Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry

Zhang, X.H.; Liu, Q.; Shi, Handuo; Wang, L.Y.; Fu, Yu; Wei, Xiuhua; Yang, Lei

doi:10.1016/j.dyepig.2013.09.011

Cited by 22 publications

(10 citation statements)

References 33 publications

(26 reference statements)

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“…There are some examples of dimethine cyanine dyes 38 – 48 available in the literature in which they are synthesized in ethanol with piperidine (Figure 11). [15, 32, 58–61] Compounds 42 – 45 were synthesized by using a microwave in yields above 90 % in less than 5 min and with absorption maxima in the presence of DNA at 483–499 nm [32] …”

Section: Synthesis Of Dimethine Cyanine Dyes Containing Quinoline Moimentioning

confidence: 99%

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Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications

Ilina

Henary

2020

Chemistry A European J

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Cyanine dyes carrying quinoline moieties are an important class of organic molecules that are of great interest for applications in many fields like medicine, pharmacology, and engineering. Despite their exceptional properties, such as stability, high molar extinction coefficients, and high pH‐sensitivity, this class of dyes has been less analyzed and reviewed in the last few decades. Therefore, this review article focuses on discussing the history of quinoline compounds, various synthetic routes to prepare quinolinium salts and symmetrical and asymmetrical mono‐, di‐, tri‐, penta‐ and heptamethine cyanine dyes, containing quinoline moieties, together with their optical properties and applications as photosensitizers in photodynamic therapy, probes in biomolecules for labeling of nucleic acids, as well as imaging agents.

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Section: Synthesis Of Dimethine Cyanine Dyes Containing Quinoline Moimentioning

confidence: 99%

“… Structures of some known dimethine cyanine dyes, synthesized from lepidine and quinaldine [15, 32, 58–61] …”

Section: Synthesis Of Dimethine Cyanine Dyes Containing Quinoline Moimentioning

confidence: 99%

Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications

Ilina

Henary

2020

Chemistry A European J

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“…Over the past decade, fluorescent dyes are used widely in bioimaging, especially for DNA detection [1,2] due to the significant advantages of fluorescent dyes, such as relative stability, low aggregation and high affinity for some biological molecules [3][4][5]. However, in order to decrease the fluorescent background interference caused by the labeled organism, the stronger fluorescent intensity is required [6,7].…”

Section: Introductionmentioning

confidence: 99%

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Fei

Lin

et al. 2015

J Fluoresc

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A novel fluorescent dye, 1-(6-carboxyhexyl)-4-(2-(9-ethyl-carbazole-3-yl) vinyl) quinolizinium bromide, was synthesized, and its structure was characterized by (1)H NMR, (13)C-NMR, IR and HRMS. The spectra properties of this dye in different solvents and under different pH value were invest'igated preliminarily, and the results showed that its fluorescent properties was affected by the polarity and the dipole moment of the solvent. The photostability and thermostability test results showed that its photoreduction rate constant was 1.64 × 10(-5) mol/Min and its fluorescent intensity decreased little after heating at 80 °C for 6 h, suggesting the dye was quite stable. In the labeling experiment of BSA and DNA with the dye, the fluorescent all intensity increased with the addition of BSA and DNA. Specially, the dye showed an excellent turn-on effect upon binding with ctDNA.

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“…Molecular probes are commonly covalently bound to peptides or other bioactive molecules for tracking their fate in cells by means of microscopy or flow cytometry. They are numerous such as fluorescein and BODIPY but only rarely are cell‐permeant . Thus, new cell permeable probes are of great interest to extend the imaging toolbox since they can illuminate biological processes and aid in the assessment of emerging therapeutic targets ‐ by perturbing biological systems in a manner distinct from other experimental approaches …”

Section: Figurementioning

confidence: 99%

“…The molecules disclosed here spontaneously penetrate into the cell. Unlike other cell‐penetrating dyes, the whole population of cells appear colored, as demonstrated by FACS monitoring. Therefore, they can be used directly for illuminating cellular processes or as shuttles by their conjugation to drug candidates that do not penetrate spontaneously into the cells.…”

Section: Figurementioning

confidence: 99%

Solid‐Phase Multicomponent Synthesis of 3‐Substituted Isoindolinones Generates New Cell‐Penetrating Probes as Drug Carriers

et al. 2020

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A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral β‐keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3‐substituted isoindolinones in one pot. Modularity was accomplished by using solid supported aldehydes and dienophiles. Optimization was achieved by using microwave as the source of energy. The reaction was also performed on a biologically relevant well‐known programed cell death‐inducing peptide D(KLAKLAK)2 on solid phase. The molecules show significant fluorescence with large Stokes shifts and fast cell penetration. The chimeric peptides can be tracked under a microscope thus proving the potential of the probes as cell sensors. They were efficiently internalized compared to unlabeled peptide, with a concomitant induction of programed cell death, thereby proving their potential as drug carriers.

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Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry

Cited by 22 publications

References 33 publications

Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications

Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications

Spectra, Stability and Labeling of a Novel Carbazole Derivative as a Fluorescent Turn-on DNA Probe

Solid‐Phase Multicomponent Synthesis of 3‐Substituted Isoindolinones Generates New Cell‐Penetrating Probes as Drug Carriers

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