呫吨染料合成方法研究进展

doi:10.11944/j.issn.1000-0518.2017.12.170308

摘要/Abstract

摘要：

呫吨染料是一类重要荧光染料,其良好的光物理性质使其得到了广泛应用。呫吨染料一般通过富电子的间苯二酚(或间氨基苯酚)与邻苯二甲酸酐在酸催化条件下缩合得到。近年来,呫吨染料在生物显微成像领域获得广泛应用,染料结构也日趋复杂,传统的合成方法不能满足需要,因而不断有新的呫吨染料合成方法见诸文献。本文简要概述了既有呫吨染料合成路线,并分析讨论了各方法的优缺点及适用底物范围。

关键词: 呫吨, 合成, 荧光染料, 分子探针

Abstract:

Xanthene dyes are a series of brilliant fluorescent dyes exhibiting superior photophysical properties, which facilitate their applications in various field. Traditionally, they are prepared via acid-catalyzed condensations between electron-rich resorcinol(m-aminophenols) and phthalic anhydride. Recently, structurally complicated xanthenes are often in need for bioimaging applications and not readily accessed with the aforementioned methods. This has promoted the development of novel pathways for their synthesis, which are summarized in this review. The scope and limitations of each methods are briefly discussed.

Key words: xanthene, synthesis, fluorophores, molecular probes

罗潇,何海红,杨有军. 呫吨染料合成方法研究进展[J]. 应用化学, 2017, 34(12): 1403-1412.

LUO Xiao,HE Haihong,YANG Youjun. Research Pregress on Synthesis of Xanthene Dyes[J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1403-1412.

