Environment-sensitive behavior of fluorescent molecular rotors

Beens H, Weller A: Excited molecular n -complexes in solution. In Organic molecular photophysics. Edited by: Birks JW. Wiley, New York; 1975. Grabowski ZR, Rotkiewicz K, Rettig W: Structural Changes Accompanying Intramolecular Electron Transfer: Focuson Twisted Intramolecular Charge-Transfer States and Structures. Chem Rev 2003,103(10):3899-4031. 10.1021/cr940745l Rettig W: Application of a simplified microstructural solvent interaction model to the solvatochromism of twisted intramolecular charge transfer (TICT) states. J Mol Struct 1982,84(3-4):303-327. 10.1016/0022-2860(82)85263-0 Allen BD, Benniston AC, Harriman A, Rostron SA, Yu C: The photophysical properties of a julolidene-based molecular rotor. Physical Chemistry Chemical Physics 2005,7(16):3035-3040. 10.1039/b507165h Haidekker MA, Nipper ME, Mustafic A, Lichlyter D, Dakanali M, Theodorakis EA: Dyes with segmental mobility: molecular rotors. In Advanced Fluorescence Reporters in Chemistry and Biology I. Edited by: Demchenko A. New York: Springer; 2010:in press. [Wolfbeis O (Series Editor): Springer series in fluorescence, vol. 8] Atsbeha T, Mohammed AM, Redi-Abshiro M: Excitation Wavelength Dependence of Dual Fluorescence of DMABN in Polar Solvents. Journal of Fluorescence 2010, in press. Haidekker MA, Ling T, Anglo M, Stevens HY, Frangos JA, Theodorakis EA: New fluorescent probes for the measurement of cell membrane viscosity. Chemistry & biology 2001,8(2):123-131. Ramadass R, Bereiter-Hahn J: Photophysical properties of DASPMI as revealed by spectrally resolved fluorescence decays. J Phys Chem B 2007,111(26):7681-7690. 10.1021/jp070378k Förster T, Hoffmann G: Die Viskositatsabhängigkeit der Fluoreszenzquantenausbeuten einiger Farbstoffsysteme [Effect of viscosity on the fluorescence quantum yield of some dye systems]. Z Phys Chem 1971, 75: 63-76. Dutta AK, Kamada K, Ohta K: Spectroscopic studies of Nile red in organic solvents and polymers. Journal of Photochemistry & Photobiology, A: Chemistry 1996, 93: 57-64. Golini CM, Williams BW, Foresman JB: Further solvatochromic, thermochromic, and theoretical studies on Nile Red. Journal of Fluorescence 1998,8(4):395-404. 10.1023/A:1020584801600 Kosower EM: Intramolecular donor-acceptor systems. 9. Photophysics of (phenylamino) naphthalenesulfonates: a paradigm for excited-state intramolecular charge transfer. Accounts of Chemical Research 1982,15(8):259-266. 10.1021/ar00080a005 Kee HL, Kirmaier C, Yu L, Thamyongkit P, Youngblood WJ, Calder ME, Ramos L, Noll BC, Bocian DF, Scheidt WR: Structural control of the photodynamics of borondipyrrin complexes. The journal of physical chemistry B 2005,109(43):20433. 10.1021/jp0525078 Rotkiewicz K, Grellmann KH, Grabowski ZR: Reinterpretation of the anomalous fluorescence of pN, N-dimethylaminobenzonitrile. Chem Phys Lett 1973, 19: 315-318. 10.1016/0009-2614(73)80367-7 Law KY: Fluorescence Probe for Microenvironments: Anomalous Viscosity Dependence of the Fluorescence Quantum Yield of P-N, N Dialkylaminobenzylidenmalononitrile in 1-Alkanols. Chem Phys Lett 1980,75(3):545-549. 10.1016/0009-2614(80)80574-4 Haidekker MA, Theodorakis EA: Molecular rotors -fluorescent biosensors for viscosity and flow. Organic & Biomolecular Chemistry 2007,5(11):1669-1678. Harkness J: The viscosity of human blood plasma; its measurement in health and disease. Biorheology 1971,8(3):171. Letcher RL, Chien S, Pickering TG, Sealey JE, Laragh JH: Direct relationship between blood pressure and blood viscosity in normal and hypertensive subjects:: Role of fibrinogen and concentration. The American Journal of Medicine 1981,70(6):1195-1202. 10.1016/0002-9343(81)90827-5 McMillan DE: Further observations on serum viscosity changes in diabetes mellitus. Metabolism 1982,31(3):274-278. 10.1016/0026-0495(82)90064-6 Otto C, Ritter MM, Richter WO, Minkenberg R, Schwandt P: Hemorrheologic abnormalities in defined primary dyslipoproteinemias with both high and low atherosclerotic risks. Metabolism 2001,50(2):166-170. 