Chemistry of Gold(III) Complexes with Nitrogen and Oxygen Ligands

Gold Chemistry: Applications and Future Directions in the Life Sciences

Volumn , Issue , 2009, Pages 47-92

  Cinellu, Maria Agostina ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

Antitumor activity; Complexes; Gold chemistry; Ligands; Nitrogen; Oxygen

Indexed keywords

EID: 84890977549     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527626724.ch2     Document Type: Chapter

References (201)

1. Hashmi, A.S.K. and Hutching, G.J. (2006) Gold catalysis. Angewandte Chemie International Edition, 45, 7896;
2. Bond, G.C., Louis, C. and Thompson, D.T. (2006) Catalytic Science Series, Vol. 6, Catalysis by Gold (ed. G.J. Hutchings), Imperial College Press, London, UK;
3. Hashmi, A.S.K. (2007) Gold-catalyzed organic reactions. Chemical Reviews, 107, 3180.
4. Guo, Z. and Sadler, P.J. (1999) Metals in medicine. Angewandte Chemie International Edition, 38, 1512;
5. Shaw, C.F. III (1999) Gold-based therapeutic agents. Chemical Reviews, 99, 2589;
6. Zhang, C.X. and Lippard, S.J. (2003) New metal complexes as potential therapeutics. Current Opinion in Chemical Biology, 7, 481;
7. Tiekink, E.R.T. (2002) Gold derivatives for the treatment of cancer. Critical Reviews in Oncology/Hematology, 42, 225;
8. Tiekink, E.R.T. (2003) Gold compounds in medicine: potential anti-tumour agents. Gold Bulletin, 36, 117;
9. Messori, L. and Marcon, G. (2004) Gold complexes as antitumour agents, in Metal Ions in Biological Systems, Vol. 42, (eds A. Sigel and H. Sigel), Marcel Dekker, Inc., New York, p. 385;
10. Messori, L. and Gabbiani, C. (2005) Recent trends in antitumor gold(III) complexes: Innovative cytotoxic metallodrugs for cancer treatment, in Metal Compounds in Cancer Chemotherapy (eds J.M. Perez, M.A. Fuertes and C. Alonso), Research Signpost, Kerala, India, p. 355;
11. Kostova, I. (2006) Gold coordination complexes as anticancer agents. Anti-Cancer Agents in Medicinal Chemistry, 6, 19.
12. Sibley, S., Thompson, M.E., Burrows, P.E. and Forrest, S.R. (1999) Electroluminescence in molecular materials, in Optoelectronic Properties of Inorganic Compounds (eds D.M. Roundhill and J.P. Jr.Fackler), Plenum Press, New York, pp. 29-54;
13. Fun, E.Y., Olmstead, M.M., Vickery, J.C. and Balch, A.L. (1998) Glowing gold rings: solvoluminescence from planar trigold(I) complexes. Coordination Chemistry Reviews, 171, 151.;
14. Chen, C.H. and Shi, J. (1998) Metal chelates as emitting materials for organic electroluminescence. Coordination Chemistry Reviews, 171, 161.;
15. Vogler, A. and Kunkely, H. (2001) Photoreactivity of gold complexes. Coordination Chemistry Reviews, 219-221, 489.;
16. Fernández, E.J., Laguna, A., López-de-Luzuriaga, J.M., Monge, M., Montiel, M., Olmos, M.E., Perez, J. and Rodríguez-Castillo, M. (2007) Pyridine gold complexes. An emerging class of luminescent materials. Gold Bulletin, 40, 172.
17. Togni, A. and Venanzi, L.M. (1994) Nitrogen donors in organometallic chemistry and homogeneous catalysis. Angewandte Chemie (International Edition in English), 33, 497.;
18. Reedijk, J. (1987) Heterocyclic nitrogen-donor ligands, in Comprehensive Coordination Chemistry, Vol 2, Ligands (eds G. Wilkinson, F.G.A. Stone and E.W. Abel), Pergamon, Oxford, UK, p. 73-98.
19. Henderson, W. (2006) The Chemistry of cyclometallated gold(III) complexes with C, N-donor ligands. Advances in Organometallic Chemistry, 54, 207.
20. Cinellu, M.A. and Minghetti, G. (2002) Gold(I) and gold(III) complexes with anionic oxygen donor ligands: hydroxo, oxo and alkoxo complexes. Gold Bulletin, 35, 11.
21. Cao, R., Anderson, T.M., Piccoli, P.M.B., Schultz, A.J., Koetzle, T.F., Geletii, Y.V., Slonkina, E., Hedman, B., Hodgson, K.O., Hardcastle, K.I., Fang, X., Kirk, M.L., Knotteenbelt, S., Kögerler, P., Musaev, D.G., Morokuma, K., Takahashi, M. and Hill, C.L. (2007) Terminalgold-oxo complexes. Journal of the American Chemical Society, 129, 11118.
22. Haruta, M. (1997) Size and support-dependency in the catalysis of gold. Catalysis Today, 36, 153.;
23. Bond, G.C. and Thompson, D.T. (2000) Gold-catalysed oxidation of carbon monoxide. Gold Bulletin, 33, 41.;
24. Monnier, J.R. (2001) The direct epoxidation of higher olefins using molecular oxygen. Applied Catalysis A: General, 221, 73.;
25. Fu, L., Wu, N.Q., Yang, J.H., Qu, F., Johnson, D.L., Kung, M.C., Kung, H.H. and Dravid, V.P. (2005) Direct evidence ofoxidized gold on supported gold catalysts. The Journal of Physical Chemistry B, 109, 3704;
26. Min, B.K., Alemozafar, A.R., Pinnaduwage, D.S. and Friend, C.M. (2006) Efficient CO oxidation at low temperature on Au(111). The Journal of Physical Chemistry B, 110, 19833.
