A Novel Turn-on Fluorescent Probe for Triphenylphosphine

doi:10.7517/j.issn.1674-0475.2017.05.013

Abstract

Abstract:

Triphenylphosphine (PPh₃) is an important organic substance and extraordinary for its nucleophilicity and reducing character.It is widely used in the synthesis of organic and organometallic compounds.The extensive use of PPh₃ is inevitable to cause phosphorous pollution to the environment and would pose a potential danger to human health.An effective and convenient detection method of PPh₃ is fairly desirable.Herein,a novel selective and sensitive off-on fluorescent probe for PPh₃ mimicking Staudinger ligation was developed.The design concept was to use a 2-azidophenylacetic ester of fluorescein to react with PPh₃ to undergo a rapid intramolecular acyl transfer through aza-ylide intermediate to release the fluorophore.The probe shows highly selective response to PPh₃ in water containing 0.5% DMSO.The probe is promising for the quantitative detection of PPh₃ with linear response from 1×10^-7 mol/L to 8×10^-7 mol/L with a detection limit of 10 nmol/L.The sensitive detection of PPh₃ can be viewed in water solutions with "naked eye".

Key words: fluorescein, fluorescent probe, turn-on fluorescent response, triphenylphosphine, Staudinger ligation

HUANG Zhentao, WANG Nannan, ZHANG Jian, ZHAO Weili. A Novel Turn-on Fluorescent Probe for Triphenylphosphine[J]. Imaging Science and Photochemistry, 2017, 35(6): 771-779.

