• 1
    Noronha, M., R. Santos, E. Paci, H. Santos and A. N. L. Maçanita (2009) Fluorescence lifetimes of tyrosine residues in cytochrome c” as local probes to study protein unfolding. J. Phys. Chem. B 113, 44664474.
  • 2
    Guzow, K., R. Ganzynkowicz, A. Rzeska, J. Mrozek, M. Szabelski, J. Karolczak, A. Liwo and W. Wiczk (2004) Photophysical properties of tyrosine and its simple derivatives studied by time-resolved fluorescence spectroscopy, global analysis, and theoretical calculations. J. Phys. Chem. B 108, 38793889.
  • 3
    Noronha, M., J. C. Lima, P. Lamosa, H. Santos, C. Maycock, R. Ventura and A. L. Maçanita (2004) Intramolecular fluorescence quenching of tyrosine by the peptide α-carbonyl group revisited. J. Phys. Chem. A 108, 21552166.
  • 4
    Willis, K. J. and A. G. Szabo (1991) Fluorescence decay kinetics of tyrosinate and tyrosine hydrogen-bonded complexes. J. Phys. Chem. 95, 15851589.
  • 5
    Creed, D. (1984) The photophysics and photochemistry of the near-UV absorbing amino acids- II. Tyrosine and its simple derivatives. Photochem. Photobiol. 39, 563575.
  • 6
    Hasselbacher, C. A., E. Waxman, L. T. Galati, P. B. Contino, J. B. A. Ross and W. R. Laws (1991) Investigation of hydrogen bonding and proton transfer of aromatic alcohols in nonaqueous solvents by steady-state and time-resolved fluorescence. J. Phys. Chem. 95, 29953005.
  • 7
    Stasiuk, M. and A. Kozubek (2010) Biological activity of phenolic lipids. Cell. Mol. Life Sci. 67, 841860.
  • 8
    Shen, J., W. Li, G. Liu, Y. Tang and H. Jiang (2009) Computational insights into the mechanism of ligand unbinding and selectivity of estrogen receptors. J. Phys. Chem. B 113, 1043610444.
  • 9
    Brzozowski, A. M., A. C. W. Pike, Z. Dauter, R. E. Hubbard, T. Bonn, O. Engstrom, L. Ohman, G. L. Greene, J.-A. Gustafsson and M. Carlquist (1997) Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389, 753758.
  • 10
    Leranth, C., T. Hajszan, K. Szigeti-Buck, J. Bober and N. J. MacLusky (2008) Bisphenol A prevents the synaptogenic response to estradiol in hippocampus and prefrontal cortex of ovariectomized nonhuman primates. Proc. Natl. Acad. Sci. U S A. 105, 1418714191.
  • 11
    Katzenellenbogen, J. A., H. J. Johnson, K. E. Carlson and H. N. Myers (1974) Photoreactivity of some light-sensitive estrogen derivatives. Use of an exchange assay to determine their photointeraction with the rat uterine estrogen binding protein. Biochemistry 13, 29862994.
  • 12
    Grabner, G., G. Köhler, J. Zechner and N. Getoff (1977) Pathways for formation of hydrated electrons from excited phenol and related compounds. Photochem. Photobiol. 26, 449458.
  • 13
    Monti, S., G. Koehler and G. Grabner (1993) Photophysics and photochemistry of methylated phenols in.beta.-cyclodextrin inclusion complexes. J. Phys. Chem. 97, 1301113016.
  • 14
    Nakashima, T., Y. Ohko, D. A. Tryk and A. Fujishima (2002) Decomposition of endocrine-disrupting chemicals in water by use of TiO2 photocatalysts immobilized on polytetrafluoroethylene mesh sheets. Photochem. Photobiol. A 151, 207212.
  • 15
    Peltonen, K., A. Zitting, H. Koskinen and A. Itkonen (1986) Free radicals from photodecomposition of bisphenol-A. Photochem. Photobiol. 43, 481484.
  • 16
    Mazellier, P., L. Méité and J. De Laat (2008) Photodegradation of the steroid hormones 17b-estradiol (E2) and 17a-ethinylestradiol (EE2) in dilute aqueous solution. Chemosphere 73, 12161223.