27. Constable, E.C. and Leese, T.A. (1989) Cycloaurated derivatives of 2-phenylpyridine. Journal of Organometallic Chemistry, 363, 419.;
28. Fan, D., Yang, C.-T., Ranford, J.D., Lee, P.F. and Vittal, J.J. (2003) Chemical and biological studies of the dichloro(2-phenylpyridine) gold(III) complex and its derivatives. Dalton Transactions, (13), 2680;
29. Fan, D., Yang, C.-T., Ranford, J.D., Vittal, J.J. and Lee, P.F. (2003) Synthesis, characterization, and biological activities of 2-phenylpyridine gold(III) complexes with thiolate ligands. Dalton Transactions, (17), 3376.
30. 2]. Journal ofthe Chemical Society, Dalton Transactions, (17), 2865.
31. 2(anp)]. Polyhedron, 16, 4039.;
32. Fuchita, Y., Ieda, H., Kayama, A., Kinoshita-Nagaoka, J., Kawano, H., Kameda, S. and Mukuriya, M. (1998) Cycloauration of 2-substituted pyridine derivatives. Synthesis, structure and reactivity of six-membered cycloaurated complexes of 2-anilino-, 2-phenoxy-and 2-(phenylsulfanyl)-pyridine. Journal ofthe Chemical Society, Dalton Transactions, (24), 4095.
33. Zhu, Z., Cameron, B.R. and Skerlj, R.T. (2003) Cycloauration of substituted 2-phenoxypyridine derivatives and X-ray crystal structure of gold, dichloro[2-[[5-[(cyclopentylamino)carbonyl]-2-pyridinyl-|N]oxy]phenyl-|C]-, (SP-4-3)-. Journal of Organometallic Chemistry, 677, 57.
34. 1, N)] [pcp = 2-(2-pyridylcarbonyl) phenyl]. Comparison with the cycloaurated complex derived from 2-benzylpyridine. Journal of the Chemical Society, Dalton Transactions, (5), 791.
35. Constable, E.C. and Sousa, L.R. (1992) Metal-ion dependent reactivity of 2-(2'-thienyl)pyridine (Hthpy). Journal of Organometallic Chemistry, 427, 125.;
36. Fuchita, Y., Ieda, H., Wada, S., Kameda, S. and Mukuriya, M. (1999) Organogold(III) complexes derived from auration reactions of thienyl-substituted pyridine derivatives. Journal of the Chemical Society, Dalton Transactions, (24), 4431.
37. Ieda, H., Fujiwara, H. and Fuchita, Y (2001) Synthesis and reactivity of the five-membered cycloaurated complex of phenylthiazole. Inorganica Chimica Acta, 319, 203.
38. Fuchita, Y., Ieda, H. and Yasutake, M. (2000) First intramolecular aromatic substitution by gold(III) of a ligand other than pyridine derivatives. Synthesis and crystal structure of the novel five-membered cycloaurated complex of 1-ethyl-2-phenylimidazole. Journal of the Chemical Society, Dalton Transactions, (3), 271.
39. Minghetti, G., Cinellu, M.A., Pinna, M.V., Stoccoro, S., Zucca, A. and Manassero, M. (1998) Gold(III) derivatives with C (4)-aurated 1-phenylpyrazole. Journal of Organometallic Chemistry, 568, 225.
40. Constable, E.C., Henney, R.P.G., Leese, T.A. and Tocher, D.A. (1990) Cyclometallation reactions of 6-phenyl-2, 2'-bipyridine; a potential C, N, N-donor analogue of 2, 2':6', 2''-terpyridine. Crystal and molecular structure of dichlorobis (6-phenyl-2, 2'-bipyridine)ruthenium(II). Journal ofthe Chemical Society, Dalton Transactions, (2), 443.
41. Constable, E.C., Henney, R.P.G. and Leese, T.A. (1989) The direct cycloauration of 6-(2''-thienyl)-2, 2'-bipyridine. Journal of Organometallic Chemistry, 361, 277.
42. Cinellu, M.A., Zucca, A., Stoccoro, S., Minghetti, G., Manassero, M. and Sansoni, M. (1996) Synthesis and characterization of gold(III) adducts and cyclometallated derivatives with 6-benzyl-and 6-alkyl-2, 2'-bipyridines. Journal ofthe Chemical Society, Dalton Transactions, (22), 4217.
43. McInnes, E.J.L., Welch, A.J. and Yellowleese, L.J. (1995) 2, 2(-Bipyridinedichlorogold(III) tetrafluoroborate. Acta Crystallographica Section C: Crystal Structure Communications, 51, 2023.
44. Robinson, W.T. and Sinn, E. (1975) Synthesis, structure, and properties of trichloro-and tribromo-(2, 9-dimethyl-1, 10-phenanthroline)gold(III). Journal of the Chemical Society, Dalton Transactions, (8), 726.
45. Abbate, F., Orioli, P., Bruni, B., Marcon, G. and Messori, L. (2000) Crystal structure and solution chemistry of the cytotoxic complex 1, 2-dichloro(o-phenanthroline) gold(III) chloride. Inorganica Chimica Acta, 311, 1.
46. 8 transition metal ions. Journal ofthe Chemical Society, Dalton Transactions, (14), 2251.
47. Cinellu, M.A., Minghetti, G., Pinna, M.V., Stoccoro, S., Zucca, A., Manassero, M. and Sansoni, M. (1998) μ-Oxo and alkoxo complexes of gold(III) with 6-alkyl-2, 2'-bipyridines. Synthesis, characterization and X-ray structures. Journal ofthe Chemical Society, Dalton Transactions, (11), 1735.
48. - (X = Cl, CN) and cytosine and guanine model nucleobases: salt formation with (hemi-) protonated bases, coordination, and oxidative degradation of guanine. Inorganica Chimica Acta, 283, 223.
