Enhancement of optical properties of new purine nucleobases containing electron-donating and -withdrawing peripheral groups

Leandro H. Zucolotto Cocca1, André G. Pelosi1, Sandrine Piguel2, Cleber Renato Mendonça1, Leonardo De Boni1
1Instituto de Física de São Carlos/Universidade de São Paulo, CP 369, 13560-970 São Carlos, SP, Brazil
2Université Paris-Saclay, Faculté de Pharmacie, CNRS UMR 8076, 92296 Châtenay-Malabry, France

Tài liệu tham khảo

Daniels, 1971, Fluorescence of the purine and pyrimidine bases of the nucleic acids in neutral aqueous solution at 300 degrees K, Science, 171, 675, 10.1126/science.171.3972.675 Nir, 2001, On the photochemistry of purine nucleobases, J. Phys. Chem. A, 105, 5106, 10.1021/jp0030645 Xu, 2017, Fluorescent nucleobases as tools for studying DNA and RNA, Nat. Chem., 9, 1043, 10.1038/nchem.2859 Zucolotto Cocca, 2022, Two-photon brightness of highly fluorescent Imidazopyridine derivatives: two-photon and ultrafast transient absorption studies, J. Mol. Liq., 348, 10.1016/j.molliq.2021.118379 Zucolotto Cocca, 2020, Two-photon emissive dyes based on push-pull purines derivatives: toward the development of new photoluminescence bioprobes, J. Phys. Chem. C, 124, 12617, 10.1021/acs.jpcc.0c01859 Kimoto, 2009, An unnatural base pair system for efficient PCR amplification and functionalization of DNA molecules, Nucleic Acids Res., 37, 10.1093/nar/gkn956 Matsunaga, 2015, Architecture of high-affinity unnatural-base DNA aptamers toward pharmaceutical applications, Sci. Report., 5, 1, 10.1038/srep18478 Ward, 1969, Fluorescence studies of nucleotides and polynucleotides. I. Formycin, 2-Aminopurine riboside, 2,6-diaminopurine riboside, and their derivatives, J. Biol. Chem., 244, 1228, 10.1016/S0021-9258(18)91833-8 Brown, 2018, Fluorescent excimers and exciplexes of the purine base derivative 8-Phenylethynyl-guanine in DNA hairpins, Faraday Discuss., 207, 217, 10.1039/C7FD00186J Bood, 2018, Pentacyclic adenine: a versatile and exceptionally bright fluorescent DNA base analogue, Chem. Sci., 9, 3494, 10.1039/C7SC05448C Butler, 2007, Highly fluorescent donor-acceptor purines, J. Mater. Chem., 17, 1863, 10.1039/B618171F Gaied, 2005, 8-vinyl-deoxyadenosine, an alternative fluorescent nucleoside analog to 2’-Deoxyribosyl-2-aminopurine with improved properties, Nucleic Acids Res., 33, 1031, 10.1093/nar/gki253 Bood, 2018, Fluorescent nucleobase analogues for Base-Base FRET in nucleic acids: synthesis, photophysics and applications, Beilstein J. Org. Chem., 14, 114, 10.3762/bjoc.14.7 Yang, 2013, Ultraviolet-violet electroluminescence from highly fluorescent purines, J. Mater. Chem. C, 1, 2867, 10.1039/c3tc00734k Matsumoto, 2011, Design and synthesis of highly solvatochromic fluorescent 2′-deoxyguanosine and 2′-deoxyadenosine analogs, Bioorg. Med. Chem. Lett., 21, 1275, 10.1016/j.bmcl.2010.11.129 Zilbershtein, 2011, 8-(p-CF3-Cinnamyl)-modified purine nucleosides as promising fluorescent probes, Org. Biomol. Chem., 9, 7763, 10.1039/c1ob05681f Huang, 2012, Dehydrogenative heck coupling of biologically relevant N-heteroarenes with alkenes: discovery of fluorescent core frameworks, Chem. Commun., 48, 2864, 10.1039/c2cc17557f Mahapatra, 2012, Fluorescence sensing of caffeine in aqueous solution with carbazole-based