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Chemiluminescence and Bioluminescence Larry J. Kricka
Department of Pathology and Laboratory Medicine, University of Pennsylvania, Philadelphia, Pennsylvania 19104 The time period covered by this review is the Chemical Abstracts citation dates October 1, 1996, to October 1, 1998. References cited in this review are drawn from the world literature and are limited to the analysis of human fluid and tissues. Chemiluminescence (CL) (light emission produced in a chemical reaction from the decay of chemiexcited species to the electronic ground state) and bioluminescence (BL) (light emission found in nature) have continued to find diverse applications in analysis but only chemiluminescence has become an established technique in routine clinical chemistry. The Proceedings of the ninth International Symposium on Bioluminescence and Chemiluminescence (B1) and a series of review articles (B2-B10) describe recent advances in the analytical applications of CL and BL. The regular literature survey in the Journal of Bioluminescence and Chemiluminescence also provides information on the fundamental and applied aspects of both CL and BL (B11-B14). A survey of commercially available luminometers and imaging devices for low-light level measurements and kits and reagents utilizing BL and CL has been updated (B15). New Reagents and Analytical Reactions. A range of new reagents have been developed for clinical assays and these include CL immunoassay labels such as acridinium esters (B16, B17) and nucleophilic polysubstituted acridinium esters (B18), di-o-bromophenylacridinium esters for use as detection reagents in an amplification cascade immunoassay (alkaline phosphatase label) (B19), acridinium esters for dual-label strategies (B20), fluorene derivatives for enhancing the CL detection of glucose oxidase labels (B21), and pyrylium compounds for detection of doublestranded DNA (B22). Further examples of 1,2-dioxetane derivatives (B23-B26), imidazopyrazinone CL superoxide probes (B27), a range of luminol and isoluminol reagents, including N-(βcarboxypropionyl)luminol (B28) and dimethylisoluminol (B29), and acridine derivatives (B30) have been described. Additional examples of enhancers for CL detection reactions for horseradish peroxidase (HRP) labels have been developed, e.g., phenothiazines (B31), aromatic amine and hydroxy compounds (B32), and boronates (B33, B34). Thiourea enhancers for CL lucigenin reactions (B35) have also been described. Sensitive analytical reactions for β-galactosidase are available using 1,2-dioxetane derivatives or 5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside (X-gal) (3 amol/assay) (B36). A mutant of Photinus pyralis luciferase (modification of residue 245) with a 5-fold increased Km for ATP has been produced and this improved reagent is useful in ATP assays (B37). Clinical Assays. CL methods continue to be applied to the analysis of body fluids and tissues for clinically important analytes (detection limit): enzymatic-based analysis of apoptotic DNA using CDP-Star (B38), serum oxalate using a coupled oxalate oxidase 10.1021/a19999022 CCC: $18.00 Published on Web 05/20/1999
© 1999 American Chemical Society
method (0.2 µmol/L) (B39), iron(III) in blood (7 × 10-3 mg/L) (B40), naproxen (15 ng/mL) (B41), and protease assays based on 1,2-dioxetanes (B42). CL assays for the messenger molecule nitric oxide (CL NO-ozone reaction), e.g., NO in exhaled air in patients with lung cancer (B43), oxidative products of NO in heart (B44), blood NO (B45), and S-nitrosothiols involved in the function of NO (10 nM) (B46, B47) continue to be an important application for CL. Also, luminol (B48), isoluminol (B49), and Cypridina luciferin-based (B50) reactions have been used as reagents in CL antioxidant assays. BL assays have also been developed for a number of analytes including ethanol in microdialyzates using the coupled NADH: FMN oxidoreductase bacterial luciferase system (analytical range, 0.05-10 mmol/L) (B51) and urea (5 µmol/L) (B52). Immunoassays. This is still one of the most active areas of exploitation for CL and BL technology. Commercialization in the