Hostname: page-component-586b7cd67f-l7hp2 Total loading time: 0 Render date: 2024-11-30T10:30:25.203Z Has data issue: false hasContentIssue false
  • English
  • Français

Tryptophan Photo-Oxidation by Clay-Adsorbed Sensitizers

Published online by Cambridge University Press:  09 July 2018

J. Cenens  and
R. A. Schoonheydt
J. Cenens
Affiliation:
Laboratorium voor Oppervlaktescheikunde, Katholieke Universiteit Leuven, Kardinaal Mercierlaan 92, 3030 Leuven (Heverlee), Belgium
R. A. Schoonheydt
Affiliation:
Laboratorium voor Oppervlaktescheikunde, Katholieke Universiteit Leuven, Kardinaal Mercierlaan 92, 3030 Leuven (Heverlee), Belgium
Get access Rights & Permissions [Opens in a new window]

Abstract

The photo-oxidation of tryptophan (TRP), photosensitized by methylene blue (MB) exchanged on hectorite, Wyoming bentonite and laponite is strongly influenced by three factors: (i) Fe(III) in the structure, which quenches the excited state of MB; (ii) the adsorption site of MB, as photo-oxidation only takes place with MB on the external surface; (iii) dye aggregation, which reduces the yield. Rose bengal (RB), chemically anchored on the external surface of Barasym does not sensitize the photo-oxidation of TRP.

Type
Research Article
Information
Clay Minerals , Volume 23 , Issue 2 , June 1988 , pp. 205 - 212
Copyright
Copyright © The Mineralogical Society of Great Britain and Ireland 1988

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Blossey, E.C., Neckers, D.C., Thayer, A.L. & Schaap, A.P. (1973) Polymer-based sensitizers for photooxidations. J. Am. Chem. Soc. 95, 5820–5822.Google Scholar
Buell, S.L. & Demas, J.N. (1983) Heterogeneous preparation of singlet oxygen using an ion-exchange-resin- bound tris(2,2,-bipyridine)ruthenium(II) photosensitizer. J. Phys. Chem. 87, 4675–4681.Google Scholar
Cenens, J. & Schoonheydt, R.A. (1988) Visible spectroscopy of methylene blue on clays in aqueous suspensions: hectorite, laponite B and barasym. Clays Clay Miner. 36 (in press).Google Scholar
Cenens, J., Vuers, D.P., Schoonheydt, R.A. & De Schryver, F.C. (1987) Spectroscopic study of the surface chemistry of proflavine on clay minerals. Proc. Int. Clay Conf. Denver, 352–358.Google Scholar
Frimer, A.A. (1979) The reaction of singlet oxygen with olefins: the question of mechanism. Chem. Rev. 79, 359–387.Google Scholar
Guy, R.D. & Narine, D.R. (1980) Organocation speciation. II. Methylene blue photosensitization as a model for speciation and toxicity of herbicides. Can. J. Chem. 58, 555–558.Google Scholar
Knowles, A. & Gurnani, S. (1972) A study of the methylene blue-sensitized oxidation of amino acids. Photochem. Photobiol. 16, 95–108.Google Scholar
Merkel, P.B. & Kearns, D.R. (1972) Radiationless decay of singlet molecular oxygen in solution. An experimental and theoretical study of electronic-to-vibrational energy transfer. J. Am. Chem. Soc. 94, 7244–7253.Google Scholar
Nakagawa, M., Yokoyama, Y., Kato, S. & Hino, T. (1985) Dye-sensitized photo-oxygenation of tryptophan. Tetrahedron 41, 2125–2132.Google Scholar
Nilsson, R., Merkel, P.B. & Kearns, D.R. (1972) Unambiguous evidence for the participation of singlet oxygen in photodynamic oxidation of amino acids. Photochem. Photobiol. 16, 117-124.Google Scholar
Schaap, A.P., Thayer, A., Zaklika, K.A. & Valenti, P.C. (1979) Photooxygenations in aqueous solution with a hydrophilic polymer-immobilized photosensitizer. J. Am. Chem. Soc. 101, 4016–4017. Google Scholar
Schoonheydt, R.A., De Pauw, P., Vliers, D. & De Schryver, F.C. (1984) Luminescence of Ru(2,2'bipy)3 2+ in aqueous clay minerals suspensions. J. Phys. Chem. 88, 5113–5118.Google Scholar
Schoonheydt, R.A., Cenens, J. & De Schryver, F.C. (1986) Spectroscopy of proflavine adsorbed on clays. J. Chem. Soc., Faraday Trans. I, 82, 281–289.Google Scholar
Spikes, J.D. (1986) Phthalocyanines as photosensitizers in biological systems and for the photodynamic therapy of tumors. Photochem. Photobiol. 43, 691–699.Google Scholar
Tamagaki, S., Liesner, C.E. & Neckers, D.C. (1980) Polymer-based sensitisers for photochemical reactions. Silica gel as a support. J. Org. Chem. 45, 1573–1576.CrossRefGoogle Scholar
Turro, N.J. (1978) Modern Molecular Photochemistry, Benjamin/Cummings, Menlo Park, California.Google Scholar
Van Olphen, H. & Fripiat, J. J. (1979) Data Handbook for Clay Minerals and other Non-Metallic Minerals. Pergamon Press, New York.Google Scholar
Wagner, J.R., Ali, H., Langlois, R., Brasseur, N. & Van Lier, J.E. (1987) Biological activities of phthalocyanines-VI. Photooxidation of L-tryptophan by selectivity sulfonated gallium phthalocyanines: singlet-oxygen yields and effect of aggregation. Photochem. Photobiol. 45, 587–594.Google Scholar
Wayne, R.P. (1969) Singlet molecular oxygen. Adv. Photochemistry 7, 311–371.Google Scholar