Probing kinetic and thermodynamic parameters as well as solvent and substituent effects on spectroscopic probes of 2-amino-1,4-naphthoquinone derivatives

Prime, 2012, A ratiometric fluorescent probe for assessing mitochondrial phospholipid peroxidation within living cells, Free Radic. Biol. Med., 53, 544, 10.1016/j.freeradbiomed.2012.05.033

Krishna Mitra, 2013, Synthesis and spectroscopic exploration of carboxylic acid derivatives of 6-hydroxy-1-keto-1,2,3,4-tetrahydrocarbazole: hydrogen bond sensitive fluorescent probes, J. Lumin., 143, 693, 10.1016/j.jlumin.2013.06.021

Laurieri, 2010, Small molecule colorimetric probes for specific detection of human arylamine N-acetyltransferase 1, a potential breast cancer biomarker, J. Am. Chem. Soc., 132, 3238, 10.1021/ja909165u

Russell, 2009, Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2, Bioorgan. Med. Chem., 17, 905, 10.1016/j.bmc.2008.11.032

Laurieri, 2013, A novel color change mechanism for breast cancer biomarker detection: naphthoquinones as specific ligands of human arylamine N-acetyltransferase 1, PLoS ONE, 8, e70600, 10.1371/journal.pone.0070600

Egleton, 2014, Structure-activity relationships and colorimetric properties of specific probes for the putative cancer biomarker human arylamine N-acetyltransferase 1, Bioorgan. Med. Chem., 22, 3030, 10.1016/j.bmc.2014.03.015

Emadi, 2011, Metabolic and electrochemical mechanisms of dimeric naphthoquinones cytotoxicity in breast cancer cells, Bioorgan. Med. Chem., 19, 7057, 10.1016/j.bmc.2011.10.005

Mancini, 2015, Excited-state proton transfer can tune the color of protein fluorescent markers, ChemPhysChem, 16, 3444, 10.1002/cphc.201500744

Laurent, 2014, ESIPT or not ESIPT? Revisiting recent results on 2,1,3-benzothiadiazole under the TD-DFT light, RSC Adv., 4, 14189, 10.1039/c4ra00991f

Rocha, 2016, Probing the ESIPT process in 2-amino-1,4-naphthoquinone: thermodynamics properties, solvent effect and chemometric analysis, Theor. Chem. Acc., 135, 39, 10.1007/s00214-015-1786-4

Paul, 2011, Density functional theory (DFT) and natural bond orbital (NBO) investigation of intramolecular hydrogen bond interaction and excited-state intramolecular proton transfer (ESIPT) reaction in a five-membered hydrogen-bonding system 2-(1H-pyrazol-5-yl)pyridi, Comput. Theor. Chem., 972, 1, 10.1016/j.comptc.2011.06.004

Azarias, 2016, Tuning ESIPT fluorophores into dual emitters, Chem. Sci., 10.1039/C5SC04826E

Bose, 2011, Excited state intramolecular proton transfer of 2-hydroxy-1-naphthaldehyde semicarbazone: a combined fluorometric and quantum chemical study, J. Photochem. Photobiol. A Chem., 222, 220, 10.1016/j.jphotochem.2011.06.001

Chaudhuri, 2009, Ground and excited state proton transfer and antioxidant activity of 7-hydroxyflavone in model membranes: absorption and fluorescence spectroscopic studies, Biophys. Chem., 139, 29, 10.1016/j.bpc.2008.09.018

Gonçalves, 2014, Dynamics, NMR parameters and hyperfine coupling constants of the Fe3O4(100)–water interface: Implications for MRI probes, Chem. Phys. Lett., 609, 88, 10.1016/j.cplett.2014.06.030

Gonçalves, 2015, Probing thermal and solvent effects on hyperfine interactions and spin relaxation rate of δ-FeOOH(100) and [MnH3buea(OH)]2−: Toward new MRI probes, Comput. Theor. Chem., 1069, 96, 10.1016/j.comptc.2015.07.006

Ramalho, 2010, Development of new acetylcholinesterase reactivators: molecular modeling versus in vitro data, Chem. Biol. Interact., 185, 73, 10.1016/j.cbi.2010.02.026

Ramalho, 2004, Solvent effects on 13 C and 15 N shielding tensors of nitroimidazoles in the condensed phase: a sequential molecular dynamics/quantum mechanics study, J. Phys.: Condens. Matter, 16, 6159

Silva, 2015, Molecular insight into the inhibition mechanism of plant and rat 4-hydroxyphenylpyruvate dioxygenase by molecular docking and DFT calculations, Med. Chem. Res., 24, 3958, 10.1007/s00044-015-1436-3

Kumar, 2016, Docking, molecular dynamics and QM/MM studies to delineate the mode of binding of CucurbitacinE to F-actin, J. Mol. Graph. Model., 63, 29, 10.1016/j.jmgm.2015.11.007

Papo, 2015, Kinetic and mechanistic investigation into the influence of substituents on the substitution reactions of Pt(II) NCN-donor complexes, Trans. Met. Chem., 40, 53, 10.1007/s11243-014-9889-7