form of immunoassay analyzers and reagent and test kits has been extensive. Acridinium ester labels, CL-based assays for alkaline phosphatase, and enhanced CL assays for peroxidase labels have been the most popular types. The diverse range of recently published assays includes the following: estrogens, e.g., 17-βestradiol (B53); hormones, e.g., calcitonin (B54), procalcitonin (B55), cortisol (B56), neonatal blood spot TSH (B57), and testosterone (B58); and viral proteins, e.g., HIV-1 p24 (B59), and p53 (B60); and new markers such as free deoxypyridinoline in urine (B61). Electrochemiluminescent (or electrogenerated) immunoassays based on a ruthenium trisbipyridyl label are also finding routine use, and clinical immunoassay analyzers have been developed for this specific purpose (B62). Various BL immunoassays (B63) have also been developed using photoproteins such as recombinant aequorin (jelly fish Aequorea victoria) for a flash-type BL immunoassay (B64), obelin (B65, B66), and a DNA (gene) label that codes for firefly luciferase (B67). In addition, an increasing number of fusion conjugates of bioluminescent proteins and binding proteins are being prepared for use in immunoassay, e.g., thermostable firefly luciferase-biotin acceptor peptide (B68) and firefly luciferase-single-chain antibody (B69). Bioluminescent reactions are also useful as sensitive methods for measuring enzyme labels, and a thermostable mutant of firefly luciferase has been utilized in the detection of an acetate kinase label (8.5 × 10-23 mol) (B70). CL and, to a much lesser extent, BL is increasingly used in Western blotting procedures for proteins. Examples of this application include blotting assays for haptoglobin (phenotyping) (B71) and immunoblotting to evaluate IgG subclass antibody to Actinobacillus actinomycetemcomitans in gingival crevicular fluid (B72). Nucleic Acid Assays. Chemiluminescence-based assays (e.g., 1,2-dioxetane substrates for alkaline phosphatase labels and the Analytical Chemistry, Vol. 71, No. 12, June 15, 1999 305R
enhanced chemiluminescent substrate for horseradish peroxidase labels) continue to have a major impact on all forms of DNA diagnostic techniques [in combination with digoxigenin-antidigoxigenin and biotin-streptavidin labeling schemes and the polymerase chain reaction (PCR)] (B73, B74), e.g., CMV DNA detection (B75) and multiplex PCR amplification techniques for detection of Chlamydia trachomatis (1 fg), Neisseria gonorrhoeae (10 fg), Ureaplasma urealyticum (10 fg), and Mycoplasma genitalium (10 fg) in first-void urine specimens (B76). PCR in conjunction with CL detection has also been used to assess maternal cell contamination of cord blood (B77). Other label detection schemes include 1-cyanobenz[f]isoindole fluorophore labels detected using the CL bis(2,6-difluorophenyl)oxalate reaction (B78). An alternative method for detecting nanogram quantities of DNA is to directly derivatize adenyl residues using methyl glyoxal dimethyl acetal and detect the CL from their reaction with tungstosilicic acid and propan-2-ol (B79). Nucleic acid sequencing based on pyrophosphate release and CL detection has also been developed (B80). CELLULAR CL AND LUMINOL- AND LUCIGENIN-ENHANCED CL Cellular CL enhanced by luminol or lucigenin remains a powerful and widely used tool for the investigation of polymorphonuclear leukocytes and for study of cellular interactions (B81B83). CL AND BL DETECTION COUPLED TO SEPARATION TECHNIQUES The sensitivity of CL detection has also been exploited in combination with HPLC, particularly with the peroxyoxalate CL reaction for postcolumn detection. Examples of assays include cyclosporine A (B84), blood glutathione (range, 5-1000 nM) (B85), methamphetamine stimulants in urine (B86), penicillamine in urine (B87), phospholipid hydroperoxides (B88), and porphyrins [uroporphyrin (40 fmol), coproporphyrin (5 fmol)] (B89). CL and BL reactions are also useful when coupled with flow injection and examples include assays for ATP (B90), sulfated bile acids (B91), vitamin C (2 × 10-10 g/mL) (B92), glucose 6-phosphate, glycerophophatidylcholine (B93), Cr(III) (0.01 µg/L) (B94), and vanadium(IV) (7 × 10-10 