49. Cossu, F., Mativic, Z., Radanovic, D. and Ponticelli, G. (1994) Cytotoxic activity of some gold(III) complexes. Il Farmaco, 49, 301.
50. Moustatih, A., and Garnier-Suillerot, A. (1989) Bifunctional antitumor compounds: synthesis and characterization of a gold(III)-streptonigrin complex with thiol-modulating properties. Journal of Medicinal Chemistry, 32, 1426.
51. Sánchez-Delgado, R.A., Navarro, M., Lazardi, K., Atencio, R., Capparelli, M., Vargas, F., Urbina, J.A., Bouillez, A., Noels, A.F. and Masi, D. (1998) Toward a novel metal based chemotherapy against tropical diseases. Synthesis and characterization of new metal-clotrimazole complexes and evaluation of their activity against Trypanosoma cruzi. Inorganica Chimica Acta, 275-276, 528.
52. Navarro, M., Vásquez, F., Sánchez-Delgado, R.A., Pérez, H., Sinou, V. and Schráevel, J. (2004) Toward a Novel Metal-Based Chemotherapy against Tropical Diseases. 7. Synthesis and in Vitro Antimalarial Activity of New Gold-Chloroquine Complexes. Journal of Medicinal Chemistry, 47, 5204.
53. Fuchita, Y., Utsunomiya, Y. and Yasutake, M. (2001) Synthesis and reactivity of arylgold(III) complexes from aromatic hydrocarbons via C-H bond activation. Journal of the Chemical Society, Dalton Transactions, (16), 2330.
54. Bardají, M., Laguna, A., Pérez, M.R. and Jones, P.G. (2002) Unexpected ring-opening reaction to a new cyanamide-thiolate ligand stabilized as a dinuclear gold complex. Organometallics, 21, 1877.
55. '-bpy-phosphine complexes: synthesis and multinuclear NMR study. Transition Metal Chemistry, 32, 314.
56. Barranco, E.M., Crespo, O., Gimeno, M.C., Jones, P.G., Laguna, A. and Villacampa, M.D. (1999) Synthesis, structure and redox behaviour of gold and silver complexes with 3-ferrocenylpyridine. Journal of Organometallic Chemistry, 592, 258.
57. Barranco, E.M., Crespo, O., Gimeno, M.C., Jones, P.G., Laguna, A. and Sarrocca, C. (2001) 1, 1'-Bis(2-pyridylthio) ferrocene: a new ligand in gold and silver chemistry. Journal of the Chemical Society, Dalton Transactions, (17), 2523.
58. Vicente, J., Chicote, M.T., Guerrero, R., Saura-Llamas, I.M., Jones, P.G. and Ramírez de Arellano, M.C. (2001) The first acetimine gold(I) and gold(III) complexes and the first acetonine complexes. Chemistry-A European Journal, 7, 638.
59. Klapötke, T.M., Krumm, B., Galvez-Ruiz, J.-C. and Nöth, H. (2005) Highly sensitive ammonium tetraazidoaurates(III). Inorganic Chemistry, 44, 9625.
60. Beck, W. and Nöoth, H. (1984) Röntgenstruktur von tetraphenylarsonium-tetraazidoaurat(III). Chemische Berichte, 117, 419.;
61. Beck, W., Klapötke, T.M., Klüfers, P., Kramer, G. and Rienäcker, C.M. (2001) X-Ray crystal structures and quantum chemical calculations of tetraphenyl-arsonium tetraazidoaurate(III) and azido (triphenylphosphine)gold(I). Zeitschrift fur Anorganische und Allgemeine Chemie, 627, 1669.
62. Wehlan, M., Thiel, R., Fuchs, J., Beck, W. and Fehlhammer, W.P. (2000) New C-tetrazolato complexes of rhodium(III), palladium(II) and gold(III). Journal of Organometallic Chemistry, 613, 159.
63. Pope, W.J. (1929) UK Patent 338506;
64. Karasch, M.S. and Isbell, H.S. (1931) The chemistry of organic gold compounds. IV. Gold imide compounds. Journal of the American Chemical Society, 53, 3059.
65. Tyabji, A.M., and Gibson, C.S. (1952) Gold imides. Journal of the Chemical Society, 450;
66. Malik, N.A., Sadler, P.J., Neidle, S. and Taylor, G.L. (1978) X-ray crystal structure of sodium bis(N-methylhydantoinato)gold(I) tetrahydrate; a linear, planar complex of pharmacological interest stabilised by two nitrogen ligands. Journal of the Chemical Society, Chemical Communications, (16), 711.
67. Oyaizu, K., Ohtani, Y., Shiozawa, A., Sugawara, K., Saito, T. and Yuasa, M. (2005) Highly stable gold(III) complex with a hydantoin ligand in alkaline media. Inorganic Chemistry, 44, 6915.
68. Teleb, S.M. (2004) Spectral and thermal studies of saccharinato complexes. The Journal of the Argentine Chemical Society, 92, 31.
69. Kilpin, K.J., Henderson, W. and Nicholson, B.K. (2007) Synthesis, characterisation and biological activity of cycloaurated organogold(III) complexes with imidate ligands. Polyhedron, 26, 204.
70. Cinellu, M.A., Minghetti, G., Pinna, M.V., Stoccoro, S., Zucca, A. and Manassero, M. (1999) Replacement of the chloride ligand in [Au(C, N, N)Cl][PF6] cyclometallated complexes by C, N, O and S donor anionic ligands. Journal ofthe Chemical Society, Dalton Transactions, (16), 2823;
71. 6H4)-6](NHC6H3Me2-2, 6)][PF6]-Oxidation of 4-methylaniline to azotoluene. European Journal of Inorganic Chemistry, 2304.
72. 4 und [(CH3)2AuN(CH3)2]2. Zeitschrift fur Anorganische und Allgemeine Chemie, 504, 7.;
73. 2. Zeitschrift fur Anorganische und Allgemeine Chemie, 529, 29.
