The synthetic and structural chemistry of heme derivatives with nitric oxide ligands

Accounts of Chemical Research

Volumn 32, Issue 4, 1999, Pages 350-359

  Scheidt, W Robert ^a   Ellison, Mary K ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HEME DERIVATIVE; IRON COMPLEX; LIGAND; METALLOPORPHYRIN; NITRIC OXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; GEOMETRY; OXIDATION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0032909508     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9700116     Document Type: Article

References (70)

1. Gibson, Q. H.; Roughton, F. J. W. Kinetics and Equilibria of Reactions of NO with Sheep Hb. J. Physiol. 1957, 136, 507-526.
2. Koshland, D. E., Jr. The Molecule of the Year. Science 1992, 258, 1861.
3. Deinum, G.; Stone, J. R.; Babcock, G. T.; Marietta, M. A. Binding of NO and CO to sGC as Observed with Resonance Raman Spectroscopy. Biochemistry 1996, 35, 1540-1547. Dierks, E. A.; Hu, S.; Vogel, K. M.; Yu, A. E.; Spiro, T. G.; Burstyn, J. N. Demonstration of the Role of Scission of the Proximal His-Fe Bond in the Activation of sGC through Metalloporphyrin Substitution Studies. J. Am. Chem. Soc. 1997, 119, 7316-7323.
4. Deinum, G.; Stone, J. R.; Babcock, G. T.; Marietta, M. A. Binding of NO and CO to sGC as Observed with Resonance Raman Spectroscopy. Biochemistry 1996, 35, 1540-1547. Dierks, E. A.; Hu, S.; Vogel, K. M.; Yu, A. E.; Spiro, T. G.; Burstyn, J. N. Demonstration of the Role of Scission of the Proximal His-Fe Bond in the Activation of sGC through Metalloporphyrin Substitution Studies. J. Am. Chem. Soc. 1997, 119, 7316-7323.
5. p, porphyrinato nitrogen.
6. Butler, A. R.; Williams, D. L. H. The Physiological Role of NO. Chem. Soc. Rev. 1993, 233-241. Moncada, S.; Palmer, R. M. J.; Higgs, E. A. NO: Physiology, Pathophysiology, Pharmacology. Pharmacol. Rev. 1991, 43, 109-142.
7. Butler, A. R.; Williams, D. L. H. The Physiological Role of NO. Chem. Soc. Rev. 1993, 233-241. Moncada, S.; Palmer, R. M. J.; Higgs, E. A. NO: Physiology, Pathophysiology, Pharmacology. Pharmacol. Rev. 1991, 43, 109-142.
8. Averill, B. A. Dissimilatory Nitrite and NO Reductases. Chem. Rev. 1996, 96, 2951-2964.
9. Ribeiro, J. M. C.; Hazzard, J. M. H.; Nussenzveig, R. H.; Champagne, D. E.; Walker, F. A. Reversible Binding of NO by a Salivary Heme Protein from a Bloodsucking Insect. Science 1993, 260, 539-541.
10. Valenzuela, J. G.; Walker, F. A.; Ribeiro, J. M. C. A Salivary Nitrophorin in the Bedbug Cimex Lectularius. J. Exp. Biol. 1995, 198, 1519-1526.
11. Palmer, G. EPR of Hemoproteins. In Iron Porphyrins, Part Two; Lever, A. B. P., Gray, H. B., Eds.; Addison-Wesley: Reading, MA, 1983; pp 77-84 and references therein.
12. Henry, Y. A.; Guissani, A.; Ducastel, B. Nitric Oxide Research from Chemistry to Biology: EPR Spectroscopy of Nitrosylated Compounds; Chapman and Hall: 1997.
13. Enemark, J. H.; Feltham, R. D. Principles of Structure, Bonding, and Reactivity for Metal Nitrosyl Complexes. Coord. Chem. Rev. 1974, 73, 339-406. Revisited by Enemark; see: Westcott, B. L.; Enemark, J. H. In Inorganic Electronic Structure and Spectroscopy; Lever, A. B. P., Solomon, E. I., Eds., in press.
14. Enemark, J. H.; Feltham, R. D. Principles of Structure, Bonding, and Reactivity for Metal Nitrosyl Complexes. Coord. Chem. Rev. 1974, 73, 339-406. Revisited by Enemark; see: Westcott, B. L.; Enemark, J. H. In Inorganic Electronic Structure and Spectroscopy; Lever, A. B. P., Solomon, E. I., Eds., in press.
