metal binding affinity by conformational restriction. Rapid discovery and structureproperty relationships of. Quinoline has also been detected in coke oven tars. In addition, the zp dyes fluoresce green when excited with blue light, thus preventing uvinduced cell damage that can occur from the nearultraviolet excitation of the quinoline based probes. No emissions of quinoline from stationary sources in california were reported, based on dataobtained from the air toxics hot spots program. Ziping liu, guangying li, qiang ma, linlin liu and xingguang su, a nearinfrared turnon fluorescent nanosensor for zincii based on cuins2 quantum dots modified with 8aminoquinoline, microchimica acta, 181, 1112, 85, 2014. Reactionbased fluorescent probes for detection of zinc mit. Zincchelating small molecules preferentially accumulate and. A quinoline based turnoff fluorescent cation sensor paramjit kaur,a hardeep kaurb and kamaljit singhb adepartment of chemistry, ugccentre of advance studiesi, borganic synthesis laboratory, department of applied chemical sciences and technology, ugcsapdrsi department, guru nanak dev university, amritsar143 005, india s1.

A compound represented by the following general formula i or a salt thereof. Excitation ratiometric fluoroscent biosensor for zinc ion. Paneth cell zinc secretion was examined in both intact animals and isolated crypt preparations using the bacterial antigen lipopolysaccharide lps and. Fourth, fluorescent sensors, especially when used intracellularly, should produce a signal with a high quantum yield. Bisquinolinebased fluorescent zinc sensors request pdf. Fluorescent sensors for zinc ii detection in biological systems stephen f. Reactionbased fluorescent probes for detection of zinc. Phosphorescent sensor for biological mobile zinc europe. To facilitate such investigations, we initiated a program in znii sensor design, largely. A highly selective quinolinebased fluorescent sensor for. A simple amide fluorescent sensor based on quinoline for. Fluorescent metal sensors, and methods of making and using the same. Quinoline based receptor in fluorometric discrimination of carboxylic acids kumaresh ghosh,1, suman. Membranepermeable and impermeable sensors of the zinpyr.

Sensors with tertiary amine based chelates are generally more emissive than those with aniline in both free and zniibound forms. Tetrakis2quinolinylmethylethylenediamine tqen as a new. An efficient quinolinebased fluorescence sensor for zinc. While most efforts were made in developing small molecule based fluorescent sensors, recent developments in dna based sensing have also been quite promising with excellent sensitivity and selectivity. Jul 17, 2019 a quinolinebased fluorescent chemosensor for distinguishing cadmium from zinc ions using cysteine as an auxiliary reagent. Yuji mikata, anna ugai, keiko yasuda, saori itami, satoshi tamotsu, hideo konno, satoshi iwatsuki. Quinolinebased twophoton fluorescent probe for nitric. Zincchelating small molecules preferentially accumulate. A quinoline moiety was used as a building block for designing a probe for the. Reactionbased probes for imaging mobile zinc in live.

Nov 09, 2012 quinoline has also been detected in coke oven tars. Data were processed on a pc using crystalclear software rigaku. Selective zinc sensor based on pyrazoles and quinoline. Quinoline based fluorescent zinc sensors with enhanced fluorescence intensity, zncd selectivity and metal binding affinity by conformational restriction yuji mikata, a yumi sato, b saaya takeuchi, b yasuko kuroda, b hideo konno c and satoshi iwatsuki d. The technology comprises a new class of reactionbased fluorescent sensors that selectively detect zinc ions in live cells. Fluorescent sensors for zinc ii detection in biological. A new red fluorescent probe 1 based on bodipy skeleton has been successfully synthesized through introduction of 2thiophen2yl quinoline moiety at meso and 3position. Zinc cations are relevant for vast majority of processes and recently.

The technology comprises a new class of reaction based fluorescent sensors that selectively detect zinc ions in live cells. Sensors with tertiary aminebased chelates are generally more emissive than those with aniline in both free and zniibound forms. A large toolbox of synthetic photoinduced electron transfer petbased fluorescent znii sensors are available, but the applicability of. Quinoline based receptor in fluorometric discrimination of carboxylic acids kumaresh ghosh,1, suman adhikari1, asoke p.