74. Messori, L., Abbate, F., Marcon, G., Orioli, P., Fontani, M., Mini, E., Mazzei, T., Carotti, S., O'Connell, T. and Zanello, P. (2000) Gold(III) complexes as potential antitumor agents: solution chemistry and cytotoxic properties of some selected gold(III) compounds. Journal of Medicinal Chemistry, 43, 3541.
75. '-monophosphate. Inorganic Chemistry, 45, 2688.
76. Carotti, S., Guerri, A., Mazzei, T., Messori, L., Mini, E. and Orioli, P. (1998) Gold(III) compounds as potential antitumor agents: Cytotoxicity and DNA binding properties of some selected polyamine-gold(III) complexes. Inorganica Chimica Acta, 281, 90.
77. Messori, L., Orioli, P., Tempi, C. and Marcon, G. (2001) Interactions of selected gold(III) complexes with calf thymus DNA. Biochemical and Biophysical Research Communications, 281, 352.
78. Liu, H.-Q., Cheung, T.-C., Peng, S.-M. and Che, C.-M. (1995) Novel luminescent cyclometaiated and terpyridine gold(III) complexes and DNA binding studies. Journal ofthe Chemical Society, Chemical Communications, (17), 1787.
79. Palanichamy, K., and Ontko, A.C. (2006) Synthesis, characterization, and aqueous chemistry of cytotoxic Au(III) polypyridyl complexes. Inorganica Chimica Acta, 359, 44.
80. '-methylsulfanyl-2, 2':6', 2''-terpyridine) gold(III) bis(trifluoromethanesulfonate). Journal ofthe Chemical Society, Dalton Transactions, (12), 2049.
81. 3[AuCl4]). Journal of the American Chemical Society, 105, 4293.
82. Yam, V.W.-W., Choi, S.W.-K., Lai, T.-F. and Lee, W.K. (1993) Syntheses, crystal structures and photophysics of organogold(III) diimine complexes. Journal of the Chemical Society, Dalton Transactions, (6), 1001.
83. Mansour, M.A., Lachicotte, R.J., Gysling, H.J. and Eisenberg, R. (1998) Syntheses, molecular structures, and spectroscopy of gold(III) dithiolate complexes. Inorganic Chemistry, 37, 4625.
84. Hayoun, R., Zhong, D.K., Rheingold, A.L. and Doerrer, L.H. (2006) Gold(III) and platinum(II) polypyridyl double salts and a general metathesis route to metallophilic interactions. Inorganic Chemistry, 45, 6120.
85. -. Inorganica Chimica Acta, 359, 721.
86. Bulak, E., Sarper, O., Dogan, A., Lissner, F., Schleid, T. and Kaim, W. (2006) Dichlorogold(III) complexes of bis(1-methyl-2-imidazolyl)ketone and related ligands: Geometrical and electronic structures. Polyhedron, 25, 2577.
87. Borkett, N.F., Bruce, M.I. and Walsh, J.D. (1980) Chemistry of the group 1B Metals. XIV Some poly(pyrazolyl)borate derivatives containing gold. Australian Journal of Chemistry, 33, 949.
88. 3, Inorganic Chemistry, 41, 1870.
89. Vicente, J., Chicote, M.T. and Bermudez, M.D. (1984) 2-[(Dimethylamino)methyl] phenylgold(III) complexes. Journal of Organometallic Chemistry, 268, 191.
90. Vicente, J., and Chicote, M.T. (1981) Synthesis and reactivity of dichloro 2-(phenylazo)phenyl gold(III). Inorganica Chimica Acta, 54, L259.
91. Schouteeten, S., Allen, O.R., Haley, A.D., Ong, G.L., Jones, G.D. and Vicic, D.A. (2006) A robust dimethylgold(III) complex stabilized by a 2-pyridyl-2-pyrrolide ligand. Journal of Organometallic Chemistry, 691, 4975.
92. Cao, L., Jennings, M.C. and Puddephatt, R.J. (2007) Amine-amide equilibrium in gold(III) complexes and a gold(III)-gold(I) aurophilic bond. Inorganic Chemistry, 46, 1361.
93. Cuadrado, J.A., Zhang, W., Hang, W. and Majidi, V. (2000) Speciation of gold (III)-L-histidine complex: a multiinstrumental approach. Journal of Environmental Monitoring, 2, 355.
94. Baddley, W.H., Basolo, F., Gray, H.B., Noölting, C. and Poeö, A.J. (1963) Acidodiethylenetriaminegold(III) complexes: preparation, solution chemistry, and electronic structure. Inorganic Chemistry, 2, 921.
95. Nardin, G., Randaccio, L., Annibale, G., Natile, G. and Pitteri, B. (1980) Comparison of structure and reactivity of bis-(2-aminoethyl)amine-and bis(2-aminoethyl)amido-chlorogold(III) complexes. Journal of the Chemical Society, Dalton Transactions, (2), 220.
96. 2trien: a dinuclear gold(III) complex with unprecedented structural features. Chemical Communications, (6), 612.
97. Fan, D., Yang, C.-T., Ranford, J.D. and Vittal, J.J. (2003) Chemical and biological studies of gold(III) complexes with uninegative bidentate N-N ligands. Dalton Transactions, (35), 4749;
98. Hill, D.T., Burns, K., Titus, D.D., Girard, G.R., Reiff, W.M. and Mascavage, L.M. (2003) Dichloro(pyridine-2-carboxamido-N1, N2)gold(III), a bis-nitrogen aurocycle: syntheses, gold-197 Mossbauer spectroscopy, and X-ray crystal structure. Inorganica Chimica Acta, 346, 1.
99. Yang, T., Tu, C., Zhang, J., Lin, L., Zhang, X., Liu, Q., Ding, J., Xu, Q. and Guo, Z. (2003) Novel Au(III) complexes of aminoquinoline derivatives: crystal structure, DNA binding and cytotoxicity against melanoma and lung tumour cells. Dalton Transactions, (24), 3419.
