Abstract:
A new family of compounds is presented as potential carbon monoxide releasing molecules (CORMs). These compounds, based on tetrachlorocarbonyliridate (III) derivatives, were synthesized and fully characterized by X-ray diffraction, electrospray mass spectrometry, IR, NMR, and density functional theory calculations. The rate of CO release was studied via the myoglobin assay. The results showed that the rate depends on the nature of the sixth ligand, trans to CO, and that a significant modulation on the release rate can be produced by changing the ligand. The reported compounds are soluble in aqueous media, and the rates of CO release are comparable with those for known CORMs, releasing CO at a rate of 0.03-0.58 μM min-1 in a 10 μM solution of myoglobin and 10 μM of the complexes. © 2011 American Chemical Society.
Registro:
Documento: |
Artículo
|
Título: | Tetrachlorocarbonyliridates: Water-soluble carbon monoxide releasing molecules rate-modulated by the sixth ligand |
Autor: | Bikiel, D.E.; Solveyra, E.G.; Di Salvo, F.; Milagre, H.M.S.; Eberlin, M.N.; Corrêa, R.S.; Ellena, J.; Estrin, D.A.; Doctorovich, F. |
Filiación: | Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, INQUIMAE-CONICET, Ciudad Universitaria, Pabellón II, C1428EHA, Buenos Aires, Argentina Institute of Biosciences, UNESP-Univ. Estadual Paulista, 13506-900 Rio Claro, SP, Brazil ThoMSon Mass Spectrometry Laboratory, Institute of Chemistry, University of Campinas, UNICAMP, 13083-970, Campinas SP, Brazil Departamento de Física e Informática, Instituto de Fisica de São Carlos, Universidad de São Paulo, Caixa Postal 369, São Carlos, SP, CEP 13560-970, Brazil
|
Palabras clave: | carbon monoxide; iridium; ligand; organometallic compound; water; article; chemical structure; chemistry; solubility; synthesis; X ray crystallography; Carbon Monoxide; Crystallography, X-Ray; Iridium; Ligands; Models, Molecular; Organometallic Compounds; Solubility; Water |
Año: | 2011
|
Volumen: | 50
|
Número: | 6
|
Página de inicio: | 2334
|
Página de fin: | 2345
|
DOI: |
http://dx.doi.org/10.1021/ic102038v |
Título revista: | Inorganic Chemistry
|
Título revista abreviado: | Inorg. Chem.
|
ISSN: | 00201669
|
CODEN: | INOCA
|
CAS: | carbon monoxide, 630-08-0; iridium, 13967-67-4, 7439-88-5; water, 7732-18-5; Carbon Monoxide, 630-08-0; Iridium, 7439-88-5; Ligands; Organometallic Compounds; Water, 7732-18-5
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00201669_v50_n6_p2334_Bikiel |
Referencias:
- Johnson, T.R., Mann, B.E., Clark, J.E., Foresti, R., Green, C.J., Motterlini, R., (2003) Angew. Chem., Int. Ed. Engl., 42, pp. 3722-3729
- Motterlini, R., Mann, B.E., Johnson, T.R., Clark, J.E., Foresti, R., Green, C., (2003) J. Curr. Pharm. Des., 9, pp. 2525-2539
- Motterlini, R., Otterbein, L.E., (2010) Nat. Rev. Drug Discovery, 9, pp. 728-743
- Morita, T., Perrella, M.A., Lee, M.E., Kourembanas, S., (1995) Proc. Natl. Acad. Sci. U. S. A, 92, pp. 1475-1479
- Motterlini, R., Clark, J.E., Foresti, R., Sarathchandra, P., Mann, B.E., Green, C., (2002) J. Circ. Res., 90, pp. E17-E24
