EPR and Quantum Chemical Studies of the pH-sensitive Imidazoline and Imidazolidine Nitroxides with Bulky Substituents

Applied Magnetic Resonance

Volumn 39, Issue 4, 2010, Pages 437-451

  Bobko, A A ^a,b   Kirilyuk, I A ^c   Gritsan, N P ^a   Polovyanenko, D N ^d   Grigor'ev, I A ^c   Khramtsov, V V ^b   Bagryanskaya, E G ^d  

^a INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

^b OHIO STATE UNIVERSITY   (United States)

^c N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^d INTERNATIONAL TOMOGRAPHY CENTER   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMEDICAL APPLICATIONS; BULKY SUBSTITUENTS; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; EPR SPECTRA; ETHYL GROUPS; FROZEN SOLUTIONS; G FACTORS; HETEROCYCLES; HIGH SENSITIVITY; HIGH STABILITY; HYDROGEN ATOMS; HYPERFINE SPLITTINGS; IMIDAZOLINES; LINE SHAPE; LOW TEMPERATURES; NITROXIDE RADICALS; NITROXIDES; PH SENSITIVE; QUANTUM CHEMICAL CALCULATIONS; QUANTUM CHEMICAL STUDIES; RING-PUCKERING; SPIN LABEL;

DEUTERIUM; HYDROGEN; NITROGEN OXIDES; PARAMAGNETIC RESONANCE; PH; QUANTUM CHEMISTRY;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

EID: 78449247077     PISSN: 09379347     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00723-010-0179-z     Document Type: Article

References (44)

