Abstract
A new family of coumarin-based pH indicators was synthesized. They are sensitive to pH in either weakly acidic or weakly basic solution. The indicators possess moderate to high brightness, excellent photostability and compatibility with light-emitting diodes. The indicators were covalently immobilized on the surface of amino-modified polymer microbeads which in turn were incorporated into a hydrogel matrix to obtain novel pH-sensitive materials. When a mixture of two different microbeads is used, the membranes are capable of optical pH sensing over a very wide range comparable to the dynamic range of the glass electrode (pH 1–11).
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Schroeder C, Weidgans BM, Klimant I (2005) Analyst 130(6):907–916
Neurauter G, Klimant I, Wolfbeis OS (2000) Fresenius’ J Anal Chem 366:481–487
Mekhail K, Khacho M, Gunaratnam L, Lee S (2004) Cell Cycle 3:1027–1029
Kojima S, Suzuki H (2003) Chem Sens 19:25–27
Juarez Tomas MS, Wiese B, Nader-Macýas ME (2005) J Appl Microbiol 99:1383–1391
Drosinos EH, Mataragas M, Nasis P, Galiotou M, Metaxopoulos J (2005) J Appl Microbiol 99:1314–1323
Marshall AJ, Blyth J, Davidson CAB, Lowe CR (2003) Anal Chem 75:4423–4431
Simova E, Simov Z, Beshkova D, Frengova G, Dimitrov Z, Spasov Z (2006) Int J Food Microbiol 107:112–123
Diwu Z, Chen CS, Zhang C, Klaubert DH, Haugland RP (1999) Chem Biol 6:411–418
Hara-Chikuma M, Wang Y, Guggino SE, Guggino WB, Verkman AS (2005) Biochem Biophys Research Commun 329:941–946
Simek M, Jisova L, Hopkins DW (2002) Soil Biol Biochem 34:1227–1234
Muhrizal S, Shamshuddin J, Fauziah I, Husni MAH (2006) Geoderma 131:110–122
Topaloglu U, Muftuoglu T, Akturk Z, Ekinci1 H, Peker O, Unalmiser S (2004) Surg Today 34:690–694
Wiczling P, Markuszewski MJ, Kaliszan M, Galer K, Kaliszan R (2005) J Pharm Biomed Anal 37:871–875
Wolfbeis OS (2006) Anal Chem 78:3859–3874, and references therein
Cajlakovic M, Lobnik A, Werner T (2002) Anal Chim Acta 455:207–213
Niu CG, Gui XQ, Zeng GM, Guan AL, Gao PF, Qin PZ (2005) Anal Bioanal Chem 383:349–357
Bernhard DD, Mall S, Pantano P (2001) Anal Chem 73:2484–2490
Leiner MJP, Wolfbeis OS (eds) (1991) Fiber optic chemical sensors and biosensors. CRC, Boca Raton, p 63
Leiner MJP, Hartmann P (1993) Sens Actuators B 11:281–289
Niu C-G, Gui X-Q, Zeng G-M, Yuan X-Z (2005) Analyst 130:1551–1556
Miliani C, Romani A, Favaro G (2000) J Phys Org Chem 13:141–150
Lin J, Liu D (2000) Anal Chim Acta 408:49–55
Netto EJ, Peterson GJ, McShane M, Hampshire V (1995) Sens Actuators B 29:157–163
Suah FBM, Ahmad M, Taib MN (2003) Sens Actuators B 90:175–181
Lobnik A, Majcena N, Niederreiterb K, Uray G (2001) Sens Actuators B 74:200–206
Nishimura G, Shiraishi Y, Hirai Y (2005) Chem Commun 5313–5315
Sartoris FJ, Bock C, Serendero I, Lannig G, Poertner HO (2003) J Fish Biol 62:1239–1253
Arain S, John GT, Krause C, Gerlach J, Wolfbeis OS, Klimant I (2006) Sens Actuators B 113:639–648
Smith JP, Drewes LR (2006) J Biol Chem 281:2053–2060
An Z, Moehwald H, Li J (2006) Biomacromolecules 7:580–585
Herrmann JM, Kantarci A, Long H, Bernardo J, Hasturk H, Wray LV, Simons ER, Van Dyke TE (2005) J Leukocyte Biol 78:612–619
Vasylevska GS, Borisov SM, Krause C, Wolfbeis OS (2006) Chem Mater 18:4609–4616
Mordon S, Devoisselle M, Soulie J (1995) J Photochem Photobiol B 1:19–23
Leiner MJP (1995) Sens Actuators B 1–3:169–173
