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Tryptophan photooxidation promoted by new hybrid materials prepared by condensation of naphthalene imides with silicate by the sol–gel process

Paper ID Volume ID Publish Year Pages File Format Full-Text
27223 44010 2009 6 PDF Available
Title
Tryptophan photooxidation promoted by new hybrid materials prepared by condensation of naphthalene imides with silicate by the sol–gel process
Abstract

Three novel hybrid organic/inorganic materials were synthesized from 4-substituted (NO2, Br, H) 1,8-naphthalene imide-N-propyltriethoxysilane by the sol–gel process. These materials were obtained as a xerogel and partially characterized. The ability to photosensitize the oxidation and degradation of tryptophan indole ring by these materials was studied through photophysical and photochemical techniques. Although the derivatives containing Br and NO2 as substituent do not cause efficient tryptophan photodamage, the hybrid material obtained from 1,8-naphthalic anhydride is very efficient to promote tryptophan photooxidation. By using laser flash photolysis it was possible to verify the presence of naphthalene imide transient radical species. The presence of oxygen causes an increase of the yield of radical formation. These results suggest that the mechanism of photodegradation of tryptophan occurs by type I, i.e. the transient radical (TrpH+) formed by the direct reaction of the triplet state of the naphthalene imide moiety with tryptophan. Thus a inorganic–organic hybrid material that can be used to promote the oxidation of biomolecules was obtained.

Keywords
Naphthalene imide; Tryptophan; Hybrid organic–inorganic material; Sol–gel
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Tryptophan photooxidation promoted by new hybrid materials prepared by condensation of naphthalene imides with silicate by the sol–gel process
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 208, Issue 1, 15 November 2009, Pages 36–41
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Price was $35.95
You save - $31
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