Limones-Herrero, D., Pérez-Ruiz, R., Lence, E., González-Bello, C., Miranda, M. A., & Jiménez, M. C. (2017). Mapping a protein recognition centre with chiral photoactive ligands. An integrated approach combining photophysics, reactivity, proteomics and molecular dynamics simulation studies. Chemical Science, 8(4), 2621-2628. doi:10.1039/c6sc04900a
O’Brien, W. M., & Bagby, G. F. (1987). Carprofen: A New Nonsteroidal Antiinflammatory Drug Pharmacology, Clinical Efficacy and Adverse Effects. Pharmacotherapy: The Journal of Human Pharmacology and Drug Therapy, 7(1), 16-24. doi:10.1002/j.1875-9114.1987.tb03500.x
Curry, S. L., Cogar, S. M., & Cook, J. L. (2005). Nonsteroidal Antiinflammatory Drugs: A Review. Journal of the American Animal Hospital Association, 41(5), 298-309. doi:10.5326/0410298
[+]
Limones-Herrero, D., Pérez-Ruiz, R., Lence, E., González-Bello, C., Miranda, M. A., & Jiménez, M. C. (2017). Mapping a protein recognition centre with chiral photoactive ligands. An integrated approach combining photophysics, reactivity, proteomics and molecular dynamics simulation studies. Chemical Science, 8(4), 2621-2628. doi:10.1039/c6sc04900a
O’Brien, W. M., & Bagby, G. F. (1987). Carprofen: A New Nonsteroidal Antiinflammatory Drug Pharmacology, Clinical Efficacy and Adverse Effects. Pharmacotherapy: The Journal of Human Pharmacology and Drug Therapy, 7(1), 16-24. doi:10.1002/j.1875-9114.1987.tb03500.x
Curry, S. L., Cogar, S. M., & Cook, J. L. (2005). Nonsteroidal Antiinflammatory Drugs: A Review. Journal of the American Animal Hospital Association, 41(5), 298-309. doi:10.5326/0410298
LEES, P., LANDONI, M. F., Giraudel, J., & TOUTAIN, P. L. (2004). Pharmacodynamics and pharmacokinetics of nonsteroidal anti-inflammatory drugs in species of veterinary interest. Journal of Veterinary Pharmacology and Therapeutics, 27(6), 479-490. doi:10.1111/j.1365-2885.2004.00617.x
T. J. Peter , All about albumin: biochemistry, genetics and medical applications , Academic press , California , 1996
He, X. M., & Carter, D. C. (1992). Atomic structure and chemistry of human serum albumin. Nature, 358(6383), 209-215. doi:10.1038/358209a0
Kragh-Hansen, U., Chuang, V. T. G., & Otagiri, M. (2002). Practical Aspects of the Ligand-Binding and Enzymatic Properties of Human Serum Albumin. Biological and Pharmaceutical Bulletin, 25(6), 695-704. doi:10.1248/bpb.25.695
Fasano, M., Curry, S., Terreno, E., Galliano, M., Fanali, G., Narciso, P., … Ascenzi, P. (2005). The extraordinary ligand binding properties of human serum albumin. IUBMB Life (International Union of Biochemistry and Molecular Biology: Life), 57(12), 787-796. doi:10.1080/15216540500404093
Carter, D. C., & Ho, J. X. (1994). Structure of Serum Albumin. Advances in Protein Chemistry, 153-203. doi:10.1016/s0065-3233(08)60640-3
Kosa, T., Maruyama, T., & Otagiri, M. (1997). Pharmaceutical Research, 14(11), 1607-1612. doi:10.1023/a:1012138604016
Chang, C.-F., & Jeng, S.-R. (1995). Isolation and characterization of the female-specific protein (vitellogenin) in mature female hemolymph of the prawn Penaeus chinensis. Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology, 112(2), 257-263. doi:10.1016/0305-0491(95)00059-3
Rahman, M. H., Maruyama, T., Okada, T., Yamasaki, K., & Otagiri, M. (1993). Study of interaction of carprofen and its enantiomers with human serum albumin—I. Biochemical Pharmacology, 46(10), 1721-1731. doi:10.1016/0006-2952(93)90576-i
Vayá, I., Pérez-Ruiz, R., Lhiaubet-Vallet, V., Jiménez, M. C., & Miranda, M. A. (2010). Drug–protein interactions assessed by fluorescence measurements in the real complexes and in model dyads. Chemical Physics Letters, 486(4-6), 147-153. doi:10.1016/j.cplett.2009.12.091
Lhiaubet-Vallet, V., Boscá, F., & Miranda, M. A. (2006). Stereodifferentiating Drug−Biomolecule Interactions in the Triplet Excited State: Studies on Supramolecular Carprofen/Protein Systems and on Carprofen−Tryptophan Model Dyads. The Journal of Physical Chemistry B, 111(2), 423-431. doi:10.1021/jp066968k
Rahman, M. H., Maruyama, T., Okada, T., Imai, T., & Otagiri, M. (1993). Study of interaction of carprofen and its enantiomers with human serum albumin—II. Biochemical Pharmacology, 46(10), 1733-1740. doi:10.1016/0006-2952(93)90577-j
