A new structure–activity relationship for cyanine dyes to improve photostability and fluorescence properties for live cell imaging

Schwechheimer, Christian; Rönicke, Franziska; Schepers, Ute; Wagenknecht, Hans‐Achim

doi:10.1039/c8sc01574k

Cited by 37 publications

(26 citation statements)

References 31 publications

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“…First of all, indole substituents, including core-substituted indoles, emerge as the most efficient in this sense, as demonstrated by several distyryls ( 1o – v ) with superior properties with respect to the prototype compound 1a . A similar effect of indole substituents was already observed in the family of mono-styryl dyes developed for detection of double-stranded DNA [68,70,91]. Moreover, pyrrole-substituted distyryls ( 1x and 7x ) also display very high fluorimetric response (up to I / I 0 = 690, for 1x –TERRA complex), albeit at the expense of somewhat lower selectivity with respect to ds DNA and ss RNA.…”

Section: Discussionsupporting

confidence: 64%

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

Xie¹,

Zuffo²,

Teulade-Fichou³

et al. 2019

Beilstein J. Org. Chem.

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A library of 52 distyryl and 9 mono-styryl cationic dyes was synthesized and investigated with respect to their optical properties, propensity to aggregation in aqueous medium, and capacity to serve as fluorescence “light-up” probes for G-quadruplex (G4) DNA and RNA structures. Among the 61 compounds, 57 dyes showed preferential enhancement of fluorescence intensity in the presence of one or another G4-DNA or RNA structure, while no dye displayed preferential response to double-stranded DNA or single-stranded RNA analytes employed at equivalent nucleotide concentration. Thus, preferential fluorimetric response towards G4 structures appears to be a common feature of mono- and distyryl dyes, including long-known mono-styryl dyes used as mitochondrial probes or protein stains. However, the magnitude of the G4-induced “light-up” effect varies drastically, as a function of both the molecular structure of the dyes and the nature or topology of G4 analytes. Although our results do not allow to formulate comprehensive structure–properties relationships, we identified several structural motifs, such as indole- or pyrrole-substituted distyryl dyes, as well as simple mono-stryryl dyes such as DASPMI [2-(4-(dimethylamino)styryl)-1-methylpyridinium iodide] or its 4-isomer, as optimal fluorescent light-up probes characterized by high fluorimetric response (I/I 0 of up to 550-fold), excellent selectivity with respect to double-stranded DNA or single-stranded RNA controls, high quantum yield in the presence of G4 analytes (up to 0.32), large Stokes shift (up to 150 nm) and, in certain cases, structural selectivity with respect to one or another G4 folding topology. These dyes can be considered as promising G4-responsive sensors for in vitro or imaging applications. As a possible application, we implemented a simple two-dye fluorimetric assay allowing rapid topological classification of G4-DNA structures.

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Section: Discussionsupporting

confidence: 64%

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

Xie¹,

Zuffo²,

Teulade-Fichou³

et al. 2019

Beilstein J. Org. Chem.

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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%

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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“…Photostability is very critical for long‐time tracking in disease diagnostics . In particular, the multiple image acquisition cycles and prolonged light exposure of probes may result in serious photobleaching and image distortion.…”

Section: Resultsmentioning

confidence: 99%

High‐Fidelity Trapping of Spatial–Temporal Mitochondria with Rational Design of Aggregation‐Induced Emission Probes

Zhang

Wang

Guo

et al. 2019

Adv Funct Materials

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High-fidelity trapping of mitochondrial dynamic activity is critical to value cellular functions and forecast disease but lack of spatial-temporal probes. Given that commercial mitochondria probes suffering from low photostability, aggregation-caused quenching effect, and limited signal-to-noise ratio from fluorescence "always on" in the process of targeting mitochondria, here, the rational design strategy of a novel aggregation-induced emission (AIE) molecular motif and unique insight into the high-fidelity targeting of mitochondria is reported, thereby illustrating the relationship between tailoring molecular aggregation state and mitochondrial targeting ability. This study focuses on how to exactly modulate the hydrophilicity and the aggregated state for realizing "off-on" fluorescence, as well as matching the charge density to go across the cell membrane for mitochondrial targeting. Probe tricyano-methylene-pyridine (TCM-1) exhibits an unprecedented high-fidelity feedback on spatial-temporal mitochondrial information with several advantages such as "off-on" near-infrared characteristic, high targeting capacity, favorable biocompatibility, as well as excellent photostability. TCM-1 also produces reactive oxygen species in situ for image-guided photodynamic anticancer therapy. Through unraveling the relationship between tuning molecular aggregation behavior and organelle-specific targeting ability, for the first time, a unique guide is provided in designing AIE-active probes to explore the hydrophilicity and membrane potential for targeting subcellular organelles.

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A new structure–activity relationship for cyanine dyes to improve photostability and fluorescence properties for live cell imaging

Abstract: A new set of cyanine-indole dyes was synthesized, characterized by optical and cytotoxic properties and subsequently applied for live cell imaging.

Cited by 37 publications

References 31 publications

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

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

High‐Fidelity Trapping of Spatial–Temporal Mitochondria with Rational Design of Aggregation‐Induced Emission Probes

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