- Burg, A.B., Schlesinger, H.I., (1937) J. Am. Chem. Soc., 59, pp. 780-787
- Motterlini, R., Sawle, P., Hammad, J., Bains, S., Alberto, R., Foresti, R., Green, C.J., (2005) FASEB J., 19, pp. 284-286
- Malone, L.J., Manley, M.R., (1967) Inorg. Chem., 6, pp. 2260-2262
- Carter, J.C., Moye, A.L., Luther, G.W., (1974) J. Am. Chem. Soc., 96, pp. 3071-3073
- Hall, I.H., Rajendran, K.G., Chen, S.Y., Wong, O.T., Sood, A., Spielvogel, B.F., (1995) Arch. Pharm. (Weinheim), 328, pp. 39-44
- Clark, J.E., Naughton, P., Shurey, S., Green, C.J., Johnson, T.R., Mann, B.E., Foresti, R., Motterlini, R., (2003) Circ. Res., 93, pp. E2-E8
- Foresti, R., Hammad, J., Clark, J.E., Johnson, T.R., Mann, B.E., Friebe, A., Green, C.J., Motterlini, R., (2004) Br. J. Pharmacol., 142, pp. 453-460
- Guo, Y., Stein, A.B., Wu, W.-J., Tan, W., Zhu, X., Li, Q.-H., Dawn, B., Bolli, R., (2004) Am. J. Physiol. Heart Circ. Physiol., 286, pp. H1649-H1653
- Foresti, R., Shurey, C., Ansari, T., Sibbons, P., Mann, B.E., Johnson, T.R., Green, C.J., Motterlini, (2005) R. Cell. Mol. Biol., 51, pp. 409-423
- Sawle, P., Foresti, R., Mann, B.E., Johnson, T.R., Green, C.J., Motterlini, R., (2005) Br. J. Pharmacol., 145, pp. 800-810
- Stein, A.B., Guo, Y., Tan, W., Wu, W.-J., Zhu, X., Li, Q., Luo, C., Bolli, R., (2005) J. Mol. Cell. Cardiol., 38, pp. 127-134
- Bani-Hani, M.G., Greenstein, D., Mann, B.E., Green, C.J., Motterlini, R., (2006) Pharmacol. Rep., 58, pp. 132-144
- Bani-Hani, M.G., Greenstein, D., Mann, B.E., Green, C.J., Motterlini, R., (2006) J. Pharmacol. Exp. Ther., 318, pp. 1315-1322
- Chlopicki, S., Olszanecki, R., Marcinkiewicz, E., Lomnicka, M., Motterlini, R., (2006) Cardiovasc. Res., 71, pp. 393-101
- Musameh, M.D., Fuller, B.J., Mann, B.E., Green, C.J., Motterlini, R., (2006) Br. J. Pharmacol., 149, pp. 1104-1112
- Sandouka, A., Fuller, B.J., Mann, B.E., Green, C.J., Foresti, R., Motterlini, R., (2006) Kidney Int., 69, pp. 239-247
- Tayem, Y., Johnson, T.R., Mann, B.E., Green, C.J., Motterlini, R., (2006) Am. J. Physiol. Renal Physiol., 290, pp. F789-F794
- Vannacci, A., Marzocca, C., Giannini, L., Mazzetti, L., Franchi-Micheli, S., Failli, P., Masini, E., Mannaioni, P.F., (2006) Inflamm. Res., 55, pp. S05-S06
- Musameh, M.D., Green, C.J., Mann, B.E., Fuller, B.J., Motterlini, R., (2007) J. Heart Lung Transplant., 26, pp. 1192-1198
- Urquhart, P., Rosignoli, G., Cooper, D., Motterlini, R., Perretti, M., (2007) J. Pharmacol. Exp. Ther., 321, pp. 656-662
- Vannacci, A., Giannini, L., Fabrizi, F., Uliva, C., Mastroianni, R., Masini, E., Motterlini, R., Mannaioni, P.F., (2007) Inflamm. Res., 56, pp. S13-S14
- Varadi, J., Lekli, I., Juhasz, B., Bacskay, I., Szabo, G., Gesztelyi, R., Szendrei, L., Tosaki, (2007) A. Life Sci., 80, pp. 1619-1626
- Fairlamb, I.J.S., Duhme-Klair, A.-K., Lynam, J.M., Moulton, B.E., O'Brien, C.T., Sawle, P., Hammad, J., Motterlini, R., (2006) Bioorg. Med. Chem. Lett., 16, pp. 995-998
- Sawle, P., Hammad, J., Fairlamb, I.J.S., Moulton, B., O'Brien, C.T., Lynam, J.M., Duhme-Klair, A.K., Motterlini, R., (2006) J. Pharmacol. Exp. Ther., 318, pp. 403-410