参考文献

[1]	Baeyer A. Uber Ein Neue Klasse von Farbstoffen(On a New Class of Dyes)[J]. Ber Dtsch Chem Ges,1871,4:555-558(in German).
[2]	Noelting E,Dziewobski K. Zur Kenntniss der Rhodamine[J]. Ber Dtsch Chem Ges,1905,38:3516-3527(in German).
[3]	Ho D T,Schlosser P,Houghton R W,et al.Comparison of SF 6 and Fluorescein as Tracers for Measuring Transport Processes in a Large Tidal River[J]. J Environ Eng,2006,132(12):1664-1669.
[4]	Robinson E,MacLeod J A,Lapple C E. A Meteorological Tracer Technique Using Uranine Dye[J]. J Atmos Sci,2010,16(1):63-67.
[5]	Wu T X,Liu G M,Zhao J C,et al.Photoassisted Degradation of Dye Pollutants.V.Self-Photosensitized Oxidative Transformation of Rhodamine B Under Visible Light Irradiation in Aqueous TiO2 Dispersions[J]. J Phys Chem B,1998,102(30):5845-5851.
[6]	Mayer U,Oberlinner A. Rhodamine Dyes:US,4647675[P].1987-03-03.
[7]	Folker K,Fritz M. Water-Soluble Reactive Xanthene Dyestuffs and Process for Preparing Them:US,3888862[P].1975-06-10.
[8]	Nestmann E R,Douglas G R,Matula T I,et al.Mutagenic Activity of Rhodamine Dyes and Their Impurities as Detected by Mutation Induction in Salmonella and DNA Damage in Chinese Hamster Ovary Cells[J]. Cancer Res,1979,39:4412-4417.
[9]	Johnson L V,Walsh M L,Chen L B. Localization of Mitochondria in Living Cells with Rhodamine 123[J]. Proc Natl Acad Sci,1980,77(2):990-994.
[10]	Widholm J M. The Use of Fluorescein Diacetate and Phenosafranine for Determining Viability of Cultured Plant Cells[J]. Stain Technol,1972,47(4):189-194.
[11]	Feenstra R P G,Tseng S C G. Comparison of Fluorescein and Rose Bengal Staining[J]. Ophthalmology,1992,99(4): 605-617.
[12]	Lee S H, Tseng S C G. Amniotic Membrane Transplantation for Persistent Epithelial Defects with Ulceration[J]. Am J Ophthalmol,1997,123(3):303-312.
[13]	Shinoda J,Yano H,Yoshimura S I,et al.Fluorescence-Guided Resection of Glioblastoma Multiforme by Using High-Dose Fluorescein Sodium[J]. J Neurosurg,2003,99(3):597-603.
[14]	Jamison J M,Krabill K,Hatwalkar A,et al.Potentiation of the Antiviral Activity of Poly R(A-U) by Xanthene Dyes[J]. Cell Biol Int Rep,1990,14:1075-1084.
[15]	Chibale K,Visser M,van Schalkwyk D, et al. Exploring the Potential of Xanthene Derivatives as Trypanothione Reductase Inhibitors and Chloroquine Potentiating Agents[J]. Tetrahedron,2003,59:2289-2296.
[16]	Sorokin P P,Lankard J R. Flashlamp Excitation of Organic Dye Lasers:A Short Communication[J]. IBM J Res Dev,1967,11(2):148-148.
[17]	Peterson O G,Webb J P, McColgin W C, et al. Organic Dye Laser Threshold[J]. J Appl Phys,1971,42(5):1917-1928.
[18]	Han J Y,Burgess K. Fluorescent Indicators for Intracellular PH[J]. Chem Rev,2009,110(5): 2709-2728.
[19]	Urano Y,Kamiya M,Kanda K,et al.Evolution of Fluorescein as a Platform for Finely Tunable Fluorescence Probes[J]. J Am Chem Soc,2005,127(13):4888-4894.
[20]	Lavis L D,Raines R T. Bright Ideas for Chemical Biology[J]. ACS Chem Biol,2008,3(3):142-155.
[21]	Lavis L D,Raines R T. Bright Building Blocks for Chemical Biology[J]. ACS Chem Biol,2014,9(4): 855-866.
[22]	Woodroofe C C,Lim M H,Bu W M,et al.Synthesis of Isomerically Pure Carboxylate- and Sulfonate-Substituted Xanthene Fluorophores[J]. Tetrahedron,2005,61(12):3097-3105.
[23]	Huang K Z,Liu M H,Liu Z G,et al.Ratiometric and Colorimetric Detection of Hydrogen Sulfide with High Selectivity and Sensitivity Using a Novel FRET-Based Fluorescence Probe[J]. Dyes Pigm,2015,118:88-94.
[24]	Sakabe M,Asanuma D,Kamiya M,et al.Rational Design of Highly Sensitive Fluorescence Probes for Protease and Glycosidase Based on Precisely Controlled Spirocyclization[J]. J Am Chem Soc,2013,135(1):409-414.
[25]	Kolmakov K,Belov V N,Bierwagen J,et al.Red-Emitting Rhodamine Dyes for Fluorescence Microscopy and Nanoscopy[J]. Chem Eur J,2010,16(1):158-166.
[26]	Chang M C Y,Pralle A,Isacoff E Y,et al. A Selevtive, Cell-Permeable Optical Probe for Hydrogen Peroxide in Living Cells[J]. J Am Chem Soc,2004,126(47):15392-15393.
[27]	Patel R G,Patel M P,Patel R G. 3,6-Disubtituted Fluorans Containing 4(3H)-quinazolinon-3-yl, Diethyl Amino Groups and Their Application in Reversible Thermochromic Materials[J]. Dyes Pigm,2005,66(1):7-13.
[28]	Hammersh j P,Pramod Kumar E K,Harris P,et al. Facile Large-Scale Synthesis of 5- and 6-Carboxyfluoresceins:Application for the Preparation of New Fluorescent Dyes[J]. Eur J Org Chem,2015,33:7301-7309.
