Hydrosulfide (HS-) coordination in iron porphyrinates

Inorganic Chemistry

Volumn 49, Issue 3, 2010, Pages 1017-1026

  Pavlik, Jeffrey W ^a   Noll, Bruce C ^a   Oliver, Allen G ^a   Schulz, Charles E ^b   Robert Scheldt, W ^b  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b KNOX COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN SULFIDE; IRON; METALLOPORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; HYDROGEN SULFIDE; IRON; METALLOPORPHYRINS; MODELS, MOLECULAR;

EID: 75649107221     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic901853p     Document Type: Article

References (74)

1. Abe, K.; Kimura, H. J. Neurosci. 1996, 16, 1066.
2. Furne, J.; Saeed, A.; Levitt, M. D. Am. J. Physiol. Regul. Integr. Comp. Physiol. 2008, 295, R1479.
3. Olson, K. R.; Dombrowski, R. A.; Russell, M. J.; Doellman, M. M.; Head, A. K.; Whitfield, N. L.; Madden, J. A. J. Exp. Biol. 2006, 209, 4011.
4. Hosoki, R.; Matsuki, N.; Kimurs, H. Biochem. Biophys. Res. Commun. 1997, 237, 527.
5. Mustafa, A. K.; Gadalla, M. M.; Snyder, S. H. Sci. Signal. 2009, 2, re2.
6. Wever, R.; Van Gelder, B. F.; Dervartanian, D. V. Biochim. Biophys. Acta 1975, 387, 189.
7. Cooper, C. E.; Brown, G. C. J. Bioenerg. Biomembr. 2008, 40, 533.
8. Billaut-Laden, I.; Allorge, D.; Crunelle-Thibaut, A.; Rat, E.; Cauffiez, C.; Chevalier, D.; Houdret, N.; Lo-Guidice, J.; Broly, F. Toxicology 2006, 225, 1.
9. Kamoun, P. Amino Acids 2004, 26, 243.
10. Blackstone, E.; Morrison, M.; Roth, M. B. Science 2005, 308, 518.
11. Leslie, M. Science 2008, 320, 1155.
12. Yang, G.; Wu, L.; Jiang, B.; Yang, W.; Qi, J.; Cao, K.; Meng, Q.; Mustafa, A.; Mu, W.; Zhang, S.; Snyder, S.; Wang, R. Science 2008, 83, 587.
13. Eto, K.; Kimura, H. J. Neurochem. 2002, 83, 80.
14. Simonsen, U.; Wadsworth, R. W.; Buus, N. H.; Mulvany, M. J. J. Physiol. 1999, 316, 271.
15. Keilin, D. Proc. R. Soc. London, Ser. B: Biol. Sci. 1933, 133, 393.
16. Hoppe-Seyler, F. Zentralbl. Med. Wiss. 1866, 4, 436.
17. Haurowitz, F. Z. Physiol. Chem. 1926, 151, 130.
18. (a) Berzofsky, J. A.; Peisach, J.; Blumberg, W. E. J. Biol. Chem. 1971, 246, 3367.
19. (b) Berzofsky, J. A.; Peisach, J.; Horecker, B. L. J. Biol. Chem. 1972, 247, 3783.
20. (a) Chatfield, M. J.; La Mar, G. N.; Lecomte, J. T. J.; Balch, A. L.; Smith, K. M.; Langry, K. C. J. Am. Chem. Soc. 1986, 108, 710.
21. (b) Chatfield, M. J.; La Mar, G. N.; Kauten, R. J. Biochemistry 1987, 26, 6939.
22. Wu, C.; Kenny, M. A. Clin. Chem. 1997, 43, 162.
23. Brittain, T.; Yosaatmadja, Y.; Henty, K. IUBMB Life 2008, 60, 135.
24. Weber, R. E.; Vinogradov, S. N. Physiol. Rev. 2001, 81, 569.
