Abstract
The aromatic diamino compound 2,3-diaminonaphthalene (DAN) has been extensively used to detect and quantify nitrite ions in biological and environmental samples. We have immobilized the DAN reagent in a porous silicate glass matrix, via previous incorporation of the dye in HP-β-CD. Changes in fluorescence intensity were used to characterize the inclusion complexes and determine the association constant and stoichiometry of the process. Fluorescence spectrum of these complexes was also used to monitor their immobilization within the sol–gel matrix. Reactivity of the immobilized complexes was evaluated with increasing concentrations of nitrite up to 10 μM (with a detection limit around 20 nM). Results show that sol–gel immobilization does not modify the reactivity of the dye against nitrite and serves to prepare a highly sensitive ready to use fluorescence-based sensor for the specific measurement of nitrite at submicromolar concentrations with no further sample pretreatment.
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Abbreviations
- DAN:
-
2,3-Diaminonaphthalene
- NATH:
-
1-(H)-Naphthotriazole
- NAT:
-
2,3-Naphthotriazole Anion
- TEOS:
-
Tetraethyl orthosilicate
- β-CD:
-
β-Cyclodextrin
- HP-β-CD:
-
2-Hydroxypropyl-β-Cyclodextrin
References
Bryan NS (2006) Nitrite in nitric oxide biology: cause or consequence? A systems-based review. Free Radic Biol Med 41(5):691–701
Damiani P, Burini G (1986) Fluorometric determination of nitrite. Talanta 33(8):649–652
Mahieuxe B, Carré MC, Viriot ML, André JC, Donner M (1994) Fiber-optic fluorescing sensors for nitrate and nitrite detection. J Fluoresc 4(1):7–10
Grisham MB, Johnson GG, Lancaster JR Jr (1996) Quantitation of nitrate and nitrite in extracellular fluids. Methods Enzymol 268:237–246
Jobgen WS, Jobgen SC, Li H, Meininger CJ, Wu G (2007) Analysis of nitrite and nitrate in biological samples using high-performance liquid chromatography. J Chromatogr B 851:71–82
Sousa AL, Santos WJ, Luz RC, Damos FS, Kubota LT, Tanaka AA, Tanaka SM (2008) Amperometric sensor for nitrite based on copper tetrasulphonated phthalocyanine immobilized with poly-l-lysine film. Talanta 75(2):333–338
Zhu X, Lin X (2007) Novel nitrite sensing using a palladium-polyphenosafranine nano-omposite. Anal Sci 23(8):981–985
Boo YC, Tressel SL, Jo H (2007) An improved method to measure nitrate/nitrite with an NO-selective electrochemical sensor. Nitric Oxide 16(2):306–312
Huang KJ, Wang H, Guo YH, Fan RL, Zhang HS (2006) Spectrofluorimetric determination of trace nitrite in food product with a new fluorescent probe 1,3,5,7-tetramethyl-2,6-dicarbethoxy-8-(3¢,4¢-diaminophenyl)-difluoroboradoaza-s-indacene. Talanta 69:73–78
Gomes A, Fernandes E, Lima JLFC (2006) Use of fluorescence probes for detection of reactive nitrogen species: a review. J Fluoresc 16:119–130
Tsikas D (2007) Analysis of nitrite and nitrate in biological fluids by assays based on the Griess reaction: appraisal of the Griess reaction in the L-arginine/nitric oxide area of research. J Chromatogr B 851:51–70
Sun J, Zhang X, Broderick M, Fein H (2003) Measurement of nitric oxide production in biological systems by using griess reaction assay. Sensors 3:276–284
Nussler AK, Glanemann M, Schirmeier A, Liu L, Nüssler NC (2006) Fluorometric measurement of nitrite/nitrate by 2,3-diaminonaphthalene. Nat Protoc 1(5):2223–2226
Kleinhenz DJ, Fan X, Rubin J, Hart CM (2003) Detection of endothelial nitric oxide release with the 2,3-diaminonapthalene assay. Free Radic Biol Med 34(7):856–861
Li H, Meininger CJ, Wu G (2000) Rapid determination of nitrite by reversed-phase high-performance liquid chromatography with fluorescence detection. J Chromatogr B 746:199–207
Marzinzig M, Nussler AK, Stadler J, Marzinzig E, Barthlen W, Nussler NC, Beger HG, Morris SM, Brückner UB (1997) Improved methods to measure end products of nitric oxide in biological fluids: nitrite, nitrate, and S-nitrosothiols. Nitric Oxide 1(2):177–189
Misko TP, Schilling RJ, Salvemini D, Moore WM, Currie MG (1993) A fluorometric assay for the measurement of nitrite in biological samples. Anal Biochem 214(1):11–16
