Abstract
A novel turn-on fluorescent dye (E)-3′,6′-bis(diethylamino)-2-((1-(naphthalen-2-ylmethyl)-2-oxoindolin-3-ylidene)amino)spiro[isoindoline-1,9′-xanthen]-3-one (RBNI) based on a rhodamine-isatin hybrid molecular architecture was synthesized by condensation of isatin derivative with rhodamine hydrazide. The dye RBNI is selective and sensitive for recognition of Cr3+ ion in aqueous CH3CN media over other tested metal ions. The sensor shows large fluorescence enhancement upon complexation with Cr3+ and simultaneous color change occurs from colorless to pink-red. Spectroscopic study predicted 1:1 binding stoichiometry between RBNI and Cr3+ ion and this was again verified through ESI-MS (Electrospray Ionisation Mass Spectrometry). Detection limit of Cr3+ ion by this dye was calculated to be 2.4 μM. Furthermore, the potential application of this dye for the monitoring of Cr3+ ions in pond water and tap water samples was demonstrated.
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Manez RM, Sancenon F (2003) Fluorogenic and chromogenic chemosensors and reagents for anions. Chem Rev 103:4419–4476
Czarnik AW (1994) Chemical communication in water using fluorescent chemosensors. Acc Chem Res 27:302–308
Kim JS, Quang DT (2007) Calixarene-derived fluorescent probes. Chem Rev 107:3780–3799
Sinkeldam RW, Greco NJ, Tor Y (2010) Fluorescent analogs of biomolecular building blocks: design, properties, and applications. Chem Rev 110:2579–2619
Czarnik AW (1992) Fluorescent chemosensors for ion and molecule recognition. Ed. American Chemical Society, Washington, DC
Numata M, Li C, Bae AH, Kaneko K, Sakurai K, Shinkai S (2005) β-1,3-Glucan polysaccharide can act as a one-dimensional host to create novel silica nanofiber structures. Chem Comm 4655–4657
Henry A (1968) The role of chromium in mammalian nutrition. J Nutr 21:230–244
Gómez V, Callao MP (2006) Chromium determination and speciation since 2000 trends. Anal Chem 25:1006–1015
Latva S, Jokiniemi J, Peraniemi S, Ahlgren M (2003) Separation of picogram quantities of Cr(III) and Cr(VI) species in aqueous solutions and determination by graphite furnace atomic absorption spectrometry. J Anal At Spectrom 18:84–86
Arakawa H, Ahmad R, Naoui M, TaJmir-Riahi HA (2000) A comparative study of calf thymus DNA binding to Cr(III) and Cr(VI) ions evidence for the guanine N-7-chromium-phosphate chelate formation. J Biol Chem 275:10150–10153
Li Z, Zhao W, Zhang Y, Zhang L, Yu M, Liu J, Zhang H (2011) An ‘off-on’ fluorescent chemosensor of selectivity to Cr3+ and its application to MCF-7 cells. Tetrahedron 67:7096–7100
Vincent JB (2000) Quest for the molecular mechanism of chromium action and its relationship to diabetes. Nutr Rev 58:67–72
Bencheikh-Latmani R, Obraztsova A, Mackey MR, Ellisman MH, Tebo BM (2006) Toxicity of Cr(III) to Shewanella sp. strain MR-4 during Cr(VI) reduction. Environ Sci Technol 41:214–220
Mahmoud ME, Yakout AA, Ahmed SB, Osman MM (2008) Development of a method for chromium speciation by selective solid phase extraction and preconcentration on alumina-functionalized thiosemicarbazide. J Liq Chromatogr Relat Technol 31:2475–2492
(1989) National research council, recommended dietary allowance, Tenth Edition. National Academy Press, Washington, D. C.
Costa M, Klein CB (2006) Toxicity and carcinogenicity of chromium compounds in humans. CRC Crit Rev Toxicol 36:155–163
Dai R, Yu C, Liu J, Lan Y, Deng B (2010) Photo-oxidation of Cr(III)-citrate complexes forms harmful Cr(VI). Environ Sci Technol 44:6959–6964
O’Brien T, Mandel HG, Pritchard DE, Patierno SR (2002) Critical role of chromium (Cr)-DNA interactions in the formation of Cr-induced polymerase arresting lesions. Biochemistry 41:12529–12537
Arar EJ, Paff JO (1991) Determination of dissolved hexavalent chromium in industrial wastewater effluents by ion chromatography and post-column derivatization with diphenylcarbazide. J Chromatogr 546:335–340
Ososkov V, Kebbekus B, Chesbro D (1996) Field determination of Cr(VI) in water at low ppb level. Anal Lett 29:1829–1850
Varnes AW, Dodson RB, Wehry EL (1972) Interactions of transition-metal ions with photoexcited states of flavines. Fluorescence quenching studies. J Am Chem Soc 94:946–950
Zhou Y, Zhang J, Zhang L, Zhang Q, Ma T, Niu J (2013) A rhodamine-based fluorescent enhancement chemosensor for the detection of Cr3+ in aqueous media. Dyes Pigments 97:148–154
Wan Y, Guo Q, Wang X, Xia A (2010) Photophysical properties of rhodamine isomers: a two-photon excited fluorescent sensor for trivalent chromium cation (Cr3+). Anal Chim Acta 665:215–220
Huang K, Yang H, Zhou Z, Yu M, Li F, Gao X, Yi T, Huang C (2008) Multisignal chemosensor for Cr3+ and its application in bioimaging. Org Lett 10:2557–2560