g) (B95) in hair, 5-hydroxytryptamine (2 × 10-9 M), 5-hydroxytryptophan (3 × 10-9 M), and 5-hydroxyindoleacetic acid (1.5 × 10-8 M) (using the potassium permanganate CL reaction) (B96), phenothiazines, e.g., fluphenazine (0.01 µg/mL) (B97), and blood and serum glucose (B98). Optical Biosensors and Imaging Assays. Various research groups continue to develop BL biosensors that exploit BL-modified bacteria, e.g., recombinant E. coli containing bacterial luciferase genes have been engineered for tetracycline assays (B99). Imaging of BL and CL has emerged as a powerful bioanalytical tool, and the spatial distribution of biomolecules can be effectively and sensitively imaged using different enzyme-labeled probes in conjunction with an optical microscope linked to a video camera and luminograph (B100). Reporter Gene-Based Assays. BL or CL detection techniques are now available for the expression products of most of the common reporter genes [e.g., secreted alkaline phosphatase (SEAP), β-galactosidase (GAL), glucuronidase (GUS), bacterial 306R
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luciferase (lux), firefly luciferase (luc)] and Vargula luciferase (B101). In addition, green fluorescent protein (GFP), a component of the BL organism A. victoria, has rapidly gained widespread and diverse applications (B5). A recent trend has been to develop dual-reporter gene assays (e.g., Renilla and firefly luciferases) (B102), or Renilla luciferase and GFP (B103), and multireporter assays, e.g., combinations of luciferase, β-galactosidase, β-glucuronidase, alkaline phosphatase, or carboxyl esterase (B104). The diverse applications for this technology include the study of single living neurons (B105), screening of immunosuppressive drug analogues (B106), and cell viability and cell growth assays (B107). Luminometers, Analyzers, Reagents, and Kits. The survey of commercially available instrumentation (luminometers) and reagents (reagents, test kits) for CL and BL assays has been updated (B15). New luminometer designs (B108) and details of CL scanning devices have been presented (B109). The utility of CL and BL assays has led to continuing development of an expanding range of analytical products that have been evaluated in different laboratories. Examples of automatic immunoassay analyzers, test methods and kits include the following: Chiron ACS:180 assays for CA125 (B110), phenytoin (B111), theophylline (B112), thyroglobulin (B113); Chiron ACS:Centaur assay for hepatitis B surface antigen (B114); GenProbe Accuprobe test for Campylobacter spp. (B115); Lumico thyroid peroxidase antibody (B116), TSH and FT4 tests (B117); DPC Immulite tests for FT4, TSH, ferritin, PSA, C-peptide, and PTH (B118, B119); and Sanofi Access estradiol assay (B120). Microchips and Microarrays. An important recent trend has been toward microminiaturization and the development of highdensity arrays of microreaction vessels, microchip-based analyzers, and microarrays of reagents. CL has found application in these new miniaturized assay formats, as exemplified by a 384-well microplate-based assay for a luciferase reporter gene (B121), simultaneous multianalyte array-type assays (B122, B123), and microchip assays (B124), particularly in conjunction with microchipbased capillary electrophoresis (B125). Larry J. Kricka is a professor of pathology and laboratory medicine at the University of Pennsylvania and Director of the General Chemistry Laboratory at the Hospital of the University of Pennsylvania. He received his B.A. and D.Phil. degrees from York University, England. His research interests include the analytical applications of bioluminescence and chemiluminescence, nonisotopic immunoassays, micromachined analytical systems, and heterophile antibodies. He is editor-in-chief of the Journal of Bioluminescence and Chemiluminescence, and a member of the editorial boards of Analytical Biochemistry, Clinical Chemistry, and the Journal of Immunoassay. Dr. Kricka is a fellow of the Royal College of Pathologists and the Royal Society of Chemistry and a member of the Association of Clinical Biochemists and the Academy of Clinical Laboratory Physicians and Scientists.