25. The following abbreviations are used in this paper:HbI, hemoglobin I from L. pectinata; OEP, dianion of 2,3,7,8,12,13,17,18-octaethylporphyrin; T-p-OMePP, dianion ofmeso-tetra-p-methoxyphenylporphyrin;TPP; dianion of meso-tetraphenylporphyrin; TMP, dianion of meso-tetramesitylporphyrin; TpivPP, dianion of α,α,α,α-tetrakis(o-pivalamidophenyl) porphyrin; Proto IX DME, dianion of protoporphyrin IX; Por, generalized porphyrin dianion; 222, 1,10-diaza-4,7,13,16,21,24-hexaoxabicyclo[8.8.8] hexacosane; Im, generalized imidazole; HIm, imidazole; 2-MeHIm, 2-methylimidazole; 1-MeIm, 1-methylimidazole; 2-MeIm, 2-methylimidazolate; cyclam, 1,4,8,11-tetraazacyclotetradecane; oespz, 2,3,7,8,12,13,17,18- octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinate dianion; dmpe, 1,2-bis(dimethylphosphino)ethane; IMes, 1,3-bis(2,4,6-trimethylphenyl)imidazol- 2-ylidene.
26. Kraus, D. W.; Wittenberg, J. B.; Jing-Fen, L.; Peisach, J. J. Biol. Chem. 1990, 265, 16054.
27. Rizzi, M.; Wittenberg, J. B.; Coda, A.; Ascenzi, P.; Bolognesi, M. J. Mol. Biol. 1996, 258, 1.
28. Pietra, R.; Lewis, A.; Leon, R. G.; Casabona, G.; Kiger, L.; Yeh, S.; Fernandez-Alberti, S.; Marden, M. C.; Cadilla, C. L.; Lopez-Garriga, J. Biochemistry 2009, 48, 4881.
29. Doeller, J. E.; Kraus, D. W.; Colacino, J. M.; Wittenberg, J. B. Biol. Bull. 1988, 175, 388.
30. Numoto, N.; Nakagawa, T.; Kita, A.; Sasayama, Y.; Fukumori, Y.; Miki, K. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 14521.
31. English, D. R.; Hendrickson, D. N.; Suslick, K. S.; Eigenbrot, C. W.; Scheidt, W. R. J. Am. Chem. Soc. 1984, 106, 7258.
32. Balch, A. L.; Cornman, C. R.; Safari, N.; Latos-Grazyński, L. Organometallics 1990, 9, 2420.
33. Cai, L.; Holm, R. H. J. Am. Chem. Soc. 1994, 116, 7177.
34. Mueting, A. M.; Boyle, P.; Pignolet, L. H. Inorg. Chem. 1984, 23, 44.
35. Ricciardi, G.; Bencini, A.; Belviso, S.; Bavaso, A.; Lelj, F. J. Chem. Soc., Dalton Trans. 1998, 1985.
36. Pleus, R. J.; Waden, H.; Saak, W.; Haase, D.; Pohl, S. J. Chem. Soc., Dalton Trans. 1999, 2601.
37. Gaffney, T. R.; Ibers, J. A. Inorg. Chem. 1982, 21, 2851.
38. Arif, A. M.; Hefner, J. G.; Jones, R. A.; Koschmieder, S. U. J. Coord. Chem. 1991, 23, 13.
39. Chatwin, S. L.; Diggle, R. A.; Jazzar, R. F.; MacGregor, S. A.; Mahon, M. F.; Whittlesey, M. K. Inorg. Chem. 2003, 42, 7695.
40. Mudalige, D. C.; Ma, E. S.; Rettig, S. J.; James, B. R.; Cullen, W. C. Inorg. Chem. 1997, 36, 5426.
41. Sellman, D.; Lechner, P.; Knoch, F.; Moll, M. J. Am. Chem. Soc. 1992, 114, 922.
42. Milgram, B. C.; Eskildsen, K.; Richter, S. M.; Scheidt, W. R.; Scheidt, K. A. J. Org. Chem. 2007, 72, 3941.
43. (a) Adler, A. D.; Longo, F. R.; Kampus, F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 32, 2443.
44. (b) Buchler, J.W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier Scientific Publishing: Amsterdam, The Netherlands, 1975; Chapter 5.
45. Lidin, R. A. Inorganic Substances Handbook; Begel House Inc.: New York, 1996; p 284.
46. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, A64, 112.
47. Legget, D. J. SQUAD: Stability Quotients from Absorbance Data. In Computational Methods for the Determination of Formation Constants; Legget, D. J., Ed.; Modern Inorganic Chemistry Series; Plenum Press: New York, 1996; pp 159-217.