1. H. M. Swartz, R. B. Clarkson, Phys. Med. Biol. 43, 1957-1975 (1998).
2. S. S. Velan, R. G. Spencer, J. L. Zweier, P. Kuppusamy, Magn. Reson. Med. 43, 804-809 (2000).
3. M. A. Foster, I. A. Grigor'ev, D. J. Lurie, V. V. Khramtsov, S. McCallum, I. Panagiotelis, J. M. Hutchison, A. Koptioug, I. Nicholson, Magn. Reson. Med. 49, 558-567 (2003).
4. V. V. Khramtsov, L. M. Weiner, A. Gogolev, I. A. Grigor'ev, V. F. Starichenko, L. B. Volodarsky, Magn. Reson. Chem. 24, 199-207 (1986).
5. V. V. Khramtsov, I. A. Grigor'ev, M. A. Foster, D. J. Lurie, Antioxid. Redox Signal. 6(3), 667-676 (2004).
6. G. I. Roshchupkina, A. A. Bobko, A. Bratasz, V. A. Reznikov, P. Kuppusamy, V. V. Khramtsov, Free Radic. Biol. Med. 45, 312-320 (2008).
7. H. M. Swartz, N. Khan, V. V. Khramtsov, Antioxid. Redox Signal. 9, 1757-1771 (2007).
8. P. Kuppusamy, H. Li, G. Ilangovan, A. J. Cardounel, J. L. Zweier, K. Yamada, M. C. Krishna, J. B. Mitchell, Cancer Res. 62, 307-312 (2002).
9. K. Yamada, D. Inoue, S. Matsumoto, H. Utsumi, Antioxid. Redox Signal. 6, 605-611 (2004).
10. W. L. Hubbel, D. Cafiso, C. Altenbach, Nat. Struct. Biol. 7, 735-739 (2000).
11. C. S. Winalski, S. Shortkroff, R. V. Mulkern, E. Schneider, G. M. Rosen, Magn. Reson. Med. 48, 965-972 (2002).
12. J. F. Keana, F. L. van Nice, Physiol. Chem. Phys. Med. NMR 16, 477-480 (1984).
13. A. I. Smirnov, A. Ruuge, V. A. Reznikov, M. A. Voinov, I. A. Grigoriev, J. Am. Chem. Soc. 126, 8872-8880 (2004).
14. M. A. Voinov, A. Ruuge, V. A. Reznikov, I. A. Grigor'ev, A. I. Smirnov, Biochemistry 47, 5626-5637 (2008).
15. A. N. Tikhonov, R. V. Agafonov, I. A. Grigor'ev, I. A. Kirilyuk, V. V. Ptushenko, B. V. Trubitsin, Biochim. Biophys. Acta 1777, 285-294 (2008).
16. K. Moebius, A. Savitsky, C. Wegener, M. Plato, M. Fuchs, A. Schnegg, A. A. Dubinskii, Y. A. Grishin, I. A. Grigor'ev, M. K̈uhn, D. Duche, H. Zimmermann, H.-J. Steinhoff, Magn. Reson. Chem. 43, 4-19 (2005).
17. V. V. Khramtsov, L. M. Weiner, I. A. Grigoriev, L. B. Volodarsky, Chem. Phys. Lett. 91, 69-72 (1982).
18. N. Kocherginsky, H. M. Swartz, Nitroxide Spin Labels, Reactions in Biology and Chemistry (CRC Press, Boca Raton, 1995).
19. R. J. Mehlhorn, J. Biol. Chem. 266, 2724-2731 (1991).
20. V. I. Yelinova, A. G. Krainev, A. Savelov, I. A. Grigor'ev, J. Chem. Soc. Perkin Trans. 2 11, 2053-2055 (1993).
21. A. A. Bobko, I. A. Kirilyuk, I. A. Grigor'ev, J. L. Zweier, V. V. Khramtsov, Free Radic. Biol. Med. 42(3), 404-412 (2007).
22. J. F. W. Keana, S. Pou, G. M. Rosen, Magn. Res. Med. 5, 525-536 (1987).
23. L. Marx, R. Chiarelli, T. Guiberteau, A. Rassat, J. Chem. Soc. Perkin Trans. 1, 1181-1182 (2000).
24. I. A. Kirilyuk, A. A. Bobko, I. A. Grigor'ev, V. V. Khramtsov, Org. Biomol. Chem. 2(7), 1025-1030 (2004).
25. S. Okazaki, M. D. M. Mannan, K. Sawai, T. Masunizu, Y. Miura, K. Takeshita, Free Radic. Res. 41, 1069-1077 (2007).
26. Y. Kinoshita, K.-I. Yamada, T. Yamasaki, H. Sadasue, K. Sakai, H. Utsumi, Free Radic. Res. 43, 565-571 (2009).
27. L. B. Volodarskii, V. A. Reznikov, V. S. Kobrin, J. Org. Chem. USSR (Engl. Transl.) 15, 364-370 (1979).
28. D. Zubenko, Yu. Tsentalovich, N. Lebedeva, I. Kirilyuk, G. Roshchupkina, I. Zhurko, V. Reznikov, S. R. A. Marque, E. Bagryanskaya, J. Org. Chem. 71, 6044-6052 (2006).
29. T. K. Sevastjanova, L. B. Volodarsky, Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 21, 2276-2280 (1972).
30. D. R. Duling, J. Magn. Reson. B 104, 105-110 (1994).
31. M. R. Fuchs, T. F. Prisner, K. Möbius, Rev. Sci. Instrum. 70, 3681-3683 (1999).
32. A. Schnegg, E. Kirilina, M. Fuchs, A. Savitsky, Y. Grishin, A. Dubinskii, M. Plato, W. Lubitz, K. Möbius, Appl. Magn. Reson. 31, 59-98 (2007).
33. S. Stoll, A. Schweiger, J. Magn. Reson. 178, 42-55 (2006).
34. A. D. Becke, J. Chem. Phys. 98, 5648-5654 (1993).
35. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 37, 785-790 (1988).
36. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople. Gaussian 03 (Revision B. 01) (Gaussian, Inc., Pittsburg PA, 2003).
37. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 105, 2999-3002 (2005).
38. V. V. Khramtsov, L. B. Volodarsky, in Spin Labeling: The Next Millenium, Biological Magnetic Resonance, vol. 14, ed. by L. J. Berliner (Plenum Press, New York, 1998).
39. R. Importa, V. Barone, Chem. Rev. 104, 1231-1253 (2004).
40. R. Importa, G. Scalmani, V. Barone, Chem. Phys. Lett. 336, 349-356 (2001).
41. R. Importa, V. Barone, T. Bally, W. T. Borden, in Reviews in Computational Chemistry, vol. 13, ed. by K. B. Lipkowitz, D. B. Boyd (Wiley, New York, 1999), pp. 1-97.
42. A. Savitsky, A. A. Dubinskii, M. Plato, Y. A. Grishin, H. Zimmermann, K. Möbius, J. Phys. Chem. B 112, 9079-9090 (2008).
43. A. F. Gullá, D. E. Budil, J. Phys. Chem. B 105, 8056-8062 (2001).
44. D. I. Potapenko, M. A. Foster, D. J. Lurie, I. A. Kirilyuk, J. M. Hutchison, I. A. Grigor'ev, E. G. Bagryanskaya, V. V. Khramtsov, J. Magn. Reson. 182, 1-11 (2006).