Divkovic, M., Pease, C. K., Gerberick, G. F., & Basketter, D. A. (2005). Hapten-protein binding: from theory to practical application in the in vitro prediction of skin sensitization. Contact Dermatitis, 53(4), 189-200. doi:10.1111/j.0105-1873.2005.00683.x
Johannesson, G., Rosqvist, S., Lindh, C. H., Welinder, H., & Jönsson, B. A. G. (2001). Serum albumins are the major site for in vivo
formation of hapten-carrier protein adducts in plasma from humans and guinea-pigs exposed to type-1 allergy inducing hexahydrophthalic anhydride. Clinical & Experimental Allergy, 31(7), 1021-1030. doi:10.1046/j.1365-2222.2001.01109.x
Lahoz, A., Hernández, D., Miranda, M. A., Pérez-Prieto, J., Morera, I. M., & Castell, J. V. (2001). Antibodies Directed to Drug Epitopes to Investigate the Structure of Drug−Protein Photoadducts. Recognition of a Common Photobound Substructure in Tiaprofenic Acid/Ketoprofen Cross-Photoreactivity. Chemical Research in Toxicology, 14(11), 1486-1491. doi:10.1021/tx0002482
P. Jones , In vitro phototoxicity assays , in Principles and Practice of Skin Toxicology , ed. R. Chilcott and S. Price , John Wiley & Sons , 2008 , p. 169
Merot, Y., Harms, M., & Saurat, J.-H. (1983). Photosensibilisation au carprofène (Imady®), un nouvel anti-inflammatoire non stéroïdien. Dermatology, 166(6), 301-307. doi:10.1159/000249894
Roelandts, G., & Goh, C. L. (1986). Photosensitivity Associated with Carprofen. Dermatology, 172(1), 64-65. doi:10.1159/000249297
Boscá, F., Marín, M. L., & Miranda, M. A. (2001). Photoreactivity of the Nonsteroidal Anti-inflammatory 2-Arylpropionic Acids with Photosensitizing Side Effects¶. Photochemistry and Photobiology, 74(5), 637. doi:10.1562/0031-8655(2001)074<0637:potnai>2.0.co;2
Kerr, A. C., Muller, F., Ferguson, J., & Dawe, R. S. (2008). Occupational carprofen photoallergic contact dermatitis. British Journal of Dermatology, 159(6), 1303-1308. doi:10.1111/j.1365-2133.2008.08847.x
Moser, J., Boscá, F., Lovell, W. W., Castell, J. V., Miranda, M. A., & Hye, A. (2000). Photobinding of carprofen to protein. Journal of Photochemistry and Photobiology B: Biology, 58(1), 13-19. doi:10.1016/s1011-1344(00)00115-9
P.-L. Toutain , A.Ferran and A.Bousquet-Mélou , Species Differences in Pharmacokinetics and Pharmacodynamics , in Handbook of Experimental Pharmacology, Vol. 199, Comparative and Veterinary Pharmacology , ed. F. Cunningan , J. Elliot and P. Lees , Springer-Verlag , Berlin, Heidelberg , 2010
Bosca, F., Encinas, S., Heelis, P. F., & Miranda, M. A. (1997). Photophysical and Photochemical Characterization of a Photosensitizing Drug: A Combined Steady State Photolysis and Laser Flash Photolysis Study on Carprofen. Chemical Research in Toxicology, 10(7), 820-827. doi:10.1021/tx9700376
Sekula, B., Ciesielska, A., Rytczak, P., Koziołkiewicz, M., & Bujacz, A. (2016). Structural evidence of the species-dependent albumin binding of the modified cyclic phosphatidic acid with cytotoxic properties. Bioscience Reports, 36(3). doi:10.1042/bsr20160089
http://www.ccdc.cam.ac.uk/solutions/csd-discovery/components/gold/
Sivertsen, A., Isaksson, J., Leiros, H.-K. S., Svenson, J., Svendsen, J.-S., & Brandsdal, B. O. (2014). Synthetic cationic antimicrobial peptides bind with their hydrophobic parts to drug site II of human serum albumin. BMC Structural Biology, 14(1). doi:10.1186/1472-6807-14-4
Pérez-Ruíz, R., Lence, E., Andreu, I., Limones-Herrero, D., González-Bello, C., Miranda, M. A., & Jiménez, M. C. (2017). A New Pathway for Protein Haptenation by β-Lactams. Chemistry - A European Journal, 23(56), 13986-13994. doi:10.1002/chem.201702643
Ghuman, J., Zunszain, P. A., Petitpas, I., Bhattacharya, A. A., Otagiri, M., & Curry, S. (2005). Structural Basis of the Drug-binding Specificity of Human Serum Albumin. Journal of Molecular Biology, 353(1), 38-52. doi:10.1016/j.jmb.2005.07.075
Curry, S., Mandelkow, H., Brick, P., & Franks, N. (1998). Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nature Structural Biology, 5(9), 827-835. doi:10.1038/1869