Bedwell DW, Rivera VR, Merrill GA, Pusateri AE (2000) Elimination of matrix-based interferences to a fluorescent nitrite/nitrate assay by a simple filtration procedure. Anal Biochem 284(1):1–5
Fernández-Cancio M, Fernández-Vitos EM, Centelles JJ, Imperial S (2001) Sources of interference in the use of 2,3-diaminonaphthalene for the fluorimetric determination of nitric oxide synthase activity in biological samples. Clin Chim Acta 312:205–212
Carré MC, Mahieuxe B, André JC, Viriot ML (1999) Fluorimetric nitrite analysis using 2,3-diaminonaphthalene: an improvement of the method. Analusis 27(10):835–838
Kandimalla VB, Tripathi VS, Ju H (2006) Immobilization of biomolecules in sol–gels: biological and analytical applications. Crit Rev Anal Chem 36(2):73–106
Gadre SY, Gouma PI (2006) Biodoped ceramics: synthesis, properties, and applications. J Am Ceram Soc 89(10):2987–3002
Dunn B, Zink JI (2007) Molecules in glass: probe, ordered assemblies and functional materials. Acc Chem Res 40(9):747–755
Zaggout FR, El-Nahhal IM, Zourab SM, El-Ashgar NM, El-Dawahedy N, Motaweh H (2005) Encapsultion of methyl red pH-indicator into a sol–gel matrix. J Dispers Sci Technol 26:629–633
Zaggout FR, Qaraman AEA, Zourab SM, Azzeez HA (2006) Spectrophotometric studies of entrapped thymol phtalein ph indicator into sol–gel matrix. J Dispers Sci Technol 27:1003–1007
Schulz-Ekloff G, Wöhrle D, van Duffel B, Schoonheydt RA (2002) Chromophores in porous silicas and minerals: preparation and optical properties. Microporous Mesoporous Mater 51:91–138
Zaggout FR, El-Ashgar NM, Zourab SM, El-Nahhal IM, Motaweh H (2005) Encapsulation of methyl orange pH-indicator into a sol–gel matrix. Mater Lett 59:2928–2931
Martinez-Pérez D, Ferrer ML, Mateo CR (2003) A reagent less fluorescent sol–gel biosensor for uric acid detection in biological fluids. Anal Biochem 322(2):238–242
Pastor I, Esquembre R, Micol V, Mallavia R, Mateo CR (2004) A ready-to-use fluorimetric biosensor for superoxide radical using superoxide dismutase and peroxidase immobilized in sol–gel glasses. Anal Biochem 334(2):335–343
Senarath-Yapa MD, Scott Saavedra S (2001) Dye leaching from a doped sol–gel is eliminated by conjugation to a dendrimer. Anal Chim Acta 432(1):89–94
Nguyen T, McNamara KP, Rosenzweig Z (1999) Optochemical sensing by immobilizing fluorophore-encapsulating liposomes in sol–gel thin films. Anal Chim Acta 400:45–54
Skrdla PJ, Saavedra SS, Armstrong NR (1999) Reduction of indicator leaching from doped sol–gels by attachment of macromolecular carriers. Appl Spectrosc 53(7):785–791
Esquembre R, Pastor I, Mallavia R, Mateo CR (2005) Detection of nitric oxide using 2,3- diaminonaphthalene incorporated in β-cyclodextrin. J Photochem Photobiol A Chem 173:384–389
Coly A, Aaron JJ (1998) Cyclodextrin-enhanced fluorescence and photochemically induced fluorescence determination of five aromatic pesticides in water. Anal Chim Acta 360:129–141
Almansa López E, Bosque-Sendra JM, Cuadros Rodríguez L, García Campaña AM, Aaron JJ (2003) Applying non-parametric statistical methods to the classical measurements of inclusion complex binding constants. Anal Bioanal Chem 375(3):414–423
Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71(8):2703–2707
Pannala AS, Mani AR, Spencer JPE, Skinner V, Bruckdorfer KR, Moore KP, Rice-Evans CA (2003) The effect of dietary nitrate on salivary, plasma, and urinary nitrate metabolism in humans. Free Radic Biol Med 34(5):576–584
Acknowledgments
The authors thank the Spanish DGI of the Ministerio de Educación y Ciencia (MEC) for grant MAT2005-01004. Rocio Esquembre acknowledges the support of a predoctoral fellowship from MEC. We are grateful for the useful insights obtained in discussions with Dr. Marisa Ferrer and Dr. Isabel Pastor. We thank David Olmo for excellent technical assistance.
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Martínez-Tomé, M.J., Esquembre, R., Mallavia, R. et al. Immobilization and Characterization of 2,3-diaminonaphthalene/cyclodextrin Complexes in a Sol–Gel Matrix: A New Fluorimetric Sensor for Nitrite. J Fluoresc 19, 119–125 (2009). https://doi.org/10.1007/s10895-008-0393-3
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DOI: https://doi.org/10.1007/s10895-008-0393-3