Abstract
While nitric oxide (NO) is an important signaling molecule and contributes to important physiological processes in humans, the one-electron reduced analogue of NO, namely nitroxyl (NO− or HNO), is quickly establishing its own unique biological role. For example, HNO has been demonstrated to increase myocardial contractility by interacting with thiols in receptor molecules of heart muscle cells. These types of properties have made this particular nitrogen oxide molecule an attractive target for certain therapeutics. Since most of the underlying chemical biology of nitroxyl is mediated by heme proteins and Fe-nitroxyl intermediates have been proposed as key intermediates in denitrifying enzymes, several iron–porphyrin–NO coordination complexes of the Enemark–Feltham {FeNO}8 notation have been pursued. Herein we describe the collective efforts on the synthetic, structural, spectroscopic, electrochemical, and theoretical work that have been performed on biologically relevant iron- and cobalt–NO complexes that afford the rare {FeNO}8 and {CoNO}9 notations. This compilation has provided a somewhat unifying picture into the electronic structure of this important {MNO} unit as well as the benchmark properties that will enable the bioinorganic community to characterize and determine the fate of these species in biology, especially at the active sites of metalloenzymes involved in the global nitrogen cycle.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Ignarro LJ (2000) Nitric oxide biology and pathobiology. Academic, San Diego
Moncada S, Higgs EA (2006) Br J Pharmacol 147:S193
Ignarro LJ (1999) Angew Chem Int Ed 38:1882
Furchgott RF (1999) Angew Chem Int Ed 38:1870
Murad F (1999) Angew Chem Int Ed 38:1856
Fukuto JM, Dutton AS, Houk KN (2005) Chembiochem 6:612
Miranda KM (2005) Coord Chem Rev 249:433
Shafirovich V, Lymar SV (2002) Proc Natl Acad Sci USA 99:7340
Irvine JC, Ritchie RH, Favaloro JL, Andrews KL, Widdop RE, Kemp-Harper BK (2008) Trends Pharmacol Sci 29:601
Flores-Santana W, Switzer C, Ridnour LA, Basudhar D, Mancardi D, Donzelli S, Thomas DD, Miranda KM, Fukuto JM, Wink DA (2009) Arch Pharm Res 32:1139
Miranda KM, Katori T, Torres de Holding CL, Thomas L, Ridnour LA, McLendon WJ, Cologna SM, Dutton AS, Champion HC, Mancardi D, Tocchetti CG, Saavedra JE, Keefer LK, Houk KN, Fukuto JM, Kass DA, Paolocci N, Wink DA (2005) J Med Chem 48:8220
Fukuto JM, Switzer CH, Miranda KM, Wink DA (2005) Annu Rev Pharmacol Toxicol 45:335
Miranda KM, Nims RW, Thomas DD, Espey MG, Citrin D, Bartberger MD, Paolocci N, Fukuto JM, Feelisch M, Wink DA (2003) J Inorg Biochem 93:52
Flores-Santana W, Salmon DJ, Donzelli S, Switzer CH, Basudhar D, Ridnour L, Cheng R, Glynn SA, Paolocci N, Fukuto JM, Miranda KM, Wink DA (2011) Antioxid Redox Signal 14:1659
Turk J, Corbett JA, Ramanadham S, Bohrer A, McDaniel ML (1993) Biochem Biophys Res Commun 197:1458
Wong PS-Y, Hyun J, Fukuto JM, Shirota FN, DeMaster EG, Shoeman DW, Nagasawa HT (1998) Biochemistry 37:5362
Doyle MP, Mahapatro SN, Broene RD, Guy JK (1988) J Am Chem Soc 110:593
Paolocci N, Jackson MI, Lopez BE, Miranda K, Tocchetti CG, Wink DA, Hobbs AJ, Fukuto JM (2007) Pharmacol Ther 113:442
Nagasawa HT, DeMaster EG, Redfern B, Shirota FN, Goon DJW (1990) J Med Chem 33:3120
Paolocci N, Katori T, Champion HC, St. John ME, Miranda KM, Fukuto JM, Wink DA, Kass DA (2003) Proc Natl Acad Sci USA 100:5537
Paolocci N, Saavedra WF, Miranda KM, Martignani C, Isoda T, Hare JM, Espey MG, Fukuto JM, Feelisch M, Wink DA, Kass DA (2001) Proc Natl Acad Sci USA 98:10463
Reisz JA, Bechtold E, King SB (2010) Dalton Trans 39:5203