48. Debrunner, P. G. Mössbauer Spectroscopy of Iron Porphyrins. In Iron Porphyrins; Lever, A. B. P., Gray, H. B., Eds.; VCH Publishers Inc.: New York, 1983; Chapter 2, Part 3.
49. Nasri, H.; Fischer, J.; Weiss, R.; Bill, E.; Trautwein, A. J. Am. Chem. Soc. 1987, 109, 2549.
50. Schappacher, M.; Weiss, R. R.; Montiel-Montoya, R.; Gonser, U.; Bill, E.; Trautwein, A. Inorg. Chim. Acta 1983, 78, L9.
51. Hu, C.; Noll, B. C.; Schulz, C. E.; Scheidt, W. R. J. Am. Chem. Soc. 2005, 127, 15018.
52. Shaevitz, B. A.; Lang, G.; Reed, C. A. Inorg. Chem. 1988, 27, 4607.
53. Bominaar, E. L.; Ding, X.; Gismelseed, A.; Bill, E.; Winkler, H.; Trautwein, A. X.; Nasri, H.; Fisher, J.; Weiss, R. Inorg. Chem. 1992, 31, 1845.
54. Collman, J. P.; Hoard, L.; Kim, N.; Lang, G.; Reed, C. A. J. Am. Chem. Soc. 1975, 97, 2676.
55. Hu, C.; Noll, B. C.; Schulz, C. E.; Scheidt, W. R. Inorg. Chem. 2007, 46, 619.
56. Strauss, S. H.; Silver, M. E.; Long, K. M.; Thompson, R. G.; Hudgens, R. A.; Spartalian, K.; Ibers, J. A. J. Am. Chem. Soc. 1985, 207, 4207.
57. Maricondi, C.; Straub, D. K.; Epstein, L. M. J. Am. Chem. Soc. 1972, 94, 4157.
58. Moss, T. H.; Bearden, A. J.; Caughey, W. S. J. Chem. Phys. 1969, 51, 2624.
59. Tang, S. C.; Koch, S.; Papaefthymiou, G. C.; Foner, S.; Frankel, R. B.; Ibers, J. A.; Holm, R. H. J. Am. Chem. Soc. 1976, 98, 2414.
60. Scheidt, W. R.; Reed, C. A. Chem. Rev. 1981, 81, 543.
61. Scheidt, W. R. Systematics of Porphyrins and Metalloporphyrins. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol.3, pp 72-73.
62. Hu, C.; Sulok, C. D.; Paulat, F.; Lehnert, N.; Zatsman, A. I.; Hendrich, M. P.; Schulz, C. E.; Scheidt, W. R., manuscript in preparation.
63. Nasri, H. Ph.D. Thesis, University of Louis Pasteur, Strasbourg, France, 1987.
64. Caron, C.; Mitschler, A.; Riviere, G.; Ricard, L.; Schappacher, M.; Weiss, R. J. Am. Chem. Soc. 1979, 101, 7401.
65. Schappacher, M.; Ricard, L.; Weiss, R. R.; Montiel-Montoya, R.; Bill, E.; Trautwein, A. X. Inorg. Chem. 1989, 28, 4639.
66. Nasri, H.; Ellison, M. K.; Shaevitz, B.; Gupta, G. P.; Scheidt, W. R. Inorg. Chem. 2006, 45, 5284.
67. Mandon, D.; Ott-Woelfel, F.; Fischer, J.; Weiss, R.; Bill, E.; Trautwein, A. X. Inorg. Chem. 1979, 101, 2442.
68. Tang, S. C.; Koch, S.; Papaefthymiou, G. C.; Foner, S.; Frankel, R. B.; Ibers, J. A.; Holm, R. H. J. Am. Chem. Soc. 1976, 98, 2414.
69. Miller, K. M.; Strouse, C. E. Acta Crystallogr., Sect. C 1984, C40, 1324.
70. Miller, K. M.; Strouse, C. E. Inorg. Chem. 1984, 23, 2395.
71. Scheidt, W. R.; Lee, Y. J. Recent Advances in the Stereochemistry of Metallotetrapyrroles. Struct. Bonding (Berlin) 1987, 64, 1-70.
72. Shelnutt, J. A.; Song, X.; Ma, J.; Jia, A.; Jentzen, W.; Medforth, C. J. Chem. Soc. Rev. 1998, 27, 31.
73. Sun, L.; Shelnutt, J. A. Program is available via the internet at http://jasheln.unm.edu.
74. See Table 3 of: Hu, C.; An, J.; Noll, B. C.; Schulz, C. E.; Scheidt, W. R. Inorg. Chem. 2006, 45, 4177.