- Fairlamb, I.J.S., Lynam, J.M., Moulton, B.E., Taylor, I.E., Duhme-Klair, A.K., Sawle, P., Motterlini, R., (2007) Dalton Trans., 33, pp. 3603-3605
- Scapens, D., Adams, H., Johnson, T.R., Mann, B.E., Sawle, P., Aqil, R., Perrior, T., Motterlini, R., (2007) Dalton Trans., 43, pp. 4962-4973
- Hewison, L., Crook, S.H., Johnson, T.R., Mann, B.E., Adams, H., Plant, S.E., Sawle, P., Motterlini, R., (2010) Dalton Trans., 39, pp. 8967-8975
- Zhang, W.Q., Atkin, A.J., Thatcher, R.J., Whitwood, A.C., Fairlamb, I.J.S., Lynam, J.M., (2009) Dalton Trans., 22, pp. 4351-4358
- Zhang, W.Q., Whitwood, A.C., Fairlamb, I.J.S., Lynam, J.M., (2010) Inorg. Chem., 49, pp. 8941-8952
- Atkin, A.J., Williams, S., Sawle, P., Motterlini, R., Lynam, J.M., Fairlamb, I.J.S., (2009) Dalton Trans., pp. 3653-3656
- Zobi, F., Degonda, A., Schaub, M.C., Bogdanova, A.Y., (2010) Inorg. Chem., 49, pp. 7313-7322
- Niesel, J., Pinto, A., N'Dongo, H.W.P., Merz, K., Ott, I., Gustb, R., Schatzschneider, U., (2008) Chem. Commun., pp. 1798-1800
- Rimmer, R.D., Richter, H., Ford, P.C., (2010) Inorg. Chem., 49, pp. 1180-1185
- Pfeiffer, H., Rojas, A., Niesel, J., Schatzschneider, U., (2009) Dalton Trans., pp. 4292-4298
- Kunz, P.C., Huber, W., Rojas, A., Schatzschneider, U., Spingler, B., (2009) Eur. J. Inorg. Chem., pp. 5358-5366
- Vandegriff, K.D., Young, M.A., Lohman, J., Bellelli, A., Samaja, M., Malavalli, A., Winslow, R.M., (2008) Br. J. Pharmacol., 154, pp. 1649-1661
- Messori, L., Marcon, G., Orioli, P., Fontani, M., Zanello, P., Bergamo, A., Sava, G., Mura, P., (2003) J. Inorg. Biochem., 95, pp. 37-46
- Alberti, F.M., Fiol, J.J., García-Raso, A., Torres, M., Terrón, A., Barceló-Oliver, M., Prieto, M.J., Molins, E., (2010) Polyhhedron, 29, pp. 34-41
- Di Salvo, F., Estrin, D.A., Leitus, G., Doctorovich, F., (2008) Qrganometallics, 27, pp. 1985-1995
- Escola, N., Llebaría, A., Leitus, G., Doctorovich, F., (2006) Qrganometallics, 25, pp. 3799-3801
- Doctorovich, F., Di Salvo, F., (2007) Acc. Chem. Res., 40, pp. 985-993
- Escola, N., Di Salvo, F., Haddad, R., Perissinotti, L., Eberlin, M.N., Doctorovich, F., (2007) Inorg. Chem., 46, pp. 4827-4834
- Perissinotti, L.L., Leitus, G., Shimon, L., Estrin, D., Doctorovich, F., (2008) Inorg. Chem., 47, pp. 4723-4733
- Perissinotti, L.L., Estrin, D.A., Leitus, G., Doctorovich, F., (2006) J. Am. Chem. Soc., 128, pp. 2512-2513
- Cleare, M.J., Griffith, W.P., (1969) J. Chem. Soc. A, pp. 372-380
- Nonius, B.V., (1997) Enraf-Nonius COLLECT, , Delft, The Netherlands
- Otwinowski, Z., Minor, W., Carter Jr., C.W., Sweet, R.M., (1997) Methods Enzymol., 276, pp. 307-326. , Eds.; Academic Press: New York
- Farrugia, L.J., (1999) J. Appl. Crystallogr., 32, pp. 837-838
- Coppens, P., Leiserowitz, L., Rabinovich, D., (1965) Acta Crystallogr., 18, pp. 1035-1038
- Sheldrick, G.M., (2008) Acta Crvstallogr, A64, pp. 112-122
- Becke, A.D., (1998) Phvs. Rev. A, 38, pp. 3098-3100
- Perdew, J.P., Wang, Y., (1992) Phvs. Rev. B, 45, pp. 13244-13249