References

[1] Cobb J E, Cribbs C M, Henke B R, Uehling D E, Hernan A G, Martin C, Rayner C M. e-EROS Encyclopedia of Reagents for Organic Synthesis[M]. New Jersey:John Wiley and Sons, 2005. 1-12.
[2] Lemieux G A, de Graffenried C L, Bertozzi C R. A fluorogenic dye activated by the Staudinger ligation[J]. Journal of the American Chemical Society, 2003,125(16):4708-4709.
[3] Chen X Q, Wang F, Hyun J Y, Wei T W, Qiang J, Ren X T, Shin I, Yoon J. Recent progress in the development of fluorescent, luminescent and colorimetric probes for detection of reactive oxygen and nitrogen species[J]. Chemical Society Reviews, 2016,45(10):2976-3016.
[4] Hangauer M J, Bertozzi C R. A FRET-based fluorogenic phosphine for live-cell imaging with the staudinger ligation[J]. Angewandte Chemie International Edition, 2008,120(13):2428-2431.
[5] Kohn M J, Breinbauer C R. The Staudinger ligation:a gift to chemical biology[J]. Angewandte Chemie International Edition, 2004,43(24):3106-3116.
[6] Saxon E, Luchansky S J, Hang H C, Yu C, Lee S C, Bertozzi C R. Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation[J]. Journal of the American Chemical Society, 2002,124(50):14893-14902.
[7] Nilsson B L, Hondal R J, Soellner M B, Raines R T. Protein assembly by orthogonal chemical ligation methods[J]. Journal of the American Chemical Society, 2003,125(18):5268-5269.
[8] Charles C, Wang Y, Seo T S, Li Z M, Ruparel H, Ju J Y. Site-specific fluorescent labeling of DNA using Staudinger ligation[J]. Bioconjugate Chemistry, 2003,14(3):697-701.
[9] Soellner M B, Dickson K A, Nilsson B L, Raines R T. Site-specific protein immobilization by Staudinger ligation[J]. Journal of the American Chemical Society, 2003,125(39):11790-11791.
[10] Kohn M, Wacker R, Peters C, Schroder H, Soulere L, Breinbauer R, Niemeyer C M, Waldmann H. Staudinger ligation:a new immobilization strategy for the preparation of small-molecule arrays[J]. Angewandte Chemie International Edition, 2003,42(47):5830-5834.
[11] Liu C Y, Wu H F, Wang Z K, Shao C X, Zhu B C, Zhang X L. A fast-response, highly sensitive and selective fluorescent probe for the ratiometric imaging of nitroxyl in living cells[J]. Chemical Communications, 2014,50(45):6013-6016.
[12] Liu P, Jing X T, Yu F B, Lv C J, Chen L X. A near-infrared fluorescent probe for the selective detection of HNO in living cells and in vivo[J]. Analyst, 2015,140(13):4576-4583.
[13] Zhang D, Chen W, Miao Z R, Ye Y, Zhao Y F, King S B, Xian M. A reductive ligation based fluorescent probe for S-nitrosothiols[J]. Chemical Communications, 2014,50(37):4806-4809.
[14] Jing X T, Yu F B, Chen L X. Visualization of nitroxyl (HNO) in vivo via a lysosome-targetable near-infrared fluorescent probe[J]. Chemical Communications, 2014,50(91):14253-14256.
[15] Gong X Y, Yang X F, Zhong Y G, Chen Y H, Li Z. A mitochondria-targetable near-infrared fluorescent probe for imaging nitroxyl (HNO) in living cells[J]. Dyes Pigments, 2016,131:24-32.
[16] Sunwoo K, Bobba K N, Lim J Y, Park T, Podder A, Heo J S, Lee S G, Bhuniya S, Kim J S. A bioorthogonal "turn-on" fluorescent probe for tracking mitochondrial nitroxyl formation[J]. Chemical Communications, 2017,53(10):1723-1726.
[17] McDonald D B, Shulman J. Spectrophotometric determination of triphenylphosphine in dilute solutions[J]. Analytical Chemistry, 1975,47(8):2023-2024.
[18] Rao V R S, Aravamudan G. Oxidimetric determination of triphenylphosphine[J]. Talanta, 1969,16(12):1594-1596.
[19] Carnes W J, Dean J A. Flame spectrophotometric study of yttrium[J]. Analytical Chemistry, 1961,33(13):1961-1962.
[20] Haky J E, Baird D M, Falzone S. Revrsed phase high performance liquid chromatographic analysis of triphenylphosphine in a reaction mixture[J]. Analytical Letters, 1989,22(11):2637-2651.
[21] Jung H S, Chen X Q, Kim J S, Yoon J. Recent progress in luminescent and colorimetric chemosensors for detection of thiols[J]. Chemical Society Reviews, 2013,42(14):6019-6031.
[22] Zhang J, Bao X L, Zhou J L, Peng F F, Ren H, Dong X C, Zhao W L. A mitochondria-targeted turn-on fluorescent probe for the detection of glutathione in living cells[J]. Biosensors and Bioelectronics, 2016,85:164-170.
[23] Zhang J, Zhou J L, Dong X C, Zheng X, Zhao W L. A near-infrared BODIPY-based fluorescent probe for the detection of hydrogen sulfide in fetal bovine serum and living cells[J]. RSC Advances, 2016,6(56):51304-51309.
[24] Shao X M, Kang R X, Zhang Y L, Huang Z T, Peng F F, Zhang J, Wang Y, Pan F C, Zhang W J, Zhao W L. Highly selective and sensitive 1 amino BODIPY-based red fluorescent probe for thiophenols with high off-to-on contrast ratio[J]. Analytical Chemistry, 2015,87(1):399-405.
[25] Zhang Y L, Shao X M, Wang Y, Pan F C, Kang R X, Peng F F, Huang Z T, Zhang W J, Zhao W L. Dual emission channels for sensitive discrimination of Cys/Hcy and GSH in plasma and cells[J]. Chemical Communications, 2015,51(20):4245-4248.
[26] Schwarzer D D, Gritsch P J, Gaich T. Mimicking dimethylallyltryptophan synthase:experimental evidence for a biosynthetic cope rearrangement process[J]. Angewandte Chemie International Edition, 2012,51(46):11514-11516.
[27] Peng B, Chen W, Liu C R, Rosser E W, Pacheco A, Zhao Y, Aguilar H C, Xian M. Fluorescent probes based on nucleophilic substitution-cyclization for hydrogen sulfide detection and bioimaging[J]. Chemistry-A European Journal, 2014,20(4):1010-1016.
[28] Zhang D, Chen W, Miao Z R, Ye Y, Zhao Y F, King S B, Xian M. A reductive ligation based fluorescent probe for S-nitrosothiols[J]. Chemical Communications, 2014,50(37):4806-4809.