The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
A group of Piloty's acid (N-hydroxybenzenesulfonamide) derivatives were synthesized and fully characterized in order to assess the rates and pH of HNO (azanone, nitroxyl) donation in aqueous media. The derivatives, with electron-withdrawing and -donating substituents include methyl, nitro, fluo...
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Elsevier Inc.
2013
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| LEADER | 08784caa a22011177a 4500 | ||
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| 001 | PAPER-11838 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204202.0 | ||
| 008 | 190411s2013 xx ||||fo|||| 00| 0 eng|d | ||
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| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JIBID | ||
| 100 | 1 | |a Sirsalmath, K. | |
| 245 | 1 | 4 | |a The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH |
| 260 | |b Elsevier Inc. |c 2013 | ||
| 270 | 1 | 0 | |m Doctorovich, F.; Departamento de Quimica Inorganica, Analitica y Quimica Fisica/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires (C1428EHA), Argentina; email: doctorovich@qi.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Farmer, P.J., Sulc, F., (2005) J. Inorg. Biochem., 99, pp. 166-184 | ||
| 504 | |a Miranda, K.M., (2005) Coord. Chem. Rev., 249, pp. 433-455 | ||
| 504 | |a Switzer, C.H., Flores-Santana, W., Mancardi, D., Donzelli, S., Basudhar, D., Ridnour, L.A., Miranda, K.M., Wink Biochim, D.A., (2009) Biochim. Biophys. Acta, 1787, pp. 835-840 | ||
| 504 | |a Adak, S., Wang, Q., Stuehr, D.J., (2000) J. Biol. Chem., 275, pp. 33554-33561 | ||
| 504 | |a Hobbs, A.J., Fukuto, J.M., Ignarro, L.J., (1994) Proc. Natl. Acad. Sci., 91, pp. 10992-10996 | ||
| 504 | |a Schmidt, H.H.H.W., Hofmann, H., Schindler, U., Shutenko, Z.S., Cunningham, D.D., Feelisch, M., (1996) Proc. Natl. Acad. Sci., 93, pp. 14492-14497 | ||
| 504 | |a Miranda, K.M., Paolocci, N., Katori, T., Thomas, D.D., Ford, E., Bartberger, M.D., Espey, M.G., Wink, D.A., (2003) Proc. Natl. Acad. Sci., 100, pp. 9196-9201 | ||
| 504 | |a Wink, D.A., Miranda, K.M., Katori, T., Mancardi, D., Thomas, D.D., Ridnour, L., Espey, M.G., Paolocci, N., (2003) Am. J. Phys., 285, pp. 2264-H2276 | ||
| 504 | |a Pagliaro, P., (2003) Life Sci., 73, pp. 2137-2149 | ||
| 504 | |a Doyle, M.P., Mahapatro, S.N., Broene, R.D., Guy, J.K., (1988) J. Am. Chem. Soc., 110, pp. 593-599 | ||
| 504 | |a Miranda, K.M., Nims, R.W., Thomas, D.D., Espey, M.G., Citrin, D., Bartberger, M.D., Paolocci, N., Wink, D.A., (2003) J. Inorg. Biochem., 93, pp. 52-60 | ||
| 504 | |a Wink, D.A., Feelisch, M., Fukuto, J., Chistodoulou, D., Jourd'Heuil, D., Grisham, M.B., Vodovotz, Y., Mitchell, J.B., (1998) Arch. Biochem. Biophys., 351, pp. 66-74 | ||
| 504 | |a Matsuo, K., Nakagawa, H., Adachi, Y., Kameda, E., Tsumoto, H., Suzuki, T., Miyata, N., (2010) Chem. Commun. (Camb. UK), 46, pp. 3788-3790 | ||
| 504 | |a Guthrie, D.A., Kim, N.Y., Siegler, M.A., Moore, C.D., Toscano, J.P., (2012) J. Am. Chem. Soc., 134, pp. 1962-1965 | ||
| 504 | |a Nagasawa, H.T., Demaster, E.G., Redfern, B., Shirota, F.N., Goon, D.J.W., (1990) J. Med. Chem., 33, pp. 3120-3122 | ||
| 504 | |a Sha, X., Isbell, T.S., Patel, R.P., Day, C.S., King, S.B., (2006) J. Am. Chem. Soc., 128, pp. 9687-9692 | ||
| 504 | |a Zeng, B.-B., Huang, J., Wright, M.W., King, S.B., (2004) Bioorg. Med. Chem. Lett., 14, pp. 5565-5568 | ||
| 504 | |a Lee, M.J., Shoeman, D.W., Goon, D.J., Nagasawa, H.T., (2001) Nitric Oxide, 5, pp. 278-287 | ||
| 504 | |a Zamora, R., Grzesiok, A., Weber, H., (1995) Biochem. J., 339, pp. 333-339 | ||
| 504 | |a Wilkins, P.C., Jacobs, H.K., Johnson, M.D., Gopalan, A.S., (2004) Inorg. Chem., 43, pp. 7877-7881 | ||
| 504 | |a Bonner, F.T., Ko, Y., (1992) Inorg. Chem., 31, pp. 2514-2519 | ||
| 504 | |a Shoeman, D.W., Nagasawa, H.T., (1998) Nitric Oxide, 2, pp. 66-72 | ||
| 504 | |a Shirota, F.N., Demaster, E.G., Lee, M.J., Nagasawa, H.T., (1999) Nitric Oxide, 3, pp. 445-453 | ||
| 504 | |a Toscano, J.P., Brookfield, F.A., Cohen, L.M., Courtney, A.D., Martin Frost, S., Kalish, V.J., WO 2007/109175 A1; Doctorovich, F., Bikiel, D., Pellegrino, J., Suárez, S.A., Larsen, A., Martí, M.A., (2011) Coord. Chem. Rev., 255, pp. 2764-2784 | ||