Dalby FW (1958) Can J Phys 36:1336
Farmer PJ, Sulc F (2005) J Inorg Biochem 99:166
Angeli A, Angelico A, Scurti F (1902) Chem Zentralbl 73:691
Angeli A (1903) Gazz Chim Ital 33:245
Bartberger MD, Liu W, Ford E, Miranda KM, Switzer C, Fukuto JM, Farmer PJ, Wink DA, Houk KN (2002) Proc Natl Acad Sci USA 99:10958
Benderskii VA, Krivenko AG, Ponomarev EA (1990) Elektrokhimiya 26:318
Clough PN, Thrush BA, Ramsay DA, Stamper JG (1973) Chem Phys Lett 23:155
Johns J, McKellar A (1977) J Chem Phys 66:1217
Sulc F, Farmer PJ (2008) Bioinorganic chemistry of HNO ligand. In: Ghosh A (ed) The smallest biomolecules: diatomics and their interactions with heme proteins. Elsevier, Amsterdam, p 429
Enemark JH, Feltham RD (1974) Coord Chem Rev 13:339
Angelo M, Hausladen A, Singel DJ, Stamler JS (2008) Methods Enzymol 436:131
Gladwin MT, Grubina R, Doyle MP (2009) Acc Chem Res 42:157
Berto TC, Lehnert N (2011) Inorg Chem 50:7361
Hopmann KH, Cardey B, Gladwin MT, Kim-Shapiro DB, Ghosh A (2011) Chem Eur J 17:6348
Tolman WB (ed) (2006) Activation of small molecules: organometallic and bioinorganic perspectives. Wiley-VCH, Weinheim
Guilard R, Kadish KM (1988) Chem Rev 88:1121
Reeder BJ (2010) Antioxid Redox Signal 13:1087
Stynes DV, Cleary Stynes H, James BR, Ibers JA (1973) J Am Chem Soc 95:4087
Wayland BB, Olson LW (1974) J Am Chem Soc 96:6037
Scheidt WR, Frisse ME (1975) J Am Chem Soc 97:17
Praneeth VKK, Näther C, Peters G, Lehnert N (2006) Inorg Chem 45:2795
Praneeth VKK, Neese F, Lehnert N (2005) Inorg Chem 44:2570
Goodrich LE, Paulat F, Praneeth VKK, Lehnert N (2010) Inorg Chem 49:6293
Olson LW, Schaeper D, Lançon D, Kadish KM (1982) J Am Chem Soc 104:2042
Choi I-K, Liu Y, Feng D, Paeng K-J, Ryan MD (1991) Inorg Chem 30:1832
Vogel KM, Kozlowski PM, Zgierski MZ, Spiro TG (1999) J Am Chem Soc 121:9915
Bayachou M, Lin R, Cho W, Farmer PJ (1998) J Am Chem Soc 120:9888
Fujita E, Fajer J (1983) J Am Chem Soc 105:6743
Wei Z, Ryan MD (2010) Inorg Chem 49:6948
Liu Y, DeSilva C, Ryan MD (1997) Inorg Chim Acta 258:247
Pellegrino J, Bari SE, Bikiel DE, Doctorovich F (2010) J Am Chem Soc 132:989
Barley MH, Takeuchi KJ, Meyer TJ (1986) J Am Chem Soc 108:5876
Barley MH, Rhodes MR, Meyer TJ (1987) Inorg Chem 26:1746
Immoos CE, Sulc F, Farmer PJ, Czarnecki K, Bocian DF, Levina A, Aitken JB, Armstrong RS, Lay PA (2005) J Am Chem Soc 127:814
Connelly NG, Geiger WE (1996) Chem Rev 96:877
Lançon D, Kadish KM (1983) J Am Chem Soc 105:5610
Waleh A, Ho N, Chantranupong L, Loew GH (1989) J Am Chem Soc 111:2767
Einsle O, Messerschmidt A, Huber R, Kroneck PMH, Neese F (2002) J Am Chem Soc 124:11737
Williams PA, Fülöp V, Garman EF, Saunders NFW, Ferguson SJ, Hajdu J (1997) Nature 389:406
Einsle O, Messerschmidt A, Stach P, Bourenkov GP, Bartunik HD, Huber R, Kroneck PMH (1999) Nature 400:476
Pellegrino J, Hübner R, Doctorovich F, Kaim W (2011) Chem Eur J 17:7868
Grinstaff MW, Hill MG, Birnbaum ER, Schaefer WP, Labinger JA, Gray HB (1995) Inorg Chem 34:4896
Bultitude J, Larkworthy LF, Mason J, Povey DC, Sandell B (1984) Inorg Chem 23:3629
Mason J, Larkworthy LF, Moore EA (2002) Chem Rev 102:913
Murphy WR Jr, Takeuchi K, Barley MH, Meyer TJ (1986) Inorg Chem 25:1041
Murphy WR Jr, Takeuchi KJ, Meyer TJ (1982) J Am Chem Soc 104:5817
Wilson RD, Ibers JA (1979) Inorg Chem 18:336
Lin R, Farmer PJ (2000) J Am Chem Soc 122:2393
Arnold EV, Bohle DS (1996) Methods Enzymol 269:41
Bazylinski DA, Goretski J, Hollocher TC (1985) J Am Chem Soc 107:7986
Bazylinski DA, Hollocher TC (1985) J Am Chem Soc 107:7982
Sulc F, Immoos CE, Pervitsky D, Farmer PJ (2004) J Am Chem Soc 126:1096