probe and imaging application in live cells, Bioorg. Med. Chem. Lett., 22, 5379, 10.1016/j.bmcl.2012.07.055 Suzuki, 2013, Naphthalene-based environmentally sensitive fluorescent 8-substituted 2′-Deoxyadenosines: application to DNA detection, Bioorg. Med. Chem. Lett., 23, 886, 10.1016/j.bmcl.2012.11.029 Nikan, 2013, An acetylene-bridged 6,8-purine dimer as a fluorescent switch-on probe for parallel G-Quadruplexes, Angew. Chem. Int. Ed., 52, 1428, 10.1002/anie.201207075 Jones, 2015, 2-Aminopurine as a fluorescent probe of DNA conformation and the DNA–enzyme Interface, Q. Rev. Biophys., 48, 244, 10.1017/S0033583514000158 Godde, 2000, 4-amino-1H-Benzo[g]Quinazoline-2-one: a fluorescent analog of cytosine to probe protonation sites in triplex forming oligonucleotides, Nucleic Acids Res., 28, 2977, 10.1093/nar/28.15.2977 Raney, 1994, A fluorescence-based assay for monitoring helicase activity, Proc. Natl. Acad. Sci. U. S. A., 91, 6644, 10.1073/pnas.91.14.6644 Okamoto, 2003, Design of base-discriminating fluorescent nucleoside and its application to T/C SNP typing, J. Am. Chem. Soc., 125, 9296, 10.1021/ja035408l Holz, 1998, 2-aminopurine as a fluorescent probe for DNA base flipping by methyltransferases, Nucleic Acids Res., 26, 1076, 10.1093/nar/26.4.1076 Liang, 2011, Pathways for fluorescence quenching in 2-aminopurine π-stacked with pyrimidine nucleobases, J. Am. Chem. Soc., 133, 6799, 10.1021/ja2007998 Vabre, 2014, Synthesis and evaluation of spectroscopic properties of newly synthesized push–pull 6-amino-8-styryl purines, Dyes Pigments, 105, 145, 10.1016/j.dyepig.2014.01.025 Fonseca, 2019, 10, 16 Xu, 2015, 4-Diphenylamino-phenyl substituted Pyrazine: nonlinear optical switching by protonation, J. Mater. Chem. C, 3, 9191, 10.1039/C5TC01657F Long, 2021, Discovery of and insights into one-photon and two-photon excited ACQ-to-AIE conversion via positional isomerization, J. Mater. Chem. C, 9, 11679, 10.1039/D1TC01963E Xu, 2021, The design strategies and applications for organic multi-branched two-photon absorption chromophores with novel cores and branches: a recent review, J. Mater. Chem. C, 9, 1520, 10.1039/D0TC05910B Liang, 2017, Recent progress on intramolecular charge-transfer compounds as photoelectric active materials, Sci. China Mater., 60, 1093, 10.1007/s40843-016-5170-2 Xu, 2020, Recent progress in efficient organic two-photon dyes for fluorescence imaging and photodynamic therapy, J. Mater. Chem. C, 8, 6342, 10.1039/D0TC00563K Bolze, 2017, Molecular photosensitisers for two-photon photodynamic therapy, Chem. Commun., 53, 12857, 10.1039/C7CC06133A Samaan, 2021, Single-molecule fluorescence detection of a tricyclic nucleoside analogue, Chem. Sci., 12, 2623, 10.1039/D0SC03903A Nobis, 2019, Single-molecule detection of a fluorescent nucleobase analogue via multiphoton excitation, J. Phys. Chem. Lett., 10, 37, 10.1021/acs.jpclett.9b02108 Mikhaylov, 2018, Two-photon absorption spectra of fluorescent isomorphic DNA base analogs, Biomed. Opt. Express, 9, 447, 10.1364/BOE.9.000447 Lane, 2012, Two-photon excitation of the fluorescent nucleobase analogues 2-AP and TC, RSC Adv., 2, 11397, 10.1039/c2ra21881j Shimada, 2015, Optical properties of disilane-bridged donor–acceptor architectures: strong effect of substituents