4-Nitroimidazole-3-hydroxyflavone conjugate as a fluorescent probe for hypoxic cells

Feng, Weipei; Wang, Yuechai; Chen, Shizhu; Wang, Chao; Wang, Shuxiang; Li, Shenghui; Li, Hongyan; Zhou, Guoqiang; Zhang, Jinchao

doi:10.1016/j.dyepig.2016.03.019

Cited by 27 publications

(12 citation statements)

References 38 publications

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“…Probe 68 was found to be cell permeable and capable of detecting changes in the levels of oxygen in HeLa cells, presumably via differences in NTR activity. 196…”

Section: Nitroreductases (Ntr)mentioning

confidence: 99%

Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents

et al. 2018

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“…Probe 68 was found to be cell permeable and capable of detecting changes in the levels of oxygen in HeLa cells, presumably via differences in NTR activity. 196…”

Section: Nitroreductases (Ntr)mentioning

confidence: 99%

Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents

et al. 2018

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“…These results provided evidence for the release of FDU and IMC-TZBCM from the prodrug IMC-FDU-TZBC-NO 2 . Based on the results above and combined with reports, ,− the process of releasing FDU with IMC-TZBCM from IMC-FDU-TZBC-NO 2 is depicted as follows: first, under the action of Na 2 S 2 O 4 the −NO 2 group was converted to −NH 2 , and IMC-FDU-TZBC-NO 2 was reduced to IMC-FDU-TZBC-NH 2 . Immediately following a series of electron transfer process and the 1,6-rearrangement-elimination reaction, small molecule 4-methylenecyclohexa-2,5-dien-1-iminium was eliminated, leading to production of IMC-FDU-TZBC.…”

Section: Resultsmentioning

confidence: 77%

Hypoxia-Activated and Indomethacin-Mediated Theranostic Prodrug Releasing Drug On-Demand for Tumor Imaging and Therapy

et al. 2019

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A smart theranostic prodrug IMC-FDU-TZBC-NO 2 , releasing active drug on-demand based on hypoxiaactivated and indomethacin-mediated, for solid tumor imaging and efficient therapy was designed. This prodrug was constructed by conjugating chemotherapy drug 5-fluoro-2-deoxyuridine (FDU), targeting moiety indomethacin (IMC), and the hypoxic trigger 4-nitrobenzyl group to a fluorescent dye precursor, which was mediated by IMC and activated by NTR under hypoxic conditions. The fluorescent dye IMC-TZBCM was generated and FDU was released at the same time in tumor cells. The rates and amounts of FDU release and IMC-TZBCM generation were regulated by hypoxia status, and increased with increasing degree of hypoxia. Nevertheless, it is "locked" in normal cells. It combined the advantages of tumor targeting, diagnosis, and chemotherapy functions, showed excellent targeting ability to cancer cells, excellent stability in physiological conditions, high cellular uptake efficiency, and on-demand drug release behavior. The in vitro and in vivo assays demonstrated that IMC-FDU-TZBC-NO 2 exhibits enhanced anticancer potency and low side effects. The novel targeted theranostic prodrug activated by hypoxia shows a great potential in cancer therapy.

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“…[104][105][106][107] Nitro-Group-Based Designs: Nitro-group-based PeT imaging probes are the most popular reductive moieties used in tumor hypoxia sensing and they include a range of nitroderivatives such as nitrobenzyl, [108][109][110][111] nitrobenzene, [112,113] and nitroimidazole. [114,115] The nitro group in these nitro-derivatives is reduced by NTRs to form electron-donating hydroxyl or amino group.…”

Section: Petmentioning

confidence: 99%

Nano versus Molecular: Optical Imaging Approaches to Detect and Monitor Tumor Hypoxia

Cheng

Zheng

2020

Adv Healthcare Materials

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Hypoxia is a ubiquitous feature of solid tumors, which plays a key role in tumor angiogenesis and resistance development. Conventional hypoxia detection methods lack continuous functional detection and are generally less suitable for dynamic hypoxia measurement. Optical sensors hereby provide a unique opportunity to noninvasively image hypoxia with high spatiotemporal resolution and enable real‐time detection. Therefore, these approaches can provide a valuable tool for personalized treatment planning against this hallmark of aggressive cancers. Many small optical molecular probes can enable analyte triggered response and their photophysical properties can also be fine‐tuned through structural modification. On the other hand, optical nanoprobes can acquire unique intrinsic optical properties through nanoconfinement as well as enable simultaneous multimodal imaging and drug delivery. Furthermore, nanoprobes provide biological advantages such as improving bioavailability and systemic delivery of the sensor to enhance bioavailability. This review provides a comprehensive overview of the physical, chemical, and biological analytes for cancer hypoxia detection and focuses on discussing the latest nano‐ and molecular developments in various optical imaging approaches (fluorescence, phosphorescence, and photoacoustic) in vivo. Finally, this review concludes with a perspective toward the potentials of these optical imaging approaches in hypoxia detection and the challenges with molecular and nanotechnology design strategies.

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4-Nitroimidazole-3-hydroxyflavone conjugate as a fluorescent probe for hypoxic cells

Cited by 27 publications

References 38 publications

Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents

Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents

Hypoxia-Activated and Indomethacin-Mediated Theranostic Prodrug Releasing Drug On-Demand for Tumor Imaging and Therapy

Nano versus Molecular: Optical Imaging Approaches to Detect and Monitor Tumor Hypoxia

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