Neutral flavin analogue inspired by FbFP’s shows efficient long- term tracking of mitochondria even in low oxygen conditions Harsha Gopal Agrawal a , Pravin Giri b , Poonam Meena a , Subha Narayan Rath* b and Ashutosh Kumar Mishra* a a Department of chemistry and b Biomedical Engineering, Indian Institute of Technology, Hyderabad Sangareddy-502285, Telangana, India, E-mail: akm@chy.iith.ac.in The luminescence of Green fluorescent proteins (GFPs) and related analogs are mainly affected by a low oxygen environment. This limits the application of GFPs in various biological studies however in this domain flavin-based fluorescent proteins (FbFPs) are an emerging class of fluorescent reporters that address the challenge of bioimaging even under a low-oxygen environment. [1] Intrigued by FbFPs where flavin plays a role as a fluorescent unit, we have designed the flavin-triphenylamine probe. The rationale behind the design is to change the photophysical property [2] and make use of it for a bioimaging application that has been less explored arena in flavin chemistry. [3] Moreover, with the plethora of mitochondrial trackers available in the market, most of them are cationic in nature and suffer from cytotoxicity. [4] While the flavin-triphenylamine probe having a neutral core can long-term track the mitochondria in the normoxia, hypoxia, and apoptosis conditions. The probe has a high affinity towards mitochondria in a short uptake period, low cytotoxicity, appreciable photostability, and efficiently penetrates the 3D structures. This excellent property of the flavin-based probe can be utilized to trail the mitochondria in varied low-oxygen conditions in clinical states. References 1. A. Losi, K. H. Gardner and A. Möglich, Chem. Rev ., 2018, 118 , 10659-10709. 2. N. Mohammed, A. A. Wiles, M. Belsley, S. S. M. Fernandes, M. Cariello, V. M. Rotello, M. M. M. Raposo and G. Cooke, RSC Adv ., 2017, 7 , 24462–24469. 3. A. Kaur and E. J. New, Acc. Chem. Res. , 2019, 52 , 623–632. 4. G. Battogtokh, Y. S. Choi, D. S. Kang, S. J. Park, M. S. Shim, K. M. Huh, Y. Y. Cho, J. Y. Lee, H. S. Lee and H. C. Kang, Acta Pharm. Sin. B , 2018, 8 , 862–880.
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