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(12) United States Patent (10) Patent No.: US 7,381,538 B2 Reardon Et Al

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(12) United States Patent (10) Patent No.: US 7,381,538 B2 Reardon Et Al US007381538B2 (12) United States Patent (10) Patent No.: US 7,381,538 B2 Reardon et al. (45) Date of Patent: Jun. 3, 2008 (54) OPTICAL BIOSENSOR WITH ENHANCED 6,060,327 A * 5/2000 Keen ..................... 204,403.14 ACTIVITY RETENTION FOR DETECTION 6,159,681 A 12/2000 Zebala .......................... 435/4 OF HALOGENATED ORGANIC COMPOUNDS OTHER PUBLICATIONS Derek W. Campbell, entitled “The Development of Biosensors for (75) Inventors: Kenneth F. Reardon, Fort Collins, CO the Detection of Halogenated Groundwater Contaminants,” avail (US); Neema Das, Murgeshpalya (IN) able from Morgan Library at the CSU in Fort Collins, Colorado, having been submitted by Derek W. Campbell in fulfillment of the (73) Assignee: Colorado State University Research requirements for the Degree of Master of Science at Colorado State Foundation (CSURF), Fort Collins, University, Spring 1998 (labeled “Attachment B” of applicants' CO (US) provisional app. filed Jun. 1, 2001 as containing general background technical information}. (*) Notice: Subject to any disclaimer, the term of this inst k Eyle A. PS SEE s past l S.s I listed under 35 12,alogenated 1998 by Reardonflydrocarbons, and Campbell, U.S. Appl. 7 pages No. (labeled,89U, “Attachment Illed Sep. M YW- (b) by ayS. C” of applicants’pp pprovisional app.pp filed Jun. 1, 2001 as containin9. general background technical information}. (21) Appl. No.: 10/478,822 Cord Müller. F. Schubert. T. Scheper,p "Multicomponentp fiberopticalp biosensor for use in hemodialysis monitoring.” Proc. SPIE vol. (22) PCT Filed: Jun. 1, 2002 2131, 555-562 Biomedical Fiber Optic Instrumentation(Jul 1994) {referenced as “Cord Müller, et al.” in applicants’ provisional app. (86). PCT No.: PCT/USO2/17407 filed Jun. 1, 2001 for its general background technical information. J. Peter, W. Buchinger, F. Karner, and W. Hampel, "Characteristics S 371 (c)(1), of a microbial assay for the detection of halogenated hydrocarbons (2), (4) Date: Aug. 9, 2004 using cells of an actinomycete-like organism as a biological com ponent.” Acta Biotechnol 17 (1997) 2 pp. 123-130 Akademie Verlag. Int’l Pub. No. WO 93/25892 (International app No. PCT/GB93/ (87) PCT Pub. No.: WO03/025627 01216) ARS Holding / J. Attridge et al. “Sensor for Optical Assay”. PCT Pub. Date: Mar. 27, 2003 * cited by examiner (65) Prior Publication Data Primary Examiner Karen Cochrane Carlson Assistant Examiner—Agnes B. Rooke US 2004/0265811 A1 Dec. 30, 2004 (74) Attorney, Agent, or Firm—Lathrop & Gage LC Related U.S. Application Data (57) ABSTRACT (60) Provisional application No. 60/295,211, filed on Jun. 1, 2001. A distal tip, and associated method of producing, of a biosensor ion sensing transducer for use in detecting an (51) Int. Cl. analyte comprising an halogenated organic compound in an CI2O I/37 (2006.01) environment Such as Soil or an aqueous environment. Fea (52) U.S. Cl. ........................................................ 435/23 tures include: a biocomponent comprising at least one (58) Field of Classification Search ..................... None enzyme for carrying out a dehalogenation of the compound; See application file for complete search history. the biocomponent is immobilized to a surface of the tip; a treatment of the biocomponent for maintaining a period of (56) References Cited enzymatic efficacy; and the biocomponent stabilized by U.S. PATENT DOCUMENTS means preferably selected from the group consisting of crosslinking a surface of the immobilized biocomponent, 4,739,380 A 4, 1988 Lauks et al. .................. 357/25 crosslinking a polymer layer to the biocomponent, adding a 5,152,758 A 10, 1992 Kaetsu et al. 604/890.1 ~. - 5,156,810 A 10/1992 Ribi ........ 422,82.01 gel-hardening agent to the biocomponent, adding a stabiliz 5,177,012 A 1/1993 Kim et al. ... ... 435/175 ing agent to the biocomponent, and modifying a component 5,250,439 A 10/1993 Musho et al. ................. 435/25 of the immobilizing means. Immobilization can be carried 5,541,057 A 7/1996 Bogart et al. .................. 435/5 out by: (a) entrapment within a hydrogel; (b) entrapment 5,629,214 A 5/1997 Crosby ....................... 436,518 within a polymeric network; (c) (micro)encapsulation; (d) 5,698,083. A 12/1997 Glass ... 204,403 covalent-bonding; and (e) adsorption. The dehalogenase of 5,798,030 A * 8, 1998 Raguse et al. ......... 204,403.08 the biocomponent may be selected from the group consisting 5,837,196 A 1 1/1998 Pinkel et al. ................. 422/55 of hydrolases, subclass EC 3.8, and lyases, subclass EC 4.5 5,837,454 A 1 1/1998 Cozzette et al. ............... 435/6 as listed in Table 2A. 5,972,199 A 10, 1999 Heller et al. .... ... 205/777.5 5,972,638 A 10/1999 Burlage et al. ............... 435/29 6,022,748 A 2/2000 Charych et al. ............ 