- Godbout, N., Salahub, D.R., Andzelm, J., Wimmer, E., (1992) Can. J. Chem., 70, pp. 560-571
- Hay, P.J., Wadt, W.R., (1985) J. Chem. Phys., 82, pp. 270-283
- Wadt, W.R., Hay, P.J., (1985) J. Chem. Phys., 82, pp. 284-298
- LeFloch, A., (1991) Mol. Phys., 72, pp. 133-144
- Adams, R.D., Trufan, E., (2010) Organometallics, 29, pp. 4346-4353
- Bach, C., Willner, H., Wang, C., Rettig, S.J., Trotter, J., Aubke, F., (1996) Angew. Chem. Int. Ed. Engl., 35, pp. 1974-1976
- Spessard, G.O., Miessler, G.L., (1996) Organometallic Chemistry, , Prentice Hall: New York
- Crabtree, R.H., (2001) The Organometallic Chemistry of the Transition Metals, , Wiley-Interscience: New York
- Elschenbroich, C., Salzer, A., (1992) Organometallics: A Concise Introduction, , VCH: New York
- Toma, S.H., Nikolaou, S., Tomazela, D.M., Eberlin, M.N., Toma, H.E., (2004) Inorg. Chim. Acta, 357, pp. 2253-2260
- Pereira, R.M.S., Paula, V.I., Buffon, R., Tomazela, D.M., Eberlin, M.N., (2004) Inorg. Chim. Acta, 357, pp. 2100-2106
- Toma, S.H., Uemi, M., Nikolaou, S., Tomazela, D.M., Eberlin, M.N., Toma, H.E., (2004) Inorg. Chem., 43, pp. 3521-3527
- Alborés, P., Slep, L.D., Eberlin, L.S., Corilo, Y.E., Eberlin, M.N., Benítez, G., Vela, M.E., Baraldo, L.M., (2009) Inorg. Chem., 41, pp. 11226-11235
- Raminelli, C., Prechtl, M.G.H., Santos, L.S., Eberlin, M.N., Comasseto, J.V., (2004) Organometallics, 23, pp. 3990-3996
- Chang, J.S., Garner, C.S., (1965) Inorg. Chem., 4, pp. 209-215
- El-Awady, A.A., Bounsall, E.J., Garner, C.S., (1967) Inorrg. Ckem, 6, pp. 79-86
- Poulsen, I.A., Garner, C.S., (1962) J. Am. Chem. Soc., 84, pp. 2032-2037
- Helm, L., Merbach, A., (1999) Coord. Chem. Rev., 187, pp. 151-181
- Motterlini, R.A., Mann, B.E., Scapens, D.A., Patent WO 2008/003953
Citas:
---------- APA ----------
Bikiel, D.E., Solveyra, E.G., Di Salvo, F., Milagre, H.M.S., Eberlin, M.N., Corrêa, R.S., Ellena, J.,..., Doctorovich, F.
(2011)
. Tetrachlorocarbonyliridates: Water-soluble carbon monoxide releasing molecules rate-modulated by the sixth ligand. Inorganic Chemistry, 50(6), 2334-2345.
http://dx.doi.org/10.1021/ic102038v---------- CHICAGO ----------
Bikiel, D.E., Solveyra, E.G., Di Salvo, F., Milagre, H.M.S., Eberlin, M.N., Corrêa, R.S., et al.
"Tetrachlorocarbonyliridates: Water-soluble carbon monoxide releasing molecules rate-modulated by the sixth ligand"
. Inorganic Chemistry 50, no. 6
(2011) : 2334-2345.
http://dx.doi.org/10.1021/ic102038v---------- MLA ----------
Bikiel, D.E., Solveyra, E.G., Di Salvo, F., Milagre, H.M.S., Eberlin, M.N., Corrêa, R.S., et al.
"Tetrachlorocarbonyliridates: Water-soluble carbon monoxide releasing molecules rate-modulated by the sixth ligand"
. Inorganic Chemistry, vol. 50, no. 6, 2011, pp. 2334-2345.
http://dx.doi.org/10.1021/ic102038v---------- VANCOUVER ----------
Bikiel, D.E., Solveyra, E.G., Di Salvo, F., Milagre, H.M.S., Eberlin, M.N., Corrêa, R.S., et al. Tetrachlorocarbonyliridates: Water-soluble carbon monoxide releasing molecules rate-modulated by the sixth ligand. Inorg. Chem. 2011;50(6):2334-2345.
http://dx.doi.org/10.1021/ic102038v