Abstract

Short Communication

Synthesis and Biological Evaluation of Fluorescein-Tagged 1-Methyl-o-carborane for Boron Neutron Capture Therapy

Lucas A Kuzmanic, Lauren E Zuidema, Jason A Misurelli, Kazuko Uno, Sherine F Elsawa*, Masao Takagaki* and Narayan S Hosmane*

Published: 26 October, 2018 | Volume 2 - Issue 1 | Pages: 075-081

Fluorescein was conjugated with 1-methyl-o-carborane and the resulting bioconjugate was biologically evaluated through microscopic and flow cytometric studies in pancreatic cancer and squamous cell carcinoma cell lines. The uniform distribution of this bioconjugate, as well as its moderate cytotoxicity and higher boron content relative to present boronated delivery agents sodium borocaptate (BSH) and boronophenylalanine (BPA), provide justification for its further evaluation as a potential delivery agent for BNCT.

Read Full Article HTML DOI: 10.29328/journal.aac.1001016 Cite this Article Read Full Article PDF

Keywords:

Boron neutron capture therapy; Carborane; Fluorescein; Bioconjugate; Theranostic

References

  1. Yinghuai Z. Hosmane NS. Applications and perspectives of boron-enriched nanocomposites in cancer therapy. Future Medicinal Chemistry. 2013; 5: 705-714. Ref.: https://goo.gl/eZRN1b
  2. Barth RF, Vicente MG, Harling OK, Kiger WS 3rd, Riley KJ, et al. Current status of boron neutron capture therapy of high grade gliomas and recurrent head and neck cancer. Radiat. Oncol. 2012; 7: 146. Ref.: https://goo.gl/9RAJEi
  3. Hosmane NS, Maguire J. Zhu Y, Takagaki M. Boron and Gadolinium Neutron Capture Therapy for Cancer Treatment. Singapore: World Scientific Pub, 2012. 272. Ref.: https://goo.gl/ZV5n9C
  4. Nakamura H. Liposomal Boron Delivery for Neutron Capture Therapy. Methods in Enzymology. 2009; 179-208. Ref.: https://goo.gl/RE4ZWR
  5. Barth RF, Soloway AH, Brugger RM. Boron Neutron Capture Therapy of Brain Tumors: Past History, Current Status, and Future Potential. Cancer Investigation. 1996; 14: 534-550. Ref.: https://goo.gl/aLjkKb
  6. Patel H, Takagaki M, Bode BP. Snajdr I, Devangi P. et al. Carborane-Appended Saccharides: Prime Candidates for Boron Neutron Capture Therapy (BNCT). Biochemical and Biophysical Journal of Neutron Capture Therapy & Cancer Treatments. 2013; 1: 15-21. Ref.: https://goo.gl/Bjm4n6
  7. Varadarajan A, Hawthorne MF. Novel carboranyl amino acids and peptides: reagents for antibody modification and subsequent neutron-capture studies. Bioconjugate Chem. 1991; 2: 242−253. Ref.: https://goo.gl/dtmX34
  8. Kusaka S, Hattori Y, Uehara K, Asano T, Tanimori S, et al. Synthesis of optically active dodecaborate-containing Lamino acids for BNCT. Appl Radiat Isot. 2011; 69: 1768−1770. Ref.: https://goo.gl/2Vemj7
  9. Hattori Y, Kusaka S, Mukumoto M, Uehara K, Asano T, et al. Biological Evaluation of Dodecaborate-Containing L-Amino Acids for Boron Neutron Capturer Therapy. J Med Chem. 2012; 55: 6980–6984. Ref.: https://goo.gl/o6bZC9
  10. Agarwal HK, Khalil A, Ishita K, Yang W, Nakkula RJ, et al. Synthesis and evaluation of thymidine-kinase 1-targeting carboranyl pyrimidine nucleoside analogs for boron neutron capture therapy of cancer. Eur J Med Chem. 2015; 100: 197-209. Ref.: https://goo.gl/iGQKtN