10.1053/meta.2001.20192 Roe PF, Harkness J: Plasma viscosity in the elderly. Gerontology 1975,17(3):168-172. Ernst E, Matria A, Schmölzl C, Magyarosy I: Dose-effect relationship between smoking and blood rheology. British journal of haematology 1987,65(4):485-487. 10.1111/j.1365-2141.1987.tb04155.x Bates DO, Levick JR, Mortimer PS: Change in macromolecular composition of interstitial fluid from swollen arms after breast cancer treatment, and its implications. Clinical science (London, England: 1979) 1993,85(6):737. Martin GS, Lewis CA: Fluid management in shock. In Seminars in Respiratory and Critical Care Medicine. Volume 25. New York: Thieme Medical Publishers; 1994:683-693. 10.1055/s-2004-860982 Haidekker MA, Tsai AG, Brady T, Stevens HY, Frangos JA, Theodorakis E, Intaglietta M: A novel approach to blood plasma viscosity measurement using fluorescent molecular rotors. American Journal of Physiology 2002,282(5):H1609-H1614. Akers WJ, Haidekker MA: Precision assessment of biofluid viscosity measurements using molecular rotors. Journal of Biomechanical Engineering 2005, 127: 450. 10.1115/1.1894366 Rosencranz R, Bogen SA: Clinical laboratory measurement of serum, plasma, and blood viscosity. American journal of clinical pathology 2006, 125: S78. Milich K, Akers W, Haidekker MA: A Ratiometric Fluorophotometer for Fluorescence-Based Viscosity Measurement with Molecular Rotors. Sensor Letters 2005,3(3):237-243. 10.1166/sl.2005.031 Loutfy RO, Teegarden DM: Effect of polymer chain tacticity on the fluorescence of molecular rotors. Macromolecules 1983,16(3):452-456. 10.1021/ma00237a022 Loutfy RO: Effect of polystyrene molecular weight on the fluorescence of molecular rotors. Macromolecules 1983,16(4):678-680. 10.1021/ma00238a035 Zhu D, Haidekker MA, Lee JS, Won YY, James CML: Application of Molecular Rotors to the Determination of the Molecular Weight Dependence of Viscosity in Polymer Melts. Macromolecules 2007,40(21):7730-7732. 10.1021/ma0702288 Hawe A, Filipe V, Jiskoot W: Fluorescent Molecular Rotors as Dyes to Characterize Polysorbate-Containing IgG Formulations. Pharmaceutical Research 2010,27(2):314-326. 10.1007/s11095-009-0020-2 Kung CE, Reed JK: Fluorescent molecular rotors: a new class of probes for tubulin structure and assembly. Biochemistry 1989,28(16):6678-6686. 10.1021/bi00442a022 Haidekker MA, Brady TP, Lichlyter D, Theodorakis EA: Effects of solvent polarity and solvent viscosity on the fluorescent properties of molecular rotors and related probes. Bioorganic Chemistry 2005,33(6):415-425. 10.1016/j.bioorg.2005.07.005 Sawada S, Iio T, Hayashi Y, Takahashi S: Fluorescent rotors and their applications to the study of GF transformation of Actin. Analytical biochemistry 1992, 204: 110-117. 10.1016/0003-2697(92)90148-Z Lindgren M, Sörgjerd K, Hammarström P: Detection and characterization of aggregates, prefibrillar amyloidogenic oligomers, and protofibrils using fluorescence spectroscopy. Biophysical journal 2005,88(6):4200-4212. 10.1529/biophysj.104.049700 Kim YH, Cho DW, Yoon M, Kim D: Observation of Hydrogen-Bonding Effects on Twisted Intramolecular Charge Transfer of p-(N, N-Diethylamino) benzoic Acid in Aqueous Cyclodextrin Solutions. J Phys Chem 1996,100(39):15670-15676. 10.1021/jp9613652 Al-Hassan KA, Khanfer MF: Fluorescence probes for cyclodextrin interiors. Journal of Fluorescence 1998,8(2):139-152. 10.1023/A:1022550409844 Albers E, Muller BW: Cyclodextrin derivatives in pharmaceutics. Crit Rev Ther Drug Carrier Syst 1995,12(4):311-337. Haidekker MA, L'Heureux N, Frangos JA: Fluid shear stress increases membrane fluidity in endothelial cells: a study with DCVJ fluorescence. American Journal of Physiology- Heart and Circulatory Physiology 2000,278(4):H1401. Kung CE, Reed JK: Microviscosity measurements of phospholipid bilayers using fluorescent dyes that undergo torsional relaxation. Biochemistry 1986,25(20):6114-6121. 