LITERATURE CITED (B1) Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds. Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Wiley: Chichester, 1997. (B2) Stott, R. A. W. Methods Mol. Biol. 1998, 80, 197-205. (B3) Billard, P.; DuBow, M. S. Clin. Biochem. 1998, 31, 1-14. (B4) Cree, I. A. Methods Mol. Biol. 1998, 102, 179-187. (B5) Kendall, J. M.; Badmiton, M. N. Trends Biotechnol. 1998, 16, 216-224. (B6) Harmon, B. J.; Regnier, F. E. Chem. Anal. 1998, 146, 925943. (B7) Favier, A. Ann. Biol. Clin. 1997, 55, 9-16. (B8) Wattre, P. Ann. Biol. Clin. 1997, 55, 25-31. (B9) Girotti, S.; Ferri, Elida N.; Ghini, S.; Fini, F.; Musiani, M.; Carrea, G.; Roda, A.; Rauch, P. Chem. Listy 1997, 917, 477482. (B10) Albrecht, S.; Zimmermann, T.; Brandl, H.; Saeger, H. D.; Distler, W. Laboratoriumsmedizin 1997, 21, 191-204; Chem. Abstr. 1997, 127, 47254.
(B11) Kricka, L. J.; Stanley, P. E. J. Biolumin. Chemilumin. 1998, 13, 41-59. (B12) Kricka, L. J.; Stanley, P. E. J. Biolumin. Chemilumin. 1998, 13, 157-184. (B13) Kricka, L. J.; Stanley, P. E. J. Biolumin. Chemilumin. 1998, 12, 113-134. (B14) Kricka, L. J.; Stanley, P. E. J. Biolumin. Chemilumin. 1998, 12, 261-270. (B15) Stanley, P. E. J. Biolumin. Chemilumin. 1997, 12, 61-78. (B16) Kawaguchi, M.; Suzuki, N. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, 1997; pp 481-484. (B17) Law, S.-J.; Sotiriou-Leventis, C.; Natrajan, A.; Jiang, Q.; Connolly, P. B.; Kilroy, J. P.; McCudden, C. R.; Tirrell, S. M. U.S. Patent 5656426, 1997; Chem. Abstr. 1997, 127, 187871. (B18) Suzuki, O.; Masuda, G.; Shiohata, N.; Matsumoto, K. Eur. Pat. Appl. EP 812823, 1997; Chem. Abstr. 1998, 128, 72655. (B19) Brown, R. C.; Weeks, I.; Fisher, M.; Harbron, S.; Taylorson, C. J.; Woodhead, J. S. Anal. Biochem. 1998, 259, 142-151. (B20) Piran, U.; Quinn, J. J. PCT Int. Appl WO 9834109, 1998; Chem. Abstr. 1998, 129, 158856. (B21) Yoda, R.; Maeda, A.; Ito, F. Jpn. Kokai Tokkyo Koho JP 10081659, 1998; Chem. Abstr. 1998, 128, 292500. (B22) Okamoto, T.; Yamamoto, N. Eur. Pat. Appl. EP 837141, 1998; Chem. Abstr. 1998, 128, 291125. (B23) Matsumoto, M. Jpn. Kokai Tokkyo Koho JP 10087651, 1998; Chem. Abstr. 1998, 128, 294773. (B24) Martin, C. S.; Olesen, C. E. M.; Liu, B.; Voyta, J. C.; Shumway, J. L.; Juo, R. R.; Bronstein, I. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, 1997; pp 525-528. (B25) Matsumoto, M.; Watanabe, N.; Kobayashi, H.; Igawa, H. Jpn. Kokai Tokkyo Koho JP 09157271, 1997; Chem. Abstr. 1997, 127, 50626. (B26) Bronstein, I.; Edwards, B.; Sparks, A.; Voyta, J. C. PCT Int. Appl. WO 9714954, 1997; Chem. Abstr. 