100. Wienken, M., Lippert, B., Zangrando, E. and Randaccio, L. (1992) Gold(III) glycyl-L-histidine dipeptide complexes. Preparation and x-ray structures of monomeric and cyclic tetrameric species. Inorganic Chemistry, 31, 1983.;
101. Carotti, S., Marcon, G., Marussich, M., Mazzei, T., Messori, L., Mini, E. and Orioli, P. (2000) Cytotoxicity and DNA binding properties of a chloro glycylhistidinate gold(III) complex (GHAu). Chemico-Biological Interactions, 125, 29.
102. 2O and HiseNH deprotonation. Journal ofthe Chemical Society, Dalton Transactions, (15), 2587.
103. 2O. Inorganica Chimica Acta, 349, 91.
104. Kilpin, K.J., Henderson, W. and Nicholson, B.K. (2007) Organogold(III) complexes containing chelating bis (amidate) ligands: Synthesis, characterisation and biological activity. Polyhedron, 26, 434.
105. Kimura, E., Kurogi, Y. and Takahashi, T. (1991) The first gold(III) macrocyclic polyamine complexes and application to selective gold(III) uptake. Inorganic Chemistry, 30, 4117.
106. Kimura, E., Kurogi, Y., Koike, T., Shionoya, M. and Iitaka, Y. (1993) Gold (III)-cyclam complexes. X-ray crystal structure and a useful macrocyclic effect on the reduction of gold(III). Journal of Coordination Chemistry, 28, 33.
107. 2 (2, 4-pentanediiminate)2](ClO4)2. Inorganic Chemistry, 17, 1304.;
108. Kim, J.-H. and Everett, G.W. (1979) Synthesis of macrocyclic complexes of gold(III) by condensation of bis (ethylenediamine)gold(III) chloride with ß-diketones. Inorganic Chemistry, 18, 3145.;
109. Kim, J.-H. and Everett, G.W. (1981) Crystal and molecular structure of a macrocyclic complex of gold(III). Inorganic Chemistry, 20, 853.
110. Park, C.H., Lee, B. and Everett, G.W. (1982) Crystal and molecular structure of a 14-π-electron macrocyclic gold(III) complex. Inorganic Chemistry, 21, 1681.
111. Afanasyeva, V.A. and Mironov, I.V. (2001) Gold(III) macrocyclic complexes in aqueous solution. Russian Journal of Coordination Chemistry, 27, 878.;
112. 4. Journal of Structural Chemistry, 46, 131.
113. 4. Journal of Structural Chemistry, 46, 876.
114. Suh, M.P., Kim, I.S., Shim, B.Y., Hong, D. and Yoon, T.-S. (1996) Extremely Facile Template Synthesis of Gold(III) Complexes of a saturated azamacrocycle and crystal structure of a six-coordinate gold(III) complex. Inorganic Chemistry, 35, 3595.;
115. Rossignoli, M., Bernhardt, P.V., Lawrance, G.A. and Maeder, M. (1997) Gold(III) template synthesis of a pendant-arm macrocycle. Journal of the Chemical Society, Dalton Transactions, (3), 323.
116. Bang, H., Lee, E.J., Lee, E.Y., Suh, J. and Suh, M.P. (2000) Transmetallation of nickel(II) ion in a nickel(II) azamacrocyclic complex with gold (III) ion. Inorganica Chimica Acta, 308, 150.
117. 4. New Journal of Chemistry, 21, 237.
118. Brun, A.M., Harriman, A., Heitz, V. and Sauvage, J.-P. (1991) Charge-transfer across oblique bisporphyrins-2-center photoactive molecules. Journal of the American Chemical Society, 113, 8657.;
119. Kilså, K., Kajanus, J., Macpherson, A.N., Mårtensson, J. and Albisson, B. (2001) Bridge-dependent electron transfer in porphyrin-based donor-bridge-acceptor systems. Journal ofthe American Chemical Society, 123, 3069.;
120. Fukuzumi, S., Ohkubo, K., Shao, J., Kadish, K.M., Hutchison, J.A., Ghiggino, K.P., Sintic, P.J. and Crossley, M.J. (2003) Metal-centered photoinduced electron transfer reduction of a gold(III) porphyrin cation linked with a zinc porphyrin to produce a long-lived charge-separated state in nonpolar solvents. Journal of the American Chemical Society, 125, 14984.;
121. Flamigni, L., Barigelletti, F., Armaroli, N., Collin, J.-P., Sauvage, J.-P. and Williams, J.A.G. (1998) Photoinduced processes in highly coupled multicomponent arrays based on a ruthenium(II) bis(terpyridine) complex and porphyrins. Chemistry-A European Journal, 4, 1744.;
122. Flamigni, L., Barigelletti, F., Armaroli, N., Ventura, B., Collins, J.-P., Sauvage, J.-P. and Williams, J.A.G. (1999) Triplet-triplet energy transfer between porphyrins linked via a ruthenium(II) bisterpyridine complex. Inorganic Chemistry, 38, 661.
123. Flamigni, L., Dixon, I.M., Collins, J.-P. and Sauvage, J.-P. (2000) A Zn(II) porphyrin-Ir(III) bis-terpyridine-Au(III) porphyrin triad with a charge-separated state in the microsecond range. Chemical Communications, (24), 2479;
124. Dixon, I.M., Collin, J.-P., Sauvage, J.-P., Barigelletti, F. and Flamigni, L. (2000) Charge separation in a molecular triad consisting of an iridium(III)-bis-terpy central core and porphyrins as terminal electron donor and acceptor groups. Angewandte Chemie International Edition, 39, 1292.
