The ability to visualize in vitro and in vivo using molecular near infrared (NIR) fluorescence is a rapidly evolving field. The BF2-chelated tetraarylazadipyrromethenes 1a,b are a class of NIR fluorescent compounds which have strong absorption and emissions in NIR region (650 – 800 nm) that most readily pass through biological tissues(1,2). The abilty to bio-conjugate is essential for in vitro and in vivo targetted imaging. The focus of my PhD research is the synthesis of maleimide substituted NIR fluorochromes (Scheme attached in next page) and the assessment of their ability to bio-conjugate via thiol to maleimide couplings.(3) The synthesised NIR fluorochromes were capable of rapid conjugation in water in the pH range of 6 - 7.5 with a variety of thiol containing biomolecules. For example, conjugation with a cystine terminally substituted 9-mer cell penetrating peptide was achieved in 10 minutes at pH 7.0 to provide the fluorophore tagged peptide 2. Confocal imaging following cell incubation for 2 hours showed a efficient cell delivery (inset). References 1. Gorman, A.; Killoran, J.; O'Shea, C.; Kenna, T.; Gallagher, W. M.; O'Shea, D. F. J. Am. Chem. Soc. 2004, 126, 10619-10631. 2. Tasior, M.; O’Shea, D.F. Bioconjugate Chem. 2010, 21, 1130-1133. 3. Wu, D.; O’Shea, D.F. Org. Lett., 2013, 15(13), 3392-3395.

Development of new BF2 azadipyrromethene near-infrared fluorochromes

249th National Meeting (2015)

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