1997, 127, 25442. (B27) Shimomura, O.; Wu, C.; Murai, A.; Nakamura, H. Anal. Biochem. 1998, 258, 230-235. (B28) Zhuang, H.-S.; Wang, Q.-E.; Zhang, F.; Huang, Q.-J.; Tang, Y.C. Chin. J. Chem. 1997, 15, 123-129. (B29) Yoshida, H.; Todoroki, K.; Zaitsu, K. Kyushu Daigaku Chuo Bunseki Senta Hokoku 1996, 14, 20-26; Chem. Abstr. 1997, 126, 327211. (B30) Akhavan-Tafti, H.; Arghavani, Z.; Desilva, R. PCT Int. Appl. WO 9726245, 1997; Chem. Abstr. 1997, 127, 176354. (B31) Davis, P. D.; Feather Henigan, K.; Hines, K. PCT Int. Appl. WO 9739142, 1997; Chem. Abstr. 1997, 127, 343580. (B32) Navas Diaz, A.; Garcia Sanchez, F.; Gonzalez Garcia, J. A. Span Patent ES 2113294, 1998; Chem. Abstr. 1998, 129, 313105. (B33) Kricka, L. J.; Ji, X. Talanta 1997, 44, 1073-1079. (B34) Ji, X., Kricka, L. J. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, 1997; pp 477-480. (B35) Maeda, A. Jpn. Kokai Tokkyo Koho JP 10087621, 1998; Chem. Abstr. 1998, 128, 319059. (B36) Arakawa, H.; Maeda, M.; Tsuji, A. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, 1997; pp 489-492. (B37) Squirrell, D. J.; White, P. J.; Lowe, C. R.; Murray, J. A. H. PCT Int. Appl. WO 9846729, 1998; Chem. Abstr. 1998, 129, 313101. (B38) Blanco, F. L.; Gonzalez-Reyes, J.; Fanjul, L. F.; Ruiz de Galarreta, C. M.; Aguiar, J. Q. BioTechniques 1998, 24, 354358. (B39) Gaulier, J. M.; Steghens, J. P.; Lardet, G.; Vallon, J. J.; Cochat, P. J. Biolumin. Chemilumin. 1997, 12, 295-298. (B40) Qin, W.; Zhang, Z. J.; Zhang, C. J. Mikrochim. Acta 1998, 129, 97-101. (B41) Campiglio, A. Analyst 1998, 123, 1571-1574. (B42) Bronstein, I.; Voyta, J.; Palmer, M.; Tillotson, B. PCT Int. Appl. WO 9839471, 1998; Chem. Abstr. 1998, 129, 225709. (B43) Liu, C.-Y.; Wang, C.-H.; Chen, T.-C.; Lin, H.-C.; Yu, C.-T.; Kuo, H.-P. Br. J. Cancer 1998, 78, 534-541. (B44) Akiyama, K.; Kimura, A.; Suzuki, H.; Takeyama, Y.; Gluckman, T. L.; Terhakopian, A.; Katagiri, T.; Suh, K.-Y.; Roseto, J.; Bing, R. J. J. Am. Coll. Cardiol. 1998, 32, 373-379. (B45) Wang, C.; Tian, Y.; Shen, W.; Jiang, C.; Wang, D.; Jiang, C.; Wang, C.; Ge, E. Zhonghua Yixue Jianyan Zazhi 1997, 20, 285-287; Chem. Abstr. 1998, 129, 158687. (B46) Samouilov, A.; Zweier, J. L. Anal. Biochem. 1998, 258, 322330. (B47) Ewing, J. F.; Janero, D. R. Free Radical Biol. Med. 1998, 25, 621-628. (B48) Landray, M. J.; Nuttall, S. L.; Maxwell, S. R. J.; Thorpe, G. H. G. Ann. Clin. Biochem. 1998, 35, 553-554. (B49) Hirayama, O.; Takagi, M.; Hukomoto, K.; Katoh, S. Anal. Biochem. 1997, 247, 237-241. (B50) Tampo, Y.; Tsukamoto, M.; Yonaha, M. FEBS Lett. 1998, 430, 348-352.
