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Excimer Emission in Norepinephrine and Epinephrine Drugs with α- and β-Cyclodextrins: Spectral and Molecular Modeling Studies

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Abstract

The inclusion complexation behavior of norepinephrine (NORE) and epinephrine (EPIN) with native cyclodextrins (α-CD and β-CD) were investigated by UV-visible, fluorimetry, time-resolved fluorescence, SEM, TEM, FT-IR, 1H NMR, DSC, powder XRD and PM3 methods. Single emission was observed in aqueous solution where as dual emission (excimer) noticed in the CD solutions. Both drugs form 1:1 drug-CD complexes in lower CD concentrations and 1:2 CD-drug2 complexes in the higher CD concentrations. Time-resolved fluorescence studies indicated that both drugs showed single exponential decay in water and biexponential decay in CD. Nano-sized self-aggregated particles of drug-CD were found by TEM studies. Molecular modeling studies indicated that aliphatic chain part of the drug was entrapped in the CD cavity. Thermodynamic parameters and binding affinity of complex formation of the CD were determined according to PM3 method. The PM3 results were in good agreement with the experimental results.

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Acknowledgments

This work is supported by the Council of Scientific and Industrial Research [No. 01(2549)/12/EMR-II] and University Grants Commission [F.No. 41-351/2012 (SR)] New Delhi, India. The authors thank Dr. P. Ramamurthy, Director, National centre for ultrafast processes, Madras University for help in the fluorescence lifetime measurements for this work.

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Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalai nagar, 608 002, Tamil Nadu, India

    N. Rajendiran, T. Mohandoss & J. Thulasidasan

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  1. N. Rajendiran
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  2. T. Mohandoss
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  3. J. Thulasidasan
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Correspondence to N. Rajendiran.

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Rajendiran, N., Mohandoss, T. & Thulasidasan, J. Excimer Emission in Norepinephrine and Epinephrine Drugs with α- and β-Cyclodextrins: Spectral and Molecular Modeling Studies. J Fluoresc 24, 1003–1014 (2014). https://doi.org/10.1007/s10895-014-1361-8

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  • DOI: https://doi.org/10.1007/s10895-014-1361-8

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