Biodistribution study of 2-nitroimidazole indocyanine green conjugate dye conjugates

Zanganeh, Saeid; Zhou, Feifei; Abuteen, Akram; Mohammad, Innus; Smith, Michael B.; Zhu, Quing

doi:10.1364/biomed.2014.bt3a.51

Cited by 2 publications

(1 citation statement)

References 13 publications

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“…17 The fluorescence signals were measured to be two-fold higher at the tumor site, relative to the untargeted dye 2 . 19 Furthermore, we showed that 3 could be detected in the tumor for 5-7 h, post-injection. We viewed the ester linkage in 3 as too labile and in an effort to improve in vivo efficacy we replaced the ethanolamine moiety with a more robust piperazine moiety, generating the second-generation dye conjugate 4 .…”

Section: Introductionmentioning

confidence: 71%

Targeting tumor hypoxia: a third generation 2-nitroimidazole-indocyanine dye-conjugate with improved fluorescent yield

et al. 2015

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Tumor hypoxia is associated with the rapid proliferation and growth of malignant tumors, and the ability to detect tumor hypoxia is important for predicting tumor response to anti-cancer treatments. We have developed a class of dye-conjugates that are related to indocyanine green (ICG, 1) to target tumor hypoxia, based on in vivo infrared fluorescence imaging using nitroimidazole moieties linked to indocyanine fluorescent dyes. We previously reported that linking 2-nitroimidazole to an indocyanine dicarboxylic acid dye derivative (2) using an ethanolamine linker (ethanolamine-2-nitroimidazole-ICG, 3), led to a dye-conjugate that gave promising results for targeting cancer hypoxia in vivo. Structural modification of the dye conjugate replaced the ethanolamine unit with a piperazineacetyl unit and led a second generation dye conjugate, piperzine-2-nitroimidazole-ICG (4). This second generation dye-conjugate showed improved targeting of tumor hypoxia when compared with 3. Based on the hypothesis that molecules with more planar and rigid structures have a higher fluorescence yield, as they could release less absorbed energy through molecular vibration or collision, we have developed a new 2-nitroimidazole ICG conjugate, 12, with two carbon atoms less in the polyene linker. Dye-conjugate 12 was prepared from our new dye (8), and coupled to 2-nitroimidazole using a piperazine linker to produce this third-generation dye-conjugate. Spectral measurements showed that the absorption/emission wavelengths of 657/670 were shifted ∼100 nm from the second-generation hypoxia dye of 755/780 nm. Its fluorescence quantum yield was measured to be 0.467, which is about 5 times higher than that of 4 (0.083). In vivo experiments were conducted with balb/c mice and 12 showed more than twice the average in vivo fluorescence intensity in the tumor beyond two hours post retro-orbital injection as compared with 4. These initial results suggest that 12 may significantly improve in vivo tumor hypoxia targeting.

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Section: Introductionmentioning

confidence: 71%

Targeting tumor hypoxia: a third generation 2-nitroimidazole-indocyanine dye-conjugate with improved fluorescent yield

et al. 2015

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Imaging Agents in Targeting Tumor Hypoxia

Zeng

Zhang³

et al. 2016

CMC

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Tissue hypoxia may occur in many diseases, specifically during the occurrence and growth of malignant solid-tumors. Targeting hypoxia is one of the most significant characteristics of tumors in diagnosis, monitoring, and treatment. This review summarizes the current oxygen-sensitive imaging agents used to target tumor hypoxia, including positron-emission computed tomography/single photon-emission computed tomography radionuclide labeled tracers, magnetic resonance imaging contrast agents for hypoxia detection, and hypoxia-sensitive optical imaging probes. Researchers have utilized nanotechnology as a useful toolkit to improve the effects of oxygen-sensitive imaging agents. We emphasize the progress and influence of nanotechnology in these materials and technologies. This review demonstrates that hypoxia imaging agents have promising prospects, and may provide helpful information for tumor diagnosis and prognosis.

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Biodistribution study of 2-nitroimidazole indocyanine green conjugate dye conjugates

Cited by 2 publications

References 13 publications

Targeting tumor hypoxia: a third generation 2-nitroimidazole-indocyanine dye-conjugate with improved fluorescent yield

Targeting tumor hypoxia: a third generation 2-nitroimidazole-indocyanine dye-conjugate with improved fluorescent yield

Imaging Agents in Targeting Tumor Hypoxia

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