Zhou Z, Yu M, Yang H, Huang K, Li F, Yi T, Huang C (2008) FRET-based sensor for imaging chromium(III) in living cells. Chem Commun 3387–3389
Rurack K, Kollmannsberger M, Resch-Genger U, Daub J (2000) A Selective and sensitive fluoroionophore for HgII, AgI, and CuII with virtually decoupled fluorophore and receptor units. J Am Chem Soc 122:968–969
Resendiz MJE, Noveron JC, Disteldorf H, Fischer S, Stang PJ (2004) A self-assembled supramolecular optical sensor for Ni(II), Cd(II), and Cr(III). Org Lett 6:651–653
Zyryanov GV, Palacios MA, Anzenbacher P (2007) Rational design of a fluorescence-turn-on sensor array for phosphates in blood serum. Angew Chem Int Ed 46:7849
Zhang M, Yu M, Li F, Zhu M, Li M, Gao Y, Li L, Liu Z, Zhang J, Zhang D (2007) A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging. J Am Chem Soc 129:10322–10323
Kim H, Lee M, Kim H, Kim J, Yoon J (2008) A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions. Chem Soc Rev 37:1465–1472
Liu H, Wan X, Liu T, Li Y, Yao Y (2014) Cascade sensitive and selective fluorescence OFF-ON-OFF sensor for Cr3+ cation and F− anion. Sensors Actuators B 200:191–197
King CIM, Bergh JJ, Petzer JP (2011) Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues. Bioorg Med Chem 19:261–274
Jiang Y, Hansen TV (2011) isatin 1,2,3-triazoles as potent inhibitors against caspase-3. Bioorg Med Chem Lett 21:1626–1629
Burdette SC, Lippard SJ (2001) ICCC34—golden edition of coordination chemistry reviews. Coordination chemistry for the neurosciences. Coord Chem Rev 216:333–361
Prodi L (2005) Luminescent chemosensors: from molecules to nanoparticles. New J Chem 29:20–31
Dhara A, Jana A, Konar S, Ghatak SK, Ray S, Das K, Bandyopadhyay A, Guchhait N, Kar SK (2013) A novel rhodamine-based colorimetric chemodosimeter for the rapid detection of Al3+ in aqueous methanol: fluorescent ‘OFF–ON’ mechanism. Tetrahedron Lett 54:3630–3634
Dhara A, Jana A, Guchhait N, Ghosh P, Kar SK (2014) Rhodamine-based molecular clips for highly selective recognition of Al3+ ions: synthesis, crystal structure and spectroscopic properties. New J Chem 38:1627–1634
Dhara A, Jana A, Guchhait N, Kar SK (2014) Isatin appended rhodamine scaffold as an efficient chemical tool to detect selectively Al3+. J Lumin 154:369–375
Anthoni U, Christophersen C, Nielsen P, Puschl A, Schaumburg K (1995) structure of red and orange fluorescein. Struct Chem 3:161–165
Xiang Y, Tong A, Jin P, Ju Y (2006) New fluorescent rhodamine hydrazone chemosensor for Cu(II) with high selectivity and sensitivity. Org Lett 8:2863–2866
Lakowicz JR (1999) Principles of fluorescence spectroscopy. Plenum, New York
Kubin RF, Fletcher AN (1952) Fluorescence quantum yields of some rhodamine dyes. J Lumin 27:455–462
Bhattacharya B, Nakka S, Guruprasad L, Samanta A (2009) Interaction of bovine serum albumin with dipolar molecules: fluorescence and molecular docking studies. J Phys Chem B 113:2143–2150
Teuchner K, Pfarrherr A, Stiel H, Freyera W, Leupold D (1993) Spectroscopic properties of potential sensitizers for new photodynamic therapy start mechanisms via two-step excited electronic states. Photochem Photobiol 57:465–471
Stiel H, Teuchner K, Paul A, Freyer W, Leupold DJ (1994) Two-photon excitation of alkyl-substituted magnesium phthalocyanine: radical formation via higher excited states. Photochem Photobiol A 80:289–298
Long GL, Winefordner JD (1983) Limit of detection a closer look at the IUPAC definition. Anal Chem 55:712A–724A
Kaur M, Kaur P, Dhuna V, Singh S, Singh K (2013) A ferrocene-pyrene based ‘turn-on’ chemodosimeter for Cr3+ - application in bioimaging. Dalton Trans 43:5707–5712
Wu S, Zhang K, Wang Y, Mao D, Liu X, Yu J, Wang L (2014) A novel Cr3+ turn-on probe based on naphthalimide and binol framework. Tetrahedron Lett 55:351–353
EPA US (1999) Integrated Risk Information System (IRIS) on chromium III. National Center for Environmental Assessment. Office of Research and Development, Washington
Vosburgh WC, Copper GR (1941) The identification of complex ions in solution by spectrophotometric measurements. J Am Chem Soc 63:437–442
Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707
Acknowledgments
A.D. thanks to CSIR, New Delhi, India for financial support by awarding senior research fellowship (Sanc. No. 01(2401)/10/EMR-II, dated 05.01. 2011).
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Dhara, A., Guchhait, N. & Kar, S.K. A Novel Cr3+ Fluorescence Turn-On Probe Based on Rhodamine and Isatin Framework. J Fluoresc 25, 1921–1929 (2015). https://doi.org/10.1007/s10895-015-1684-0
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DOI: https://doi.org/10.1007/s10895-015-1684-0