An insight into the role of ESIPT/TICT-based antioxidant flavone analogues in fluoro-probing diabetes-induced viscosity changes: a unified experimental and theoretical endeavour

• Published in: Photochemical & photobiological sciences 2024-09, Vol.23 (9), p.1771-1782
• Main Authors: Samanta, Trisha, Mandal, Samanwita, Karmakar, Abhijit, Pramanik, Anup, Kundu, Rakesh, Begum, Naznin Ara
• Format: Article
• Language: English
• Subjects: Biochemistry; Biomaterials; Chemistry; Chemistry and Materials Science; Original Papers; Physical Chemistry; Plant Sciences
• ISSN: 1474-905X; 1474-9092; 1474-9092
• DOI: 10.1007/s43630-024-00630-6

Potent antioxidants, like 3-hydroxy flavones, attracted considerable attention due to their excited state intramolecular proton transfer (ESIPT)-based fluorescence behaviour. This article is an interesting demonstration of a series of synthetic 3-hydroxy flavone analogues having high antioxidant activity as molecular rotor-like viscosity probes. Among these flavone analogues, 4′- N,N -dimethylamino-3-hydroxy flavone ( 3 ) is the most potent one, showing the twisted intramolecular charge transfer (TICT)-dependent fluoroprobing activity toward the blood viscosity changes associated with diabetes and free fatty acids (FFA)-induced nuclear viscosity changes of MIN6 cells. The TICT dynamics of ( 3 ), which instigates its viscosity probing activity, was comprehended with the help of DFT-based computational studies. Abnormal cellular viscosity changes are the pathological traits for various diseases, and non-toxic flavone-based viscosity probes can be useful for diagnosing such pathological conditions. Graphical abstract