  11. Swenson DH. Laster BH. Metzger RL. Synthesis and evaluation of boronated nitroimidazole for boron neutron capture therapy. J Med Chem. 1996; 39: 1540–1544. Ref.: https://goo.gl/oBKk2D
  12. Mathew T, Kundan S, Abdulsamad MI, Menon S, Dharan BS, et al. Multiple muscular ventricular septal defects: use of fluorescein dye to identify residual defects. Ann Thorac Surg. 2014; 97: 27-28. Ref.: https://goo.gl/m6Hi89
  13. Hui F, Nguyen CT, Bedggood PA, He Z, Fish RL, et al. Quantitative Spatial and Temporal Analysis of Fluorescein Angiography Dynamics in the Eye. PLoS One. 2014; 9: 11. Ref.: https://goo.gl/DjBKJM
  14. Francaviglia N, Iacopino DG, Costantino G, Villa A, Impallaria P, et al. Fluorescein for resection of high-grade gliomas: A safety study control in a single center and review of the literature. Surg Neurol Int. 2017; 8: 145. Ref.: https://goo.gl/ToXJhB
  15. Acerbi F, Cavallo C, Broggi M, Cordella R, Anghileri E, et al. Fluorescein-guided surgery for malignant gliomas: a review. Neurosurg Rev. 2014; 37: 547-57. Ref.: https://goo.gl/5QZGXw
  16. Xuan S, Zhao N, Zhou Z, Fronczek FR, Vicente MG. Synthesis and in Vitro Studies of a Series of CarboraneContaining Boron Dipyrromethenes (BODIPYs). J Med Chem. 2016; 59: 2109−2117. Ref.: https://goo.gl/ccX6Y8
  17. Gibbs JH, Wang H, Bhupathiraju NV, Fronczek FR, Smith KM, et al. Synthesis and properties of a series of carboranyl-BODIPYs. J Organomet Chem. 2015; 798: 209−213. Ref.: https://goo.gl/RWZsft
  18. Chaari M, Gaztelumendi N, Cabrera-González J, Peixoto-Moledo P, Viñas C, et bl. Fluorescent BODIPY-Anionic Boron Cluster Conjugates as Potential Agents for Cell Tracking. Bioconjugate Chemistry. 2018; 29: 1763-1773. Ref.: https://goo.gl/kvwmai
  19. Li Y, Rey-Dios R, Roberts DW, Valdés PA, Cohen-Gadol AA. Intraoperative fluorescence-guided resection of high-grade gliomas: a comparison of the present techniques and evolution of future strategies. World Neurosurg. 2014; 82: 175-185. Ref.: https://goo.gl/wZkoRa
  20. Maugeri R, Villa A, Pino M, Imperato A, Giammalva GR, et al. With a Little Help from My Friends: The Role of Intraoperative Fluorescent Dyes in the Surgical Management of High-Grade Gliomas. Brain Sci. 2018; 8: pii: E31. Ref.: https://goo.gl/FRVgdU
  21. Yinghuai Z, Peng AT, Carpenter K, Maguire JA, Hosmane NS, et al. Substituted Carborane-Appended Water-Soluble Single-Wall Carbon Nanotubes: New Approach to Boron Neutron Capture Therapy Drug Delivery. J Am Chem Soc. 2005; 127: 9875 – 9880. Ref.: https://goo.gl/n2DftV
  22. Williamson Ether Synthesis. Williamson, A. Theory of Aetherification. Philosophical Magazine. 1850; 37: 350-356. Ref.: https://goo.gl/dXNNMg
  23. Fotakis G, Timbrell JA. In vitro cytotoxicity assays: Comparison of LDH, neutral red, MTT and protein assay in hepatoma cell lines following exposure to cadmium chloride. Toxicology Letters. 2006; 160: 171-177. Ref.: https://goo.gl/wpCtu2

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