[29]	Wang C Y, Wong K M-C. Selevtive Hg2+ Sensing Behaviors of Rhodamine Derivatives with Extended Conjugation Based on Two Successive Ring-Opening Process[J]. Inorg Chem,2013,52(23):13432-13441.
[30]	Sen R N,Sinha N N. Condensations of Aldehydes with Resorcinol and Some Other Aromatic Hydroxy Compounds[J]. J Am Chem Soc,1923,45(12):2984-2996.
[31]	Hilderbrand S A,Weissleder R. One-Pot Synthesis of New Symmetric and Asymmetric Xanthene Dyes[J]. Tetra Lett,2007,48(25):4383-4385.
[32]	Chevalier A,Renard P Y,Romieu A. Straightforward Access to Water-Soluble Unsymmetrical Sulfoxanthene Dyes:Application to the Preparation of Far-Red Fluorescent Dyes with Large Stokes' Shifts[J]. Chem Eur J,2014,20(27):8330-8337.
[33]	Jiao G S,Thoresen L H,Burgess K. Fluorescent, Through-Bond Energy Transfer Cassettes for Labelling Mutiple Biological Molecules in One Experiment[J]. J Am Chem Soc,2003,125(48):14668-14669.
[34]	Sibrian-Vazquez M,Escobedo J O,Lowry M,et al.Field Effects Induce Bathochromic Shifts in Xanthene Dyes[J]. J Am Chem Soc,2012,134(25):10502-10508.
[35]	Miller E W,Bian S X,Chang C J. A Fluorescent Sensor for Imaging Reversible Redox Cycles in Living Cells[J]. J Am Chem Soc,2007,129(12):3458-3459.
[36]	Shindo Y,Fujii T,Komatsu H,et al.Newly Developed Mg2+-Selective Fluorescent Probe Enables Visualization of Mg2+ Dynamics in Mitochondria[J]. PLoS One,2011,6(8):e23684.
[37]	Cardoso I C S,Amorim A L,Queir s C,et al. Microwave-Assisted Synthesis and Spectroscopic Properties of 4'-Substituted Rosamine Fluorophores and Naphthyl Analogues[J]. Eur J Org Chem,2012,2012(29):5810-5817.
[38]	Lin W Y,Yuan L,Cao Z M,et al.Through-Bond Energy Transfer Cassettes with Minimal Spectral Overlap Between the Donor Emission and Acceptor Absorption: Coumarin-Rhodamine Dyads with Large Pseudo-Stokes Shifts and Emission Shifts[J]. Angew Chem Int Ed,2010,49(2):375-379.
[39]	Minta A,Kao J P,Tsien R Y. Fluorescent Indicators for Cytosolic Calcium Based on Rhodamine and Fluorescein Chromophores[J]. J Biol Chem,1989,264(14):8171-8178.
[40]	Hirano T,Kikuchi K,Urano Y,et al.Novel Zinc Fluorescent Probes Excitable with Visible Light for Biological Applications[J]. Angew Chem Int Ed,2000,112(6):1094-1096.
[41]	Komatsu H,Iwasawa N,Citterio D,et al.Design and Synthesis of Highly Sensitive and Selective Fluorescein-Derived Magnesium Fluorescent Probes and Application to Intracellular 3D Mg2+ Imaging[J]. J Am Chem Soc,2004,126(50):16353-16360.
[42]	Ahn Y H,Lee J S,Chang Y T. Combinatorial Rosamine Library and Application to in vivo Glutathione Probe[J]. J Am Chem Soc,2007,129(15):4510-4511.
[43]	Yoon S,Miller E W,He Q W,et al.A Bright and Specific Fluorescent Sensor for Mercury in Water, Cells, and Tissue[J]. Angew Chem Int Ed,2007,46(35):6658-6661.
[44]	Wu L X,Burgess K. Synthesis and Spectroscopic Properties of Rosamines with Cyclic Amine Substituents[J]. J Org Chem,2008,73(22):8711-8718.
[45]	Beacham D,Dzubay J,Gee K,et al. Fluorogenic pH Sensitive Dyes and Their Method of Use:US.Patent Application 14/455,550[P].2014-08-08.
[46]	Carpenter R D,Verkman A S. Synthesis of a Sensitive and Selective Potassium-Sensing Fluoroionophore[J]. Org Lett,2010,12(6):1160-1163.
[47]	Yang Y J,Escobedo J O,Wong A,et al.A Convenient Preparation of Xanthene Dyes[J]. J Org Chem,2005,70(17):6907-6912.
[48]	Yang Y J,Lowry M,Schowalter C M,et al.An Organic White Light-Emitting Fluorophore[J]. J Am Chem Soc,2006,128(43):14081-14092.
[49]	Yang Y J,Lowry M,Xu X Y,et al.Seminaphthofluorones are a Family of Water-Soluble, Low Molecular Weight, NIR-Emitting Fluorophores[J]. Proc Natl Acad Sci,2008,105(26):8829-8834.
[50]	Sezukuri K,Suzuki M,Hayashi H,et al.A Laterally Π-Expanded Fluorone Dye as an Efficient Near Infrared Fluorophore[J]. Chem Commun,2016,52(27):4872-4875.
[51]	Gaillard S,Yakovlev A,Luccardini C,et al.Synthesis and Characterization of a New Red-Emitting Ca2+ Indicator, Calcium Ruby[J]. Org Lett,2007,9(14):2629-2632.
[52]	Anzalone A V,Wang T Y,Chen Z X,et al.A Common Diaryl Ether Intermediate for the Gram-Scale Synthesis of Oxazine and Xanthene Fluorophores[J]. Angew Chem Int Ed,2013,52(2):650-654.
[53]	Lei Z H,Yang Y J. A Concise Colorimetric and Fluorimetric Probe for Sarin Related Threats Designed via the “Covalent-Assembly” Approach[J]. J Am Chem Soc,2014,136(18):6594-6597.
[54]	Lei Z H,Li X R,Li Y,et al.Synthesis of Sterically Protected Xanthene Dyes with Bulky Groups at C-3' and C-7'[J]. J Org Chem,2015,80(22):11538-11543.