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A new member of tetranuclear dinitrosyl iron complexes (DNICs) with 2-mercaptothiazoline ligand: synthesis, structure and properties

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Abstract

A new tetranuclear dinitrosyliron complex [(μ-SC3H4SN)Fe(NO)2]4 (2), each of a Fe center coordinated with two S or two N, was prepared by CO replacement from the reduced precursor (CO)2Fe(NO)2 with 1 equiv of HSC3H4SN (2-mercaptothiazoline) in the presence of O2(g). The structure of 2 is similar to [(Imid-iPr)Fe(NO)2]4 (Imid-iPr = 2-isopropylimidazole) (Hess et al. J Am Chem Soc 133:20426–20434, 2011), and both complexes comprise a quadrilateral plane of irons with corresponding ligands, SC3H4SN− or Imid-iPr−, bridging the edges and two nitrosyl ligands capping the irons at the corners. An additional equiv of SC3H4SN− was added to 2, which results in the mononuclear {Fe(NO)2}9 (SC3H4SN)2Fe(NO) −2 (3), in the manner of N bound-[SC3H4SN]. Reaction of (TMEDA)IFe(NO)2 (TMEDA = tetramethylethylenediamine) and complex 3 leads to the formation of complex 2. Dinuclear complex [(μ-C5H7N2)Fe(NO)2]2 (4) can be synthesized by the ligand displacement of SC3H4SN− to C5H7N2 − (3,5-dimethylpyrazolate) of 2 (Chong et al. Can J Chem 57:3119–3125, 1979). Complexes 2–4 were characterized by IR and UV–Vis. The molecular structures of 2 and 3 were determined by X-ray single crystal diffraction.

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References

  1. R. Morphy, C. Kay, Z. Rankovic, Drug Discov. Today 9, 641–651 (2004)

    Article  CAS  Google Scholar 

  2. K–.K. Lin, S.-C. Wu, K.-M. Hsu, C.-H. Hung, W.-F. Liaw, Y.-M. Wang, Org. Lett. 15, 4242–4245 (2013)

    Article  CAS  Google Scholar 

  3. T.D. Bradshaw, S. Wrigley, D.-F. Shi, R.J. Schultz, K.D. Paul, M.F.G. Stevens, Br. J. Cancer 77, 745–752 (1998)

    Article  CAS  Google Scholar 

  4. E.A. Jaimes, D. del Castillo, M.S. Rutherford, L. Raij, J. Am. Chem. Soc. 12, 1204–1210 (2001)

    CAS  Google Scholar 

  5. G.C.P. May, P.K. Moore, C.P. Page, Br. J. Pharmacol. 102, 759–763 (1991)

    Article  CAS  Google Scholar 

  6. Y.P. Tao, T.P. Misko, A.C. Howlette, C. Klein, Development 124, 3587–3595 (1997)

    CAS  Google Scholar 

  7. J. MacMicking, Q. Xie, C. Nathan, Annu. Rev. Immunol. 15, 323–350 (1997)

    Article  CAS  Google Scholar 

  8. J.A. McCleverty, Chem. Rev. 104, 403–418 (2004)

    Article  CAS  Google Scholar 

  9. C. Badorff, B. Fichtlscherer, A. Muelsch, A.M. Zeiher, S. Dimmeler, Nitric Oxide 6, 305–312 (2002)

    Article  CAS  Google Scholar 

  10. J.S. Stamler, D.J. Singel, J. Loscalzo, Science 258, 1898–1902 (1992)

    Article  CAS  Google Scholar 

  11. J.S. Stamler, Cell 78, 931–936 (1994)

    Article  CAS  Google Scholar 

  12. M. Boese, P.I. Mordvintcev, A.F. Vanin, R. Busse, A. Muelsch, J. Biol. Chem. 270, 29244–29249 (1995)

    Article  CAS  Google Scholar 

  13. Y. Henry, M. Lepoivre, J.C. Drapier, C. Ducrocq, J.L. Boucher, A. Guissani, FASEB J. 7, 1124–1134 (1993)

    CAS  Google Scholar 

  14. R. Radi, J.S. Beckman, K.M. Bush, B.A. Freeman, J. Biol. Chem. 266, 4244–4250 (1991)

    CAS  Google Scholar 

  15. A. Mulsch, Drug Res. 44, 408–411 (1994)

    CAS  Google Scholar 

  16. A.F. Vanin, P.I. Mordvintcev, S. Hauschildt, A. Muelsch, Biochim. Biophys. Acta Mol. Cell Res. 1177, 37–42 (1993)

    Article  CAS  Google Scholar 

  17. E. Cesareo, L.J. Parker, J.Z. Pedersen, M. Nuccetelli, A.P. Mazzetti, A. Pastore, G. Federici, A.M. Caccuri, G. Ricci, J.J. Adams, M.W. Parker, M.J. Lo, Bello. Biol. Chem. 280, 42172–42180 (2005)