Knaeble, 2016, Kinetic and theoretical insights into the mechanism of alkanol dehydration on solid Brønsted acid catalysts, J. Phys. Chem. C, 10.1021/acs.jpcc.5b11127

Jacquemin, 2008, Fast and reliable theoretical determination of pKa∗ for photoacids, J. Phys. Chem. A, 112, 794, 10.1021/jp7105814

Hessz, 2014, Solvation and protonation of coumarin 102 in aqueous media: a fluorescence spectroscopic and theoretical study, J. Phys. Chem. A, 118, 5238, 10.1021/jp504496k

Marciniak, 1992, Estimation of pKa∗ in the first excited singlet state. A physical chemistry experiment that explores acid-base properties in the excited state, J. Chem. Educ., 69, 247, 10.1021/ed069p247

Borg, 2007, Relative ground and excited-state pKa values of phytochromobilin in the photoactivation of photochrome: a computational study, J. Phys. Chem. B, 111, 11554, 10.1021/jp0727953

Silva, 2014, Prototropic studies in vitreous and in solid phases: Pyranine and 2-naphthol excited state proton transfer, J. Lumin., 146, 57, 10.1016/j.jlumin.2013.09.038

Idoux, P., Hancock, K., 1967. The Correlation of the Electronic Spectra, Ground-State p, 4858.

Dixit, 2016, Thermodynamic and kinetic studies of LiNi0.5Co0.2Mn0.3O2 as a positive electrode material for Li-ion batteries using first principles, Phys. Chem. Chem. Phys., 18, 6799, 10.1039/C5CP07128C

Qi, 2016, Kinetic mechanism of effects of hydrogen addition on methane catalytic combustion over Pt(111) surface: a DFT study with cluster modeling, Comput. Mater. Sci., 111, 430, 10.1016/j.commatsci.2015.09.002

Wang, 2014, Mechanistic insights into the stereoselective C2-functionalization of 1-substituted imidazoles with cyanophenylacetylene and aldehydes, Comput. Theor. Chem., 1049, 35, 10.1016/j.comptc.2014.09.015

Mariam, 2000, DFT computational studies of intramolecular hydrogen-bonding interactions in a model system for 5-iminodaunomycin, J. Mol. Struct. Theochem., 529, 83, 10.1016/S0166-1280(00)00535-2

Mariam, 2001, A B3LYP study of intramolecular hydrogen bonding and proton transfer in naphthazarin: a model system for daunomycin/adriamycin, J. Mol. Struct. Theochem., 549, 123, 10.1016/S0166-1280(01)00487-0

Lamoureux, 2008, Reactivity and structure of derivatives of 2-hydroxy-1,4-naphthoquinone (lawsone), J. Phys. Org. Chem., 21, 1022, 10.1002/poc.1435

Budzák, 2016, Optical properties of V-shaped bis-coumarins: Ab initio insights, 1076, 57

Jayabharathi, 2012, Potential fluorescent chemosensor based on L-tryptophan derivative: DFT based ESIPT process, Spectrochim. Acta. A Mol. Biomol. Spectrosc., 95, 446, 10.1016/j.saa.2012.04.017

Niu, 2016, Dry (CO2) reforming of methane over Pt catalysts studied by DFT and kinetic modeling, Appl. Surf. Sci., 10.1016/j.apsusc.2016.01.212

Guseva, 2015, Theoretical studies on the electronic structure and spectroscopic properties of zinc(II) bis(dipyrrinate)s, Comput. Theor. Chem., 1054, 88, 10.1016/j.comptc.2014.12.018

Li, 2016, Excited state intramolecular proton transfer (ESIPT) of 6-amino-2-(2′-hydroxyphenyl)benzoxazole in dichloromethane and methanol: a TD-DFT quantum chemical study, J. Lumin., 172, 29, 10.1016/j.jlumin.2015.11.026

Bermejo-Bescós, 2010, In vitro antiamyloidogenic properties of 1,4-naphthoquinones, Biochem. Biophys. Res. Commun., 400, 169, 10.1016/j.bbrc.2010.08.038

De Castro, 2013, Júnior, synthesis of quinoidal molecules: strategies towards bioactive compounds with an emphasis on lapachones, Eur. J. Med. Chem., 69, 678, 10.1016/j.ejmech.2013.07.057

Basheer, 2016, Spectroscopic and TD-DFT studies on the turn-off fluorescent chemosensor based on anthraldehyde N(4) cyclohexyl thiosemicarbazone for the selective recognition of fluoride and copper ions, Polyhedron, 10.1016/j.poly.2016.01.021

Jacquemin, 2010, Visible spectrum of naphthazarin investigated through time-dependent density functional theory, Chem. Phys. Lett., 493, 67, 10.1016/j.cplett.2010.04.071

Lan, 2013, Time-dependent density functional theory (TD-DFT) study on the excited-state intramolecular proton transfer (ESIPT) in 2-hydroxybenzoyl compounds: Significance of the intramolecular hydrogen bonding, Spectrochim. Acta – Part A Mol. Biomol. Spectrosc., 102, 281, 10.1016/j.saa.2012.10.017