10.1021/bi00368a042 Furuno T, Isoda R, Inagaki K, Iwaki T, Noji M, Nakanishi M: A fluorescent molecular rotor probes the kinetic process of degranulation of mast cells. Immunology letters 1992,33(3):285-288. 10.1016/0165-2478(92)90074-X Viriot ML, Carré MC, Geoffroy-Chapotot C, Brembilla A, Muller S, Stoltz JF: Molecular rotors as fluorescent probes for biological studies. Clinical Hemorheology and Microcirculation 1998,19(2):151-160. Lukac S: Thermally induced variations in polarity and microviscosity of phospholipids and surfactant vesicles monitored with a probe forming an intramolecular charge-transfer complex. Journal of the American Chemical Society 1984,106(16):4386-4392. 10.1021/ja00328a016 Nipper ME, Majd S, Mayer M, Lee JCM, Theodorakis EA, Haidekker MA: Characterization of changes in the viscosity of lipid membranes with the molecular rotor FCVJ. Biochimica et Biophysica Acta (BBA)-Biomembranes 2008,1778(4):1148-1153. 10.1016/j.bbamem.2008.01.005 Axelrod D, Koppel DE, Schlessinger J, Elson E, Webb WW: Mobility measurement by analysis of fluorescence photobleaching recovery kinetics. Biophysical Journal 1976,16(9):1055-1069. 10.1016/S0006-3495(76)85755-4 Shinitzky M, Yuli I: Lipid fluidity at the submacroscopic level: determination by fluorescence polarization. Chemistry and Physics of Lipids 1982,30(2-3):261-282. 10.1016/0009-3084(82)90054-8 Schuddeboom W, Jonker SA, Warman JM, Leinhos U, Kühnle W, Zachariasse KA: Excited-State Dipole Moments of Dual Fluorescent 4-(Dialkylamino) Benzonitriles. Influence of Alkyl Chain Length and Effective Solvent Polarity. J Phys Chem 1992, 96: 10809-10819. 10.1021/j100205a041 Ghoneim N, Suppan P: Solvation of TICT states in solvent mixtures. Pure and applied chemistry 1993, 65: 1739-1739. 10.1351/pac199365081739 Grabowski ZR, Dobkowski J: Twisted intramolecular charge transfer (tict) excited states: energy and molecular structure. Pure Appl Chem 1983, 55: 245. 10.1351/pac198855020245 Gregoire G, Dimicoli I, Mons M, donder Lardeux C, Jouvet C, Martrenchard S, Solgadi D: Femtosecond Dynamics of "TICT" State Formation in Small Clusters: The Dimethylaminobenzomethyl Ester Acetonitrile System. J Phys Chem A 1998,102(41):7896-7902. 10.1021/jp9818378 Rullière C, Grabowski ZR, Dobkowski J: Picosecond absorption spectra of carbonyl derivatives of dimethylaniline: the nature of the TICT excited states. Chemical Physics Letters 1987,137(5):408-413. 10.1016/0009-2614(87)80224-5 Guilbault GG: Practical fluorescence. CRC; 1990. Iwaki T, Torigoe C, Noji M, Nakanishi M: Antibodies for fluorescent molecular rotors. Biochemistry 1993,32(29):7589-7592. 10.1021/bi00080a034 Wang K, Shi W, Jia J, Chen S, Ma H: Characterization of 2-phenylbenzo [g] quinoxaline derivatives as viscosity-sensitive fluorescent probes. Talanta 2009,77(5):1795-1799. 10.1016/j.talanta.2008.10.021 Kuimova MK, Yahioglu G, Levitt JA, Suhling K: Molecular rotor measures viscosity of live cells via fluorescence lifetime imaging. J Am Chem Soc 2008,130(21):6672-6673. 10.1021/ja800570d Kuimova MK, Botchway SW, Parker AW, Balaz M, Collins HA, Anderson HL, Suhling K, Ogilby PR: Imaging intracellular viscosity of a single cell during photoinduced cell death. Nature Chemistry 2009, 1: 69-73. 10.1038/nchem.120 Levitt JA, Kuimova MK, Yahioglu G, Chung PH, Suhling K, Phillips D: Membrane-Bound Molecular Rotors Measure Viscosity in Live Cells via Fluorescence Lifetime Imaging. The Journal of Physical Chemistry C 2009, 113: 11634-11642. 10.1021/jp9013493 Wang D, Miyamoto R, Shiraishi Y, Hirai T: BODIPY-Conjugated Thermoresponsive Copolymer as a Fluorescent Thermometer Based on Polymer Microviscosity. Langmuir 2009,25(22):13176-13182. 10.1021/la901860x Vogel M, Rettig W: Excited state dynamics of triphenylmethane-dyes used for investigation of microviscosity effects. Berichte der Bunsengesellschaft für Physikalische Chemie 1987,91(11):1241-1247. Gierer Av, Wirtz K: Molekulare Theorie der Mikroreibung [Molecular theory of microfriction]. Zeitschrift für Naturforschung 1953, 8: 532-538. Loutfy RO: Fluorescence probes for polymer free-volume. NATO ASI series. Series C, Mathematical and physical sciences 1986, 182: 429-448. Loutfy RO, Arnold BA: Effect of viscosity and temperature on torsional relaxation of molecular rotors. The Journal of Physical Chemistry 1982,86(21):4205-4211. 