  • 17
    Lin, A. Y.-C. and M. Reinhard (2005) Photodegradation of common environmental pharmaceuticals and estrogens in river water. Environ. Toxicol. Chem. 24, 13031309.
  • 18
    Feng, X., S. Ding, J. Tu, F. Wu and N. Deng (2005) Degradation of estrone in aqueous solution by photo-fenton system. Sci. Total Environ. 345, 229237.
  • 19
    Jürgens, M. D., K. I. E. Holthaus, A. C. Johnson, J. J. L. Smith, M. Hetheridge and R. J. Williams (2002) The potential for estradiol and ethinylestradiol degradation in english rivers. Environ. Toxicol. Chem. 21, 480488.
  • 20
    Albini, A. and E. Fasani (1998) Photochemistry of drugs: An overview and practical problems. In Drugs: Photochemistry and Photostability, Vol. 225. (Edited by A. Albini and E. Fasani), pp. 173. The Royal Society of Chemistry, Cambridge, UK.
  • 21
    Leech, D. M., M. T. Snyder and R. G. Wetzel (2009) Natural organic matter and sunlight accelerate the degradation of 17ß-estradiol in water. Sci. Total Environ. 407, 20872092.
  • 22
    Koh, Y. K. K., T. Y. Chiu, A. Boobis, E. Cartmell, M. D. Scrimshaw and J. N. Lester (2008) Treatment and removal strategies for estrogens from wastewater. Environ. Technol. 29, 245267.
  • 23
    Liu, Z.-h., J. A. Ogejo, A. Pruden and K. F. Knowlton (2011) Occurrence, fate and removal of synthetic oral contraceptives (SOCs) in the natural environment: A review. Sci. Total Environ. 409, 51495161.
  • 24
    Kuster, M., M. J. López de Alda, M. D. Hernando, M. Petrovic, J. Martín-Alonso and D. Barceló (2008) Analysis and occurrence of pharmaceuticals, estrogens, progestogens and polar pesticides in sewage treatment plant effluents, river water and drinking water in the Llobregat river basin (Barcelona, Spain). J. Hydrol. 358, 112123.
  • 25
    Johnson, A. C., T. Ternes, R. J. Williams and J. P. Sumpter (2008) Assessing the concentrations of polar organic microcontaminants from point sources in the aquatic environment: Measure or model? Environ. Sci. Technol. 42, 53905399.
  • 26
    Kidd, K. A., P. J. Blanchfield, K. H. Mills, V. P. Palace, R. E. Evans, J. M. Lazorchak and R. W. Flick (2007) Collapse of a fish population after exposure to a synthetic estrogen. Proc. Natl. Acad. Sci. U S A. 104, 88978901.
  • 27
    Chen, C.-Y., T.-Y. Wen, G.-S. Wang, H.-W. Cheng, Y.-H. Lin and G.-W. Lien (2007) Determining estrogenic steroids in Taipei waters and removal in drinking water treatment using high-flow solid-phase extraction and liquid chromatography/tandem mass spectrometry. Sci. Total Environ. 378, 352365.
  • 28
    Auriol, M., Y. Filali-Meknassi and R. Dayal Tyagi (2007) Occurrence and fate of steroid hormones in wastewater treatment plants. Rev. Sci. Eau 20, 89108.
  • 29
    Zuo, Y., K. Zhang and Y. Deng (2006) Occurrence and photochemical degradation of 17[alpha]-ethinylestradiol in Acushnet River Estuary. Chemosphere 63, 15831590.
  • 30
    Wen, Y., B.-S. Zhou, Y. Xu, S.-W. Jin and Y.-Q. Feng (2006) Analysis of estrogens in environmental waters using polymer monolith in-polyether ether ketone tube solid-phase microextraction combined with high-performance liquid chromatography. J. Chromatr. A 1133, 2128.
  • 31
    Swartz, C. H., S. Reddy, M. J. Benotti, H. Yin, L. B. Barber, B. J. Brownawell and R. Rudel (2006) Steroid estrogens, nonylphenol ethoxylate metabolites, and other wastewater contaminants in groundwater affected by a residential septic system on cape cod MA. Environ. Sci. Technol. 40, 48944902.