125. Kadish, K.M., Wenbo, E., Ou, Z., Shao, J., Sintic, P.J., Ohkubo, K., Fukuzumi, S. and Crossley, M.J. (2002) Evidence that gold (III) porphyrins are not electrochemically inert: facile generation of gold(II) 5, 10, 15, 20-tetrakis(3, 5-di-tert-butylphenyl)porphyrin. Chemical Communications, (4), 356.
126. Ou, Z., Kadish, K.M., Wenbo E., Shao, J., Sintic, P.J., Ohkubo, K., Fukuzumi, S. and Crossley, M.J. (2004) Substituent effects on the site of electron transfer during the first reduction for gold(III) porphyrins. Inorganic Chemistry, 43, 2078.
127. Knöor, G. (2000) Molecular design of cationic sensitizers carrying redox active intercalator substituents: Towards recognition and photocatalytic cleavage of DNA. Journal of Information Recording, 25, 111.
128. Knör, G. (2001) Intramolecular charge transfer excitation of meso-tetrakis (1-pyrenyl) porphyrinato gold(III) acetate. Photosensitized oxidation of guanine. Inorganic Chemistry Communications, 4, 160.
129. Che, C.-M., Sun, R.W.-Y., Yu, W.-Y., Ko, C.-B., Zhu, N. and Sun, H. (2003) Gold(III) porphyrins as a new class of anticancer drugs: cytotoxicity, DNA binding and induction of apoptosis in human cervix epitheloid cancer cells. Chemical Communications, (14), 1718;
130. Wang, Y., He, O.-Y., Sun, R.W.-Y., Che, C.-M. and Chiu, J.-F. (2007) Cellular pharmacological properties of gold(III) porphyrin 1a, a potential anticancer drug lead. European Journal of Pharmacology, 554, 113.
131. Sun, R.W.-Y., Yu, W.-Y., Sun, H. and Che, C.-M. (2004) In vitro inhibition of human immunodeficiency virus type-1 (HIV-1) reverse transcriptase by gold(III) porphyrins. ChemBioChem, 5, 1293.
132. Zhou, C.-Y., Chan, P.W.H. and Che, C.-M. (2006) Gold(III) porphyrin-catalyzed cycloisomerization of allenones. Organic Letters, 8, 325.
133. Miles, M.G., Glass, G.E. and Tobias, R.S. (1966) Structure of dimethylgold(III) compounds. Spectroscopic studies on the aquo ion and several coordination compounds. Journal of the American Chemical Society, 88, 5738.
134. Glass, G.E., Konnert, J.H., Miles, M.G., Britton, D. and Tobias, R.S. (1968) Crystal and molecular structure and the solution conformation of dimethylgold(III) hydroxide, inorganic intermediate ring compound. Journal of the American Chemical Society, 90, 1131.
135. Harris, S.J. and Tobias, R.S. (1969) Inorganic condensation reactions. Hydrolysis of dimethylgold(III) and the growth of tetrakis(dimethylgold hydroxide). Inorganic Chemistry, 8, 2259.
136. Braye, E.H., Hübel, W. and Caplier, I. (1961) New unsaturated heterocyclic systems. I. Journal of the American Chemical Society, 83, 4406.;
137. 2. Acta Crystallographica Section C: Crystal Structure Communications, 4, 375.
138. 2O. Journal of Organometallic Chemistry, 508, 53.
139. 2. Journal ofthe Chemical Society, Dalton Transactions, (5), 677.
140. Bortoluzzi, M., De Faveri, E., Daniele, S. and Pitteri, B. (2006) Synthesis of a new tetrakis(2-pyridinyl)pyrazine complex of gold(III) and its computational, spectroscopic and electrochemical characterization. European Journal of Inorganic Chemistry, 3393.
141. Pinna, M.V. (2000) PhD. Thesis, University of Sassari, Italy.
142. Cinellu, M.A., Minghetti, G., Pinna, M.V., Stoccoro, S., Zucca, A. and Manassero, M. (1998) The first gold(III) dinuclear cyclometallated derivatives with a single oxo bridge. Chemical Communications, (21), 2397.
143. Marcon, G., Carotti, S., Coronnello, M., Messori, L., Mini, E., Orioli, P., Mazzei, T., Cinellu, M.A. and Minghetti, G. (2002) Gold(III) complexes with bipyridyl ligands: solution chemistry, cytotoxicity, and DNA binding properties. Journal of Medicinal Chemistry, 45, 1672.;
144. Coronnello, M., Mini, E., Caciagli, B., Cinellu, M.A., Bindoli, A., Gabbiani, C. and Messori, L. (2005) Mechanisms of cytotoxicity of selected organogold(III) compounds. Journal of Medicinal Chemistry, 48, 6761.
145. 6]. Journal ofthe Chemical Society, Dalton Transactions, (8), 1261.
146. Cocco, F.S.(2007) PhD Thesis, University of Sassari.
147. 0-bipyridine and oxygen ligands. Inorganica Chimica Acta, 310, 34.
148. Nesmeyanov, A.N., Perevalova, E.G., Struchkov, Yu.T., Antipin, M.Yu., Grandberg, K.I. and Dyadchenko, V.P. (1980) Tris(triphenylphosphinegold) oxonium salts. Journal of Organometallic Chemistry, 201, 343.
149. Sharp, P.R. (1999) Late transition metal oxo and imido chemistry. Comments on Inorganic Chemistry, 21, 85.
150. Gabbiani, C., Casini, A., Messori, L., Guerri, A., Cinellu, M.A., Minghetti, G., Corsini, M., Rosani, C., Zanello, P. and Arca, M. (2008) Structural characterization, solution studies, and DFT calculations on a series of binuclear gold(III) oxo complexes: relationships to biological properties. Inorganic Chemistry, 47, 2368.
151. Jones, P.G., Rumpel, H., Schwarzmann, E., Sheldrick, G.M. and Paulus, H. (1979) Gold(III) oxide. Acta Crystallographica Section B: Structural Science, 35, 1435.