15. 6.
16. Wayland, B. B.; Olson, L. W. Spectroscopic Studies and Bonding Model for NO Complexes of Iron Porphyrins. J. Am. Chem. Soc. 1974, 96, 6037-6041.
17. Hoffmann, R.; Chen, M. M. L.; Elian, M.; Rossi, A. R.; Mingos, D. M. P. Pentacoordinate Nitrosyls. Inorg. Chem. 1974, 13, 2666-2675 and references therein.
18. Scheldt, W. R.; Hoard, J. L. Structure and Bonding in a Nitrosylcobalt Porphyrin and Their Bearing on One Rational Model for the Oxygenated Protoheme. J. Am. Chem. Soc. 1973, 95, 8281-8288.
19. Scheidt, W. R.; Frisse, M. E. Synthesis and Molecular Stereochemistry of Nitrosyl-α,β,γ,δ-tetraphenylporphinatoiron(II). J. Am. Chem. Soc. 1975, 97, 17-21.
20. 15N CPMAS NMR Spectroscopy. Inorg. Chem. 1993, 32, 379-380.
21. (a) Ellison, M. K.; Scheidt, W. R. Tilt/Asymmetry in Nitrosyl Metalloporphyrin Complexes: The Cobalt Case. Inorg. Chem. 1998, 37, 382-383.
22. (b) Richter-Addo, G. B.; Hodge, S. J.; Yi, G.-B.; Khan, M. A.; Ma, T.; Van Caemelbecke, E.; Guo, N.; Kadish, K. M. Synthesis, Characterization, and Spectroelectrochemistry of Cobalt Porphyrins Containing Axially Bound NO. Inorg. Chem. 1996, 35, 6530-6538. Correction. Ibid. 1997, 36, 2696.
23. (c) Buchler, J. W.; Lay, K.-L.; Tonn, B.; Lee, Y. J.; Scheidt, W. R. Unpublished results.
24. Chien, J. C. W. Reactions of NO with Methemoglobin. J. Am. Chem. Soc. 1969, 91, 2166-2168.
25. DiFeo, T. J.; Addison, A. W.; Stephanos, J. J. Kinetic and Spectroscopic Studies of Hb and Mb from Urechis Caupo. Biochem. J. 1990, 269, 739-747.
26. Hoshino, M.; Maeda, M.; Konishi, R.; Seki, H.; Ford, P. C. Studies on the Reaction Mechanism for Reductive Nitrosylation of Ferrihemoproteins in Buffer Solutions. J. Am. Chem. Soc. 1996, 118, 5702-5707.
27. Scheidt, W. R.; Hatano, K.; Rupprecht, G. A.; Piciulo, P. L. Molecular Stereochemistry of Nitrosyl-α,β,γ,-δ-tetratolylporphinatomanganese(II) and Nitrosyl(4-methylpiperidine)-α,β,γ,δ- tetraphenylporphinatomanganese(II). Inorg. Chem. 1979, 18, 292-299.
28. Scheidt, W. R.; Lee, Y. J.; Hatano, K. Preparation and Structural Characterization of Nitrosyl Complexes of Ferric Porphyrinates. Molecular Structure of Aquonitrosyl(meso-tetraphenylporphinato)iron-(III) Perchlorate and Nitrosyl(octaethylporphinato)-iron(III) Perchlorate. J. Am. Chem. Soc. 1984, 106, 3191-3198.
29. Nasri, H.; Haller, K. J.; Wang, Y.; Huynh, B. H.; Scheidt, W. R. Reactions of Bis(nitro) [α,α,α,α-mesotetrakis(o-pivalamidophenyl)porphinato] iron(III)with 2,3,5,6-Tetrafluorothiophenol and 2,3,5,6-Tetrafluorothiophenolate. Inorg. Chem. 1992, 31, 3459-3467.
30. Bohle, D. S.; Hung, C.-H. Ligand-Promoted Rapid NO Dissociation from Ferrous Porphyrin Nitrosyls. J. Am. Chem. Soc. 1995, 117, 9584-9585.
31. Ellison, M. K.; Scheidt, W. R. Structural Distortion in Five-Coordinate Nitrosyl Iron Porphyrins. Axial Ligand Tilting and its Effect on Equatorial Geometry. J. Am. Chem. Soc. 1997, 119, 7404-7405.
