Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Developing Tamoxifen-Based Chemical Probes for Use with a Dual-Modality Fluorescence and Optical Coherence Tomography Imaging Needle

Louisa A. Ho A , Loretta Scolaro B C D , Elizabeth Thomas E , Bryden C. Quirk B C D , Rodney W. Kirk B C D , Robert A. McLaughlin https://orcid.org/0000-0001-6947-5061 B C D and Rebecca O. Fuller https://orcid.org/0000-0003-3926-8680 A F G H
+ Author Affiliations
- Author Affiliations

A School of Molecular Sciences M310, The University of Western Australia, 35 Stirling Hwy, Crawley, WA 6009, Australia.

B Australian Research Council Centre of Excellence for Nanoscale Biophotonics, Adelaide Medical School, The University of Adelaide, North Terrace, Adelaide, SA 5005, Australia.

C Institute for Photonics and Advanced Sensing, The University of Adelaide, North Terrace, Adelaide, SA 5005, Australia.

D School of Engineering, The University of Western Australia, 35 Stirling Hwy, Crawley, WA 6009, Australia.

E School of Surgery M507, The University of Western Australia, QEII Medical Center, Monash Ave, Nedlands, WA 6009, Australia.

F School of Molecular and Life Sciences, Curtin University, Bentley, WA 6102, Australia.

G Current address: School of Natural Sciences – Chemistry, University of Tasmania, Hobart, Tas. 7001, Australia.

H Corresponding author. Email: rebecca.fuller@utas.edu.au

Australian Journal of Chemistry 73(10) 903-910 https://doi.org/10.1071/CH19364
Submitted: 5 August 2019  Accepted: 1 October 2019   Published: 12 December 2019

Abstract

Fluorescent small molecules based on the chemotherapeutic tamoxifen have been synthesised for use with an imaging needle capable of acquiring simultaneous fluorescence and optical coherence tomography (OCT) images. The chemical probes are based on the active metabolite of the drug, 4-hydroxytamoxifen that is coupled with a diamine linker to commercially available Alexa Fluor or 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes. The tamoxifen derivatives were then added to cultures of live oestrogen receptor positive MCF-7 human breast cancer cells and imaged using the miniaturised fibre-optic device enclosed within a 23-gauge needle (outer diameter 640 μm). The OCT images showed the micro-architecture of the cell culture, while the fluorescence identified oestrogen receptor positive cells. Both dyes were found to have suitable excitation and emission properties and are good candidates to further develop as probes for fluorescence-guided surgery.


References

[1]  E. A. Specht, E. Braselmann, A. E. Palmer, Annu. Rev. Physiol. 2017, 79, 93.
         | Crossref | GoogleScholarGoogle Scholar | 27860833PubMed |

[2]  Y. Fu, N. S. Finney, RSC Adv. 2018, 8, 29051.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  H.-W. Liu, L. Chen, C. Xu, Z. Li, H. Zhang, X.-B. Zhang, W. Tan, Chem. Soc. Rev. 2018, 47, 7140.
         | Crossref | GoogleScholarGoogle Scholar | 30140837PubMed |

[4]  V. C. Jordan, S. Koerner, Eur. J. Cancer 1975, 11, 205.
         | Crossref | GoogleScholarGoogle Scholar | 165942PubMed |

[5]  R. M. O’Regan, V. C. Jordan, Lancet Oncol. 2002, 3, 207.
         | Crossref | GoogleScholarGoogle Scholar | 12067682PubMed |

[6]  V. C. Jordan, Endocr. Relat. Cancer 2014, 21, R235.
         | Crossref | GoogleScholarGoogle Scholar | 24659478PubMed |

[7]  Ahmad I. Shagufta, Eur. J. Med. Chem. 2018, 143, 515.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  P. Y. Maximov, R. E. McDaniel, V. C. Jordan, P. Y. Maximov, R. E. McDaniel, V. C. Jordan, Tamoxifen: Pioneering Medicine in Breast Cancer 2013 (Springer: Basel).

[9]  E. L. Rickert, S. Oriana, C. Hartman-Frey, X. Long, T. T. Webb, K. P. Nephew, R. V. Weatherman, Bioconjug. Chem. 2010, 21, 903.
         | Crossref | GoogleScholarGoogle Scholar | 20420372PubMed |

[10]  F. Abendroth, M. Solleder, D. Mangoldt, P. Welker, K. Licha, M. Weber, O. Seitz, Eur. J. Org. Chem. 2015, 2157.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  L. A. Ho, E. Thomas, R. A. McLaughlin, G. R. Flematti, R. O. Fuller, Bioorg. Med. Chem. Lett. 2016, 26, 4879.
         | Crossref | GoogleScholarGoogle Scholar | 27662800PubMed |

[12]  T. Yogo, K. Umezawa, M. Kamiya, R. Hino, Y. Urano, Bioconjug. Chem. 2017, 28, 2069.
         | Crossref | GoogleScholarGoogle Scholar | 28691803PubMed |

[13]  H. Zhu, J. Fan, J. Du, X. Peng, Acc. Chem. Res. 2016, 49, 2115.
         | Crossref | GoogleScholarGoogle Scholar | 27661761PubMed |

[14]  J. Blagg, P. Workman, Cancer Cell 2017, 32, 9.
         | Crossref | GoogleScholarGoogle Scholar | 28697345PubMed |

[15]  P. A. Valdés, A. Kim, M. Brantsch, C. Niu, Z. B. Moses, T. D. Tosteson, B. C. Wilson, K. D. Paulsen, D. W. Roberts, B. T. Harris, Neuro-Oncology 2011, 13, 846.
         | Crossref | GoogleScholarGoogle Scholar | 21798847PubMed |

