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Synthesis, Structure, and Properties of the Iron Nitrosyl Complex with 2-Ethyl-4-pyridinecarbothioamide

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Abstract

The synthesis and data on the physicochemical characteristics and biological activity of the new iron nitrosyl complex (Q+)2[Fe2(S2O3)2(NO)4]2– (I), where Q+ is protonated 2-ethyl-4-pyridinecarbothioamide (C8H11N2S), are presented. The structure and properties of the complex were studied by X-ray diffraction, elemental analysis, IR and Mössbauer spectroscopy, and amperometry. The complex showed antibacterial activity and efficiently inhibited cyclic guanosine monophosphate phosphodiesterase (cGMP PDE), which may suggest its antihypertensive, anti-aggregation, and vasodilator activities.

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REFERENCES

  1. Benencia, F. and Courreges, M.C., Immunology, 1999, vol. 98, no. 3, p. 363.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Mehta, D.R., Ashkar, A.A., and Mossman, K.L., PLoS One, 2012, vol. 7, no. 2, p. e31688.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. McMullin, B.B., Chittock, D.R., Roscoe, D.L., et al., Respiratory Care, 2005, vol. 50, no. 11, p. 1451.

    PubMed  Google Scholar 

  4. Jones-Carson, J., Zweifel, A.E., Tapscott, T., et al., PLoS Negl. Trop. Dis., 2014, vol. 8, no. 8, p. e3079.

    Article  PubMed  PubMed Central  Google Scholar 

  5. Fang, F.C., J. Clin. Invest., 1997, vol. 99, no. 12, p. 2818.

    Article  CAS  Google Scholar 

  6. De Groote, M.A. and Fang, F.C., Clin. Infect. Dis., 1995, vol. 21, no. 2, p. S162.

    Article  CAS  PubMed  Google Scholar 

  7. Schairer, D.O., Chouake, J.S., Nosanchuk, J.D., et al., Virulence, 2012, vol. 3, p. 271.

    Article  PubMed  PubMed Central  Google Scholar 

  8. Jones, M.L., Ganopolsky, J.G., Labbe, A., et al., Appl. Microbiol. Biotechnol., 2010, vol. 88, no. 2, p. 401.

    Article  CAS  PubMed  Google Scholar 

  9. Jones, M.L., Ganopolsky, J.G., Labbe, A., et al., Appl. Microbiol. Biotechnol., 2010, vol. 87, no. 2, p. 509.

    Article  CAS  PubMed  Google Scholar 

  10. Fox, S., Wilkinson, T.S., Wheatley, P.S., et al., Acta Biomater., 2010, vol. 6, no. 4, p. 1515.

    Article  CAS  PubMed  Google Scholar 

  11. Narin, G., Albayrak, C.B., and Ulku, S., Appl. Clay Sci., 2010, vol. 50, no. 4, p. 560.

    Article  CAS  Google Scholar 

  12. Weller, R., Ormerod, A.D., Hobson, R.P., et al., J. Am. Acad. Dermatol., 1998, vol. 38, no. 4, p. 559.

    Article  CAS  PubMed  Google Scholar 

  13. Ormerod, A.D., White, M.I., Shah, S.A., et al., Br. J. Dermatol., 1999, vol. 41, no. 6, p. 1051.

    Article  Google Scholar 

  14. Phillips, R., Adjei, O., Lucas, S., et al., Antimicrob. Agents Chemother., 2004, vol. 48, no. 8, p. 2866.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Ormerod, A.D., Shah, A.A., Li, H., et al., BMC Res. Notes, 2011, vol. 4, p. 458.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Davidson, R.N., Yardley, V., Croft, S.L., et al., Trans. R. Soc. Trop. Med. Hyg., 2000, vol. 94, no. 3, p. 319.

    Article  CAS  PubMed  Google Scholar 

  17. Daiber, A., Wenzel, P., Oelze, M., et al., Clin. Res. Cardiol., 2008, vol. 97, no. 1, p. 12.

    Article  CAS  PubMed  Google Scholar 

  18. Deupree, S.M. and Schoenfisch, M.H., Acta Biomater., 2009, vol. 5, no. 5, p. 1405.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Schairer, D.O., Chouake, J.S., Nosanchuk, J.D., and Friedman, A.J., Virulence, 2012, vol. 3, no. 3, p. 271.

