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A Fluorescence Study on Binding Interaction of N-acetylated Dansylamide Conjugates with β-cyclodextrin, Tween-20 and DPPC Lipid Bilayer Membrane

Journal of Fluorescence volume 28, pages 409–417 (2018)Cite this article

Abstract

The present work describes the photophysical behavior of a saturated fatty acid (palmitic acid) containing N-acetylated dansylamide derivative (DAN-PA) into biologically important organized assembly such as β-cyclodextrin (β-CD), Tween-20 (T-20) and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) lipid bilayer membrane. The results were compared by using another N-acetylated dansylamide conjugate having a short hydrophobic tail, DAN-ACYL. Long hydrophobic tail (saturated fatty acid) containing dansylamide conjugate (DAN-PA) shows more efficient binding interactions with the β-CD as compared to the short tail containing dansylamide derivative (DAN-ACYL). The calculated binding constants values of DAN-PA and DAN-ACYL probes are 1.35 × 102 M −1 and 0.31 × 102 M −1 respectively. The DAP-PA is a sensitive fluorophore for understanding the micellization process in T-20, as compared to the DAN-ACYL because it shows a significant change in fluorescent properties (steady-state and time-resolved both) with changing in T-20 concentrations. The calculated CMC value for T-20 surfactant is 0.07 mM. While the DAN-ACYL does not show any change in the fluorescent properties while changing the T-20 concentrations. Fluorescent parameters like steady-state and time-resolved of DAN-PA are quite sensitive towards the thermo-tropic phase transitional changes into lipid bilayer membrane properties. And the calculated thermo-tropic phase transition temperature by using DAN-PA fluorophore is 42 °C.

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Acknowledgements

We thank DST, New Delhi for financial support. The high-performance computing facility of IIT Madras is greatly acknowledged. A. K. T thanks to Prof. A. K. Mishra (IIT Madras) to provides lab facility and his valuable suggestion. Dr. A. K. T. thanks, UGC, New Delhi for a research fellowship.

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  1. Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, Tamil Nadu, India

    Alok Kumar Tripathi

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  1. Alok Kumar Tripathi
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Correspondence to Alok Kumar Tripathi.

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10895_2017_2202_MOESM1_ESM.docx

Fluorescence spectra of N-acylated dansyl derivatives, Fluorescence lifetime decay profile of N-acylated dansyl derivatives in β-CD, T-20, Fluorescence intensity DAN-ACYL DPPC liposome. (DOCX 2330 KB)

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Tripathi, A.K. A Fluorescence Study on Binding Interaction of N-acetylated Dansylamide Conjugates with β-cyclodextrin, Tween-20 and DPPC Lipid Bilayer Membrane. J Fluoresc 28, 409–417 (2018). https://doi.org/10.1007/s10895-017-2202-3

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  • DOI: https://doi.org/10.1007/s10895-017-2202-3

Keywords

  • Steady-state and time-resolved fluoroecence
  • β-Cyclodextrin
  • Tween-20
  • DPPC lipid bilayer membrane
  • Micellization
  • Thermo-tropic phase transition
  • Binding constant