Miller, B. R., McGee, T. D., Swails, J. M., Homeyer, N., Gohlke, H., & Roitberg, A. E. (2012). MMPBSA.py: An Efficient Program for End-State Free Energy Calculations. Journal of Chemical Theory and Computation, 8(9), 3314-3321. doi:10.1021/ct300418h
Wang, Z., Ho, J. X., Ruble, J. R., Rose, J., Rüker, F., Ellenburg, M., … Carter, D. C. (2013). Structural studies of several clinically important oncology drugs in complex with human serum albumin. Biochimica et Biophysica Acta (BBA) - General Subjects, 1830(12), 5356-5374. doi:10.1016/j.bbagen.2013.06.032
Zunszain, P. A., Ghuman, J., Komatsu, T., Tsuchida, E., & Curry, S. (2003). BMC Structural Biology, 3(1), 6. doi:10.1186/1472-6807-3-6
Kelley, L. A., Mezulis, S., Yates, C. M., Wass, M. N., & Sternberg, M. J. E. (2015). The Phyre2 web portal for protein modeling, prediction and analysis. Nature Protocols, 10(6), 845-858. doi:10.1038/nprot.2015.053
Vanquelef, E., Simon, S., Marquant, G., Garcia, E., Klimerak, G., Delepine, J. C., … Dupradeau, F.-Y. (2011). R.E.D. Server: a web service for deriving RESP and ESP charges and building force field libraries for new molecules and molecular fragments. Nucleic Acids Research, 39(suppl_2), W511-W517. doi:10.1093/nar/gkr288
http://upjv.q4md-forcefieldtools.org/RED/
Dupradeau, F.-Y., Pigache, A., Zaffran, T., Savineau, C., Lelong, R., Grivel, N., … Cieplak, P. (2010). The R.E.D. tools: advances in RESP and ESP charge derivation and force field library building. Physical Chemistry Chemical Physics, 12(28), 7821. doi:10.1039/c0cp00111b
Cornell, W. D., Cieplak, P., Bayly, C. I., Gould, I. R., Merz, K. M., Ferguson, D. M., … Kollman, P. A. (1995). A Second Generation Force Field for the Simulation of Proteins, Nucleic Acids, and Organic Molecules. Journal of the American Chemical Society, 117(19), 5179-5197. doi:10.1021/ja00124a002
Case, D. A., Cheatham, T. E., Darden, T., Gohlke, H., Luo, R., Merz, K. M., … Woods, R. J. (2005). The Amber biomolecular simulation programs. Journal of Computational Chemistry, 26(16), 1668-1688. doi:10.1002/jcc.20290
Wang, J., Wolf, R. M., Caldwell, J. W., Kollman, P. A., & Case, D. A. (2004). Development and testing of a general amber force field. Journal of Computational Chemistry, 25(9), 1157-1174. doi:10.1002/jcc.20035
Wang, J., Wang, W., Kollman, P. A., & Case, D. A. (2006). Automatic atom type and bond type perception in molecular mechanical calculations. Journal of Molecular Graphics and Modelling, 25(2), 247-260. doi:10.1016/j.jmgm.2005.12.005
Gordon, J. C., Myers, J. B., Folta, T., Shoja, V., Heath, L. S., & Onufriev, A. (2005). H++: a server for estimating pKas and adding missing hydrogens to macromolecules. Nucleic Acids Research, 33(Web Server), W368-W371. doi:10.1093/nar/gki464
http://biophysics.cs.vt.edu/H++
Götz, A. W., Williamson, M. J., Xu, D., Poole, D., Le Grand, S., & Walker, R. C. (2012). Routine Microsecond Molecular Dynamics Simulations with AMBER on GPUs. 1. Generalized Born. Journal of Chemical Theory and Computation, 8(5), 1542-1555. doi:10.1021/ct200909j
Le Grand, S., Götz, A. W., & Walker, R. C. (2013). SPFP: Speed without compromise—A mixed precision model for GPU accelerated molecular dynamics simulations. Computer Physics Communications, 184(2), 374-380. doi:10.1016/j.cpc.2012.09.022
Darden, T., York, D., & Pedersen, L. (1993). Particle mesh Ewald: AnN⋅log(N) method for Ewald sums in large systems. The Journal of Chemical Physics, 98(12), 10089-10092. doi:10.1063/1.464397
Ryckaert, J.-P., Ciccotti, G., & Berendsen, H. J. . (1977). Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. Journal of Computational Physics, 23(3), 327-341. doi:10.1016/0021-9991(77)90098-5
W. L. DeLano , The PyMOL Molecular Graphics System , DeLano Scientific LLC , Palo Alto, CA, USA , 2008 . http://www.pymol.org/
Roe, D. R., & Cheatham, T. E. (2013). PTRAJ and CPPTRAJ: Software for Processing and Analysis of Molecular Dynamics Trajectory Data. Journal of Chemical Theory and Computation, 9(7), 3084-3095. doi:10.1021/ct400341p
http://www.amber.utah.edu/AMBER-workshop/London-2015/pca/
[-]
![[Cerrado]](/themes/UPV/images/candado.png)
Miranda Alonso, Miguel Ángel