  • 32
    Falconer, I. R., H. F. Chapman, M. R. Moore and G. Ranmuthugala (2006) Endocrine-disrupting compounds: A review of their challenge to sustainable and safe water supply and water reuse. Environ. Toxicol. 21, 181191.
  • 33
    de Mes, T., G. Zeeman and G. Lettinga (2005) Occurrence and fate of estrone, 17β-estradiol and 17α-ethynylestradiol in STPs for domestic wastewater. Rev. Environ. Sci. Biotechnol. 4, 275311.
  • 34
    Rodriguez-Mozaz, S., M. J. López de Alda and D. Barceló (2004) Monitoring of estrogens, pesticides and bisphenol A in natural waters and drinking water treatment plants by solid-phase extraction-liquid chromatography-mass spectrometry. J. Chromatr. A 1045, 8592.
  • 35
    Hohenblum, P., O. Gans, W. Moche, S. Scharf and G. Lorbeer (2004) Monitoring of selected estrogenic hormones and industrial chemicals in groundwaters and surface waters in Austria. Sci. Total Environ. 333, 185193.
  • 36
    Williams, R. J., A. C. Johnson, J. J. L. Smith and R. Kanda (2003) Steroid estrogens profiles along river stretches arising from sewage treatment works discharges. Environ. Sci. Technol. 37, 17441750.
  • 37
    Baronti, C., R. Curini, G. D'Ascenzo, A. Di Corcia, A. Gentili and R. Samperi (2000) Monitoring natural and synthetic estrogens at activated sludge sewage treatment plants and in a receiving river water. Environ. Sci. Technol. 34, 50595066.
  • 38
    Routledge, E. J., D. Sheahan, C. Desbrow, G. C. Brighty, M. Waldock and J. P. Sumpter (1998) Identification of estrogenic chemicals in STW effluent. 2. In Vivo responses in trout and roach. Environ. Sci. Technol. 32, 15591565.
  • 39
    Jobling, S., M. Nolan, C. R. Tyler, G. Brighty and J. P. Sumpter (1998) Widespread sexual disruption in wild fish. Environ. Sci. Technol. 32, 24982506.
  • 40
    Hansen, P. D., H. Dizer, B. Hock, A. Marx, J. Sherry, M. McMaster and C. Blaise (1998) Vitellogenin - a biomarker for endocrine disruptors. Trends Anal. Chem. 17, 448451.
  • 41
    Coleman, H. M., M. I. Abdullah, B. R. Eggins and F. L. Palmer (2005) Photocatalytic degradation of 17[beta]-oestradiol, oestriol and 17[alpha]-ethynyloestradiol in water monitored using fluorescence spectroscopy. Appl. Catal. B 55, 2330.
  • 42
    Chan, K. Y., B. M. Gavaghan, A. W. Stoeckel, K. Irizarry and P. M. Hare (2012) Solvent effects on the steady state photophysics of estrone and 17β-estradiol. Photochem. Photobiol. 88, 295303.
  • 43
    Weinreb, A. and A. Werner (1969) On the intrinsic fluorescence of estrone. Chem. Phys. Lett. 3, 231232.
  • 44
    Weinreb, A. and A. Werner (1974) On the luminescence of estrogens. Photochem. Photobiol. 20, 313321.
  • 45
    Ashfold, M. N. R., B. Cronin, A. L. Devine, R. N. Dixon and M. G. D. Nix (2006) The role of ps* excited states in the photodissociation of heteroaromatic molecules. Science 312, 1637.
  • 46
    Ashfold, M. N. R., A. L. Devine, R. N. Dixon, G. A. King, M. G. D. Nix and T. A. A. Oliver (2008) Exploring nuclear motion through conical intersections in the UV photodissociation of phenols and thiophenol. Proc. Natl. Acad. Sci. U S A. 105, 1270112706.
  • 47
    Vieuxmaire, O. P. J., Z. Lan, A. L. Sobolewski and W. Domcke (2008) Ab initio characterization of the conical intersections involved in the photochemistry of phenol. J. Chem. Phys. 129, 22430710.
