Abstract
The electrochemical method and quantum chemical modeling were used to study the NO-donor activity of the mononuclear nitrosyl complex with the thiourea ligand and the influence of the pH of the medium on the reaction. It is shown experimentally that this complex evolves nitrogen monoxide and the character of this process depends on the pH of the medium. For a neutral medium, the curve of nitrogen monoxide evolution reaches a plateau, whereas the curve increases linearly with time for an alkaline medium. The quantum chemical modeling (using DFT methods with the B3LYP and BP86 functionals) of possible processes in an aqueous solution of the complex in neutral and alkaline media allowed us to propose the schemes of the NO-donation reaction, which explain the experimental data on the pH effect.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
S. Moccelin, Curr. Cancer Drug Targets, 2009, 9, 214.
B. Brune, N. Scheneiderhan, Toxicol Lett., 2003, 193, 19.
L. Liu, M. Welliver, S. Kanagula, H. E. Pegg, Canser. Res., 2002, 62, 3037.
D. Wink, J. Vodovoz, J. Cook, Biochemistry, 1998, 63, 948.
A. Millet, A. Bettaieb, F. Renaud, L. Prevotat, A. Hammann, E. Solary, B. Mignotte, J. F. Jeannin, Gastroenterology, 2002, 123, 235.
V. J. Findlay, D. M. Townsend, J. E. Saavedra, G. S. Buzard, M. L. Citro, L. K. Keefer, X. Ji, K. D. Tew, Mol. Pharmacol., 2004, 65, 1070.
S. L. Pan, J. H. Guh, C. Y. Peng, S. W. Wang, Y. L. Chang, F. C. Cheng, J. H. Chang, S. C. Kuo, F. Y. Lee, C. M. Teng, J. Pharmacol. Exp. Ther., 2005, 314, 35.
E. J. Yeo, Y. S. Chun, Y. S. Cho, M. S. Kim, J. W. Park, J. Natl. Cancer. Inst., 2003, 95, 516.
B. Rigas, K. Kashfi, Trends Mol. Med., 2004, 10, 324.
J. L. Williams, S. Borgo, I. Hasan, E. Castillo, F. Traganos, B. Rigas, Cancer Res., 2001, 61, 3285.
N. A. Sanina, S. M. Aldoshin, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 2428 [Izv. Akad. Nauk, Ser. Khim., 2004, 2326].
J. L. Bourassa, P. C. Ford, Coord. Chem. Rev., 2000, 200–202, 887.
N. A. Sanina, L. A. Syrtsova, N. I. Shkondina, T. N. Rudneva, E. S. Malkova, T. A. Bazanov, A. I. Kotelnikov, S. M. Aldoshin, Nitric Oxide: Biology and Chemistry, 2007, 16, 181.
N. A. Sanina, T. N. Rudneva, I. V. Sulimenkov, N. P. Konovalova, T. E. Sashenkova, S. M. Aldoshin, Ross. Khim. Zh., 2009, 53, 164 [Mendeleev Chem. J. (Engl. Transl.), 2009, 53].
N. A. Sanina, O. S. Zhukova, Z. S. Smirnova, L. M. Borisova, M. P. Kiseleva, S. M. Aldoshin, Ross. Bioterap. Zh. [Russian Biotherapeutical Journal], 2008, 1, 52 (in Russian).
Pat. RF 2429242, 2011; http://www.findpatent.ru/patent/ 242/2429242.html.
Pat. US 8,067,628 B2, 2011; http://www.google.com/ patents/US8067628.
J. L. Hess, C h.-H. Hsieh, J. H. Reibenspies, M. Y. Darensbourg, Inorg. Chem., 2011, 50, 8541.
Ch.-H. Hsieh, M. Y. Darensbourg, J. Am. Chem. Soc., 2010, 132, 14118.
L. Wang, G. Wang, H. Qu, C. Wang, M. Zhou, J. Phys. Chem. A, 2014, 118, 1841.
Ch.-H. Hsieh, R. B. Chupik, T. A. Pinder, M. Y. Darensbourg, Polyhedron, 2013, 58, 151.
N. A. Sanina, N. S. Emelyanova, A. N. Chekhlov, A. F. Shestakov, I. V. Sulimenkov, S. M. Aldoshin, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 1126 [Izv. Akad. Nauk, Ser. Khim., 2010, 1104].
N. S. Emelýanova, A. F. Shestakov, I. V. Sulimenkov, T. N. Rudneva, N. A. Sanina, S. M. Aldoshin, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 1 [Izv. Akad. Nauk, Ser. Khim., 2012, 1].
N. A. Sanina, G. I. Kozub, O. S. Zhukova, N. S. Emelyanova, T. A. Kondrateva, D. V. Korchagin, G. V. Shilov, N. S. Ovanesyan, S. M. Aldoshin, J. Coord. Chem., 2013, 66, 3602.
N. Yu. Shmatko, N. A. Sanina, D. V. Korchagin, G. V. Shilov, N. S. Avanesyan, S. M. Aldoshin, III Vseross. nauchn. konf. (s mezhdunarodnym uchastiem) “Uspekhi sinteza i kompleksoobrazovaniya” [Proc. III All-Russia Scientific Conf. (with international participation) “Success in Synthesis and Complex Formation”] (April 21–25, 2014, Moscow), Russia University of People´s Friendship, Moscow, 2014, p. 49 (in Russian).
G. Gomori, Methods Enzymology, 1955, 1, 138.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, 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, V. Bakken, 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. NanayakkaReceived May 28, 2014; in revised form April 16, 2015 ra, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford (CT), 2004.
J. A. Hrabie, L. K. Keefer, Chem. Rev., 2002, 102, 1135.
N. A. Sanina, Doct. Sci. (Chem.) Thesis, Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, 2011 (in Russian).
A. F. Shestakov, Yu. M. Shulğa, N. S. Emelýanova, N. A. Sanina, S. M. Aldoshin, Russ. Chem. Bull. (Int. Ed.), 2007, 62, 1289 [Izv. Akad. Nauk, Ser. Khim., 2007, 1244].
N. S. Emelýanova, N. Yu. Shmatko, N. A. Sanina, S. M. Aldoshin, Comput. Theor. Chem., 2015, 1060, 1–9.
N. S. Emelýanova, A. F. Shestakov, N. A. Sanina, S. M. Aldoshin, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 355 [Izv. Akad. Nauk, Ser. Khim., 2013, 359].
Author information
Authors and Affiliations
Corresponding author
Additional information
Based on the materials of the XXVI Symposium “Modern Chemical Physics” (September 20–October 1, 2014, Tuapse, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2344–2350, October, 2015.
Rights and permissions
About this article
Cite this article
Emel’yanova, N.S., Shmatko, N.Y., Sanina, N.A. et al. Experimental and quantum chemical modeling of the influence of the pH of the medium on the NO-donor activity of the mononuclear nitrosyl iron complex [Fe(SC(NH2)2)2(NO)2]Сl•H2O. Russ Chem Bull 64, 2344–2350 (2015). https://doi.org/10.1007/s11172-015-1162-5
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-015-1162-5