The pursuit of polymethine fluorophores with NIR-II emission and high brightness for<i>in vivo</i>applications

Zhang, Xuan; Zhang, Fan; Lei, Zuhai

doi:10.1039/d2sc03136a

Cited by 52 publications

(32 citation statements)

References 82 publications

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“…, the instability of conventional dyes and the low brightness of polymers). 76–78 Chan and coworkers designed and synthesized three types of polymethine-based SPs (Pttc-SeBTa-NIR1125/1270/1380) with narrow absorption and emission bands for NIR-IIb (1500–1700 nm) fluorescence imaging of whole-body blood vessels and the mouse brain. 79 They synthesized a SP with anti-ACQ properties because the rigid three-dimensional structure of the Pttc monomer and the steric hindrance of the SeBTa monomer were both conducive to preventing the ACQ effect.…”

Section: High-performance Nir-ii Sps For High-resolution In Vivo Fluo...mentioning

confidence: 99%

NIR-II semiconducting polymers forin vivohigh-resolution imaging and theranostics

et al. 2023

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Section: High-performance Nir-ii Sps For High-resolution In Vivo Fluo...mentioning

confidence: 99%

NIR-II semiconducting polymers forin vivohigh-resolution imaging and theranostics

et al. 2023

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“…[14][15][16] However, the long flexible conjugated chains also cause some problems, including insufficient fluorescence brightness, poor molecular stability, and unsatisfactory biocompatibility. 17 Nevertheless, xanthenoid dyes usually have high brightness and excellent stability, 18 with maximum emission wavelengths redshifted to the near-infrared window by using some structural modification strategies, such as -conjugation extension, replacement of the oxygen atom with other atoms, and cyclization, 19 although the wavelengths often remain below 800 nm. 20 Based on these observations, we have designed a series of shortwave infrared fluorescent dyes CX 21 and Chrodol, 22 with adjustable wavelengths, by creatively combining the respective advantages of cyanine and xanthenoid dyes.…”

Section: Account Synlett 3 Fluorescent Dyes and Fluorescent Probes Co...mentioning

confidence: 99%

New High-Performance Fluorescent Dye Scaffolds: Applications for Bioimaging and Biosensing

Cheng

Lei

2023

Synlett

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Fluorescence imaging in the short-wave infrared region (SWIR, 850-2500 nm) window has become an indispensable tool in biomedical research with weaker absorption, less light scattering, and less background fluorescence in this window. As we know, the design and synthesis of fluorescent dyes and fluorescent probes are the cores of fluorescence imaging and biosensing. Thus, their photophysical mechanisms exploring and bioanalytical applications are multidisciplinary and cutting-edge research topics. In this regard, we have been working on high-performance fluorescent dyes and fluorescent probes for years. In short, we have developed a series of bright, stable, aggregation-resistant, SWIR fluorescent dyes ECXs, based on a carbon-bridged spiro ring strategy. Besides, we also developed a series of high-performance SWIR fluorescent dyes CXs and Chrodols, which combine the structural advantages of cyanine and xanthenoid dyes. Based on these new SWIR scaffolds, we further constructed some activatable SWIR fluorescent probes with OFF-ON or ratiometric properties for biosensing in vivo. Therefore, the mainline of our work is to deeply understand the photophysical mechanisms of fluorescent dyes, to create high-performance luminescent dyes, and further develop fluorescent probes for bioimaging and biosensing.

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“…As an important class of near-infrared chromophores, despite their relatively poor photostability, heptamethine cyanine dyes have aroused great interest due to the ease of structural modifications to extend these chromophores’ fluorescence into the NIR-II range and their high absorption coefficient. − But their long conjugation architecture and hydrophobicity usually prevent them from being renal clearable, thus limiting their applications in the detection and imaging of kidney diseases. Attempts to improve the water solubility of these dyes by introducing hydrophilic group(s) at both ends of the dyes may not make them kidney clearable. − For example, indocyanine green (ICG), which has been approved by the FDA for clinical applications, is water soluble because hydrophilic sulfonate groups have been introduced on both sides of the conjugation architecture, and yet it remains hepatic clearable instead of renal clearable; − this is because the conjugation skeleton in the middle remains hydrophobic and easily binds with proteins in vivo, resulting in the formation of particles too large to be renal clearable; the same is true for the hydrophilic group PEG n ( n = 3–45), − as displayed in Scheme A.…”

Section: Introductionmentioning

confidence: 99%

Renal-Clearable Probe with Water Solubility and Photostability for Biomarker-Activatable Detection of Acute Kidney Injuries via NIR-II Fluorescence and Optoacoustic Imaging

Zeng

Tan

Sun

et al. 2023

ACS Appl. Mater. Interfaces

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Acute kidney injuries (AKI) have serious short-term or long-term complications with high morbidity and mortality rate, thus posing great health threats. Developing high-performance NIR-II probes for noninvasive in situ detection of AKI via NIR-II fluorescent and optoacoustic dual-mode imaging is of great significance. Yet NIR-II chromophores often feature long conjugation and hydrophobicity, which prevent them from being renal clearable, thus limiting their applications in the detection and imaging of kidney diseases. To fully exploit the advantageous features of heptamethine cyanine dye, while overcoming its relatively poor photostability, and to strive to design a NIR-II probe for the detection and imaging of AKI with dual-mode imaging, herein, we have developed the probe PEG3-HC-PB, which is renal clearable, water soluble, and biomarker activatable and has good photostability. As for the probe, its fluorescence (900−1200 nm) is quenched due to the existence of the electron-pulling phenylboronic group (responsive element), and it exhibits weak absorption with a peak at 830 nm. Meanwhile, in the presence of the overexpressed H 2 O 2 in the renal region in the case of AKI, the phenylboronic group is converted to the phenylhydroxy group, which enhances NIR-II fluorescent emission (900−1200 nm) and absorption (600−900 nm) and eventually produces conspicuous optoacoustic signals and NIR-II fluorescent emission for imaging. This probe enables detection of contrast-agent-induced and ischemia/reperfusion-induced AKI in mice using real-time 3D-MSOT and NIR-II fluorescent dual-mode imaging via response to the biomarker H 2 O 2 . Hence, this probe can be used as a practicable tool for detecting AKI; additionally, its design strategy could provide insight into the design of other large-conjugation NIR-II probes with multifarious biological applications.

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The pursuit of polymethine fluorophores with NIR-II emission and high brightness forin vivoapplications

Abstract: Polymethine cyanine dyes, as the most important class of organic near-Infrared-II (NIR-II) fluorophores, recently received increasing attention due to their high molar extinction coefficients, intensive fluorescence brightness, and flexible wavelength...

Cited by 52 publications

References 82 publications

NIR-II semiconducting polymers forin vivohigh-resolution imaging and theranostics

NIR-II semiconducting polymers forin vivohigh-resolution imaging and theranostics

New High-Performance Fluorescent Dye Scaffolds: Applications for Bioimaging and Biosensing

Renal-Clearable Probe with Water Solubility and Photostability for Biomarker-Activatable Detection of Acute Kidney Injuries via NIR-II Fluorescence and Optoacoustic Imaging

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