Excited‐State Proton Transfer Can Tune the Color of Protein Fluorescent Markers
作者： Daiana T. Mancini , Kakali Sen , Mario Barbatti , Walter Thiel , Teodorico C. Ramalho
关键词: Amino acid 、 Binding site 、 Proton 、 Excited state 、 Photochemistry 、 Fluorescence 、 Benzothiazole 、 Enol 、 Molecular dynamics 、 Chemistry
摘要: We show by quantum mechanical/molecular mechanical (QM/MM) simulations that phenylbenzothiazoles undergoing an excited-state proton transfer (ESPT) can be used to probe protein binding sites. For 2-(2'-hydroxy-4'-aminophenyl)benzothiazole (HABT) bound a tyrosine kinase, the absolute and relative intensities of fluorescence bands arising from enol keto forms are found strongly dependent on active-site conformation. The emission properties tuned hydrogen-bonding interactions HABT with neighboring amino acid T766 water. use ESPT tuners opens possibility creating two-color fluorescent markers for sites, potential applications in detection mutations cancer cell lines.
mpg.de
sci-hub.se 参考文章(40)
Daiana T. Mancini, Eugenio F. Souza, Melissa S. Caetano, Teodorico C. Ramalho, 99Tc NMR as a promising technique for structural investigation of biomolecules: theoretical studies on the solvent and thermal effects of phenylbenzothiazole complex. Magnetic Resonance in Chemistry. ,vol. 52, pp. 129- 137 ,(2014) , 10.1002/MRC.4043
William L. Jorgensen, Jayaraman Chandrasekhar, Jeffry D. Madura, Roger W. Impey, Michael L. Klein, Comparison of simple potential functions for simulating liquid water The Journal of Chemical Physics. ,vol. 79, pp. 926- 935 ,(1983) , 10.1063/1.445869
Valeriano Antonio Corbellini, Maria Lúcia Scroferneker, Mariana Carissimi, Fabiano Severo Rodembusch, Valter Stefani, A fast and cost-effective methodology for Fonsecaea pedrosoi ATCC46428 staining using ESIPT fluorescent dyes. Journal of Photochemistry and Photobiology B-biology. ,vol. 99, pp. 126- 132 ,(2010) , 10.1016/J.JPHOTOBIOL.2010.03.007
Dong-Fang Shi, Tracey D. Bradshaw, Samantha Wrigley, Carol J. McCall, Peter Lelieveld, Iduna Fichtner, Malcolm F. G. Stevens, Antitumor Benzothiazoles. 3.1 Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo Journal of Medicinal Chemistry. ,vol. 39, pp. 3375- 3384 ,(1996) , 10.1021/JM9600959
Paul Sherwood, Alex H. de Vries, Martyn F. Guest, Georg Schreckenbach, C.Richard A. Catlow, Samuel A. French, Alexey A. Sokol, Stefan T. Bromley, Walter Thiel, Alex J. Turner, Salomon Billeter, Frank Terstegen, Stephan Thiel, John Kendrick, Stephen C. Rogers, John Casci, Mike Watson, Frank King, Elly Karlsen, Merethe Sjøvoll, Adil Fahmi, Ansgar Schäfer, Christian Lennartz, QUASI: A general purpose implementation of the QM/MM approach and its application to problems in catalysis Journal of Molecular Structure: THEOCHEM. ,vol. 632, pp. 1- 28 ,(2003) , 10.1016/S0166-1280(03)00285-9
Kakali Sen, Rachel Crespo-Otero, Oliver Weingart, Walter Thiel, Mario Barbatti, Interfacial States in Donor-Acceptor Organic Heterojunctions: Computational Insights into Thiophene-Oligomer/Fullerene Junctions. Journal of Chemical Theory and Computation. ,vol. 9, pp. 533- 542 ,(2013) , 10.1021/CT300844Y
K. Vanommeslaeghe, E. Prabhu Raman, A. D. MacKerell, Automation of the CHARMM General Force Field (CGenFF) II: Assignment of Bonded Parameters and Partial Atomic Charges Journal of Chemical Information and Modeling. ,vol. 52, pp. 3155- 3168 ,(2012) , 10.1021/CI3003649
Geoffrey Wells, Tracey D Bradshaw, Patrizia Diana, Angela Seaton, Dong-Fang Shi, Andrew D Westwell, Malcolm FG Stevens, None, Antitumour benzothiazoles. Part 10: the synthesis and antitumour activity of benzothiazole substituted quinol derivatives. Bioorganic & Medicinal Chemistry Letters. ,vol. 10, pp. 513- 515 ,(2000) , 10.1016/S0960-894X(00)00027-5
Hemal A. Bhuva, Suvarna G. Kini, Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors Journal of Molecular Graphics & Modelling. ,vol. 29, pp. 32- 37 ,(2010) , 10.1016/J.JMGM.2010.04.003
Gernot Kieseritzky, E. W. Knapp, Improved pKaprediction: Combining empirical and semimicroscopic methods Journal of Computational Chemistry. ,vol. 29, pp. 2575- 2581 ,(2008) , 10.1002/JCC.20999