(B51) Anderstam, B.; Gutierrez, A.; Lundin, A.; Alvestrand, A. Scand. J. Clin. Lab. Invest. 1998, 58, 89-96. (B52) Naslund, B.; Stahle, L.; Lundin, A.; Anderstam, B.; Arner, P.; Bergstrom, J. Clin. Chem. 1998, 44, 1964-1973. (B53) Bohm, R.; Hagedorn, H.; Hasselbach, G.; Zoulek, G.; Wetzel, E.; Wetzel, V. Clin. Lab. 1997, 43, 863-874. (B54) Suzuki, H. J. Clin. Lab. Anal. 1998, 12, 218-222. (B55) Rau, B.; Steinbach, G.; Gansauge, F.; Mayer, J. M.; Grunert, A.; Beger, H. G. Gut 1997, 41, 832-840. (B56) Elmlinger, M. W.; Ranke, M. B.; Weber, M. M. Clin. Lab. 1997, 43, 857-862. (B57) John, R.; Henley, R.; Oversby, N. Ann. Clin. Biochem. 1997, 34, 396-399. (B58) Luppa, P.; Bruckner, C.; Schwab, I.; Hauck, S.; Schmidmayr, S.; Birkmayer, C.; Paulus, B.; Hauptmann, H. Clin. Chem. 1997, 43, 2345-2352. (B59) Schlederer, T.; Himmler, G. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, 1997; pp 533-536. (B60) Dittadi, R.; Brazzale, A.; Mione, R.; Difresco, S.; Gatti, C.; Vinante, O.; Bassan, F.; Nascimben, O.; Gion, M. Anticancer Res. 1997, 17, 4691-4696. (B61) Seibel, M. J.; Woitge, H. W.; Auler, B.; Kissling, C.; Ziegler, R. Clin. Lab. 1998, 44, 269-275. (B62) Erler, K. Wien. Klin. Wochenschr. 1998, 110(Suppl. 3), 5-10. (B63) Price, R. L.; Squirrell, D. J.; Murphy, M. J.; White, P. J. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, 1997; pp 220-223. (B64) Actor, J. K.; Kuffner, T.; Dezzutti, C. S.; Hunter, R. L.; McNicholl, J. M. J. Immunol. Methods 1998, 211, 65-77. (B65) Frank, L. A.; Vysotskii, E. S.; Petunin, A. I.; Nevdaev, A. V. Immunologiya (Moscow) 1997, 1, 55-57; Chem. Abstr. 1998, 128, 280525. (B66) Frank, L. A.; Vysotski, E. S. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, 1997; pp 439-442. (B67) Laios, E.; Ioannou, P. C.; Christopoulos, T. K. Clin. Biochem. 1998, 31, 151-158. (B68) Tatsumi, H.; Fukuda, S.; Kikuchi, M.; Koyama, Y. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, 1997; pp 232-235. (B69) Billiald, P.; Mousli, M.; Goyffon, M.; Vaux, D. Biotechnol. Lett. 1997, 19, 1037-1041. (B70) Murakami, S.; Ito, K.; Goto, T.; Kamada, S.; Maeda, M. Anal. Chim. Acta 1998, 361, 19-26. (B71) Ouyang, J.; Delanghe, J.; Baeyens, W. R. G.; Langlois, M. Anal. Chim. Acta 1998, 362, 113-120. (B72) Dibart, S.; Eftimiadi, C.; Socransky, S.; Taubman, M. A.; Van Dyke, T. E. Oral Microbiol. Immunol. 1998, 13, 166-172. (B73) Taoufik, Y.; Froger, D.; Benoliel, S.; Wallon, C.; Dussaix, E.; Delfraissy, J. F.; Lantz, O. Eur. Cytokine Network 1998, 9, 197-204. (B74) Verhaegen, M.; Christopoulos, T. K. Anal. Chem. 1998, 70, 4120-4125 (B75) Alexandre, I.; Zammatteo, N.; Moris, P.; Brancart, F.; Remacle, J. J. Virol. Methods 1997, 66, 113-122. (B76) Mahony, J. B.; Jang, D.; Chong, S.; Luinstra, K.; Sellors, J.; Tyndall, M.; Chernesky, M. Mol. Diagn. 1997, 2, 161-168. (B77) Poli, F.; Crespiatico, L.; Lecchi, L.; Sirchia, G.; Scalamogna, M.; Sirchia, S. M.; Garagiola, I.; Pedranzini, L. Blood 1997, 89, 3061-3062. (B78) Kuroda, N.; Hosoki, S.; Nakashima, K.; Akiyama, S.; Givens, R. S. J. Biolumin. Chemilumin. 1998, 13, 101-105. (B79) Kuroda, N.; Nakashima, K.; Akiyama, S.; Sato, N.; Imi, N.; Shirakawa, K.; Uemura, A. J. Biolumin. Chemilumin. 