    Article  CAS  Google Scholar 

  18. A.F. Vanin, Open Conf. Proc. J. 4, 47–53 (2013)

    Article  Google Scholar 

  19. S.M. Aldoshin, K.A. Lyssenko, M.Y. Antipin, N.A. Sanina, V.V. Gritsenko, J. Mol. Struct. 875, 309–315 (2008)

    Article  CAS  Google Scholar 

  20. N.A. Sanina, T.N. Rudneva, S.M. Aldoshin, G.V. Shilov, D.V. Kortchagin, Y.M. Shulga, V.M. Martynenko, N.S. Ovanesyan, Inorg. Chim. Acta 359, 570–576 (2006)

    Article  CAS  Google Scholar 

  21. O.A. Rakova, N.A. Sanina, S.M. Aldoshin, N.V. Goncharova, G.V. Shilov, Y.M. Shulga, N.S. Ovanesyan, Inorg. Chem. Commun. 6, 145–148 (2003)

    Article  CAS  Google Scholar 

  22. N. A.Sanina, T.N. Roudneva, G.V. Shilov, R. Morgunov, N.S. Ovanesyan, S. M. Aldoshin, Dalton Trans. 1703–1706 (2009)

  23. N.A. Sanina, O.A. Rakova, S.M. Aldoshin, G.V. Shilov, Y.M. Shulga, A.V. Kulikov, N.S. Ovanesyan, Mendeleev Commun. 14, 7–8 (2004)

    Article  Google Scholar 

  24. J.L. Hess, C.-H. Hsieh, J.H. Reibenspies, M.Y. Darensbourg, Inorg. Chem. 50, 8541–8552 (2011)

    Article  CAS  Google Scholar 

  25. K. Chong, T. Rettiga, L. Torra, N.J. Rotter, Can. J. Chem. 57, 3119–3125 (1979)

    Article  CAS  Google Scholar 

  26. J.H. Enemark, R.D. Feltham, Coord. Chem. Rev. 13, 339–406 (1974)

    Article  CAS  Google Scholar 

  27. M.-C. Hung, M.-C. Tsai, W.-F. Liaw, Inorg. Chem. 45, 6041–6047 (2006)

    Article  CAS  Google Scholar 

  28. M.-L. Tsai, W.-F. Liaw, Inorg. Chem. 45, 6583–6585 (2006)

    Article  CAS  Google Scholar 

  29. Z.J. Tonzetich, L.H. Do, S.J. Lippard, J. Am. Chem. Soc. 131, 7964 (2009)

    Article  CAS  Google Scholar 

  30. J.L. Hess, C.-H. Hsieh, S.M. Brothers, M.B. Hall, M.Y. Darensbourg, J. Am. Chem. Soc. 133, 20426–20434 (2012)

    Article  Google Scholar 

  31. APEX2, version 2009.7-0; (Bruker AXS, Inc., Madison, 2007)

  32. SAINTPLUS: Program for Reduction of Area Detector Data, version 6.63; (Bruker AXS, Inc., Madison, 2007)

  33. G.M. Sheldrick, SADABS: Program for Absorption Correction of Area Detector Frames (Bruker AXS Inc., Madison, 2001)

    Google Scholar 

  34. G.M. Sheldrick, SHELXS-97: Program for Crystal Structure Solution; Germany (1997)

  35. G.M. Sheldrick, SHELXL-97: Program for Crystal Structure Refinement; Germany (1997)

  36. C.F. Macrae, P.R. Edgington, P. McCabe, E. Pidcock, G.P. Shields, R. Taylor, M. Towler, J. van de Streek, J. Appl. Crytsallogr. 39, 453–457 (2006)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge financial support from the National Science Council of Taiwan. The authors thank Dr. Gene-Hsiang Lee for the single-crystal X-ray structural determinations.

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Authors and Affiliations

  1. School of Applied Chemistry, Chung Shan Medical University, Taichung, 40201, Taiwan

    Chien-Hong Chen & Jheng-Hong Wang

  2. Department of Medical Education, Chung Shan Medical University Hospital, Taichung, 40201, Taiwan

    Chien-Hong Chen

  3. Department of Chemistry, Tamkang University, New Taipei City, 25137, Taiwan

    Jing-Yi Huang & Chung-Hung Hsieh

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  1. Chien-Hong Chen
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  2. Jheng-Hong Wang
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Correspondence to Chien-Hong Chen or Chung-Hung Hsieh.

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Chen, CH., Wang, JH., Huang, JY. et al. A new member of tetranuclear dinitrosyl iron complexes (DNICs) with 2-mercaptothiazoline ligand: synthesis, structure and properties. Res Chem Intermed 40, 2217–2227 (2014). https://doi.org/10.1007/s11164-014-1599-4

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