Photoisomerization of Heptamethine Cyanine Dyes Results in Red-Emissive Species: Implications for Near-IR, Single-Molecule, and Super-Resolution Fluorescence Spectroscopy and Imaging DOI Creative Commons
Elin Sandberg, Joachim Piguet, Uliana Kostiv

et al.

The Journal of Physical Chemistry B, Journal Year: 2023, Volume and Issue: 127(14), P. 3208 - 3222

Published: April 3, 2023

Photoisomerization kinetics of the near-infrared (NIR) fluorophore Sulfo-Cyanine7 (SCy7) was studied by a combination fluorescence correlation spectroscopy (FCS) and transient state (TRAST) excitation modulation spectroscopy. A photoisomerized with redshifted emission identified, consistent three-state photoisomerization model. Combining TRAST spectrofluorimetry (spectral-TRAST) further confirmed an excitation-induced redshift in spectrum SCy7. We show how this red-emissive contributes to blinking different bands NIR cyanine dyes, it can influence single-molecule, super-resolution, as well Förster resonance energy transfer (FRET) multicolor readouts. Since also be populated at moderate intensities, more broadly readouts, readouts not relying on high conditions. However, additional its photodynamics, identified characterized work, used strategy push dyes into enhance photosensitization nanoparticles absorption spectra NIR. Finally, we that SCy7 formation photoisomer depend strongly local environmental conditions, such viscosity, polarity, steric constraints, which suggests use other sensors. Such information monitored TRAST, NIR, low autofluorescence scattering conditions broad range samples experimental

Language: Английский

Xanthene, cyanine, oxazine and BODIPY: the four pillars of the fluorophore empire for super-resolution bioimaging DOI
Soham Samanta, Kaitao Lai,

Feihu Wu

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(20), P. 7197 - 7261

Published: Jan. 1, 2023

In the realm of biological research, invention super-resolution microscopy (SRM) has enabled visualization ultrafine sub-cellular structures and their functions in live cells at nano-scale level, beyond diffraction limit, which opened up a new window for advanced biomedical studies to unravel complex unknown details physiological disorders level with unprecedented resolution clarity. However, most SRM techniques are highly reliant on personalized special photophysical features fluorophores. recent times, there been an surge development robust fluorophore systems various imaging techniques. To date, xanthene, cyanine, oxazine BODIPY cores have authoritatively utilized as basic units small-molecule-based organic fluorescent probe designing strategies owing excellent characteristics easy synthetic acquiescence. Since future next-generation will be decided by availability probes these four building blocks play important role progressive design, is urgent need review advancements fluorophores different methods based dye cores. This article not only includes comprehensive discussion about developments emphasis effective integration into cell bio-imaging applications but also critically evaluates background each highlight merits demerits towards developing newer SRM.

Language: Английский

Citations

63

Super-photostable organic dye for long-term live-cell single-protein imaging DOI
Dohyeon Kim, Hong Minh Triet, Sun Hyeok Lee

et al.

Nature Methods, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 15, 2025

Language: Английский

Citations

3

Recent Advances in Cyanine-Based Phototherapy Agents DOI Creative Commons

Kübra Bilici,

Sultan Cetin, Eda Celikbas

et al.

Frontiers in Chemistry, Journal Year: 2021, Volume and Issue: 9

Published: June 24, 2021

Phototherapies, in the form of photodynamic therapy (PDT) and photothermal (PTT), are very promising treatment modalities for cancer since they provide locality turn-on mechanism toxicity, both which critical reducing off-site toxicity. Irradiation photosensitive agents demonstrated successful therapeutic outcomes; however, each approach has its limitations needs to be improved clinical success. The combination PTT PDT may work a synergistic way overcome method indeed improve efficacy. development single capable inducing is, therefore, extremely advantageous highly desired. Cyanine dyes shown have such potential, hence been popular recent years. Luminescence cyanine renders them as phototheranostic molecules, reporting localization agent prior irradiation induce phototoxicity, allowing image-guided phototherapy. In this review, we mainly focus on dye–based phototherapy different cells, concentrating advancements achieved last ten

Language: Английский

Citations

64

Long-Wavelength Photoconvertible Dimeric BODIPYs for Super-Resolution Single-Molecule Localization Imaging in Near-Infrared Emission DOI
Qingbao Gong, Xinfu Zhang, Wanwan Li

et al.

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(48), P. 21992 - 21999

Published: Nov. 22, 2022

Sulfoxide-bridged dimeric BODIPYs were developed as a new class of long-wavelength photoconvertible fluorophores. Upon visible-light irradiation, sulfoxide moiety was released to generate the corresponding α,α-directly linked BODIPYs. The extrusion SO from sulfoxides mainly through an intramolecular fashion involving reactive triplet states. By this photoconversion, not only more than 100 nm red shifts absorption and emission maxima (up 648/714 nm) achieved but also stable products with bright fluorescence produced high efficiency. combination photoactivation red-shifted excitation/emission offered optimal contrast eliminated interference biological autofluorescence. More importantly, in situ these visible-light-induced reactions demonstrated ideal single-molecule properties near-infrared region. Therefore, photoconversion could be powerful method achieving super-resolution localization imaging living cell without using UV illumination cell-toxic additives.

