Research Pregress on Synthesis of Xanthene Dyes
- Corresponding author: YANG Youjun, youjunyang@ecust.edu.cn
Citation:
LUO Xiao, HE Haihong, YANG Youjun. Research Pregress on Synthesis of Xanthene Dyes[J]. Chinese Journal of Applied Chemistry,
;2017, 34(12): 1403-1412.
doi:
10.11944/j.issn.1000-0518.2017.12.170308
Baeyer A. Uber Ein Neue Klasse von Farbstoffen(On a New Class of Dyes)[J]. Ber Dtsch Chem Ges, 1871,4:555-558. doi: 10.1002/(ISSN)1099-0682
Noelting E, Dziewobski K. Zur Kenntniss der Rhodamine[J]. Ber Dtsch Chem Ges, 1905,38:3516-3527. doi: 10.1002/(ISSN)1099-0682
Ho D T, Schlosser P, Houghton R W. 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. doi: 10.1061/(ASCE)0733-9372(2006)132:12(1664)
Robinson E, MacLeod J A, Lapple C E. A Meteorological Tracer Technique Using Uranine Dye[J]. J Atmos Sci, 2010,16(1):63-67.
Wu T X, Liu G M, Zhao J C. 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. doi: 10.1021/jp980922c
Mayer U, Oberlinner A. Rhodamine Dyes:US, 4647675[P]. 1987-03-03.
Folker K, Fritz M. Water-Soluble Reactive Xanthene Dyestuffs and Process for Preparing Them:US, 3888862[P]. 1975-06-10.
Nestmann E R, Douglas G R, Matula T I. 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.
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. doi: 10.1073/pnas.77.2.990
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. doi: 10.3109/10520297209116483
Feenstra R P G, Tseng S C G. Comparison of Fluorescein and Rose Bengal Staining[J]. Ophthalmology, 1992,99(4):605-617. doi: 10.1016/S0161-6420(92)31947-5
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. doi: 10.1016/S0002-9394(14)70125-4
Shinoda J, Yano H, Yoshimura S I. Fluorescence-Guided Resection of Glioblastoma Multiforme by Using High-Dose Fluorescein Sodium[J]. J Neurosurg, 2003,99(3):597-603. doi: 10.3171/jns.2003.99.3.0597
Jamison J M, Krabill K, Hatwalkar A. Potentiation of the Antiviral Activity of Poly R(A-U) by Xanthene Dyes[J]. Cell Biol Int Rep, 1990,14:1075-1084. doi: 10.1016/0309-1651(90)90015-Q
Chibale K, Visser M, van Schalkwyk D. Exploring the Potential of Xanthene Derivatives as Trypanothione Reductase Inhibitors and Chloroquine Potentiating Agents[J]. Tetrahedron, 2003,59:2289-2296. doi: 10.1016/S0040-4020(03)00240-0
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. doi: 10.1147/rd.112.0148
Peterson O G, Webb J P, McColgin W C. Organic Dye Laser Threshold[J]. J Appl Phys, 1971,42(5):1917-1928. doi: 10.1063/1.1660468
Han J Y, Burgess K. Fluorescent Indicators for Intracellular PH[J]. Chem Rev, 2009,110(5):2709-2728.
Urano Y, Kamiya M, Kanda K. Evolution of Fluorescein as a Platform for Finely Tunable Fluorescence Probes[J]. J Am Chem Soc, 2005,127(13):4888-4894. doi: 10.1021/ja043919h
Lavis L D, Raines R T. Bright Ideas for Chemical Biology[J]. ACS Chem Biol, 2008,3(3):142-155. doi: 10.1021/cb700248m
Lavis L D, Raines R T. Bright Building Blocks for Chemical Biology[J]. ACS Chem Biol, 2014,9(4):855-866. doi: 10.1021/cb500078u
Woodroofe C C, Lim M H, Bu W M. Synthesis of Isomerically Pure Carboxylate-and Sulfonate-Substituted Xanthene Fluorophores[J]. Tetrahedron, 2005,61(12):3097-3105. doi: 10.1016/j.tet.2005.01.024
Huang K Z, Liu M H, Liu Z G. 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. doi: 10.1016/j.dyepig.2015.03.007
Sakabe M, Asanuma D, Kamiya M. 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. doi: 10.1021/ja309688m
Kolmakov K, Belov V N, Bierwagen J. Red-Emitting Rhodamine Dyes for Fluorescence Microscopy and Nanoscopy[J]. Chem Eur J, 2010,16(1):158-166. doi: 10.1002/chem.v16:1
Chang M C Y, Pralle A, Isacoff E Y. A Selevtive, Cell-Permeable Optical Probe for Hydrogen Peroxide in Living Cells[J]. J Am Chem Soc, 2004,126(47):15392-15393. doi: 10.1021/ja0441716
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. doi: 10.1016/j.dyepig.2004.08.004
Hammersh j P, Pramod Kumar E K, Harris P. 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.