436,527 18 Claims, 4 Drawing Sheets U.S. Patent Jun. 3, 2008 Sheet 1 of 4 US 7,381,538 B2 CIET CVamazine Propazine SIT s ' CEET Prometry Simazine - h N's 1. Cvromazine E. NH2 ar N24N 1s! 1s! '4la HO1N1 YOH NH1N12 NNH2 N?silla NN Ho / AOOT IrN\o N lay N Ammelide NHSN'oha O /6 OOOT anuric acid N Overview of E.egradation acid 3CO+6H2O+3NH3 FIG. 1 FG, 2 C atrazine OH als chlorohydrolase NSN U.S. Patent Jun. 3, 2008 Sheet 2 of 4 US 7,381,538 B2 45 Atrazine-degrading Microorganism FIG. 4 FIG. 5 U.S. Patent Jun. 3, 2008 Sheet 3 of 4 US 7,381,538 B2 pH Electrode Aglago Electrolyte 0.5myv EnzymeZyme LayLayer F.G. 6 Enzyme Layer Solution FIG. 8 s-s-s-s (SSSSS. S. Adsorption Microencapsulation N / N / N / C C C f -- - Key: Cross-linking Covalent-bonding SBiocomponent-enzyme C Crosslinker U.S. Patent Jun. 3, 2008 Sheet 4 of 4 US 7,381,538 B2 SN FIG. 9 Enzyme Membrane FIG 10 US 7,381,538 B2 1. 2 OPTICAL BIOSENSOR WITH ENHANCED the requirements for the Degree of Master of Science at ACTIVITY RETENTION FOR DETECTION Colorado State University, available from Morgan Library at OF HALOGENATED ORGANIC the Colorado State University in Fort Collins, Colo., refer COMPOUNDS ence is made to a pH optode structure featuring the reaction BACKGROUND OF THE INVENTION illustrated schematically in Campbell, 1998 (labeled FIG. 2.4): the cleavage of halide ion X and proton H" from a This application claims priority under 35 USC S 119(e) halogenated hydrocarbon by the appropriate hydrolytic and 37 C.F.R. S1.78 to pending provisional patent applica dehalogenase. An earlier reference entitled “Multicompo tion No. 60/259,211, filed 01 Jun. 2001. 10 nent fiberoptical biosensor for use in hemodialysis monitor In general, the present invention relates to techniques for ing' (Cord Muller, et al.) employed a pH optode-type monitoring halogenated organic chemicals (pollutants, pes biosensor structure limited to the use of urease as a catalyst ticides, etc.) in Soil, as well as groundwater, waste waters, (urea is split into ammonia & CO): the bifunctional reagent glutaraldehyde was used to bind the urease directly to the and other aqueous environments. More particularly, the 15 invention is directed to an improved distal tip having a head of a pH optode. transducer to which a biocomponent comprising a dehalo Chemical biosensors are miniaturized analytical devices, genase (selected for dehalogenation of a selected analyte of which can deliver real-time and on-line information on the interest) is immobilized, treated, and/or stabilized for moni presence of specific compounds or ions in complex samples. toring continuously in situ Soil oran aqueous environment to Usually an analyte recognition process takes place followed detect the presence and/or concentration of the analyte. Such by the conversion of chemical information into an electrical as any of the S-triazine pesticides, including the chlorinated or optical signal. Two popular classes of chemical sensors herbicide atrazine (used to control broadleaf and grassy used today are electrochemical transduction type. (ampero weeds), Simazine, terbuthylazine, propazine, cyanazine, 25 metric, potentiometric, including ion-selective electrodes deethylatrazine, and deisopropylatrazine, plus other S-triaz (ISE), field effect transistors (FETs), gas-sensing electrodes, ines (including those in TABLE 1), lindane, and DDT. etc., and conductimetric) and optical transduction type (in Disclosed is a novel technique of measuring an analyte and cluding pH optodes). They are used during laboratory analy associated biosensor capable of measuring pH (hydrogen sis as well as in industry, process control, physiological ion) and halide ion concentration in Soil and aqueous envi 30 measurements, and environmental monitoring. The basic ronments to detect the concentration, or collect other infor principles of operation of the chemical sensors utilizing mation about, the analyte. In one aspect of the invention, electrochemical and optical transduction are quite well focus is on a unique biosensor including a fiber optic understood. In developing biosensors for general manufac element (an optical fiber or bundle), the tip of which has a ture and commercial use, longevity and Stabilization of the layer of a bacteria atop a layer of a pH-sensitive fluorophore 35 biocomponent are critical. It is preferable to have a stable, (dye). The bacteria is selected Such that it carries an enzyme long-lived biosensor that can stand prolonged storage as to catalyze a reaction with the halogenated compound of the well as perform well in use for a selected period of time. analyte, releasing either protons (and causing a detectable Among the biocomponent possibilities, enzymes, though pH change) or a measurable halide ion concentration. Fur 40 very selective, fall on the lower end of the stability spec ther, prior to being glued (immobilized or otherwise trum.s affixed) to the tip of the fiber optic transducer, the bacteria The S-triazine compounds include many pesticides.
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