[16]  M. L. Gabriele, G. Wollstein, H. Ishikawa, L. Kagemann, J. Xu, L. S. Folio, J. S. Schuman, Invest. Ophthalmol. Vis. Sci. 2011, 52, 2425.
         | Crossref | GoogleScholarGoogle Scholar | 21493951PubMed |

[17]  G. J. Tearney, E. Regar, T. Akasaka, T. Adriaenssens, P. Barlis, H. G. Bezerra, B. Bouma, N. Bruining, J.-m. Cho, S. Chowdhary, M. A. Costa, R. de Silva, J. Dijkstra, C. Di Mario, D. Dudeck, E. Falk, M. D. Feldman, P. Fitzgerald, H. Garcia, N. Gonzalo, J. F. Granada, G. Guagliumi, N. R. Holm, Y. Honda, F. Ikeno, M. Kawasaki, J. Kochman, L. Koltowski, T. Kubo, T. Kume, H. Kyono, C. C. S. Lam, G. Lamouche, D. P. Lee, M. B. Leon, A. Maehara, O. Manfrini, G. S. Mintz, K. Mizuno, M.-a. Morel, S. Nadkarni, H. Okura, H. Otake, A. Pietrasik, F. Prati, L. Räber, M. D. Radu, J. Rieber, M. Riga, A. Rollins, M. Rosenberg, V. Sirbu, P. W. J. C. Serruys, K. Shimada, T. Shinke, J. Shite, E. Siegel, S. Sonada, M. Suter, S. Takarada, A. Tanaka, M. Terashima, T. Troels, S. Uemura, G. J. Ughi, H. M. M. van Beusekom, A. F. W. van der Steen, G.-A. van Es, G. van Soest, R. Virmani, S. Waxman, N. J. Weissman, G. Weisz, J. Am. Coll. Cardiol. 2012, 59, 1058.
         | Crossref | GoogleScholarGoogle Scholar | 22421299PubMed |

[18]  M. J. Suter, S. K. Nadkarni, G. Weisz, A. Tanaka, F. A. Jaffer, B. E. Bouma, G. J. Tearney, JACC Cardiovasc. Imaging 2011, 4, 1022.
         | Crossref | GoogleScholarGoogle Scholar | 21920342PubMed |

[19]  D. Huang, E. A. Swanson, C. P. Lin, J. S. Schuman, W. G. Stinson, W. Chang, M. R. Hee, T. Flotte, K. Gregory, C. A. Puliafito, et al. Science 1991, 254, 1178.
         | Crossref | GoogleScholarGoogle Scholar | 1957169PubMed |

[20]  L. Scolaro, R. A. McLaughlin, B. F. Kennedy, C. M. Saunders, D. D. Sampson, Photonics Lasers Med. 2014, 3, 225.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  R. K. Wang, Phys. Med. Biol. 2002, 47, 2281.
         | Crossref | GoogleScholarGoogle Scholar | 12164587PubMed |

[22]  J. Welzel, Skin Res. Technol. 2001, 7, 1.
         | Crossref | GoogleScholarGoogle Scholar | 11301634PubMed |

[23]  D. Lorenser, B. C. Quirk, M. Auger, W.-J. Madore, R. W. Kirk, N. Godbout, D. D. Sampson, C. Boudoux, R. A. McLaughlin, Opt. Lett. 2013, 38, 266.
         | Crossref | GoogleScholarGoogle Scholar | 23381406PubMed |

[24]  L. Scolaro, D. Lorenser, W.-J. Madore, R. W. Kirk, A. S. Kramer, G. C. Yeoh, N. Godbout, D. D. Sampson, C. Boudoux, R. A. McLaughlin, Biomed. Opt. Express 2015, 6, 1767.
         | Crossref | GoogleScholarGoogle Scholar | 26137379PubMed |

[25]  L. Scolaro, D. Lorenser, R. A. McLaughlin, B. C. Quirk, R. W. Kirk, D. D. Sampson, Opt. Lett. 2012, 37, 5247.
         | Crossref | GoogleScholarGoogle Scholar | 23258067PubMed |

[26]  M. F. Dillon, A. D. K. Hill, C. M. Quinn, E. W. McDermott, N. O’Higgins, Ann. Surg. Oncol. 2006, 13, 333.
         | Crossref | GoogleScholarGoogle Scholar | 16474911PubMed |

[27]  D. D. Yu, B. M. Forman, J. Org. Chem. 2003, 68, 9489.
         | Crossref | GoogleScholarGoogle Scholar | 14629178PubMed |

[28]  A. K. Shiau, D. Barstad, P. M. Loria, L. Cheng, P. J. Kushner, D. A. Agard, G. L. Greene, Cell 1998, 95, 927.
         | Crossref | GoogleScholarGoogle Scholar | 9875847PubMed |

[29]  J. A. Katzenellenbogen, K. E. Carlson, B. S. Katzenellenbogen, J. Steroid Biochem. 1985, 22, 589.
         | Crossref | GoogleScholarGoogle Scholar | 4010284PubMed |

[30]  W. L. F. Armarego, C. Chai, Purification of Laboratory Chemicals, 5th edn 2003 (Butterworth-Heinemann: Cornwall).

[31]  H. E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 1997, 62, 7512.
         | Crossref | GoogleScholarGoogle Scholar | 11671879PubMed |

[32]  J. P. Trebley, E. L. Rickert, P. T. Reyes, R. V. Weatherman, in Chemical Genomics (Eds S. Jaroch, H. Weinmann) 2006, pp. 75–87 (Springer: Berlin)