NIR-emitting styryl dyes with large Stokes’ shifts for imaging application: From cellular plasma membrane, mitochondria to zebrafish neuromast

Dahal, Dipendra; Ojha, Krishna R.; Pokhrel, Sabita; Paruchuri, Sailaja; Konopka, Michael; Liu, Qin; Pang, Yi

doi:10.1016/j.dyepig.2021.109629

Cited by 12 publications

(7 citation statements)

References 52 publications

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“…The studied compounds have large Stokes’ shift values ( Table 3 , entry 3 )—around 195 nm for compounds 6a and b ; 240 nm for compound 6e ; 325 and 352 nm for compounds 6d and 6c , respectively. The revealed properties of the reported fluorescent compounds are in line with the results of recent articles on NIR styryl dyes [ 46 ], where it is indicated that very large Stokes’ shifts are crucial in bioimaging applications. Synthesis and studies of styryl dyes are continuing with the purpose of searching for efficient plasma membrane probes [ 47 ], highly selective fluorescent probes for lysosome visualisation in live cells [ 48 ], probes to visualise the nucleus in live cells [ 49 ], and probes for mitochondria imaging in live cells [ 50 ].…”

Section: Resultssupporting

confidence: 85%

Styrylpyridinium Derivatives for Fluorescent Cell Imaging

Putralis,

Korotkaja,

Kaukulis

et al. 2023

Pharmaceuticals

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A set of styrylpyridinium (SP) compounds was synthesised in order to study their spectroscopic and cell labelling properties. The compounds comprised different electron donating parts (julolidine, p-dimethylaminophenyl, p-methoxyphenyl, 3,4,5-trimethoxyphenyl), conjugated linkers (vinyl, divinyl), and an electron-withdrawing N-alkylpyridinium part. Geminal or bis-compounds incorporating two styrylpyridinium (bis-SP) moieties at the 1,3-trimethylene unit were synthesised. Compounds comprising a divinyl linker and powerful electron-donating julolidine donor parts possessed intensive fluorescence in the near-infrared region (maximum at ~760 nm). The compounds had rather high cytotoxicity towards the cancerous cell lines HT-1080 and MH-22A; at the same time, basal cytotoxicity towards the NIH3T3 fibroblast cell line ranged from toxic to harmful. SP compound 6e had IC50 values of 1.0 ± 0.03 µg/mL to the cell line HT-1080 and 0.4 µg/mL to MH-22A; however, the basal toxicity LD50 was 477 mg/kg (harmful). The compounds showed large Stokes’ shifts, including 195 nm for 6a,b, 240 nm for 6e, and 325 and 352 nm for 6d and 6c, respectively. The highest photoluminescence quantum yield (PLQY) values were observed for 6a,b, which were 15.1 and 12.2%, respectively. The PLQY values for the SP derivatives 6d,e (those with a julolidinyl moiety) were 0.5 and 0.7%, respectively. Cell staining with compound 6e revealed a strong fluorescent signal localised in the cell cytoplasm, whereas the cell nuclei were not stained. SP compound 6e possessed self-assembling properties and formed liposomes with an average diameter of 118 nm. The obtained novel data on near-infrared fluorescent probes could be useful for the development of biocompatible dyes for biomedical applications.

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Section: Resultssupporting

confidence: 85%

Styrylpyridinium Derivatives for Fluorescent Cell Imaging

Putralis,

Korotkaja,

Kaukulis

et al. 2023

Pharmaceuticals

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“…Compared to commercial CM dye FM1-43, probe 3 exhibited high fluorescence quantum yield and Stokes shift, enabling probe 3 to be used in a lower concentration. In 2021, using a similar molecular construction strategy, they obtained NIR CM-targeting probe 4 with 260 nm Stokes shift by integrating the ESIPT unit 2-(2-hydroxyphenyl)benzoxazole (HBO) into pyridinium-derived cyanine [ 55 ]. Application of this probe in live cells showed that this probe could stain inner CM in prokaryotic cells, E. coli ( Figure 3 ).…”