Yang, 2016, Theoretical investigation on ESIPT mechanism of a new fluorescent sensor in different solvents, Spectrochim. Acta. A. Mol. Biomol. Spectrosc., 159, 30, 10.1016/j.saa.2016.01.025

Barman, 2016, A p-hydroxyphenacyl-benzothiazole-chlorambucil conjugate as a real-time-monitoring drug-delivery system assisted by excited-state intramolecular proton transfer, Angew. Chem. Int. Ed., 55, 4194, 10.1002/anie.201508901

Kumar, 2009, Cytotoxic, genotoxic and oxidative stress induced by 1,4-naphthoquinone in B16F1 melanoma tumor cells, Toxicol. Vitr., 23, 242, 10.1016/j.tiv.2008.12.004

Gornostaev, 2014, Synthesis of 2-amino(alkylamino)-3-nitro-1,4-naphthoquinones, Russ. J. Org. Chem., 50, 205, 10.1134/S1070428014020110

da Rocha, 2016, Insights into the value of statistical models and relativistic effects for the investigation of halogenated derivatives of fluorescent probes, Theor. Chem. Acc., 135, 135, 10.1007/s00214-016-1862-4

Elkechai, 2014, Redox properties of biscyclopentadienyl uranium(V) imido-halide complexes: a relativistic DFT study, J. Mol. Model., 20, 2294, 10.1007/s00894-014-2294-5

Reinen, 2010, Jahn-Teller coupling and the influence of strain in Tg and Eg ground and excited states – a ligand field and DFT study on halide MIIIX6 model complexes [M=TiIII–CuIII; X=F−, Cl−], Coord. Chem. Rev., 254, 2703, 10.1016/j.ccr.2010.04.015

Daniel, 2014, Photochemistry and photophysics of transition metal complexes: quantum chemistry, Coord. Chem. Rev., 282–283, 19

Wilbraham, 2015, Describing excited state intramolecular proton transfer in dual emissive systems: a density functional theory based analysis, J. Phys. Chem. B, 119, 2459, 10.1021/jp507425x

Neese, 2012, The ORCA program system, Wiley Interdiscip. Rev. Comput. Mol. Sci., 2, 73, 10.1002/wcms.81

Zhurko, 2015, Chemcraft program, Academic version

Ghadari, 2015, A study on the interactions of amino acids with nitrogen doped graphene; docking, MD simulation, and QM/MM studies, Phys. Chem. Chem. Phys., 18

Ferreira, 2002, Multivariate QSAR, J. Braz. Chem. Soc., 13, 742, 10.1590/S0103-50532002000600004

Barboza, 2012, A TD-DFT basis set and density functional assessment for the calculation of electronic excitation energies of fluorene, Int. J. Quantum Chem., 112, 3434, 10.1002/qua.24300

Lena do Nascimento Silva, 2015, Quantitation of organic acids in wine and grapes by direct infusion electrospray ionization mass spectrometry, Anal. Methods, 7, 53, 10.1039/C4AY00114A

Nascimento, 2010, Análise screening de vinhos empregando um analisador fluxo-batelada, espectroscopia UV-VIS e quimiometria, Quim. Nova, 33, 351, 10.1590/S0100-40422010000200022

Li, 2012, Efficient detection of secondary structure folded nucleic acids related to Alzheimer’s disease based on junction probes, Biosens. Bioelectron., 36, 142, 10.1016/j.bios.2012.04.003

Scharnagl, 2004, Solution pKa values of the green fluorescent protein chromophore from hybrid quantum-classical calculations, J. Phys. Chem. B, 108, 477, 10.1021/jp036411u

Lukeš, 2015, Electronic structure and spectroscopic properties of (2S,3S)-2,3-diphenyl-5,6-diheteroaryl-2,3-dihydropyrazines and their model oligomers, Synth. Met., 199, 319, 10.1016/j.synthmet.2014.11.035

Chen, 2014, TDDFT study of UV–vis spectra of permethrin, cypermethrin and their beta-cyclodextrin inclusion complexes: A comparison of dispersion correction DFT (DFT-D3) and DFT, Spectrochim, Acta Part A Mol. Biomol. Spectrosc., 128, 461, 10.1016/j.saa.2014.02.193

Szafran, 2015, Structural, spectroscopic and theoretical studies of dimethylphenyl betaine complex with two molecules of 2,6-dichloro-4-nitro-phenol, Spectrochim, Acta Part A Mol. Biomol. Spectrosc., 136, 1216, 10.1016/j.saa.2014.10.007

Ballester, 2010, Prospective virtual screening with Ultrafast Shape Recognition: the identification of novel inhibitors of arylamine N-acetyltransferases, J. R. Soc. Interface, 7, 335, 10.1098/rsif.2009.0170

Jali, 2013, Selectivity in changes of fluorescence emission of 1,4-naphthoquinone derivatives by manganese and cadmium ions, Polyhedron, 51, 75, 10.1016/j.poly.2012.12.018