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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

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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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References

  1. Rohacova J, Marin ML, Miranda MA (2010) Complexes between fluorescent cholic acid derivatives and human serum albumin. A photophysical approach to investigate the binding behavior. J Phys Chem B 114:4710–4716

    Article  CAS  PubMed  Google Scholar 

  2. Shamsuzzaman, Dar AM, Khan Y, Sohail A (2013) Synthesis and biological studies of steroidal pyran based derivatives. J Photochem Photobiol B 129:36–47

    Article  CAS  PubMed  Google Scholar 

  3. Rao HSP, Desai A, Sarkar I, Mohapatra M, Mishra AK (2014) Photophysical behavior of a new cholesterol attached coumarin derivative and fluorescence spectroscopic studies on its interaction with bile salt systems and lipid bilayer membranes. Phys Chem Chem Phys 16:1247–1256

    Article  CAS  PubMed  Google Scholar 

  4. Cardin AD, Jackson RL, Johnson JD (1982) 5-Dimethylaminonaphthalene-1-sulfonyl 3-aminotyrosyl apolipoprotein C-III preparation, characterization and interaction with vesicles. J Biol Chem 257:4987–4992

    CAS  PubMed  Google Scholar 

  5. Tewari N, Joshi NK, Rautela R, Gahlaut R, Joshi HC, Pant S (2011) On the ground and excited state dipole moments of dansylamide from solvatochromic shifts of absorption and fluorescence spectra. J Mol Liq 160:150–153

    Article  CAS  Google Scholar 

  6. Kikuchi T, Narita M, Hamada F (2001) Synthesis of bis dansyl-modified β-cyclodextrin liner trimer having multi-recognition sites and high hydrophobic environment. Tetrahedron 57:9317–9324

    Article  CAS  Google Scholar 

  7. Gomez-Mendoza M, Marin ML, Miranda MA (2011) Dansyl derivatives of cholic acid as tools to build speciation diagrams for sodium cholate aggregation. J Phys Chem Lett 2:782–785

    Article  CAS  Google Scholar 

  8. Gomez-Mendoza M, Marin ML, Miranda MA (2012) Dansyl-labeled cholic acid as a tool to build speciation diagrams for the aggregation of bile acids. J Phys Chem B 116:14776–14780

    Article  CAS  PubMed  Google Scholar 

  9. Zheng Y, Hashidzume A, Harada A (2013) pH-responsive self-assembly by molecular recognition on a macroscopic scale. Macromol Rapid Commun 34:1062–1066

    Article  CAS  PubMed  Google Scholar 

  10. Yuan D, Kitagawa Y, Fukudome M, Fujita K (2007) A vector-selective reaction enables efficient construction of specific topology upon the primary side of β-cyclodextrin. Org Lett 9:5267–5270

    Article  Google Scholar 

  11. Wang J, Pham D, Kee T, Clafton S, Guo X, Clements P, Lincoln S, Home R and Easton CJ (2011) Aggregation and host-guest interactions in dansyl-substituted poly (acrylate)s in the presence of β-cyclodextrin and a β-cyclodextrin dimer in aqueous solution: A UV-Vis, fluorescence, 1H NMR, and rheological study. Macromolecules 44:9782–9791

    Article  CAS  Google Scholar 

  12. Bugler J, Engbersen JFJ, Reinhoudt DN (1998) Novel water-soluble β-cyclodextrin-calix[4]arene couples as fluorescent sensor molecules for the detection of neutral analytes. J Org Chem 63:5339–5344

    Article  Google Scholar 

  13. Flink S, Veggel FCJM, Reinhoudt DN (1999) A self-assembled monolayer of a fluorescent guest for the screening of host molecules. Chem Commun 0:2229–2230

    Article  CAS  Google Scholar 

  14. Pham D, Wang J, Kee TW, Guo X, Clements P, Lincoln SF, Prud RK (2010) Dansyl substituted poly(acrylate)s: synthesis, host-guest complexation and viscosity study at molecular and macroscopic levels. Polym Prepr 51:450–451

    CAS  Google Scholar 

  15. Faucon JF, Dufourcq J, Lussan C, Bernon R (1976) Lipid-protein interactions in membrane models fluorescence polarization study of cytochrome b5-phospholipids complexes. Biochim Biophys Acta 436:283–294

    Article  CAS  PubMed  Google Scholar 

  16. Kimura K, Arata Y, Yasuda T, Kinoshita K, Nakanishi M (1992) Fluorescence quenching measurements of the membrane-bound lipid haptens with different length spacers. Biochim Biophys Acta 1104:9–14

    Article  CAS  PubMed  Google Scholar 

  17. Luzardo MDC, Bernik DL, Pazos IF, Figueroa S, Lanio ME, Verez V, Disalvo EA (1999) Phase and surface properties of lipid bilayers containing neoglycolipids. Arch Biochem Biophys 363:81–90

