Electrolysis: processes – compositions used therein – and methods – Electrolytic coating – Forming nonmetal coating
Reexamination Certificate
1999-11-30
2003-06-24
Alexander, Lyle A. (Department: 1743)
Electrolysis: processes, compositions used therein, and methods
Electrolytic coating
Forming nonmetal coating
C205S198000, C204S403010, C204S415000, C204S418000, C435S287200, C435S287900, C435S817000, C422S082030
Reexamination Certificate
active
06582583
ABSTRACT:
BACKGROUND OF THE INVENTION
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FIELD OF THE INVENTION
The present invention relates to the field of biosensors and, in particular, to biosensors comprising a catalytically active cyclodextrins.
DESCRIPTION OF RELATED TECHNOLOGY
Many chemicals in common use in industrialized societies contain aromatic esters. Examples of the types of chemicals containing aromatic esters include detergents, antioxidants and agricultural chemicals. Upon degradation of these aromatic esters whether through enzymatic hydrolysis or bacterial degradation, toxic phenols and phenol derivatives are produced. Research has shown that these toxic chemicals can accumulate in food, soil, and water. In addition, it has been shown that the presence of these chemicals can be dangerous to humans and animals as they can have adverse effects on reproduction and have been implicated in the development of tumors (Certa et al. 1996). The United States Environmental Protection Agency (US-EPA) has listed phenolic compounds as priority pollutants due to their toxicity and persistence in the environment (EPA method 604, Phenols in Federal Register, Oct. 26, 1984, Environment Protection Agency, Part VIII, 40 CFR Part 136, 58-66; EPA method 625, Base
eutrals and acids in Federal Register, Oct. 26, 1984. Environment Protection Agency, Part VIII, 40 CFR Part 136, 154-174). Furthermore, European Community Directive 76/464/EEC recommends that the maximum level of phenolic compounds in surface water for drinking purposes should be in the 1-10 &mgr;g/L range (Puig et al.). Therefore, developing a sensitive, reliable, and fast testing method for the detection of phenolic compounds is an issue of importance to the entire industrialized world.
Current methods for the detection of phenolic compounds include liquid chromatography with electrochemical (LCEC) detection and a coupled gas chromatography/mass spectrometry (GC/MS) method which requires sample pretreatment (Puig et al. 1996; Li et al. 1997). These currently employed methods suffer from various limitations. For example, the LCEC method is subject to interference because of the high applied potential (around 1V) required for electrochemical detection of the phenolic compounds. The high polarizing potential causes oxidation of other matrix compounds; hence, an increase in background current is frequently observed. In addition, the LCEC method has problems with signal stability, pH dependence, and time consuming experimental protocols. The GC/MS method usually requires sample derivatization prior to analysis. For example, Li and co-workers (Li et al. 1997) converted phenols to phenyl acetate prior to analyzing with GC/MS. It has been suggested by Puig (Puig et al. 1996) that the US-EPA method for derivatization of nitrophenols for GC/MS may often lead to incorrect results.
Conventional electrochemical methods used to detect toxic phenols suffer from signal drift, and the probes need frequent cleaning because of polymerization caused by oxidation of phenols (Puig et al. 1996). Because traditional electrochemical methods are sensitive to pH they have limited practical application. To date, no satisfactory approach exists for measuring phenols. Cyclodextrins (CDs) and modified CDs have been used as biomimetic enzyme (BMZ) catalysts for several decades (Bender et al. 1978; Breslow et al. 1980; Szejtli et al. 1988; Editor Sant'e, D.
Minutes of the Sixth International Symposium on Cyclodextrins
, Paris, 1992; Editor Bethell, D.
Advances in Physical Organic Chemistry,
1994, Volume 29, 1-85, Academic Press, N.Y.). CDs are cyclic carbohydrates made up of six (&agr;-CD), seven (&bgr;-CD) or eight (&ggr;-CD) linked D-glucopyranose units. They look like hollow truncated cones, where the interior cavity is hydrophobic and the outside is hydrophilic. The cavities can entrap a variety of chemicals having suitable size and hydrophobicity. Functional groups can be attached to the CDs enabling them to mimic enzyme catalysis. For example, one or two imidazolyl groups attached on the C-3 position of the dimethyl-&bgr;-cyclodextrin (&bgr;-DMCD) can enhance catalysis of the hydrolysis of paranitrophenyl acetate (p-NPA) to para-nitrophenolate (p-NPO
−
) with rate increases up to several thousand times the un-catalyzed rate (Chen et al.
Alexander Lyle A.
Cole Monique T.
Haddaway Keith G.
The United States of America as represented by the Department of
Venable
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