Progress in Resorufin-Based Spectroscopic Probes

doi:10.7517/j.issn.1674-0475.2014.01.060

Abstract

Abstract:

Spectroscopic probes may be defined as the reagents that can react with analytes, accompanied by the changes of their spectroscopic (chromogenic, or luminescent including chemiluminescent) properties; based on such changes the analytes can thus be determined. Spectroscopic probes have attracted continually growing attention because of their powerful ability to improve analytical sensitivity, and especially to offer greater temporal and spatial resolution for in vivo imaging studies. In recent years, resorufin-based spectroscopic probes have been developed greatly, possibly resulting from its superior properties such as long analytical wavelength, high quantum yield, good water-solubility and non-cytotoxicity. In particular, the spectroscopic signal of resorufin is easily quenched via 7-hydroxy substitution, which provides a convenient platform for preparing a spectroscopic probe with extremely low background signal. So far, this behavior has been widely used to design excellent resorufin-based spectroscopic probes for various analytes, such as enzymes, ions and reactive oxygen species. In the present paper, we will briefly review the progress of resorufin-based spectroscopic probes, including their design strategies, reaction mechanisms and analytical applications.

Key words: spectroscopic probes, resorufin, enzymes, ions, reactive oxygen species, fluorescence imaging

LI Zhao, MA Huimin. Progress in Resorufin-Based Spectroscopic Probes[J]. Imaging Science and Photochemistry, 2014, 32(1): 60-68.

