Skip to main content
SpringerLink
Log in

Permeability Studies of Redox-Sensitive Nitroxyl Spin Probes Through Lipid Membranes Using an L-Band ESR Spectrometer

  • Published:
Applied Magnetic Resonance Aims and scope Submit manuscript

Abstract

Electron spin resonance (ESR) studies were carried out for 2 mM 14N-labeled deuterated 3-methoxycarbonyl-2,2,5,5-tetramethyl-pyrrolidine-1-oxyl (MC-PROXYL) and 3-carboxy-2,2,5,5,-tetramethyl-pyrrolidin-1-oxyl (carboxy-PROXYL) in pure water and various concentrations of liposomal solution by using an L-band ESR spectrometer. The ESR parameters, such as the line width, hyperfine coupling constant, g-factor, rotational correlation time and partition parameter, were reported for the samples. The changes in the line width were observed for 14N-labeled deuterated MC-PROXYL and carboxy-PROXYL in liposomal solution. The hyperfine coupling constant was observed for both nitroxyl spin probes. The permeable and impermeable nature of nitroxyl radicals was demonstrated using the ESR L-band spectra. The rotational correlation time increases with increasing concentration of liposome. The partition parameter for 14N-labeled deuterated MC-PROXYL in liposomal solution increases with increasing concentration of liposome, which reveals that the nitroxyl spin probe permeates into lipid membrane. The lipid peaks were observed for 2 mM 14N-labeled deuterated MC-PROXYL in 200, 300 and 400 mM liposomal concentration. The lipid peaks were not observed for 14N-labeled deuterated carboxy-PROXYL. These results indicate the permeable and impermeable nature of 14N-labeled deuterated nitroxyl spin probe.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. V.P. Torchilin, Nat. Rev. Drug. Discov. 4, 145 (2005)

    Article  Google Scholar 

  2. B. Tiwari Sandip, N. Udupa, B.S.S. Rao, P. Uma Devi, Indian J. Pharm. Sci. 32, 214 (2000)

    Google Scholar 

  3. T. Lian, R.J.Y. Ho, J. Pharm. Sci. 90, 667 (2001)

    Article  Google Scholar 

  4. C. Ropert, J. Braz, Med. Biol. Res. 32, 163 (1999)

    Google Scholar 

  5. S.-L. Huang, Adv. Drug Deliver. Rev. 60, 1167 (2008)

    Article  Google Scholar 

  6. A.S. Ulrich, Biosci. Rep. 22, 129 (2002)

    Article  Google Scholar 

  7. A. Grammenos, M.A. Bahri, P.H. Guelluy, G. Piel, M. Hoebeke, Biochem. Biophys. Res. Commun. 390, 5 (2009)

    Article  Google Scholar 

  8. D. Man, R. Slota, M.A. Broda, G. Mele, J. Li, J. Biol. Inorg. Chem. 16, 173 (2011)

    Article  Google Scholar 

  9. V.D. Fedotov, N.N. Vylegzhanina, A.E. Altshuler, V.I. Shlenkin, YuF Zuev, N. Garti, Appl. Magn. Reson. 14, 479 (1998)

    Article  Google Scholar 

  10. R. Bartucci, G. Montesano, L. Sportelli, Appl. Magn. Reson. 12, 41 (1997)

    Article  Google Scholar 

  11. D. Marsh, Appl. Magn. Reson. 31, 387 (2007)

    Article  Google Scholar 

  12. K. Kasazaki, K. Yasukawa, H. Sano, K. Yamada, H. Utsumi, Appl. Magn. Reson. 23, 585 (2003)

    Article  Google Scholar 

  13. K. Takeshita, C. Chi, H. Hirata, M. Ono, T. Ozawa, Free Radic. Biol. Med. 40, 876 (2006)

    Article  Google Scholar 

  14. M.C. Krishna, S. English, K. Yamada, J. Yoo, R. Murugesan, N. Devasahayam, J.A. Cook, K. Golaman, J.H. Ardenkjaer-Larsen, S. Subramanian, J.B. Mitchell, Proc. Natl. Acad. Sci. USA. 99, 1758 (2002)

    Article  Google Scholar 

  15. H. Utsumi, K. Yamada, K. Ichikawa, K. Sakai, Y. Kinoshita, S. Matsumoto, M. Nagai, Proc. Natl. Acad. Sci. USA. 103, 1463 (2006)

    Article  ADS  Google Scholar 

  16. A. Milton Franklin Benial, K. Ichikawa, R. Murugesan, K.-I. Yamada, H. Utsumi, J. Magn. Reson. 182, 273 (2006)

    Article  ADS  Google Scholar 

  17. R. Bartucci, D.A. Erilov, R. Guzzi, L. Sportelli, S.A. Dzuba, D. Marsh, Chem. Phys. Lipids 141, 142 (2006)

    Article  Google Scholar 

  18. K. Mirosavljevic, V. Noethig-Laslo, Chem. Phys. Lipids 155, 74 (2008)

    Article  Google Scholar 

  19. J. Zhao, J. Wu, F.A. Heberle, T.T. Mills, P. Klawitter, G. Huang, G. Costanza, G.W. Feigenson, Biochim. Biophys. Acta 1768, 2764 (2007)