152. Casini, A., Cinellu, M.A., Minghetti, G., Gabbiani, C., Coronnello, M., Mini, E. and Messori, L. (2006) Structural and solution chemistry, antiproliferative effects, and DNA and protein binding properties of a series of dinuclear gold(III) compounds with bipyridyl ligands. Journal of Medicinal Chemistry, 49, 5524.
153. ip = 6-isopropyl-2, 2-bipyridine). Chemical Communications, (14), 1618;
154. Cinellu, M.A., Minghetti, G., Cocco, F., Stoccoro, S., Zucca, A. and Manassero, M. (2005) Reactions of gold(III) oxo complexes with cyclic alkenes. Angewandte Chemie International Edition, 44, 6892;
155. +. Dalton Transactions, (48), 5703.
156. Jørgensen, K.A. and Schiøtt, B. (1990) Metallaoxetanes as intermediate in oxygen-transfer reactions-reality or fiction? Chemical Reviews, 90, 1483.
157. Deng, X., and Friend, C.M. (2005) Selective oxidation of styrene on an oxygen-covered Au(111). Journal of the American Chemical Society, 127, 17178.
158. Shul'pin, G.B., Shilov, A. and Suss-Fink, G. (2001) Alkane oxygenation catalysed by gold complexes. Tetrahedron Letters, 42, 7253.
159. Schmidbaur, H., and Bergfeld, M. (1966) Trimethylsiloxydimethylgold. Inorganic Chemistry, 5, 2069.
160. Uchida, H., Saito, N., Sato, M., Take, M. and Ogi, K. (1994) (Mitsubishi Material Corp) Manufacture of gold thin film by chemical vapor deposition, Jpn. Kokai Tokkyo Koho JP 06, 101, 046.
161. Sone, T., Iwata, M., Kasuga, N. and Komiya, S. (1991) Dimethylgod(III) aryloxides and alkoxides having a triphenylphosphine ligand. Chemistry Letters, 20, 1949.
162. Usui, Y., Hirano, M., Fukuoka, A. and Komiya, S. (1997) Hydrogen abstraction from transition metal hydrides by gold alkoxides giving gold-containing heterodinuclear complexes. Chemistry Letters, 26, 981.
163. Komiya, S., Sone, T., Usui, Y., Hirano, M. and Fukuoka, A. (1996) Condensation reactions of benzaldehyde catalysed by gold alkoxides. Gold Bulletin, 29, 131.
164. Usui, Y., Noma, J., Hirano, M. and Komiya, S. (2000) C-Si bond cleavage of trihalomethyltrimethylsilane by alkoxo-and aryloxogold or-copper complexes. Inorganica Chimica Acta, 309, 151.
165. Komiya, S., Ishikava, M. and Ozaki, S. (1988) Isolation of cis-dimethyl (methoxycarbonyl)(triphenylphosphine) gold(III). Organometallics, 7, 2238.;
166. Komiya, S., Sone, T., Ozaki, S., Ishikava, M. and Kasuga, N. (1992) Synthesis, structure and properties of dimethyl(alkoxycarbonyl)gold(III) complexes having a triphenylphosphine ligand. Journal of Organometallic Chemistry, 428, 303.
167. 1-allyl)gold(III) complex. Diastereoselective allylation of aromatic aldehyde. Bulletin of the Chemical Society of Japan, 68, 1523.
168. Goss, C.H.A., Henderson, W., Wilkins, A.L. and Evans, C. (2003) Synthesis, characterisation and biological activity of gold(III) catecholate and related complexes. Journal of Organometallic Chemistry, 679, 194.
169. Pal, B., Sen, P.K. and Sen Gupta, K.K. (2001) Reactivity of alkanols and aryl alcohols towards tetrachloroaurate(III) in sodium acetate-acetic acid buffer medium. Journal of Physical Organic Chemistry, 14, 284.
170. Parish, R.V., Boyer, P., Fowler, A., Kahn, T.A., Cross, W.I. and Pritchard, R.G. (2000) Gold complexes derived from diphenyl-2-styrylphosphine. Journal ofthe Chemical Society, Dalton Transactions, (14), 2287.
171. 2 (M = Na, K, Rb). Zeitschrift för Naturforschung B. A Journal of Chemical Sciences, 56b, 1340.
172. 2. Zeitschrift fur Anorganische und Allgemeine Chemie, 628, 911.
173. Jones, P.G., Schelbach, R., Schwarzmann, E., Thöorne, C. and Vielmöader, A. (1988) Darstellung und kristallstruktur einiger tetracarboxylatoaurate(III). Zeitschrift fur Naturforschung B. A Journal of Chemical Sciences, 43b, 807.;
174. 2O. Acta Crystallographica Section C: Crystal Structure Communications, 40, 804.
175. 4. Synthesis and molecular and crystal structure analysis. Inorganic Chemistry, 41, 4173.
176. Buckley, R.G., Elsome, A.M., Fricker, S.P., Henderson, G.R., Theobald, B.R.C., Parish, R.V., Howe, B.P. and Kelland, L.R. (1996) Antitumor properties of some 2-[(dimethylamino)methyl]phenyl-gold(III) complexes. Journal of Medicinal Chemistry, 39, 5208.
177. Bessonov, A.A., Baidina, I.A., Morozova, N.B., Semyannikov, P.P., Trubin, S.V., Gel'fond, N.V. and Igumenov, I.K. (2007) Synthesis, crystal structure, and thermal behavior of dimethylgold(III) acetate. Journal of Structural Chemistry, 48, 282.;
178. Bessonov, A.A., Morozova, N.B., Kuraťeva, N.V., Baidina, I.A., Gel'fond, N.V. and Igumenov, I.K. (2008) Synthesis and crystal structure of dimethylgold(III) carboxylates. Russian Journal of Coordination Chemistry, 34, 70.