    Article  PubMed  PubMed Central  Google Scholar 

  20. Cariello, A.J. and Bispo, P.J., de Souza, et al., Clin. Ophthalmol., 2012, vol. 6, p. 1907.

  21. Williams, D.L.H., Acc. Chem. Res., 1999, vol. 32, no. 10, p. 869.

    Article  CAS  Google Scholar 

  22. Laver, J.R., Stevanin, T.M., Messenger, S.L., et al., FASEB J., 2010, vol. 24, no. 1, p. 286.

    Article  PubMed  PubMed Central  Google Scholar 

  23. Jaouen, G. and Salmain, M., The Bioorganometalic Chemistry: Applications in Drug Discovery, Biocatalysis and Imaging, Weinheim: Wiley-VCH, 2014.

    Book  Google Scholar 

  24. Hsiao, H., Chung, C., Santos, J.H., et al., Dalton Trans., 2019, vol. 48, p. 9431.

    Article  CAS  PubMed  Google Scholar 

  25. Gould, N., Doulias, P.-T., Tenopoulou, M., et al., J. Biol. Chem., 2013, vol. 288, no. 37, p. 26473.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Stupina, T.S., Antonova, N.O., Balalaeva, I.V., et al., Intern. Sci. J. Med. Biol. Sci., 2014, vol. 1, no. 1, p. 23.

    Google Scholar 

  27. Grigor’ev, A.I. and Vladimirov, Yu.A., Fundamental’nye nauki — meditsine: Biofizicheskie meditsinskie tekhnologii (Fundamental Sciences for Medicine: Biophysical Medical Technologies), Moscow: MAKS Press, 2015.

  28. Sanina, N.A., Kozub, G.I., Kondrat’eva, T.A., et al., Russ. Chem. Bull., 2017, no. 9, p. 1706.

  29. Mumyatova, V.A., Kozub, G.I., Kondrat’eva, T.A., et al., Russ. Chem. Bull., 2019, no. 5, p. 1025.

  30. Sanina, N.A., Mumyatova, V.A., Terent’ev, A.A., et al., Russ. Chem. Bull., 2019, no. 12, p. 2225.

  31. Hanoulle, X., Wieruszeski, J.M., Rouseelot-Pailley, P., et al., Biochem. Biophys. Res. Commun., 2005, vol. 331, p. 452.