32. 7 Complexes: X-ray Structure of [Fe-(OETAP)(NO)]. J. Chem. Soc., Chem. Commun. 1997, 91-92.
33. Autret, M.; Will, S.; Van Caemelbecke, E.; Lex, J.; Gisselbrecht, J. P.; Gross, M.; Vogel, E.; Kadish, K. Synthesis and Electrochemistry of Fe(III) Corroles Containing a Nitrosyl Axial Ligand. J. Am. Chem. Soc. 1994, 116, 9141-9149.
34. Duval, H.; Ellison, M. K.; Leader, T. J.; Scheidt, W. R. To be submitted for publication.
35. Piciulo, P. L.; Rupprecht, G.; Scheidt, W. R. Stereochemistry of Nitrosyl-α,β,γ,δ-tetraphenylporphinato-(1- methylimidazole)iron and Nitrosyl-α,β,γδ-tetraphenylporphinato(4-methylpiperidine) manganese. J. Am. Chem. Soc. 1974, 96, 5293-5295.
36. Piciulo, P. L.; Scheidt, W. R. Synthesis and Molecular Stereochemistry of Nitrosyl-α,β,γ,δ-tetraphenylporphinato(1-methylimidazole) iron(II). J. Am. Chem. Soc. 1976, 93, 1913-1919.
37. Scheidt, W. R.; Brinegar, A. C.; Ferro, E. B.; Kirner, J. F. Molecular Stereochemistry of Two Crystalline Forms of Nitrosyl-α,β,γ,δ-tetraphenylporphinato(4- methylpiperidine)iron(II). J. Am. Chem. Soc. 1977, 99, 7315-7322.
38. Nasri, H.; Ellison, M. K.; Chen, S.; Huynh, B. H.; Scheidt, W. R. Sharing the π-Bonding. An Iron Porphyrin Derivative with Trans, π-Accepting Axial Ligands. J. Am. Chem. Soc. 1997, 119, 6274-6283.
39. Safo, M. K.; Scheidt, W. R.; Gupta, G. P. Axial Ligand Orientation in Iron(II) Porphyrinates. Inorg. Chem. 1990, 29, 626-633.
40. (a) Steffen, W. L.; Chun, H. K.; Hoard, J. L.; Reed, C. A. Abstracts of Papers, 175th National Meeting of the American Chemical Society, Anaheim, CA, March 13-17, 1978; American Chemical Society: Washington, DC, 1978; INOR 15.
41. (b) Hoard, J. L. Personal communication.
42. Radonovich, L. J.; Bloom, A.; Hoard, J. L. Stereochemistry of Low-Spin Iron Porphyrins. Bis(piperidine)-α,β,γ,δ-tetraphenylporphinatoiron(II). J. Am. Chem. Soc. 1972, 94, 2073-2078.
43. 3OPor Capped Porphyrins. Inorg. Chem. 1996, 35, 3607-3613.
44. Kon, H.; Kataoka, N. EPR of NO-Protoheme Complexes with Some Nitrogenous Base. Model Systems of NO Hemoproteins. Biochemistry 1969, 8, 4757-4762.
45. 2 with Co(II) and Fe(II) Porphyrins. J. Am. Chem. Soc. 1974, 96, 2795-2801.
46. The presence of a nitrogen base significantly increases the oxygen sensitivity of the five-coordinate cobalt nitrosyl, leading to the production of a six-coordinate cobalt(III) nitrite derivative: Kaduk, J. A.; Scheidt, W. R. The Molecular Stereochemistry of Nitro-α,β,γ,δ-tetraphenylporphinato(3,5-lutidine)- cobalt(III). Inorg. Chem. 1974, 13, 1875-1880.
47. Maxwell, J. C.; Caughey, W. S. Biochemistry 1976, 15, 388. Szabo, A.; Barron, L. D. Resonance Raman Studies of Nitric Oxide Hemoglobin. J. Am. Chem. Soc. 1975, 97, 660-662. Szabo, A.; Perutz, M. F. Equilibrium between 6-and 5-Coordinated Hemes in Nitrosylhemoglobin: Interpretation of ESR Spectra. Biochemistry 1976, 15, 4427.
