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Boron Tracedrug: Design, Synthesis, and Pharmacological Activity of Phenolic BODIPY-Containing Antioxidants as Traceable Next-Generation Drug Model

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Oxygen Transport to Tissue XXXIII

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 737))

Abstract

We designed and synthesized phenolic BODIPY-containing antioxidants as traceable next-generation drug model named boron tracedrugs, UTX-42, UTX-43, and UTX-44. These drugs are basically composed of phenolic antioxidant moiety and stable boron-containing BODIPY moiety. Their antioxidant activities were evaluated by spectroscopic analysis with ABTS radical cations and inhibitory activity on lipid peroxidation of rat liver mitochondria. The reactivity of them with ABTS radical cations showed to be higher than trolox, which is one of the well-known antioxidants. These trace drugs, especially UTX-44, also showed much higher inhibitory activity than trolox against RLM lipid peroxidation. These results demonstrated that UTX-44 had the most potent boron-containing antioxidant among these drugs.

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References

  1. Hori H, Uto Y, Nakata E (2010) Medicinal electronomics bricolage design of hypoxia-targeting antineoplastic drugs and invention of boron tracedrugs as innovative future-architectural drugs. Anticancer Res 30:3233–3242

    PubMed  CAS  Google Scholar 

  2. Nagasawa H, Uto Y, Kirk KL et al (2006) Design of hypoxia-targeting drugs as new cancer ­chemotherapeutics. Biol Pharm Bull 29:2335–2342

    Article  PubMed  CAS  Google Scholar 

  3. Lee JS, Kang NY, Kim YK et al (2009) Synthesis of a BODIPY library and its application to the development of live cell glucagon imaging probe. J Am Chem Soc 131:10077–10082

    Article  PubMed  CAS  Google Scholar 

  4. Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian, Inc., Wallingford CT, Gaussian 03, Revision B.04, 2004

    Google Scholar 

  5. Flükiger HP, Lüthi S, Portmann J (2000) Weber. Swiss National Supercomputing Centre CSCS, Manno, Switzerland

    Google Scholar 

  6. Re R, Pellegrini N, Proteggente A, Pannala A et al (1999) Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 26:1231–1237

    Article  PubMed  CAS  Google Scholar 

  7. Myers DK, Slater EC (1957) The enzymatic hydrolysis of adenosine triphosphate by liver mitochondria I. Activities at different pH values. Biochem J 67:558–572

    PubMed  CAS  Google Scholar 

  8. Uto Y, Ae S, Koyama D et al (2006) Artepillin C isoprenomics: design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity. Bioorg Med Chem 14:5721–5728

    Article  PubMed  CAS  Google Scholar 

  9. Muller R. The organic chemistry portal home page, chemistry tools, The OSIRIS Property Explorer. http://www.organic-chemistry.org/prog/peo/

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Acknowledgments

We thank Ms. Maki Nakamura, Ms. Emiko Okayama, and the staff of our faculty for measurement of NMR and elemental analyses. We also thank Prof. Toshihiro Hashimoto and Ms. Yasuko Okamoto for measurement of FAB-MS.

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Correspondence to Hitoshi Hori .

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© 2012 Springer Science+Business Media, LLC

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Nakata, E., Koizumi, M., Yamashita, Y., Uto, Y., Hori, H. (2012). Boron Tracedrug: Design, Synthesis, and Pharmacological Activity of Phenolic BODIPY-Containing Antioxidants as Traceable Next-Generation Drug Model. In: Wolf, M., et al. Oxygen Transport to Tissue XXXIII. Advances in Experimental Medicine and Biology, vol 737. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-1566-4_44

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