Section: Nir Molecular Probes For CM Imagingmentioning

confidence: 99%

Molecular Engineering of Near-Infrared Fluorescent Probes for Cell Membrane Imaging

Pan

Song

et al. 2023

Molecules

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Cell membrane (CM) is a phospholipid bilayer that maintains integrity of a whole cell and relates to many physiological and pathological processes. Developing CM imaging tools is a feasible method for visualizing membrane-related events. In recent decades, small-molecular fluorescent probes in the near-infrared (NIR) region have been pursued extensively for CM staining to investigate its functions and related events. In this review, we summarize development of such probes from the aspect of design principles, CM-targeting mechanisms and biological applications. Moreover, at the end of this review, the challenges and future research directions in designing NIR CM-targeting probes are discussed. This review indicates that more efforts are required to design activatable NIR CM-targeting probes, easily prepared and biocompatible probes with long retention time regarding CM, super-resolution imaging probes for monitoring CM nanoscale organization and multifunctional probes with imaging and phototherapy effects.

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“…Styryl dyes consist of an electron donor (D) and electron acceptor (A) building block linked together through a π-conjugated system, forming D-π-A architectures [1,2]. In general, they present high absorption capacity in the blue to green region of the visible spectrum and highly red-shifted fluorescence, as the emission takes place from an intramolecular charge-transfer state (ICT), exhibiting rather large Stokes shifts, an important feature to minimize inner-filter effects (reabsorption and re-emission) [3][4][5][6]. Their strong push-pull character makes them very promising organic molecules for advanced optical applications, including nonlinear optics (NLO), sensing, and bioimaging [3,[6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Confinement of a Styryl Dye into Nanoporous Aluminophosphates: Channels vs. Cavities

Oliden-Sánchez,

Sola-Llano,

Pérez-Pariente

et al. 2024

IJMS

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Styryl dyes are generally poor fluorescent molecules inherited from their flexible molecular structures. However, their emissive properties can be boosted by restricting their molecular motions. A tight confinement into inorganic molecular sieves is a good strategy to yield highly fluorescent hybrid systems. In this work, we compare the confinement effect of two Mg-aluminophosphate zeotypes with distinct pore systems (the AEL framework, a one-dimensional channeled structure with elliptical pores of 6.5 Å × 4.0 Å, and the CHA framework, composed of large cavities of 6.7 Å × 10.0 Å connected by eight-ring narrower windows) for the encapsulation of 4-DASPI styryl dye (trans-4-[4-(Dimethylamino)styryl]-1-methylpyridinium iodide). The resultant hybrid systems display significantly improved photophysical features compared to 4-DASPI in solution as a result of tight confinement in both host inorganic frameworks. Molecular simulations reveal a tighter confinement of 4-DASPI in the elliptical channels of AEL, explaining its excellent photophysical properties. On the other hand, a singular arrangement of 4-DASPI dye is found when confined within the cavity-based CHA framework, where the 4-DASPI molecule spans along two adjacent cavities, with each aromatic ring sitting on these adjacent cavities and the polymethine chain residing within the narrower eight-ring window. However, despite the singularity of this host–guest arrangement, it provides less tight confinement for 4-DASPI than AEL, resulting in a slightly lower quantum yield.

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NIR-emitting styryl dyes with large Stokes’ shifts for imaging application: From cellular plasma membrane, mitochondria to zebrafish neuromast

Cited by 12 publications

References 52 publications

Styrylpyridinium Derivatives for Fluorescent Cell Imaging

Styrylpyridinium Derivatives for Fluorescent Cell Imaging

Molecular Engineering of Near-Infrared Fluorescent Probes for Cell Membrane Imaging

Confinement of a Styryl Dye into Nanoporous Aluminophosphates: Channels vs. Cavities

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