Bellerby RGJ, Olsen A, Johannessen T, Croot P (2002) Talanta 1:61–69
Martz TR, Carr JJ, French CR, DeGrandpre MD (2003) Anal Chem 8:1844–1850
Whitaker JE, Haugland RP, Prendergast FG (1991) Anal Biochem 2:330–344
Parker JW, Laksin O, Yu C, Lau ML, Klima S, Fisher R, Scott I, Atwater BW (1993) Anal Chem 17:2329–2334
Karasev AA, Lukatskaya LL, Rubtsov MI, Zhykol EK, Yarmolenko SN, Ponomarev OA (1995) Russ J Gen Chem 65:1416–1425
Rajagopal R, Shenoy VU, Padmanabhan S, Sequeira S, Seshadri S (1990) Dyes Pigm 13:167–175
Swindlehurst BR, Narayanaswamy R (eds) (2004) Optical sensing of pH in low ionic strength waters. Optical Sensors, Manchester, pp 281–308
Hermanson GT (1996) Bioconjugate techniques. Academic, New York
Huber C, Werner T, Krause C, Leiner MJP, Wolfbeis OS (1999) Anal Chim Acta 398:137–143
Demas JN, Crosby GA (1971) J Phys Chem 76:991–1024
Krause C, Werner T, Huber C, Wolfbeis OS, Leiner MJP (1999) Anal Chem 71:1544–1548
Perrin DD, Dempsey B (1974) Laboratory manuals. Chapmann & Hall, London
Syzova ZA, Doroshenko AO, Lukatskaya LL, Rubtsov MI, Karasyov AA (2004) J Photochem Photobiol A 165:59–68
Park EJ, Brasuel M, Behrend C, Philbert MA, Kopelman R (2003) Anal Chem 75:3784–3791
Park EJ, Reid KR, Tang W, Kennedy RT, Kopelman R (2005) J Mater Chem 15:2913–2919
Klimant I, Huber C, Liebsch G, Neurauter G, Stangelmayer A, Wolfbeis OS (eds) (2001) Dual lifetime referencing (DLR)—a new scheme for converting fluorescence intensity into a frequency-domain or time-domain information. Springer, Berlin
Lakowicz JR, Castellano FN, Dattelbaum JD, Tolosa L, Rao G, Gryczynski I (1998) Anal Chem 70:5115–5121
von Bueltzingsloewen C, McEvoy AK, McDonagh C, MacCraith BD, Klimant I, Krause C, Wolfbeis OS (2002) Analyst 127:1478–1483
Peppas NA (1986) Preparation, methods & structures of hydrogels. CRC, Boca Raton
Drummen GPC, van Liebergen LCM, Op den Kamp JAF, Post JA (2002) Free Radical Biol Med 33:473–490
Weidgans BM, Krause C, Klimant I, Wolfbeis OS (2004) Analyst 129:645–650
Shortreed M, Kopelman R, Kuhn M, Hoyland B (1996) Anal Chem 68:1414–1418
Tan W, Shi ZY, Kopelman R (1992) Anal Chem 64:2985–2990
Kostov Y, Tzonkov S, Yotovan L, Krysteva M (1993) Anal Chem Acta 280:15–19
Jones TP, Porter MD (1988) Anal Chem 60:404–406
Opitz N, Luebbers DW (1983) Sens Actuators B 4:473–479
Niu C-G, Gui X-Q, Zeng G-M, Guan A-L, Gao P-F, Qin P-Z (2005) Anal Bioanal Chem 383:349–357
Sanchez-Barragan I, Costa-Fernandez JM, Sanz-Medel A (2005) Sens Actuators B 107:69–76
Liebsch G, Klimant I, Krause C, Wolfbeis O S (2001) Anal Chem 73:4354–4363
Brandrup J, Immergut EH, Grulke EA (eds) (1999) Polymer handbook. Wiley, New York
Liebsch G, Klimant I, Wolfbeis OS (1999) Adv Mater 11:1296–1299
Borisov SM, Vasylevska AS, Krause C, Wolfbeis OS (2006) Adv Funct Mater 16:1536–1542
Borisov SM, Krause C, Arain S, Wolfbeis OS (2006) Adv Mater 18:1511–1516
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We thank the BMBF for financial support within the project BP28 (HYBOP).
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Vasylevska, A.S., Karasyov, A.A., Borisov, S.M. et al. Novel coumarin-based fluorescent pH indicators, probes and membranes covering a broad pH range. Anal Bioanal Chem 387, 2131–2141 (2007). https://doi.org/10.1007/s00216-006-1061-6
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DOI: https://doi.org/10.1007/s00216-006-1061-6