48. Maxwell, J. C.; Caughey, W. S. Biochemistry 1976, 15, 388. Szabo, A.; Barron, L. D. Resonance Raman Studies of Nitric Oxide Hemoglobin. J. Am. Chem. Soc. 1975, 97, 660-662. Szabo, A.; Perutz, M. F. Equilibrium between 6-and 5-Coordinated Hemes in Nitrosylhemoglobin: Interpretation of ESR Spectra. Biochemistry 1976, 15, 4427.
49. Maxwell, J. C.; Caughey, W. S. Biochemistry 1976, 15, 388. Szabo, A.; Barron, L. D. Resonance Raman Studies of Nitric Oxide Hemoglobin. J. Am. Chem. Soc. 1975, 97, 660-662. Szabo, A.; Perutz, M. F. Equilibrium between 6-and 5-Coordinated Hemes in Nitrosylhemoglobin: Interpretation of ESR Spectra. Biochemistry 1976, 15, 4427.
50. 44 appears to be too small, and we would regard it as unlikely to be correct. However, our studies lead us to expect that an Fe-N-O angle that small should be recognizable from IR and EPR parameters and would strongly urge that these be measured in all structurally characterized nitrosyl hemoproteins.
51. Harutyunyan, E. H.; Safonova, T. N.; Kuranova, I. P.; Popov, A. N.; Teplyakov, A. V.; Obmolova, G. V.; Vainshtein, B. K.; Dodson, G. G.; Wilson, J. C. The Binding of CO and NO to Leghaemoglobin in Comparison with Other Haemoglobins. J. mol. Biol. 1996, 264, 152-161.
52. Brucker, E. A.; Olson, J. S.; Ikeda-Saito, M.; Phillips, G. N., Jr. NO Myoglobin: Crystal Structure and Analysis of Ligand Geometry. Proteins: Struct., Funct., Genet. 1998, 30, 352-356.
53. Nasri, H.; Goodwin, J. A.; Scheidt, W. R. Protected Binding Sites for Nitrite Binding in Iron(III) Porphyrinates. Inorg. Chem. 1990, 29, 185-191. Nasri, H.; Wang, Y.; Huynh, B. H.; Scheidt, W. R. Nitrite-Bound Five-Coordinate Low-Spin Iron(II) Model Complex for the Prosthetic Group of Nitrite Reductase with an Unusually Large Quadrupole Splitting. J. Am. Chem. Soc. 1991, 113, 717-719. Nasri, H.; Wang, Y.; Huynh, B. H.; Walker, F. A.; Scheidt, W. R. Reactions of Bis(nitro)(tetra-α,α,α,α-o-pivalamidophenylporphinato) iron(III) with Pyridine and Imidazole. Inorg. Chem. 1991, 30, 1483-1489.
54. Nasri, H.; Goodwin, J. A.; Scheidt, W. R. Protected Binding Sites for Nitrite Binding in Iron(III) Porphyrinates. Inorg. Chem. 1990, 29, 185-191. Nasri, H.; Wang, Y.; Huynh, B. H.; Scheidt, W. R. Nitrite-Bound Five-Coordinate Low-Spin Iron(II) Model Complex for the Prosthetic Group of Nitrite Reductase with an Unusually Large Quadrupole Splitting. J. Am. Chem. Soc. 1991, 113, 717-719. Nasri, H.; Wang, Y.; Huynh, B. H.; Walker, F. A.; Scheidt, W. R. Reactions of Bis(nitro)(tetra-α,α,α,α-o-pivalamidophenylporphinato) iron(III) with Pyridine and Imidazole. Inorg. Chem. 1991, 30, 1483-1489.
55. Nasri, H.; Goodwin, J. A.; Scheidt, W. R. Protected Binding Sites for Nitrite Binding in Iron(III) Porphyrinates. Inorg. Chem. 1990, 29, 185-191. Nasri, H.; Wang, Y.; Huynh, B. H.; Scheidt, W. R. Nitrite-Bound Five-Coordinate Low-Spin Iron(II) Model Complex for the Prosthetic Group of Nitrite Reductase with an Unusually Large Quadrupole Splitting. J. Am. Chem. Soc. 1991, 113, 717-719. Nasri, H.; Wang, Y.; Huynh, B. H.; Walker, F. A.; Scheidt, W. R. Reactions of Bis(nitro)(tetra-α,α,α,α-o-pivalamidophenylporphinato) iron(III) with Pyridine and Imidazole. Inorg. Chem. 1991, 30, 1483-1489.