    Article  CAS  PubMed  Google Scholar 

  32. Vilchèze, C., Weisbrod, T.R., Chen, B., et al., Antimicrob. Agents Chemother., 2005, vol. 49, p. 708.

    Article  PubMed  PubMed Central  Google Scholar 

  33. Yu, K.L., Torri, A.F., Luo, G., et al., Bioorg. Med. Chem. Lett., 2002, vol. 12, no. 23, p. 3379.

    Article  CAS  PubMed  Google Scholar 

  34. Hitotsuyanagi, Y., Hasuda, T., Matsumoto, Y., et al., Chem. Commun., 2000, no. 17, p. 1633.

  35. Nakagawa, Y., Irie, K., Ohigashi, H., et al., Bioorg. Med. Chem. Lett., 2000, vol. 10, no. 18, p. 2087.

    Article  CAS  PubMed  Google Scholar 

  36. Wei, Q.L., Zhang, S.S., Gao, J., et al., Bioorg. Med. Chem., 2006, vol. 14, no. 21, p. 7146.

    Article  CAS  PubMed  Google Scholar 

  37. Wentland, M.P., Sun, X., Bu, Y., et al., Bioorg. Med. Chem. Lett., 2005, vol. 15, no. 10, p. 2547.

    Article  CAS  PubMed  Google Scholar 

  38. Krinková, J., Doležal, M., Hartl, J., et al., Il Farmaco, 2002, vol. 57, no. 1, p. 71.

    Article  PubMed  Google Scholar 

  39. Yu, K.L., Torri, A.F., Luo, G., et al., Bioorg. Med. Chem. Lett., 2002, vol. 12, no. 23, p. 3379.

    Article  CAS  PubMed  Google Scholar 

  40. Davies, D.J., Faust, R., Garratt, P.J., et al., Bioorg. Chem., 2004, vol. 32, no. 1, p. 1.

    Article  CAS  PubMed  Google Scholar 

  41. Boström, J., Olsson, R.I., Tholander, J., et al., Bioorg. Med. Chem. Lett., 2010, vol. 20, no. 2, p. 479.

    Article  PubMed  Google Scholar 

  42. Thanigaimalai, P., Sharma, V.K., Lee, K.C., et al., Bioorg. Med. Chem. Lett., 2010, vol. 20, no. 16, p. 4771.

    Article  CAS  PubMed  Google Scholar 

  43. Brunhofer, G., Studenik, C., Ecker, G.F., et al., Eur. J. Pharm. Sci., 2011, vol. 42, nos. 1−2, p. 37.

    Article  CAS  PubMed  Google Scholar 

  44. Shimotori, Y., Hoshi, M., Ogawa, N., et al., Heterocycl. Commun., 2020, vol. 26, p. 84.

    Article  CAS  Google Scholar 

  45. Registr lekarstvennykh sredstv Rossii: Entsiklopediya lekarstv. Vyp. 29 (Register of Pharmaceutical Products of Russia: Drug Encyclopedia. Issue 29), Vyshkovskii, G.L., Ed., Moscow: Vedanta, 2021.

    Google Scholar 

  46. Mahantaa, N., Szantai-Kisc, M., Peterssonc, E.J., et al., ACS Chem. Biol., 2019, vol. 14, no. 2, p. 142.

    Article  Google Scholar 

  47. Vale, N., Gomes, P., and Santos, H., Curr. Drug Metab., 2013, vol. 14, no. 1, p. 151.

    Article  CAS  PubMed  Google Scholar 

  48. Mills III, T. and Roberson, J.C., Instrumental Data for Drug Analysis, New York: Elsevier, 1992, vol. 2.

  49. Eccles, K.S., Morrison, R.E., Maguire, A.R., et al., Cryst. Growth Des., 2014, vol. 14, p. 2753.

    Article  CAS  Google Scholar 

  50. Wysokinski, R., Michalska, D., Bienko, D.C., et al., J. Mol. Struct., 2006, vol. 791, nos. 1–3, p. 70.

    Article  CAS  Google Scholar 

  51. Vale, N., Makila, E., Salonen, J., et al., Eur. J. Pharm. Biopharm., 2012, vol. 81, p. 314.

    Article  CAS  PubMed  Google Scholar 

  52. Sanina, N.A., Starostina, A.A., Utenyshev, A.N., et al., Molecules, 2022, vol. 27, p. 6886.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. Karyakin, Yu.V. and Angelov, I.I., Chistye khimicheskie veshchestva (Pure Chemicals), Moscow: Khimiya, 1974.

  54. Sanina, N.A., Aldoshin, S.M., and Rudneva, T.N., Russ. J. Coord. Chem., 2005, vol. 31, no. 5, p. 301. https://doi.org/10.1007/s11173-005-0093-3

    Article  CAS  Google Scholar 

  55. Weissberger, A., Proskauer, E., Riddick, J.A., et al., Organic Solvents: Physical Properties and Methods of Purification, New York: Intercscience, 1955.

    Google Scholar 

  56. Agilent. CrysAlis PRO, Yarnton–Oxfordshire: Agilent Technologies UK Ltd., 2011.

  57. Sheldrick, G.M., SHELXTL. Version 6.14. Structure Determination Software Suite, Madison (WI, USA): Bruker AXS, 2000.

    Google Scholar 

  58. MUK 4.2.1890-04. Opredelenie chuvstvitel’nosti mikroorganizmov k antibakterial’nym preparatam. Metodicheskie ukazaniya: data vvedeniya 2014-03-04 (MUK 4.2.1890-04. Determination of Bacterial Sensitivity to Antiibacterial Agents. Methodical Guidelines: Issued April 3, 2014) Moscow: Federal’nyi tsentr gossanepidnadzora Minzdrava Rossii, 2004.