1998, 13, 25-29. (B80) Ronaghi, M.; Uhlen, M.; Nyren, P. Science 1998, 281, 363365. (B81) Nishida, A.; Ushijima, Y.; Nakano, M. Photomed. Photobiol. 1996, 18, 51-52. (B82) Farinelli, A.; Setti, M.; Puppo, F.; Scudeletti, M.; De Martini, D.; Balestra, V.; Indiveri, F. APMIS 1996, 104, 500-508. (B83) Crocnan, D.; Olinescu, R.; Turcu, G. R. Rom. J. Biophys. 1997, 7, 87-93. (B84) Katayama, M.; Taniguchi, H.; Matsuda, Y.; Akihama, S.; Kaneko, S.; Ishikawa, H.; Aikawa, A.; Sandou, M.; Kuroda, Y.; Nozawa, S. Anal. Lett. 1998, 31, 621-629. (B85) Cecchettin, M.; Cbapanzano, C.; Aversa, E. V.; Gaizigna, L. Eur. J. Lab. Med. 1997, 5, 58-60. (B86) Takayama, N.; Tanaka, S.; Hayakawa, K. Curr. Top. Forensic Sci. 1997, 2, 344-347. (B87) Zhang, Z.; Baeyens, W. R. G.; Zhang, X.; Zhao, Y.; Van Der Weken, G. Anal. Chim. Acta 1997, 347, 325-332. (B88) Yamamoto, Y.; Kambayashi, Y.; Ueda, T. Methods Mol. Biol. 1998, 108, 63-70. (B89) Lin, M.; Huie, C. W. J. Liq. Chromatogr. Relat. Technol. 1997, 20, 681-691 (B90) Fujiwara, T.; Kurahashi, K.; Kumamaru, T. Anal. Chim. Acta 1997, 349, 159-164.
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(B91) Gao, X.-F.; Ikebukuro, K.; Karube, I.; Li, Y.-S. Lab. Rob. Autom. 1997, 9, 69-79. (B92) Chen, H.; Qin, W.; Zhang, Z. Fenxi Huaxue 1997, 25, 10791081; Chem. Abstr. 1997, 127, 314254. (B93) Yaqoob, M.; Nabi, A.; Masoom-Yasinzai, M. J. Biolumin. Chemilumin. 1997, 12, 1-5. (B94) Escobar, R.; Garcia-Dominguez, M. S.; Guiraum, A.; De la Rosa, F. F. Fresenius’ J. Anal. Chem. 1998, 361, 509-511. (B95) Li, W.; Wang, Z.; Li, J.; Zhang, Z. Fenxi Shiyanshi 1998, 17, 41-44; Chem. Abstr. 1998, 129, 297651. (B96) Barnett, N. W.; Hindson, B. J.; Lewis, S. W. Anal. Chim. Acta 1998, 362, 131-140. (B97) Aly, F. A.; Alarfaj, N. A.; Slwarthan, A. A. Anal. Chim. Acta 1998, 358, 255-262. (B98) Perez-Ruiz, T.; Martinez-Lozano, C.; Tomas, V.; Sanz, A. Anal. Lett. 1998, 31, 1837-1855. (B99) Korpela, M. T.; Kurittu, J. S.; Karvinen, J. T.; Karp, M. T. Anal. Chem. 1998, 70, 4457-4462. (B100) Roda, A.; Pasini, P.; Baraldini, M.; Musiani, M.; Gentilomi, G.; Robert, C. Anal. Biochem. 1998, 257, 53-62. (B101) Tanahashi, Y.; Fujieda, K. Kenkyu Nenpo-Seicho Kagaku Kyokai 1997, 21, 305-314; Chem. Abstr. 1998, 129, 286456. (B102) Grentzmann, G.; Ingram, J. A.; Kelly, P. J.; Gesteland, R. F.; Atkins, J. F. RNA 1998, 44, 479-486. (B103) Szalay, A. A.; Wang, G.; Wang, Y. PCT Int. Appl. WO 9814605, 1998; Chem. Abstr. 1998, 128, 291113. (B104) Bronstein, I. Y.; Fortin, J. J.; Martin, C. S.; Voyta, J. C. PCT Int. Appl. WO 9724460, 1997; Chem. Abstr. 1997, 127, 119320. (B105) Nunez, L.; Faught, W. J.; Frawley, L. S. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 9648-9653. (B106) Baldari, C. T.; Di Somma, M. M.; Majolini, M. B.; Ulivieri, C.; Milia, E.; Telford, J. L. Biologicals 1998, 26, 1-5. (B107) Coombe, D. R.; Nakhoul, A.-M.; Stevenson, S. M.; Peroni, S. E.; Sanderson, C. J. J. Immunol. Methods 1998, 215, 145150. (B108) Eppler, J.; Leistner, H. Ger. Offen. DE 19704731, 1998; Chem. Abstr. 1998, 129, 197307. (B109) Imai, T.; Nishiguchi, Y.; Takada, S.; Yoshida, M. Seibutsu Shiryo Bunseki 1997, 20, 243-248.