Language: Английский

Citations

53

Photochemical Mechanisms of Fluorophores Employed in Single‐Molecule Localization Microscopy DOI Creative Commons
Kai Kikuchi, Liam D. Adair, Jiarun Lin

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(1)

Published: Sept. 30, 2022

Decoding cellular processes requires visualization of the spatial distribution and dynamic interactions biomolecules. It is therefore not surprising that innovations in imaging technologies have facilitated advances biomedical research. The advent super-resolution has empowered researchers with ability to answer long-standing questions about at an entirely new level. Fluorescent probes greatly enhance specificity resolution experiments. Here, we introduce key technologies, a brief discussion on single-molecule localization microscopy (SMLM). We evaluate chemistry photochemical mechanisms fluorescent employed SMLM. This Review provides guidance identification adoption single molecule inspire design next-generation amenable imaging.

Language: Английский

Citations

39

Heptamethine Cyanine Dyes with Ultra‐Efficient Excited‐State Nonradiative Decay for Synergistic Photothermal Immunotherapy DOI
Xiang Xia, Chao Shi, Yang Zi

et al.

Advanced Functional Materials, Journal Year: 2023, Volume and Issue: 33(38)

Published: May 26, 2023

Abstract Organic dyes in the excited singlet state (S 1 ) decay via intersystem crossing (ISC) to triplet state, radiative dissipation as fluorescence, or nonradiative for thermal deactivation. Although many studies are conducted improve ISC and fluorescence efficiency, few have optimized S deactivation, which is crucial designing photothermal agents. A strategy inhibiting by introducing electron withdraw groups (EWGs) into meso position of heptamethine cyanines (Cy7) reported here, allows energy relaxation. The decrease density Cy7 caused EWGs improved photostability, important biological applications because conventional cyanine easily photobleached. EWG substitutes acted efficient rotation with low‐energy barriers, narrowing gap between ground considerably improving conversion efficiency (PCE). PCE CF 3 cy strongest increased up 83%. Liposome used a carrier biocompatibility tumor retention cy, combined toll‐like receptor agonist resiquimod (R848) synergistic immunotherapy against both primary distant tumors elicits long‐lasting immunological memory effect.

Language: Английский

Citations

36

Method To Diversify Cyanine Chromophore Functionality Enables Improved Biomolecule Tracking and Intracellular Imaging DOI
Syed Muhammad Usama, Sierra C. Marker, Dong‐Hao Li

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(27), P. 14647 - 14659

Published: June 27, 2023

Heptamethine indocyanines are invaluable probes for near-infrared (NIR) imaging. Despite broad use, there only a few synthetic methods to assemble these molecules, and each has significant limitations. Here, we report the use of pyridinium benzoxazole (PyBox) salts as heptamethine indocyanine precursors. This method is high yielding, simple implement, provides access previously unknown chromophore functionality. We applied this create molecules address two outstanding objectives in NIR fluorescence First, used an iterative approach develop protein-targeted tumor When compared common fluorophores, optimized probe increases specificity monoclonal antibody (mAb) nanobody conjugates. Second, developed cyclizing with goal improving cellular uptake fluorogenic properties. By modifying both electrophilic nucleophilic components, demonstrate that solvent sensitivity ring-open/ring-closed equilibrium can be modified over wide range. then show chloroalkane derivative compound tuned cyclization properties undergoes particularly efficient no-wash live cell imaging using organelle-targeted HaloTag self-labeling proteins. Overall, chemistry reported here broadens scope accessible functionality, and, turn, enables discovery promising advanced applications.

Language: Английский

Citations

32

Red-Shifted Coumarin Luciferins for Improved Bioluminescence Imaging DOI
Anna Love, Donald R. Caldwell, Bethany Kolbaba‐Kartchner

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(6), P. 3335 - 3345

Published: Feb. 6, 2023

Multicomponent bioluminescence imaging in vivo requires an expanded collection of tissue-penetrant probes. Toward this end, we generated a new class near-infrared (NIR) emitting coumarin luciferin analogues (CouLuc-3s). The scaffolds were easily accessed from commercially available dyes. Complementary mutant luciferases for the CouLuc-3 also identified. brightest probes enabled sensitive vivo. are orthogonal to popular bioluminescent reporters and can be used multicomponent applications. Collectively, work showcases set tools that readily implemented multiplexed variety biological settings.

Language: Английский

Citations

24

Recent advances in self‐immobilizing fluorescent probes for in vivo imaging DOI Creative Commons
Yong Zhang,

Xuemei Lv,

Yafu Wang

et al.

Smart Molecules, Journal Year: 2024, Volume and Issue: 2(3)

Published: Aug. 23, 2024

Abstract In situ precise detection of bioactive molecules with high sensitivity and spatiotemporal resolution is essential for studying physiological events disease diagnosis. The utilization versatile fluorescent probes in fluorescence imaging offers a powerful tool vivo biomarkers closely associated pathological conditions. However, the dynamic behavior leading to rapid clearance small molecule from regions interest severely compromises their potential imaging. Notably, self‐immobilizing that selectively recognize diseased tissues while improving retention enrichment enable accurate high‐fidelity this review, we aim summarize strategies employed recent advances performance precision using techniques. Lastly, discuss prospects challenges promote further development application more delicate probes.

Language: Английский

Citations

13

Near-infrared photocatalysis with cyanines: synthesis, applications and perspectives DOI Creative Commons
Nicolas Sellet, Johanna Frey, Morgan Cormier

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(23), P. 8639 - 8650

Published: Jan. 1, 2024

Cyanines are organic dyes bearing two aza-heterocycles linked by a polymethine chain.

Language: Английский

Citations

12