on fluorescence and nonlinear optical properties, J. Am. Chem. Soc., 137, 1024, 10.1021/ja511177e Sheik-Bahae, 1990, Sensitive measurement of optical nonlinearities using a single beam, IEEE J. Quantum Electron., 26, 760, 10.1109/3.53394 Sheik-bahae, 1989, High-sensitivity, single-beam N_2 measurements, Opt. Lett., 14, 955, 10.1364/OL.14.000955 Meath, 1984, On the importance of permanent moments in multiphoton absorption using perturbation theory, J. Phys. B At. Mol. Phys., 17, 763, 10.1088/0022-3700/17/5/017 Vivas, 2013, Two-photon circular–linear dichroism of perylene in solution: a theoretical–experimental study, J. Phys. Chem. B, 117, 2742, 10.1021/jp311065n Vivas, 2013, Revealing the electronic and molecular structure of randomly oriented molecules by polarized two-photon spectroscopy, J. Phys. Chem. Lett., 16, 13 Vabre, 2014, Palladium-catalyzed cross-coupling between 8-substituted 6-Thiophenyl­purines and boronic acids, Synthesis-Stuttgart, 46, 933, 10.1055/s-0033-1340734 Lakowicz, 2008, Principles of fluorescence spectroscopy, third edition, J. Biomed. Opt., 13, 10.1117/1.2904580 2006, 353 Belfield, 2007, Solvent effect on the steady-state fluorescence anisotropy of two-photon absorbing fluorene derivatives, J. Lumin., 126, 14, 10.1016/j.jlumin.2006.04.012 Gvishi, 1993, Spectroscopy and laser action of the “red Perylimide dye” in various solvents, Chem. Phys. Lett., 213, 338, 10.1016/0009-2614(93)85142-B Sadrai, 1992, Lasing action in a family of perylene derivatives: singlet absorption and emission spectra, triplet absorption and oxygen quenching constants, and molecular mechanics and semiempirical molecular orbital calculations, J. Phys. Chem., 96, 7988, 10.1021/j100199a032 Brouwer, 2016, Standards for photoluminescence quantum yield measurements in solution Hashimoto, 1993, Mechanism of fluorescence quenching of pyrene with purines in polar media. formation of the pyrene triplet state via exciplex formation, J. Phys. Chem., 97, 3662, 10.1021/j100117a005 Neves, 2007, Two-photon absorption spectra of Salen dye complexes with Azo dyes, Chem. Phys. Lett., 441, 221, 10.1016/j.cplett.2007.05.021 Lippert, 1957, Spektroskopische Bestimmung Des Dipolmomentes Aromatischer Verbindungen Im Ersten Angeregten Singulettzustand, Zeitschrift für Elektrochemie, Berichte der Bunsengesellschaft für Phys. Chemie, 61, 962, 10.1002/bbpc.19570610819 Mataga, 1956, Solvent effects upon fluorescence spectra and the dipolemoments of excited molecules, Bull. Chem. Soc. Jpn., 29, 465, 10.1246/bcsj.29.465 Islam, 2006, Einstein–Smoluchowski diffusion equation: A discussion, Phys. Scr., 70, 120, 10.1088/0031-8949/70/2-3/008 Cohen, 2004, Strickler–berg analysis of excited singlet state dynamics in DNA and RNA nucleosides, Faraday Discuss., 127, 137, 10.1039/B316939A Larsen, 2003, Electronic states in 2-Aminopurine revealed by ultrafast transient absorption and target analysis, Chem. Phys. Lett., 371, 157, 10.1016/S0009-2614(03)00212-4 Fonseca, 2018, First-order hyperpolarizability of triphenylamine derivatives containing cyanopyridine: molecular branching effect, J. Phys. Chem. C, 122, 1770, 10.1021/acs.jpcc.7b05829 Drobizhev, 2011, Two-photon absorption properties of fluorescent proteins, Nat. Methods, 8, 393, 10.1038/nmeth.1596