| 504 | |a Piloty, O., (1896) Ber. Dtsch. Ges., 29, p. 1559 | ||
| 504 | |a Angeli, A., (1902) Chem. Zentralbl., 73, p. 691 | ||
| 504 | |a Bonner, F.T., Hughes, M.N., (1988) Comments Inorg. Chem., 7, pp. 215-234 | ||
| 504 | |a Seel, F., Bliefert, C., (1974) Z. Anorg. Allg. Chem., 406, pp. 277-281 | ||
| 504 | |a Exner, O., Juska, T., (1984) Collect. Czech. Chem. Commun., 49, p. 51 | ||
| 504 | |a Exner, O., (1964) Collect. Czech. Chem. Commun., 29, p. 1337 | ||
| 504 | |a Exner, O., Kalkac, B., (1963) Collect. Czech. Chem. Commun., 28, p. 1656 | ||
| 504 | |a Bonner, F.T., Wang, N.Y., (1986) Inorg. Chem., 25, pp. 1858-1862 | ||
| 504 | |a Wang, N.Y., Bonner, F.T., (1986) Inorg. Chem., 25, pp. 1863-1866 | ||
| 504 | |a Porcheddu, A., De Luca, L., Giacomelli, G., (2009) Synlett, pp. 2149-2153 | ||
| 504 | |a Blackburn, G.M., Mann, B.E., Taylor, B.F., Worrall, A.F., (1985) Eur. J. Biochem., 153, pp. 553-558 | ||
| 504 | |a Scholz, J.N., Engel, P.S., Glidewell, C., Whitmire, K.H., (1989) Tetrahedron, 45, pp. 7695-7708 | ||
| 504 | |a Lindberg, B.J., (1967) Acta Chem. Scand., 21, pp. 2215-2234 | ||
| 504 | |a Suárez, S.A., Fonticelli, M.H., Rubert, A.A., De La Llave, E., Scherlis, D., Salvarezza, R.C., Martí, M.A., Doctorovich, F., (2010) Inorg. Chem., 49, pp. 6955-6966 | ||
| 504 | |a French, D.C., Crumrine, D.S., (1990) J. Org. Chem., 55, pp. 5494-5496 | ||
| 504 | |a Luna, A., Merch, M., Srn, B., Roos, O., (1995) Chem. Phys., 196, pp. 437-445 | ||
| 520 | 3 | |a A group of Piloty's acid (N-hydroxybenzenesulfonamide) derivatives were synthesized and fully characterized in order to assess the rates and pH of HNO (azanone, nitroxyl) donation in aqueous media. The derivatives, with electron-withdrawing and -donating substituents include methyl, nitro, fluoro, tri-isopropyl, trifluoromethyl and methoxy groups. The most interesting modulation observed is the change in pH range in which the compounds are able to donate HNO. UV-visible kinetic measurements at different pH values were used to evaluate the decomposition rate of the donors. A novel technique based on electrochemical measurements using a Co-porphyrin sensor was used to assess the release of HNO as a function of pH, by direct measurement of [HNO]. The results were contrasted with DFT calculations in order to understand the electronic effects exerted by the ring substituents, which drastically modify the pH range of donation. For example, while Piloty's acid donates HNO from pH 9.3, the corresponding fluoro derivative starts donating at pH 4.0. © 2012 Elsevier Inc. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Fondo para la Investigación Científica y Tecnológica, PICT 2010-2649 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PME-2006-01113, PIP 112-201001-00125 | ||
| 536 | |a Detalles de la financiación: This work was financially supported by UBA ( UBACYT W583 ), FONCyT ( PICT 2010-2649 ), CONICET ( PIP 112-201001-00125 ) and PME-2006-01113 . Appendix A | ||
| 593 | |a Departamento de Quimica Inorganica, Analitica y Quimica Fisica/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires (C1428EHA), Argentina | ||
| 690 | 1 | 0 | |a AZANONE DONORS |
| 690 | 1 | 0 | |a NITROXYL DONORS |
| 690 | 1 | 0 | |a PILOTY'S ACID |
| 690 | 1 | 0 | |a RING SUBSTITUENTS |
| 690 | 1 | 0 | |a BENZENESULFONAMIDE DERIVATIVE |
| 690 | 1 | 0 | |a PHENOL DERIVATIVE |
| 690 | 1 | 0 | |a PILOTY ACID DERIVATIVE |
| 690 | 1 | 0 | |a PORPHYRIN |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ACIDITY |
| 690 | 1 | 0 | |a AQUEOUS SOLUTION |
| 690 | 1 | 0 | |a DECOMPOSITION |
| 690 | 1 | 0 | |a DENSITY FUNCTIONAL THEORY |
| 690 | 1 | 0 | |a ELECTROCHEMICAL ANALYSIS |
| 690 | 1 | 0 | |a ELECTRON TRANSPORT |
| 690 | 1 | 0 | |a ENTHALPY |
| 690 | 1 | 0 | |a MODULATION |
| 690 | 1 | 0 | |a PKA |
| 690 | 1 | 0 | |a PROTON TRANSPORT |
| 690 | 1 | 0 | |a REVIEW |
| 690 | 1 | 0 | |a SENSOR |
| 650 | 1 | 7 | |2 spines |a PH |
| 700 | 1 | |a Suárez, S.A. | |
| 700 | 1 | |a Bikiel, D.E. | |
| 700 | 1 | |a Doctorovich, F. | |
| 773 | 0 | |d Elsevier Inc., 2013 |g v. 118 |h pp. 134-139 |p J. Inorg. Biochem. |x 01620134 |w (AR-BaUEN)CENRE-818 |t Journal of Inorganic Biochemistry | |
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