10.1021/j100218a023 Loutfy RO, Law KY: Electrochemistry and Spectroscopy of Intramolecular Charge-Transfer Complexes.p -N,N-Dialkylamlnobenzylidenemalononitrlles. J Phys Chem 1980, 84: 2803-2808. 10.1021/j100458a027 Doolittle AK: Studies in Newtonian Flow. III. The Dependence of the Viscosity of Liquids on Molecular Weight and Free Space (in Homologous Series). Journal of Applied Physics 1952, 23: 236. 10.1063/1.1702182 Williams ML, Landel RF, Ferry JD: The temperature dependence of relaxation mechanisms in amorphous polymers and other glass-forming liquids. Journal of the American Chemical Society 1955,77(14):3701-3707. 10.1021/ja01619a008 Lang JM, Dreger ZA, Drickamer HG: A high pressure study of the effect of viscosity on the light induced isomerization of DMABN in three linear alcohols, iso-butanol and glycerol. Chemical Physics Letters 1995,243(1-2):78-84. 10.1016/0009-2614(95)00775-Y Zachariasse KA, Grobys M, von der Haar T, Hebecker A, Il'ichev YV, Jiang YB, Morawski O, Knhnle W: Intramolecular charge transfer in the excited state. Kinetics and configurational changes. Journal of Photochemistry & Photobiology, A: Chemistry 1996,102(1S1):59-70. Kuimova MK, Yahioglu G, Ogilby PR: Singlet Oxygen in a Cell: Spatially Dependent Lifetimes and Quenching Rate Constants. Journal of the American Chemical Society 2009, 131: 332-340. 10.1021/ja807484b Kumar S, Singh AK, Krishnamoorthy G, Swaminathan R: Thioflavin T displays enhanced fluorescence selectively inside anionic micelles and mammalian cells. Journal of Fluorescence 2008,18(6):1199-1205. 10.1007/s10895-008-0378-2 White CR, Frangos JA: The shear stress of it all: the cell membrane and mechanochemical transduction. Philosophical Transactions B 2007,362(1484):1459. 10.1098/rstb.2007.2128 Mukherjee S, Raghuraman H, Chattopadhyay A: Membrane localization and dynamics of Nile Red: effect of cholesterol. BBA-Biomembranes 2007, 1768: 59-66. 10.1016/j.bbamem.2006.07.010 Haidekker MA, Brady T, Wen K, Okada C, Stevens HY, Snell JM, Frangos JA, Theodor-akis EA: Phospholipid-bound molecular rotors: synthesis and characterization. Bioorganic & medicinal chemistry 2002,10(11):3627-3636. Haidekker MA, Lichlyter D, Johny MB, Grimes CA: Probing polymerization dynamics with fluorescent molecular rotors and magnetoelastic sensors. Sensor Letters 2006,4(3):257-261. 10.1166/sl.2006.031 Bur AJ, Wang FW, Thomas CL, Rose JL: In-line optical monitoring of polymer injection molding. Polymer Engineering and Science 2004,34(8):671-679. 10.1002/pen.760340809 Bosch P, Catalina F, Corrales T, Peinado C: Fluorescent probes for sensing processes in polymers. Chemistry-A European Journal 2005,11(15):4314. 10.1002/chem.200401349 Roos Y, Karel M: Crystallization of amorphous lactose. Journal of food science 2006,57(3):775-777. 10.1111/j.1365-2621.1992.tb08095.x Yildiz ME, Kokini JL: Determination of Williams-Landel-Ferry constants for a food polymer system: Effect of water activity and moisture content. Journal of Rheology 2001, 45: 903-912. 10.1122/1.1380425 Dutta P, Bhattacharyya K: Ultrafast chemistry in complex and confined systems. Journal of Chemical Sciences 2004, 116: 5-16. 10.1007/BF02708207 Hara K, Bulgarevich DS, Kajimoto O: Pressure tuning of solvent viscosity for the formation of twisted intramolecular charge transfer state in 4, 4 diaminodiphenyl sulfone in alcohol solution. The Journal of chemical physics 1996,104(23):9431. 10.1063/1.471687 Suhling K, French PMW, Phillips D: Time-resolved fluorescence microscopy. Photochemical & Photobiological Sciences 2005, 4: 13-22. Haidekker MA, Brady TP, Lichlyter D, Theodorakis EA: A ratiometric fluorescent viscosity sensor. Journal of the American Chemical Society 2006,128(2):398-399. 10.1021/ja056370a