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Interaction of an Aldose Sugar with Photoinduced Electron Transfer (PET) and Non-PET Based Acridinedione Dyes in Water: Hydrogen-bonding Evidences from Fluorescence Spectral Techniques Assisted by Molecular Docking Approach

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Abstract

Fluorescence spectral techniques aided by molecular docking (Mol.Doc) approach were employed in probing the molecular interactions existing between D-glucose and resorcinol based acridinedione (ADR) dyes. ADR dyes has been classified into PET and non-PET dyes based on the substitution in the 9th position of acridinedione ring structure. Addition of glucose to PET dye (ADR1) resulted in a decrease in the absorbance whereas to that of ADR2 dye (non-PET character in aqueous medium) resulted in a significant increase in the absorbance. The formation of an isosbestic point reveals the existence of a ground state interaction existing between the dye and sugar molecule. Addition of glucose to PET dye resulted in a drastic increase in the fluorescent enhancement (FE) and subsequent addition resulted in a marked decrease in the fluorescent intensity with no apparent shift of emission maximum. Interestingly, neither characteristic shift nor variation in emission intensity was observed in the case of ADR2 dye. Fluorescence lifetime studies of ADR1 dye in the presence of glucose illustrate the existence of multiple distinguishable micro environments of dye. Mol.Doc studies authenticate the co-existence of hydrogen bonding (HB) and hydrophobic interaction wherein the dye and sugar molecule acts as HB donor and acceptor resulting in a stable conformer. These conformers are governed predominantly by HB interactions. The nature of interaction of a simple sugar with ADR dyes are explored in depth by fluorescent techniques in coordination with docking studies is imparted in the present study.

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Acknowledgements

R.K. thank Dr C. Selvaraju, Director, National Centre for Ultrafast Processes, University of Madras, Taramani campus, Chennai, for permitting and assisting us to avail the instrument facilities. S.M.V and M.S.S thank Mrs. Shoba Gunasekaran for aiding us in MOL.DOC techniques. The authors also thank Principal, Dr. S. Santhosh Baboo and Shri. Ashok Kumar Mundra, Secretary, D.G. Vaishnav College (Autonomous), Chennai, for permitting us to avail the laboratory and instrumentation facilities.

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Rajendran Kumaran, Perumal Tamizhdurai and Chinnadurai Raghupathi: Conceptualization, Methodology. Seba Merin Vinod, Murugan Sridevi Sangeetha: Software. Rajendran Kumaran, Seba Merin Vinod and Krishnan Anju: Data curation, Writing- Original draft preparation. Rajendran Kumaran: Visualization, Investigation. Rajendran Kumaran and Seba Merin Vinod: Writing- Reviewing and Editing, Rajendran Kumaran: Supervision.

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Correspondence to Kumaran Rajendran.

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Vinod, S., Murugan Sreedevi, S., Krishnan, A. et al. Interaction of an Aldose Sugar with Photoinduced Electron Transfer (PET) and Non-PET Based Acridinedione Dyes in Water: Hydrogen-bonding Evidences from Fluorescence Spectral Techniques Assisted by Molecular Docking Approach. J Fluoresc 33, 471–486 (2023). https://doi.org/10.1007/s10895-022-03062-6

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