A Two‐Photon Excitation Based Fluorogenic Probe for Sialome Imaging in Living Systems

Rong, Lei; Zhang, Chi; Lei, Qi; Qin, Si‐Yong; Feng, Jun; Zhang, Xian‐Zheng

doi:10.1002/advs.201500211

Cited by 8 publications

(8 citation statements)

References 16 publications

(18 reference statements)

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“… 18 As anticipated, pure DBB-NO possesses a maximum δ of 270 GM at 710 nm. Although such a value is comparable to the TP-imaging contrast in other reports, 19 the ultralow Φ F makes DBB-NO unusable for TP-imaging due to its low brightness ( δ × Φ F ). In sharp contrast, upon responding to NO, an extremely elevated δ (2800 GM at 710 nm) was observed, which nearly reached the maximum δ of DBB (3300 GM at 710 nm).…”

Section: Resultssupporting

confidence: 60%

Nitric oxide activatable photosensitizer accompanying extremely elevated two-photon absorption for efficient fluorescence imaging and photodynamic therapy

Xie

Zhao

et al. 2018

Chem. Sci.

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Section: Resultssupporting

confidence: 60%

Nitric oxide activatable photosensitizer accompanying extremely elevated two-photon absorption for efficient fluorescence imaging and photodynamic therapy

Xie

Zhao

et al. 2018

Chem. Sci.

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“…Interestingly, a fluorogenic CuAAC adduct was demonstrated to exhibit a considerable response to two-photon excitation. Herein, Ac 4 ManNAz was clicked with Naph-yne, an alkyne-functionalized turn-on fluorophore synthesized from 4-bromo-1,8-naphthalic anhydride . This bioconjugation may find application in deeper tissue imaging, although to date, it has been applied to only the embryonic surfaces.…”

Section: Glycansmentioning

confidence: 99%

“…Herein, Ac 4 ManNAz was clicked with Naph-yne, an alkynefunctionalized turn-on fluorophore synthesized from 4-bromo-1,8-naphthalic anhydride. 39 This bioconjugation may find application in deeper tissue imaging, although to date, it has been applied to only the embryonic surfaces. Zebrafish embryos metabolically labeled with N-azidogalactosamine (GalNAz) were spatially labeled through focused ultraviolet irradiation 72 hpf using 4,5-dimethoxy-2-nitrobenzyl (DMNB)-caged phos- phine (Figure 2, 1).…”

Section: ■ Glycansmentioning

confidence: 99%

Clicking a Fish: Click Chemistry of Different Biomolecules in Danio rerio

Chandrasekaran

Rentmeister

2018

Biochemistry

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Click chemistry has found remarkable applications in imaging biomacromolecules in cellular systems and even organisms. Over the past few years, bioorthogonal click reactions have been improved and tailored for specific applications, allowing the selective labeling of biomolecules like DNA, RNA, proteins, glycans, and lipids. The zebrafish, Danio rerio, is a prime model organism for vertebrate development and has gained importance in experimental biology and biochemistry for its ease of handling and appreciable genetic homology to mammals. With respect to biomolecular labeling, the zebrafish represents the next level of complexity relative to in vitro cell line models, challenging researchers to further improve the specificity and targeting of their labeling approaches, and to reduce the level of interference with the host. At the same time, bioorthogonal labeling has facilitated an improved understanding of embryonic zebrafish development. Highlighted in this Perspective are click chemistry approaches that rely on (i) designing analogues of endogenous target molecules, (ii) utilizing the conjugation moiety on these analogues to attach fluorophores by clicking them outside or inside living systems, and finally, (iii) imaging the cells or tissue or, sometimes, the whole organism. While glycans and proteins have been extensively studied in D. rerio using bioorthogonal click chemistry for their intimate involvement in embryonic development, DNA and RNA remain less investigated. Together with the formulation of strategies to perform click reactions with the weakest impact on the host system, bioorthogonal approaches have enormous potential to visualize organisms in all their molecular splendor.

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“…Zhang and co-workers treated living cells by mild periodate oxidation to selectively generate aldehydes on SAs followed by chemoselective ligation of fluorescein-5-thiosemicarbazide toward aldehydes, achieving in situ two-photon imaging of sialylated glycoproteins on living cells . Rong and co-workers synthesized an alkyne-functionalized and two-photon excited fluorogenic probe for the sialylated glycans imaging through copper(I)-catalyzed azido-alkyne cycloaddition . Zheng et al developed a two-photon bioorthogonal functionalized terbium complex and metabolic precursor Ac 4 ManNTCO to profile SAs on living cells .…”

Section: Introductionmentioning

confidence: 99%

Self-Assembled Nanorods of Phenylboronic Acid Functionalized Pyrene for In Situ Two-Photon Imaging of Cell Surface Sialic Acids and Photodynamic Therapy

Liu

2021

Anal. Chem.

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Sialic acid (SA) plays important roles in various biological and pathological processes. Methods for monitoring and detection of SA are of great significance in terms of fundamental research, cancer diagnostics, and therapeutics, which are still limited until now. Here, a phenylboronic acid (PBA)-functionalized pyrene derivative, 4-(4-(pyren-1-yl)butyramido)phenylboronic acid (Py-PBA), was synthesized and used as a building block for selfassembling into hydrophilic nanorods. The Py-PBA nanorods (Py-PBA NRs) featured highly specific and efficient imaging of SA on living cells with the advantages of excellent fluorescence stability, good biocompatibility, and unique two-photon fluorescence properties. Meanwhile, the assembled Py-PBA NRs could efficiently generate 1 O 2 under two-photon irradiation, making it an excellent candidate for photodynamic therapy. This nanoplatform realized in situ recognition and two-photon imaging of SA on the cell surface as well as effective cancer cell therapy, providing a potential method for simple and selective analysis of SA in living cells and a new prospect for image-guided therapy.

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A Two‐Photon Excitation Based Fluorogenic Probe for Sialome Imaging in Living Systems

Abstract: Taking advantage of the fluorescence property of alkyne‐modified naphthalimide, the two‐photon excited fluorogenic probe Naph‐yne is used for azide‐tagged mannosyl glycoprotein imaging both at the cellular level and for vertebrate model organisms.

Cited by 8 publications

References 16 publications

Nitric oxide activatable photosensitizer accompanying extremely elevated two-photon absorption for efficient fluorescence imaging and photodynamic therapy

Nitric oxide activatable photosensitizer accompanying extremely elevated two-photon absorption for efficient fluorescence imaging and photodynamic therapy

Clicking a Fish: Click Chemistry of Different Biomolecules in Danio rerio

Self-Assembled Nanorods of Phenylboronic Acid Functionalized Pyrene for In Situ Two-Photon Imaging of Cell Surface Sialic Acids and Photodynamic Therapy

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