  • 48
    Sobolewski, A. L., W. Domcke, C. Dedonder-Lardeux and C. Jouvet (2002) Excited-state hydrogen detachment and hydrogen transfer driven by repulsive 1πσ* states: A new paradigm for nonradiative decay in aromatic biomolecules. Phys. Chem. Chem. Phys. 4, 10931100.
  • 49
    Hurwitz, A. R. and S. T. Liu (1977) Determination of aqueous solubility and pKa values of estrogens. J. Pharm. Sci. 66, 624627.
  • 50
    Shareef, A., M. J. Angove, J. D. Wells and B. B. Johnson (2006) Aqueous solubilities of estrone, 17β-estradiol, 17α-ethynylestradiol, and bisphenol A. J. Chem. Eng. Data 51, 879881.
  • 51
    Lakowicz, J. R. (2006) Principles of Fluorescence Spectroscopy. Springer, New York.
  • 52
    Lide, D. R. (2007) CRC Handbook of Chemistry and Physics. Taylor and Francis, Boca Raton, FL.
  • 53
    Kamlet, M. J., J. L. M. Abboud, M. H. Abraham and R. W. Taft (1983) Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, pi.*, alpha., and.beta., and some methods for simplifying the generalized solvatochromic equation. J. Org. Chem. 48, 28772887.
  • 54
    Kaneko, S., S. Yotoriyama, H. Koda and S. Tobita (2009) Excited-state proton transfer to solvent from phenol and cyanophenols in water. J. Phys. Chem. A 113, 30213028.
  • 55
    Grégoire, G., C. Dedonder-Lardeux, C. Jouvet, S. Martrenchard, A. Peremans and D. Solgadi (2000) Picosecond hydrogen transfer in the phenol-(NH3)n = 1-3 excited state. J. Phys. Chem. A 104, 90879090.
  • 56
    Lipert, R. J., G. Bermudez and S. D. Colson (1988) Pathways of S1 decay in phenol, indoles, and water complexes of phenol and indole in a free jet expansion. J. Phys. Chem. 92, 38013805.
  • 57
    Sur, A. and P. M. Johnson (1986) Radiationless transitions in gas phase phenol and the effects of hydrogen bonding. J. Chem. Phys. 84, 12061209.
  • 58
    Magde, D., G. E. Rojas and P. G. Seybold (1999) Solvent dependence of the fluorescence lifetimes of xanthene dyes. Photochem. Photobiol. 70, 737744.
  • 59
    Magde, D., R. Wong and P. G. Seybold (2002) Fluorescence Quantum yields and their relation to lifetimes of rhodamine 6G and fluorescein in nine solvents: Improved absolute standards for quantum yields. Photochem. Photobiol. 75, 327334.
  • 60
    Lewis, K. M. and R. D. Archer (1979) pKa values of estrone, 17beta-estradiol, and 2-methoxyestrone. Steroids 34, 485499.
  • 61
    Renge, I. (2009) Solvent dependence of n-pi* absorption in acetone. J. Phys. Chem. A 113, 1067810686.
  • 62
    Schuster, D. I., J. Eriksen, P. S. Engel and M. A. Schexnayder (1976) Photochemistry of ketones in solution. 50. Fluorescence lifetimes of.beta., gamma.-unsaturated ketones. Structural dependence of rate constants for reaction and decay of singlet excited states. J. Am. Chem. Soc. 98, 50255027.
  • 63
    O'Sullivan, M. P. and A. C. Testa (1970) Fluorescence of aliphatic ketones. J. Am. Chem. Soc. 92, 58425844.
  • 64
    Zechner, J., G. Köhler, G. Grabner and N. Getoff (1980) The role of the molecular environment for the primary photoprocesses of phenol in solution. Can. J. Chem. 58, 20062010.
  • 65
    Stasiuk, M. and A. Kozubek (2008) Membrane perturbing properties of natural phenolic and resorcinolic lipids. FEBS Lett. 582, 36073613.
  • 66
    Kamlet, M. J., M. H. Abraham, R. M. Doherty and R. W. Taft (1984) Solubility properties in polymers and biological media. 4. Correlation of octanol/water partition coefficients with solvatochromic parameters. J. Am. Chem. Soc. 106, 464466.