Development of NIR Fluorescent Dyes Based on Si–rhodamine for in Vivo Imaging

Koide, Yuichiro; Urano, Yasuteru; Hanaoka, Kenjiro; Piao, Wen; Kusakabe, Moriaki; Saito, Noriko; Terai, Takuya; Okabe, Takayoshi; Nagano, Tetsuo

doi:10.1021/ja210375e

Cited by 276 publications

(198 citation statements)

References 19 publications

Supporting

Mentioning

187

Contrasting

Unclassified

Order By: Relevance

“…As illustrated by the x- and y- axes in Fig. 3a, substituting the 10-position of xanthene from O atom to C and Si 23 (Fig. 3a, green marked), gradually expanding the xanthene rings (Fig.…”

mentioning

confidence: 99%

Super-multiplex vibrational imaging

Chen

Shi

et al. 2017

Nature

433

452

View full text Add to dashboard Cite

The ability to directly visualize a large number of distinct molecular species inside cells is increasingly essential for understanding complex systems and processes. Even though existing methods have been used successfully to explore structural-functional relationships in nervous systems, profile RNA in situ, reveal tumor microenvironment heterogeneity or study dynamic macromolecular assembly1–4, it remains challenging to image many species with high selectivity and sensitivity under biological conditions. For instance, fluorescence microscopy faces a “color barrier” due to the intrinsically broad (~1500 cm−1) and featureless nature of fluorescence spectra5 that limits the number of resolvable colors to 2 to 5 (or 7-9 if using complicated instrumentation and analysis)6–8. Spontaneous Raman microscopy probes vibrational transitions with much narrower resonances (peak width ~10 cm−1) and thus doesn’t suffer this problem, but its feeble signals make many demanding bio-imaging applications impossible. And while surface-enhanced Raman scattering offers remarkable sensitivity and multiplicity, it cannot be readily used to quantitatively image specific molecular targets inside live cells9. Here we show that carrying out stimulated Raman scattering under electronic pre-resonance conditions (epr-SRS) enables imaging with exquisite vibrational selectivity and sensitivity (down to 250 nM with 1-ms) in living cells. We also create a palette of triple-bond-conjugated near-infrared dyes that each display a single epr-SRS peak in the cell-silent spectral window, and that with available fluorescent probes give 24 resolvable colors with potential for further expansion. Proof-of-principle experiments on neuronal co-cultures and brain tissues reveal cell-type dependent heterogeneities in DNA and protein metabolism under physiological and pathological conditions, underscoring the potential of this super-multiplex optical imaging approach for untangling intricate interactions in complex biological systems.

show abstract

“…As illustrated by the x- and y- axes in Fig. 3a, substituting the 10-position of xanthene from O atom to C and Si 23 (Fig. 3a, green marked), gradually expanding the xanthene rings (Fig.…”

mentioning

confidence: 99%

Super-multiplex vibrational imaging

Chen

Shi

et al. 2017

Nature

433

452

View full text Add to dashboard Cite

show abstract

“…22 2-Me TeR, a NIRF dye that selectively probed reactive oxygen species (ROS) utilizing tellurium, could monitor dynamically in vivo endogenous ROS levels. 23 Unique NIR-absorbing xanthene chromophores could also be synthesized by modulating the HOMO-LUMO (highest occupied molecular orbital-lowest unoccupied molecular orbital) gap in xanthene dyes.…”

mentioning

confidence: 99%

Near-infrared fluorescent probes in cancer imaging and therapy: an emerging field

Yi¹,

Wang²,

Qin³

et al. 2014

IJN

213

149

View full text Add to dashboard Cite

Near-infrared fluorescence (NIRF) imaging is an attractive modality for early cancer detection with high sensitivity and multi-detection capability. Due to convenient modification by conjugating with moieties of interests, NIRF probes are ideal candidates for cancer targeted imaging. Additionally, the combinatory application of NIRF imaging and other imaging modalities that can delineate anatomical structures extends fluorometric determination of biomedical information. Moreover, nanoparticles loaded with NIRF dyes and anticancer agents contribute to the synergistic management of cancer, which integrates the advantage of imaging and therapeutic functions to achieve the ultimate goal of simultaneous diagnosis and treatment. Appropriate probe design with targeting moieties can retain the original properties of NIRF and pharmacokinetics. In recent years, great efforts have been made to develop new NIRF probes with better photostability and strong fluorescence emission, leading to the discovery of numerous novel NIRF probes with fine photophysical properties. Some of these probes exhibit tumoricidal activities upon light radiation, which holds great promise in photothermal therapy, photodynamic therapy, and photoimmunotherapy. This review aims to provide a timely and concise update on emerging NIRF dyes and multifunctional agents. Their potential uses as agents for cancer specific imaging, lymph node mapping, and therapeutics are included. Recent advances of NIRF dyes in clinical use are also summarized.

show abstract

“…A dramatic red-shift to NIR emission was observed due to the relatively low lying LUMO levels of the group 14 elements allowing the fluorescent properties to be readily controlled. [89][90][91] Recent studies have been carried out by both Urano and Nagano in the area of enzyme-activated photosensitizers. The Nagano group reported bGal activated photosensitizers based on thiazole orange, PhoTo-Gal, and fluorescein, TGI-bGal.…”

Section: Rhodaminementioning

confidence: 99%

Recent advances in the development of synthetic chemical probes for glycosidase enzymes

2015

View full text Add to dashboard Cite

The emergence of synthetic glycoconjugates as chemical probes for the detection of glycosidase enzymes has resulted in the development of a range of useful chemical tools with applications in glycobiology, biotechnology, medical and industrial research. Critical to the function of these probes is the preparation of substrates containing a glycosidic linkage that when activated by a specific enzyme or group of enzymes, irreversibly releases a reporter molecule that can be detected. Starting from the earliest examples of colourimetric probes, increasingly sensitive and sophisticated substrates have been reported. In this review we present an overview of the recent advances in this field, covering an array of strategies including chromogenic and fluorogenic substrates, lanthanide complexes, gels and nanoparticles. The applications of these substrates for the detection of various glycosidases and the scope and limitations for each approach are discussed.

show abstract

Development of NIR Fluorescent Dyes Based on Si–rhodamine for in Vivo Imaging

Cited by 276 publications

References 19 publications

Super-multiplex vibrational imaging

Super-multiplex vibrational imaging

Near-infrared fluorescent probes in cancer imaging and therapy: an emerging field

Recent advances in the development of synthetic chemical probes for glycosidase enzymes

Contact Info

Product

Resources

About