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. doi: 10.1021/ic401810x
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. doi: 10.1021/ja01665a026
Hilderbrand S A, Weissleder R. One-Pot Synthesis of New Symmetric and Asymmetric Xanthene Dyes[J]. Tetra Lett, 2007,48(25):4383-4385. doi: 10.1016/j.tetlet.2007.04.088
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. doi: 10.1002/chem.201402306
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. doi: 10.1021/ja037193l
Sibrian-Vazquez M, Escobedo J O, Lowry M. Field Effects Induce Bathochromic Shifts in Xanthene Dyes[J]. J Am Chem Soc, 2012,134(25):10502-10508. doi: 10.1021/ja302445w
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. doi: 10.1021/ja0668973
Shindo Y, Fujii T, Komatsu H. Newly Developed Mg2+-Selective Fluorescent Probe Enables Visualization of Mg2+ Dynamics in Mitochondria[J]. PLoS One, 2011,6(8)e23684. doi: 10.1371/journal.pone.0023684
Cardoso I C S, Amorim A L, Queir s C. Microwave-Assisted Synthesis and Spectroscopic Properties of 4'-Substituted Rosamine Fluorophores and Naphthyl Analogues[J]. Eur J Org Chem, 2012,2012(29):5810-5817. doi: 10.1002/ejoc.201200783
Lin W Y, Yuan L, Cao Z M. 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. doi: 10.1002/anie.200904515
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.
Hirano T, Kikuchi K, Urano Y. Novel Zinc Fluorescent Probes Excitable with Visible Light for Biological Applications[J]. Angew Chem Int Ed, 2000,112(6):1094-1096. doi: 10.1002/(ISSN)1521-3757
Komatsu H, Iwasawa N, Citterio D. 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. doi: 10.1021/ja049624l
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. doi: 10.1021/ja068230m
Yoon S, Miller E W, He Q W. A Bright and Specific Fluorescent Sensor for Mercury in Water, Cells, and Tissue[J]. Angew Chem Int Ed, 2007,46(35):6658-6661. doi: 10.1002/(ISSN)1521-3773
Wu L X, Burgess K. Synthesis and Spectroscopic Properties of Rosamines with Cyclic Amine Substituents[J]. J Org Chem, 2008,73(22):8711-8718. doi: 10.1021/jo800902j
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.
Carpenter R D, Verkman A S. Synthesis of a Sensitive and Selective Potassium-Sensing Fluoroionophore[J]. Org Lett, 2010,12(6):1160-1163. doi: 10.1021/ol902836c
Yang Y J, Escobedo J O, Wong A. A Convenient Preparation of Xanthene Dyes[J]. J Org Chem, 2005,70(17):6907-6912. doi: 10.1021/jo051002a
Yang Y J, Lowry M, Schowalter C M. An Organic White Light-Emitting Fluorophore[J]. J Am Chem Soc, 2006,128(43):14081-14092. doi: 10.1021/ja0632207
Yang Y J, Lowry M, Xu X Y. Seminaphthofluorones are a Family of Water-Soluble, Low Molecular Weight, NIR-Emitting Fluorophores[J]. Proc Natl Acad Sci, 2008,105(26):8829-8834. doi: 10.1073/pnas.0710341105
Sezukuri K, Suzuki M, Hayashi H. A Laterally Π-Expanded Fluorone Dye as an Efficient Near Infrared Fluorophore[J]. Chem Commun, 2016,52(27):4872-4875. doi: 10.1039/C6CC00237D
Gaillard S, Yakovlev A, Luccardini C. Synthesis and Characterization of a New Red-Emitting Ca2+ Indicator, Calcium Ruby[J]. Org Lett, 2007,9(14):2629-2632. doi: 10.1021/ol070648h
Anzalone A V, Wang T Y, Chen Z X. 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. doi: 10.1002/anie.201205369
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. doi: 10.1021/ja502945q
Lei Z H, Li X R, Li Y. Synthesis of Sterically Protected Xanthene Dyes with Bulky Groups at C-3' and C-7'[J]. J Org Chem, 2015,80(22):11538-11543. doi: 10.1021/acs.joc.5b01746
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
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