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Artificial Chemical Reporter Targeting Strategy Using Bioorthogonal Click Reaction for Improving Active-Targeting Efficiency of Tumor

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Center for Theragnosis, Biomedical Research Institute, Korea Institute of Science and Technology, 5, Hwarang-ro 14-gil, Seongbuk-gu, Seoul 02792, Republic of Korea
Department of Bioengineering, Hanyang University, 222, Wangsimni-ro, Seongdong-gu, Seoul, 04763, Republic of Korea
§ Department of Pharmacy, Graduate School, Kyung Hee University, 26, Kyungheedae-ro, Dongdaemun-gu, Seoul 02447, Republic of Korea
# KU-KIST Graduate School of Converging Science and Technology, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul, 02841, Republic of Korea
College of Pharmacy, Graduate School of Pharmaceutical Science, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-gu, Seoul 03760, Republic of Korea
Department of Medical Lifescience, College of Medicine, The Catholic University of Korea, 222, Banpo-daero, Seocho-gu, Seoul 06591, Republic of Korea
*Tel: +82-2-958-5912. Fax: +82-2-958-5909. E-mail: [email protected]
*Tel: +82-2-958-5916. Fax: +82-2-958-5909. E-mail: [email protected]
Cite this: Mol. Pharmaceutics 2017, 14, 5, 1558–1570
Publication Date (Web):February 13, 2017
https://doi.org/10.1021/acs.molpharmaceut.6b01083
Copyright © 2017 American Chemical Society
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Abstract

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Biological ligands such as aptamer, antibody, glucose, and peptide have been widely used to bind specific surface molecules or receptors in tumor cells or subcellular structures to improve tumor-targeting efficiency of nanoparticles. However, this active-targeting strategy has limitations for tumor targeting due to inter- and intraheterogeneity of tumors. In this study, we demonstrated an alternative active-targeting strategy using metabolic engineering and bioorthogonal click reaction to improve tumor-targeting efficiency of nanoparticles. We observed that azide-containing chemical reporters were successfully generated onto surface glycans of various tumor cells such as lung cancer (A549), brain cancer (U87), and breast cancer (BT-474, MDA-MB231, MCF-7) via metabolic engineering in vitro. In addition, we compared tumor targeting of artificial azide reporter with bicyclononyne (BCN)-conjugated glycol chitosan nanoparticles (BCN–CNPs) and integrin αvβ3 with cyclic RGD-conjugated CNPs (cRGD–CNPs) in vitro and in vivo. Fluorescence intensity of azide-reporter-targeted BCN–CNPs in tumor tissues was 1.6-fold higher and with a more uniform distribution compared to that of cRGD–CNPs. Moreover, even in the isolated heterogeneous U87 cells, BCN–CNPs could bind artificial azide reporters on tumor cells more uniformly (∼92.9%) compared to cRGD–CNPs. Therefore, the artificial azide-reporter-targeting strategy can be utilized for targeting heterogeneous tumor cells via bioorthogonal click reaction and may provide an alternative method of tumor targeting for further investigation in cancer therapy.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.molpharmaceut.6b01083.

  • MFI results and images of U87 tumor cells (PDF)

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