308R
Analytical Chemistry, Vol. 71, No. 12, June 15, 1999
(B110) Roth, H. J.; Zahn, I. Clin. Lab. 1997, 43, 515-526. (B111) Dasgupta, A.; Datta, P.; Redlich, G.; Limmany, A. Ther. Drug Monit. 1997, 19, 191-194. (B112) Malliaros, D. P.; Wong, S. S.; Wu, A. H. B.; Campbell, J.; Leonard, H.; Houser, S.; Berg, M.; Gornet, T.; Brown, C.; Feng, Y. J. Ther. Drug Monit. 1997, 19, 224-229. (B113) Kaczur, V.; Vereb, Gy.; Molnar, I.; Krajczar, G.; Kiss, E.; Farid, N. R.; Balazs, Cs. Clin. Chem. 1997, 43, 1392-1396. (B114) Hall, J.; Jilg, W.; Hottentraeger, B.; Bonnar, P.; Fang, C.; Baker, L. Clin. Lab. 1998, 44, 349-354. (B115) Houlakis, V.; Charvalos, E.; Tselentis, J. Delt. Ell. Mikrobiol. Etair. 1997, 42, 792-795; Chem. Abstr. 1998, 129, 271168. (B116) Yasui, T.; Sato, M.; Okamoto, M.; Kaino, M.; Omote, M.; Matsushima, H. Igaku to Yakugaku 1997, 38, 1243-1249; Chem. Abstr. 1998, 129, 38282. (B117) Noh, J. Y. Igaku to Yakugaku 1998, 39, 1003-1009; Chem. Abstr. 1998, 129, 270714. (B118) Cecchettin, M.; Cbapanzano, C.; Aversa, E. V.; Gaizigna, L. Eur. J. Lab. Med. 1997, 5, 58-60. (B119) Saadeddin, S. M.; Sobki, S. H. Med. Sci. Res. 1997, 25, 579581. (B120) Dancoine, F.; Couplet, G.; Buvat, J.; Guittard, C.; Marcolin, G.; Fourlinnie, J.-C. Clin. Chem. 1997, 43, 1165-1171. (B121) Kolb, A. J. Stud. Org. Chem. (Amsterdam) 1998, 53, 111119. (B122) Eggers, M. D.; Balch, W. J.; Hogan, M. E.; Mendoza, L. G. PCT Int. Appl. WO 9829736, 1998; Chem. Abstr. 1998; 129, 106256. (B123) Akhavan-Tafti, H.; Reddy, L. V.; Siripurapu, S.; Schoenfelner, B. A.; Handley, R. S.; Schaap, A. P. Clin. Chem. 1998, 44, 2065-2066. (B124) Bryan, B. J.; Gaalema, S.; Murphy, R. B. PCT Int. Appl. WO 9826277, 1998; Chem. Abstr. 1998, 129, 65194. (B125) Mangru, S. D.; Harrison, D. Electrophoresis 1998, 19, 2301-2307.
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