56. Yi, G.-B.; Chen, L.; Khan, M. A.; Richter-Addo, G. B. Activation of Thionitrites and Isoamyl Nitrite by Group 8 Metalloporphyrins and the Subsequent Generation of Nitrosyl Thiolates and Alkoxides of Ru and Os Porphyrins. Inorg. Chem. 1997, 36, 3876-3885.
57. Ellison, M. K.; Scheidt, W. R. Submitted for publication.
58. 2)(NO)]. Inorg. Chem. 1999, 38, 100-108.
59. Higgins, T. B.; Safo, M. K.; Scheidt, W. R. Molecular Structure of Bis(1-methylimidazole)(meso-tetraphenylporphinato)iron(III) Perchlorate. Inorg. Chim. Acta 1990, 178, 261-267.
60. Yoshimura, T. Reaction of Nitrosylporphyrinatoiron-(II) with NO. Inorg. Chim. Acta 1984, 83, 17-21.
61. 52,53
62. Finnegan, M. G.; Lappin, A. G.; Scheidt, W. R. Instability of the Nitrite/Iron(III) Porphyrinate System. Inorg. Chem. 1990, 29, 181-185.
63. Munro, O. Q.; Scheidt, W. R. (Nitro)Iron(III) Porphyrins. EPR Detection of a Transient Low-Spin Iron (III) Complex and Structural Characterization of an O Atom Transfer Product. Inorg. Chem. 1998, 37, 2308-2316.
64. Settin, M. F.; Fanning, J. C. Reaction of Certain Nitrogen Oxides with Fe(III) Porphyrin μ-Oxo Complexes. Inorg. Chem. 1988, 27, 1431-1435.
65. Richter-Addo, G. B.; Legzdins, P. Metal Nitrosyls; Oxford University Press: NY, 1992; p 65.
66. Ellison, M. K.; Scheidt, W. R. Manuscript in preparation.
67. Lang, G.; Marshall, W. Mössbauer Effect in some Hemoglobin Compounds. J. Mol. Biol. 1966, 18, 385-404.
68. 1 from T. Denitrificans. Eur. J. Biochem 1987, 169, 253-258. Christner, J. A.; Münck, E.; Janick, P. A.; Siegel, L. M. Mössbauer Evidence for Exchange-coupled Siroheme and [4Fe-4S] Prosthetic Groups in E. Coli Sulfate Reductase. J. Biol. Chem. 1983, 250, 11147-11156. Costa, C.; Moura, J. J. G.; Moura, I.; Liu, M. Y.; Peck, H. D., Jr.; LeGall, J.; Wang, Y.; Huynh, B. H. Hexaheme Nitrite Reductase from D. Desulfuricans. Mössbauer and EPR Characterization of the Heme Groups. J. Biol. Chem. 1990, 265, 14382-14388.
69. 1 from T. Denitrificans. Eur. J. Biochem 1987, 169, 253-258. Christner, J. A.; Münck, E.; Janick, P. A.; Siegel, L. M. Mössbauer Evidence for Exchange-coupled Siroheme and [4Fe-4S] Prosthetic Groups in E. Coli Sulfate Reductase. J. Biol. Chem. 1983, 250, 11147-11156. Costa, C.; Moura, J. J. G.; Moura, I.; Liu, M. Y.; Peck, H. D., Jr.; LeGall, J.; Wang, Y.; Huynh, B. H. Hexaheme Nitrite Reductase from D. Desulfuricans. Mössbauer and EPR Characterization of the Heme Groups. J. Biol. Chem. 1990, 265, 14382-14388.
70. 1 from T. Denitrificans. Eur. J. Biochem 1987, 169, 253-258. Christner, J. A.; Münck, E.; Janick, P. A.; Siegel, L. M. Mössbauer Evidence for Exchange-coupled Siroheme and [4Fe-4S] Prosthetic Groups in E. Coli Sulfate Reductase. J. Biol. Chem. 1983, 250, 11147-11156. Costa, C.; Moura, J. J. G.; Moura, I.; Liu, M. Y.; Peck, H. D., Jr.; LeGall, J.; Wang, Y.; Huynh, B. H. Hexaheme Nitrite Reductase from D. Desulfuricans. Mössbauer and EPR Characterization of the Heme Groups. J. Biol. Chem. 1990, 265, 14382-14388.