References

[1] Shi W, Ma H M. Spectroscopic probes with changeable π-conjugated systems[J]. Chemical Communications,2012, 48(70):8732-8744.
[2] Li X H, Gao X H, Shi W, et al. Design strategies for water-soluble small molecular chromogenic and fluorogenic probes[J].Chemical Reviews, 2013, ASAP (doi: 10.1021/cr300508p).
[3] 邱波, 于天君, 陈金平, 等. 水相氟离子"turn-on"型荧光传感器[J]. 影像科学与光化学, 2013, 31(5): 383-389. Qiu B, Yu T J, Chen J P, et al. A rapid aqueous fluoride anion sensor with turn-on fluorescence mode[J]. Imaging Science and Photochemistry, 2013, 31(5): 383-389.
[4] 胡睿, 郭旭东, 杨国强. 激发态分子内质子转移化合物的性能及作为荧光化学传感器的应用研究[J]. 影像科学与光化学, 2013, 31(5): 335-348. Hu R, Guo X D, Yang G Q. Investigation on the property of the excited state intramolecular proton transfer compounds and its application as fluorescence chemical sensor[J]. Imaging Science and Photochemistry, 2013, 31(5): 335-348.
[5] Kim H N, Guo Z, Zhu W, et al. Recent progress on polymer-based fluorescent and colorimetric chemosensors[J]. Chemical Society Reviews, 2011, 40: 79-93.
[6] Chen X Q, Sun M, Ma H M. Progress in spectroscopic probes with cleavable active bonds[J]. Current Organic Chemistry,2006, 10: 477-489.
[7] Bueno C, Villegas M L, Bertolotti S G, et al. The excited-state interaction of resazurin and resorufin with amines in aqueous solutions. Photophysics and photochemical reaction[J].Photochemistry Photobiology, 2002, 76(4): 385-390.
[8] Zhang Y Y, Chen W, Feng D, et al. A spectroscopic off-on probe for simple and sensitive detection of carboxylesterase activity and its application to cell imaging[J]. Analyst, 2012, 137:716-721.
[9] 宋延超,刘俊秀,张阳阳,等. 纳米材料在生物分析应用中存在的若干问题[J].化学学报, 2013, 71: 1607-1610. Song Y C, Liu J X, Zhang Y Y, et al. Some problems of nanomaterials in bioanalytical applications[J]. Acta Chimica Sinica, 2013, 71: 1607-1610.
[10] Albers A E, Rawls K E, Chang C J. Activity-based fluorescent reporters for monoamine oxidases in living cells[J]. Chemical Communication,2007, 4647-4649.
[11] Li Z, Li X H, Gao X H, et al. Nitroreductase detection and hypoxic tumor cell imaging by a designed sensitive and selective fluorescent probe, 7--3H- phenoxazin-3-one[J]. Analytical Chemistry,2013, 85: 3926-3932.
[12] Li Z, Gao X H, Shi W, et al. 7-((5-Nitrothiophen-2-yl)methoxy)-3H-phenoxazin-3-one as a spectroscopic off-on probe for highly sensitive and selective detection of nitroreductase[J]. Chemical Communication, 2013, 49: 5859-5861.
[13] Hofmann J, Sernetz M. Immobilized enzyme kinetics analyzed by flow-through microfluorimetry: resorufin-β-D-galactopyranoside as a new fluorogenic substrate for β-galactosidase[J]. Analytica Chimica Acta,1984, 163: 67-72.
[14] Motabar O, Shi Z D, Goldin E, et al. A new resorufin-based β-glucosidase assay for high-throughput screening[J]. Analytical Biochemitry,2009, 390: 79-84.
[15] Gao W, Xing B, Tsien R Y, et al. Novel fluorogenic substrates for imaging lactamase gene expression[J]. Journal of American Chemical Society,2003, 125:11146-11147.
[16] Lavis L D, Chao T Y, Raines R T. Synthesis and utility of fluorogenic acetoxymethyl ethers[J]. Chemical Science,2011, 2: 521-530.
[17] Cui K, Chen Z L, Wang Z, et al. A naked-eye visible and fluorescence "turn-on'' probe for acetyl-cholinesterase assay and thiols as well as imaging of living cells[J]. Analyst, 2011, 136: 191-195.
[18] Sun M, Shangguan D H, Ma H M, et al. Simple Pb^II fluorescent probe based on the Pb^II-catalyzed hydrolysis of phosphodiester[J]. Biopolymers,2003,72: 413-420.
[19] Ma X, Wang J, Du Y, et al. A "Turn-on" fluorescent Hg²⁺chemosensor based on ferrier carbocyclization[J]. Organic Letters,2012, 14: 820-823.
[20] Ren W X, Pradhan T, Yang Z, et al. Rapid responsive palladium sensor under mild condition[J]. Sensors and Actuators B, 2012, 171-172: 1277-1282.
[21] Kim S Y, Hong J I. Chromogenic and fluorescent chemodosimeter for detection of fluoride in aqueous solution[J]. Organic Letters,2007, 9: 3109-3112.
[22] Chen W, Li Z, Shi W, et al. A new resorufin-based spectroscopic probe for simple and sensitive detection of benzoyl peroxide via deboronation[J]. Chemical Communication,2012, 48: 2809-2811.
[23] Choi M G, Cha S, Park J E, et al. Selective perborate signaling by deprotection of fluorescein and resorufin acetates[J]. Organic Letters,2010, 12: 1468-1471.
[24] Choi M G, Hwang J, Eor S, et al. Chromogenic and fluorogenic signaling of sulfite by selective deprotection of resorufin levulinate[J]. Organic Letters,2010, 12: 5624-5627.
[25] 陈巍, 马会民. 检测活性氧物种的氧杂蒽类光学探针的研究进展[J].分析化学,2012,40(9): 1311-1321. Chen W, Ma H M. Progress in xanthene-based spectroscopic probes for reactive oxygen species[J]. Chinese Journal of Analytical Chemistry, 2012,40(9): 1311-1321.
[26] Miller E W, Tulyathan O, Isacoff E Y, et al.Molecular imaging of hydrogen peroxide produced for cell signaling[J]. Nature Chemical Biology, 2007, 3: 263-267.
[27] Newton G L, Milligan J R. Fluorescence detection of hydroxyl radicals[J]. Radiation Physics and Chemistry, 2006, 75: 473-478.
[28] Zhang Y Y, Shi W, Li X H, et al. Sensitive detection of ozone by a practical resorufin-based spectroscopic probe with extremely low background signal[J]. Scientific Reports,2013, 3: 2830.