Daiber A, Nauser T, Takaya N, Kudo T, Weber P, Hultschig C, Shoun H, Ullrich V (2002) J Inorg Biochem 88:343
Sulc F, Fleischer E, Farmer PJ, Ma D, La Mar GN (2003) J Biol Inorg Chem 8:348
Yu N-T, Kerr EA (1988) In: Spiro TG (ed) Biological applications of Raman spectroscopy, vol 3. Wiley, New York
Silvernail NJ, Olmstead MM, Noll BC, Scheidt WR (2009) Inorg Chem 48:971
Wyllie GRA, Schulz CE, Scheidt WR (2003) Inorg Chem 42:5722
Lehnert N, Praneeth VKK, Paulat F (2006) J Comput Chem 27:1338
Rich AM, Armstrong RS, Ellis PJ, Lay PA (1998) J Am Chem Soc 120:10827
Linder DP, Rodgers KR (2005) Inorg Chem 44:8259
Brucker EA, Olson JS, Ikeda-Saito M, Phillips GN Jr (1998) Proteins Struct Funct Genet 30:352
Copeland DM, West AH, Richter-Addo GB (2003) Proteins Struct Funct Genet 53:182
Copeland DM, Soares AS, West AH, Richter-Addo GB (2006) J Inorg Biochem 100:1413
Scheidt WR, Barabanschikov A, Pavlik JW, Silvernail NJ, Sage JT (2010) Inorg Chem 49:6240
Ye S, Price JC, Barr EW, Green MT, Bollinger JM Jr, Krebs C, Neese F (2010) J Am Chem Soc 132:4739
Di Vaira M, Ghilardi CA, Sacconi L (1976) Inorg Chem 15:1555
Di Vaira M, Tarli A, Stoppioni P, Sacconi L (1975) Cryst Struct Commun 4:653
Stephens FS (1972) J Chem Soc Dalton Trans 2257
Mašek J, Mášlová E (1974) Collect Czech Chem Commun 39:2141
González-Lebrero MC, Scherlis DA, Estiú GL, Olabe JA, Estrin DA (2001) Inorg Chem 40:4127
Serres RG, Grapperhaus CA, Bothe E, Bill E, Weyhermüller T, Neese F, Wieghardt K (2004) J Am Chem Soc 126:5138
Hauser C, Glaser T, Bill E, Weyhermüller T, Wieghardt K (2000) J Am Chem Soc 122:4352
Schwane JD, Ashby MT (2002) J Am Chem Soc 124:6822
Patra AK, Dube KS, Sanders BC, Papaefthymiou GC, Conradie J, Ghosh A, Harrop TC (2012) Chem Sci 3:364
Montenegro AC, Amorebieta VT, Slep LD, Martín DF, Roncaroli F, Murgida DH, Bari SE, Olabe JA (2009) Angew Chem Int Ed 48:4213
McCleverty JA (2004) Chem Rev 104:403
Conradie J, Ghosh A (2011) Inorg Chem 50:4223
Boulet P, Buchs M, Chermette H, Daul C, Gilardoni F, Rogemond F, Schläpfer CW, Weber J (2001) J Chem Phys A 105:8991
Boulet P, Buchs M, Chermette H, Daul C, Furet E, Gilardoni F, Rogemond F, Schläpfer CW, Weber J (2001) J Chem Phys A 105:8999
Wyllie GRA, Scheidt WR (2002) Chem Rev 102:1067
Richter-Addo GB, Legzdins P (1992) Metal nitrosyls. Oxford University Press, New York
Scheidt WR, Hoard JL (1973) J Am Chem Soc 95:8281
Kadish KM, Mu XH, Lin XQ (1988) Inorg Chem 27:1489
Hess JL, Conder HL, Green KN, Darensbourg MY (2008) Inorg Chem 47:2056
Wang X, Andrews L (2001) J Phys Chem A 105:4403
Feltham RD, Enemark JH (1981) Structures of metal nitrosyls, vol 12. Topics in inorganic and organometallic stereochemistry. Wiley, New York
Thyagarajan S, Incarvito CD, Rheingold AL, Theopold KH (2003) Inorg Chim Acta 345:333
Tomson NC, Crimmin MR, Petrenko T, Rosebrugh LE, Sproules S, Boyd WC, Bergman RG, DeBeer S, Toste FD, Wieghardt K (2011) J Am Chem Soc 133:18785
Blanchard AA, Rafter JR, Adams WB Jr (1934) J Am Chem Soc 56:16
Coleman GW, Blanchard AA (1936) J Am Chem Soc 58:2160
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Sanders, B.C., Rhine, M.A., Harrop, T.C. (2013). Properties of {FeNO}8 and {CoNO}9 Metal Nitrosyls in Relation to Nitroxyl Coordination Chemistry. In: Rabinovich, D. (eds) Molecular Design in Inorganic Biochemistry. Structure and Bonding, vol 160. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_2012_87
Download citation
DOI: https://doi.org/10.1007/430_2012_87
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-43598-4
Online ISBN: 978-3-662-43599-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)