179. Bessonov, A.A., Morozova, N.B., Gel'fond, N.V., Semyannikov, P.P., Trubin, S.V., Shevtsov, Yu.V., Shubin, Yu.V. and Igumenov, I.K. (2007) Dimethylgold(III) carboxylates as new precursors for gold CVD. Surface & Coatings Technology, 201, 9099.
180. Brain, F.H. and Gibson, G.S. (1939) The organic compounds of gold. Part VII. Methyl and ethyl compounds. Journal of the Chemical Society, 762.
181. Komiya, S., and Kochi, J.K. (1977) Reversible linkage isomerisms of ß-diketonato ligands. Oxygen-bonded and carbon-bonded structures in gold(III) acetylacetonate complexes induced by phosphines. Journal of the American Chemical Society, 99, 3695.
182. Puddephatt, R.J. (1999) Gold metal and gold alloys in electronics and thin film technology, in Gold: Progress in Chemistry, Biochemistry and Technology (ed. H. Schmidbaur), John Wiley & Sons, Ltd, Chichester, UK, p. 237-256.
183. Baum, T.H. (1987) Laser chemical vapor deposition of gold. Journal ofthe Electrochemical Society, 134, 2616.
184. Guzman, J., and Gates, B.C. (2004) A mononuclear gold complex catalyst supported on MgO: spectroscopic characterization during ethylene hydrogenation catalysis. Journal of Catalysis, 226, 111.
185. 2, [Au(K-C, N-C6H4CH2NMe2-2)(K-N, O-NC9H6O)] BF4, and [Au(K-C, N-C6H4CH2NMe2-2) (K-N, S-H2NC6H4S)]ClO4. Journal ofthe Chemical Society, Dalton Transactions, (11), 2361.
186. Bessonov, A.A., Morozova, N.B., Semyannikov, P.P., Trubin, S.V., Gel'fond, N.V. and Igumenov, I.K. (2008) Thermal properties of dimethylgold(III) 8-hydroxyquinolinate and 8-mercaptoquinolinate. Russian Journal of Coordination Chemistry, 34, 186.
187. Canovese, L., Cattalini, L., Marangoni, G. and Tobe, M.L. (1985) Displacement of pyridine-2-methanol from dichloro (pyridine-2-methanolato)gold(III) in acidic solution. Ring opening at Oxygen. Journal of the Chemical Society, Dalton Transactions, (4), 731;
188. Dar, A., Moss, K., Cottrill, S.M., Parish, R.V., McAuliffe, C.A., Pritchard, R.G., Beagley, B. and Sandbank, J. (1992) Complexes of gold(III) with mononegative bidentate N, O-ligands. Journal of the Chemical Society, Dalton Transactions, (12), 1907.
189. Annibale, G., Canovese, L., Cattalini, L., Marangoni, G., Michelon, G. and Tobe, M.L. (1984) Displacement by chloride of pyridine-2-carboxylate from dichloro(pyridine-2-carboxylato)gold(III) in acidic solution; the position of ring opening. Journal of the Chemical Society, Dalton Transactions, (8), 1641.
190. Bertolasi, V., Annibale, G., Marangoni, G., Paolucci, G. and Pitteri, B. (2003) Syntheses, characterization and X-ray structures of gold(III) complexes obtained by addition of bases to gold(III)(2-pyridinecarboxaldehyde). Journal of Coordination Chemistry, 56, 397.;
191. Marangoni, G., Pitteri, B., Annibale, G. and Bortoluzzi, M. (2006) Ring opening and displacement by chloride of the bidentate chelate ligand from dichloro [pyridine-2-(methoxymethanolato)]gold (III)-A kinetic and mechanistic study. European Journal of Inorganic Chemistry, 29, 765.
192. 2 (pm). Journal of Inorganic Biochemistry, 66, 103;
193. Calamai, P., Carotti, S., Guerri, A., Mazzei, T., Messori, L., Mini, E., Orioli, P. and Speroni, G.P. (1998) Cytotoxic effects of gold(III) complexes on established human tumor cell lines sensitive and resistant to cisplatin. Anti-Cancer Drug Design, 13, 67.;
194. 2(esal)]. Inorganica Chimica Acta, 285, 309.
195. Hashmi, A.S.K., Rudolph, M., Weyrauch, J.P., Wölfe, M., Frey, W. and Bats, J.W. (2005) Gold catalysis: proof of arene oxides as intermediates in the phenol synthesis. Angewandte Chemie International Edition, 44, 2798.
196. Hashmi, A.S.K., Weyrauch, J.P., Rudolph, M. and Kurpejovic, E. (2004) Gold catalysis: the benefits of N and N, O ligands. Angewandte Chemie International Edition, 43, 6545.
197. 6. Inorganic Chemistry, 40, 972.
198. Comas-Vives, A., González-Arellano, C., Corma, A., Iglesias, M., Sanchez, F. and Ujaque, G. (2006) Single-site homogeneous and heterogeneized gold(III) hydrogenation catalysts: mechanistic implications. Journal of the American-Chemical Society, 128, 4756.
199. González-Arellano, C., Corma, A., Iglesias, M. and Sáanchez, F. (2005) Homogeneous and heterogenized Au(III) Schiff base-complexes as selective and general catalysts for self-coupling of aryl boronic acids. Chemical Communications, (15), 1990.
200. Corma, A., González-Arellano, C., Iglesias, M. and Sáanchez, F. (2007) Gold nanoparticles and gold(III) complexes as general and selective hydrosilylation catalysts. Angewandte Chemie International Edition, 46, 7820.
201. Kolev, Ts., Koleva, B.B., Zareva, S.Y. and Spiteller, M. (2006) Au(III)-complexes of the alanyl-containing peptides glycylalanine and glycylalanylalanine-Synthesis, spectroscopic and structural characterization. Inorganica Chimica Acta, 359, 4367.