    Article  Google Scholar 

  20. J. Zhao, J. Wu, H. Shao, F. Kong, N. Jain, G.G. Hunt, G.W. Feigenson, Biochim. Biophys. Acta 1768, 2777 (2007)

    Article  Google Scholar 

  21. A.N. Cimato, L.L. Piehl, G.B. Facorro, H.B. Torti, A.A. Hager, Free Radic. Biol. Med. 37, 2042 (2004)

    Article  Google Scholar 

  22. M. Brgles, K. Mirosavljevic, V. Noethig-Laslo, R. Frkanec, J. Tomasic, Int. J. Biol. Macromol. 40, 312 (2007)

    Article  Google Scholar 

  23. A. Wisniewska, A. Wolnicka-Glubisz, Biophys. Chem. 11, 43 (2004)

    Article  Google Scholar 

  24. I. Voszka, Z. Szabo, G. Csik, P. Maillard, P. Grof, J. Photochem. Photobiol. B 79, 83 (2005)

    Article  Google Scholar 

  25. R. Weissleder, U. Mahmood, Radiology 219, 316 (2001)

    Google Scholar 

  26. I.J. Hildebrandt, S.S. Gambhir, Cl. Immunol. 111, 210 (2004)

    Article  Google Scholar 

  27. T.F. Massoud, S.S. Gambhir, Gene. Dev. 17, 545 (2003)

    Article  Google Scholar 

  28. M. Yamato, T. Egashira, H. Utsumi, Free Radic. Biol. Med. 35, 1619 (2003)

    Article  Google Scholar 

  29. A. Milton Franklin Benial, H. Utsumi, K. Ichikawa, R. Murugesan, K.-I. Yamada, Y. Kinoshita, T. Naganuma, M. Kato, J. Magn. Reson. 204, 131 (2010)

    Article  ADS  Google Scholar 

  30. H. Sano, K. Matsumoto, H. Utsumi, Biochem. Mol. Biol. Int. 42, 641 (1997)

    Google Scholar 

  31. A. Milton Franklin Benial, M. Kumara Dhas, A. Jawahar, Appl. Magn. Reson. 40, 311 (2011)

    Article  Google Scholar 

  32. A. Cruz, D. Marsh, J. Perez-Gil, Biochim. Biophys. Acta. 1415, 125 (1998)

    Article  Google Scholar 

  33. P.F. Knowles, D. Marsh, H.W.E. Rattle, Magnetic Resonance of Biomolecules: An Introduction to the Theory and Practice of NMR and ESR in Biological Systems (Wiley, London, 1976)

    Google Scholar 

  34. M.J.G.W. Roozen, M.A. Hemminga, J. Phys. Chem. 94, 7326 (1990)

    Article  Google Scholar 

  35. Z.-N. Wang, R.-L. You, Environ. Exp. Bot. 43, 219 (2000)

    Article  Google Scholar 

  36. E.A. Golovina, A.N. Tikhonov, F.A. Hoekstra, Plant Physiol. 114, 383 (1997)

    Google Scholar 

  37. M. Kveder, G. Pifat, S. Pecar, M. Schara, P. Ramos, H. Esterbauer, Chem. Phys. Lipids 85, 1 (1997)

    Article  Google Scholar 

Download references

Acknowledgments

The authors A. Milton Franklin Benial, A. Jawahar and M. Kumara Dhas thank the college management for encouragement and permission to carry out this work. This work was supported by the UGC, New Delhi (Major Research Project: F.No.38-140/2009(SR)). This work was also supported by the Grant-in-Aid for JSPS Postdoctoral Fellowship for Foreign Researchers (ID No. P 04489).

Author information

Authors and Affiliations

  1. Department of Physics, NMSSVN College, Nagamalai, Madurai, 625 019, Tamilnadu, India

    A. Milton Franklin Benial & M. Kumara Dhas

  2. Department of Bio-functional Science, Faculty of Pharmaceutical Sciences, Kyushu University, Maidashi 3-1-1, Higashi-ku, Fukuoka, 812-8582, Japan

    Kazuhiro Ichikawa, Ken-ichi Yamada & Hideo Utsumi

  3. Innovation Center for Medical Redox Navigation, Kyushu University, Fukuoka, Japan

    Fuminori Hyodo

  4. Department of Chemistry, NMSSVN College, Nagamalai, Madurai, 625 019, Tamilnadu, India

    A. Jawahar

Authors
  1. A. Milton Franklin Benial
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Kumara Dhas
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kazuhiro Ichikawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ken-ichi Yamada
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Fuminori Hyodo
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. Jawahar
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Hideo Utsumi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hideo Utsumi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Milton Franklin Benial, A., Kumara Dhas, M., Ichikawa, K. et al. Permeability Studies of Redox-Sensitive Nitroxyl Spin Probes Through Lipid Membranes Using an L-Band ESR Spectrometer. Appl Magn Reson 44, 439–447 (2013). https://doi.org/10.1007/s00723-012-0383-0

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00723-012-0383-0

Keywords

Search

Navigation