A novel nitro-substituted benzothiadiazole as fluorescent probe for tumor cells under hypoxic condition

Jiang, Qian; Zhang, Zhanyuan; Lu, Jiao; Huang, Yan; Lu, Zhiyun; Tan, Yanfei; Jiang, Qing

doi:10.1016/j.bmc.2013.10.019

Cited by 44 publications

(29 citation statements)

References 28 publications

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“… 20 By using BTD-based fluorophores, some interesting applications were described. For instance, tumor cells under hypoxic condition were labeled, 21 ligand trafficking in artificial and living cell systems could be probed, 22 and other applications are found. 23 − 27 Among these new applications, selective LDs staining was described by us 28 and by others.…”

Section: Introductionmentioning

confidence: 99%

From Live Cells to Caenorhabditis elegans: Selective Staining and Quantification of Lipid Structures Using a Fluorescent Hybrid Benzothiadiazole Derivative

et al. 2018

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The current article describes the synthesis, characterization, and application of a designed hybrid fluorescent BTD–coumarin (2,1,3-benzothiadiazole-coumarin) derivative (named BTD-Lip). The use of BTD-Lip for live-cells staining showed excellent results, and lipid droplets (LDs) could be selectively stained. When compared with the commercially available dye (BODIPY) for LD staining, it was noted that the designed hybrid fluorescence was capable of staining a considerable larger number of LDs in both live and fixed cells (ca. 40% more). The new dye was also tested on live Caenorhabditis elegans (complex model) and showed an impressive selectivity inside the worm, whereas the commercial dye showed no selectivity in the complex model.

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Section: Introductionmentioning

confidence: 99%

From Live Cells to Caenorhabditis elegans: Selective Staining and Quantification of Lipid Structures Using a Fluorescent Hybrid Benzothiadiazole Derivative

et al. 2018

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“…[17,[25][26][27][28][29] The other mechanism for the design of hypoxia-sensitive imaging probes was by exploiting the bioreductive microenvironmento fh ypoxia,r esulting in excess expression of nitro reductase (NTR), azo reductase, quinone reductase, and so forth. [30] Several hypoxia-sensitive probes, the luminescence intensity of which changes depending on bioreductionu nder hypoxia,h ave been developed by employing nitro groups, [31][32][33] azo groups, [8,10,34] quinone groups, [19,35] or QSY-21 [9] as the hypoxia-sensing moiety.…”

Section: Introductionmentioning

confidence: 99%

Iridium(III) Anthraquinone Complexes as Two‐Photon Phosphorescence Probes for Mitochondria Imaging and Tracking under Hypoxia

Sun

Chen

Kuang

et al. 2016

Chemistry A European J

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In the present study, four mitochondria-specific and two-photon phosphorescence iridium(III) complexes, Ir1-Ir4, were developed for mitochondria imaging in hypoxic tumor cells. The iridium(III) complex has two anthraquinone groups that are hypoxia-sensitive moieties. The phosphorescence of the iridium(III) complex was quenched by the functions of the intramolecular quinone unit, and it was restored through two-electron bioreduction under hypoxia. When the probes were reduced by reductase to hydroquinone derivative products under hypoxia, a significant enhancement in phosphorescence intensity was observed under one- (λ=405 nm) and two-photon (λ=720 nm) excitation, with a two-photon absorption cross section of 76-153 GM at λ=720 nm. More importantly, these probes possessed excellent specificity for mitochondria, which allowed imaging and tracking of the mitochondrial morphological changes in a hypoxic environment over a long period of time. Moreover, the probes can visualize hypoxic mitochondria in 3D multicellular spheroids and living zebrafish through two-photon phosphorescence imaging.

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“…An example of smooth cyclization in high yield by phosphoric acid is the formation of 2-benzamido-5-phenyl-1,3,4-thiadiazole from 1,4-dibenzoylthiosemicarbazide 23 .…”

Section: Methodsmentioning

confidence: 99%

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

Asif¹

2016

Mediterr.J.Chem.,

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Thiadiazoles are an important class of heterocyclic compounds that exhibit diverse applications in organic synthesis, pharmaceutical and biological applications. They are also useful as oxidation inhibitors, cyanine dyes, metal chelating agents, anti-corrosion agents. Researchers across the globe are working on this moiety due to their broad spectrum of applications of thiadiazole chemistry. This article provides information about developments, exploration, synthetic strategies, techniques for the synthesis of thiadiazoles and their diverse biological activities, structure-activity relationship of the compounds and physical properties. This article is an important tool for organic and medicinal chemists to develop newer thiadiazole compounds that could be better agents in terms of efficacy and safety.

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A novel nitro-substituted benzothiadiazole as fluorescent probe for tumor cells under hypoxic condition

Cited by 44 publications

References 28 publications

From Live Cells to Caenorhabditis elegans: Selective Staining and Quantification of Lipid Structures Using a Fluorescent Hybrid Benzothiadiazole Derivative

From Live Cells to Caenorhabditis elegans: Selective Staining and Quantification of Lipid Structures Using a Fluorescent Hybrid Benzothiadiazole Derivative

Iridium(III) Anthraquinone Complexes as Two‐Photon Phosphorescence Probes for Mitochondria Imaging and Tracking under Hypoxia

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

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