    Article  CAS  PubMed  Google Scholar 

  18. Ramirez DMC, Ogilvie WW, Johnston LJ (2010) NBD-cholesterol probes to track cholesterol distribution in model membranes. Biochim Biophys Acta 1798:558–568

    Article  CAS  PubMed  Google Scholar 

  19. Samanta A, Guchhait N, Bhattacharya SC (2014) Preferential molecular encapsulation of an ICT fluorescence probe in the supramolecular cage of cucurbit[7]uril and β-cyclodextrin: an experimental and theoretical approach. J Phys Chem B 118:13279–13289

    Article  CAS  PubMed  Google Scholar 

  20. Gilla HS, Prausnitz MR (2008) Microneedles for drug delivery to the skin. J Phys Chem Solids 69:1537–1541

    Article  Google Scholar 

  21. Helisto P, Korpela T (1998) Effects of detergents on the activity of microbial lipases as measured by the nitrophenyl alkanoate esters method. Enzym Microb Technol 23:113–117

    Article  CAS  Google Scholar 

  22. Bernik DL, Negri RMA (1998) Local polarity at the polar head level of lipid vesicles using dansyl fluorescent probes. J Colloid Interface Sci 203:97–105

    Article  CAS  Google Scholar 

  23. Asaia Y, Watanabe S (1999) Formation and structure of stably dispersed particles composed of retinal with dipalmitoylphosphatidylcholine: coexistence of emulsion particles with bilayer vesicles. Eur J Pharm Biopharm 48:77–83

    Article  Google Scholar 

  24. Tripathi AK, Mohapatra M, Mishra AK (2015) Fluorescence of N-acylated dansylamide with a long hydrophobic tail: sensitive response to premicellar aggregation of sodium deoxycholate. Phys Chem Chem Phys 17:29985–29994

    Article  CAS  PubMed  Google Scholar 

  25. Bramhall J (1986) Use of the fluorescent weak acid dansylglycine to measure transmembrane proton concentration gradients. Biochemistry 25:3958–3962

    Article  CAS  PubMed  Google Scholar 

  26. Carrier RL, Miller LA, Ahmed I (2007) The utility of cyclodextrins for enhancing oral bioavailability. J Control Release 123:78–99

    Article  CAS  PubMed  Google Scholar 

  27. Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707

    Article  CAS  Google Scholar 

  28. Rajendiran N, Jenita MJ (2015) Encapsulation of 4-hydroxy-3-methoxy benzoic acid and 4-hydroxy-3,5-dimethoxy benzoic acid with native and modified cyclodextrins. Spectrochim Acta Part A 136:1349–1357

    Article  CAS  Google Scholar 

  29. Ghosh S, Burman AD, De GC, Das AR (2011) Interfacial, and self-aggregation of binary mixtures of anionic and nonionic amphiphiles in the aqueous medium. J Phys Chem B 115:11098–11112

    Article  CAS  PubMed  Google Scholar 

  30. Ruiz-Pena M, Oropesa-Nunez R, Ponsb T, Louroc SRW, Pérez-Gramatgesa A (2010) Physico-chemical studies of molecular interactions between non-ionic surfactants and bovine serum albumin. Colloids Surf B 75:282–289

    Article  CAS  Google Scholar 

  31. Acharya S and Sharma R (2014) Fluorescence study of p-nitroacetophenone in different micellar media. J Appl Chem 3:1649–1654

    Google Scholar 

  32. Andrianov AK, Marin A, DeCollibus DP (2011) Microneedles with intrinsic immunoadjuvant properties: microfabrication, protein stability, and modulated release. Pharm Res 28:58–65

    Article  CAS  PubMed  Google Scholar 

  33. Matsubara N, Terabe S (1994) Separation of 24 dansylamino acids by capillary electrophoresis with a non-ionic surfactant. J Chromatogr A 680:311–315

    Article  CAS  PubMed  Google Scholar 

  34. Roodsari FS, Wu D, Pum GS, Hajdu JA (1999) New approach to the stereospecific synthesis of phospholipids. The use of L-glyceric acid for the preparation of diacylglycerols, phosphatidylcholines, and related derivatives. J Org Chem 64:7727–7737

    Article  CAS  Google Scholar 

  35. Peetla C, Stine A, Labhasetwar V (2009) Biophysical interactions with model lipid membranes: applications in drug discovery and drug delivery. Mol Pharm 6:1264–1276

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. Miyazaki M, Nakano M, Fukuda M, Handa T (2009) Smaller discoidal high-density lipoprotein particles form saddle surfaces, but not planar bilayers. Biochemistry 48:7756–7763

    Article  CAS  PubMed  Google Scholar 

  37. Kimura Y, Ikegami A (1985) Local dielectric properties around polar region of lipid bilayer membranes. J Membr Biol 85:225–231

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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

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