  59. Libinzon, R.E., Shchekoldina, T.G., Batolkina, O.E., et al., Voprosy meditsinskoi khimii, 1977, vol. 23, no. 4, p. 526.

    CAS  PubMed  Google Scholar 

  60. Tat’yanenko, L.V., Kotel’nikov, A.I., Dobrokhotova, O.V., et al., Khim.-Farm. Zh., 2009, vol. 43, no. 9, p. 45.

    Google Scholar 

  61. Berezin, I.V. and Klesov, A.A., Prakticheskii kurs khimicheskoi i fermentativnoi kinetiki (Practical Course of Chemical and Enzymatic Kinetics), Moscow: Izd-vo Mosk. un-ta, 1976.

  62. Glidewell, C., Hursthouse, M.B., Lambert, R.J., et al., Dalton Trans., 1989, p. 2061.

  63. Sanina, N.A., Rakova, O.A., Aldoshin, S.M., et al., Russ. J. Coord. Chem., 2001, vol. 27, no. 3, p. 179. https://doi.org/10.1023/A:1009598228585

    Article  CAS  Google Scholar 

  64. Sanina, N.A., Emel’yanova, N.S., Chekhlov, A.N., et al., Russ. Chem. Bull., 2010, vol. 59, p. 1126.

    Article  CAS  Google Scholar 

  65. Sanina, N.A., Sulimenkov, I.V., Rudneva, T.N., et al., Dokl. Chem., 2009, vol. 425, Pt. 1, p. 60.

    Article  CAS  Google Scholar 

  66. Chan, C., Hardin, T.C., and Smart, J.I., Future Microbiol., 2015, vol. 10, p. 1325.

    Article  CAS  PubMed  Google Scholar 

  67. Omori, K. and Kotera, J., Circ. Res., 2007, vol. 100, p. 309.

    Article  CAS  PubMed  Google Scholar 

  68. Hardman, J.G., Robison, G.A., and Sutherland, E.W., Annu. Rev. Physiol., 1971, vol. 33, p. 311.

    Article  CAS  PubMed  Google Scholar 

  69. Padda, I.S. and Tripp, J., Phosphodiesterase Inhibitors, Treasure Island (FL): StatPearls, 2022.

    Google Scholar 

  70. Baillie, G.S., Tejeda, G.S., and Kelly, M.P., Nat. Rev. Drug Discov., 2019, vol. 18, p. 770.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. Miller, M.S., J. Receptor Ligand Channel Res., 2015, vol. 8, p. 19.

    Google Scholar 

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Funding

This study was supported by the Ministry of Science and Higher Education of the Russian Federation (State Assignment no. AAAA-A19-119071890015-6).

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Authors and Affiliations

  1. Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Russia

    N. A. Sanina, G. V. Shilov, N. S. Ovanesyan, V. A. Mumyatova, A. A. Balakina, A. A. Terent’ev, O. V. Pokidova & S. M. Aldoshin

  2. Research and Education Center “Medicinal Chemistry” in Chernogolovka, State University of Education, Mytishchi, Moscow oblast, Russia

    N. A. Sanina & A. A. Terent’ev

  3. Moscow State University, Moscow, Russia

    N. A. Sanina & A. A. Terent’ev

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  1. N. A. Sanina
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  2. G. V. Shilov
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  3. N. S. Ovanesyan
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  4. V. A. Mumyatova
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Correspondence to N. A. Sanina.

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Translated by Z. Svitanko

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Sanina, N.A., Shilov, G.V., Ovanesyan, N.S. et al. Synthesis, Structure, and Properties of the Iron Nitrosyl Complex with 2-Ethyl-4-pyridinecarbothioamide. Russ J Coord Chem 49, 542–554 (2023). https://doi.org/10.1134/S1070328423600523

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